Water soluble additive composition

Abstract

To provide a new composition including cyclic carboxylic acid.SOLUTION: A water soluble additive composition is provided, which includes cyclic carboxylic acid and satisfies one or more of the following conditions 1-4: (condition 1) the water soluble additive composition includes a component (A) of cyclic carboxylic acid excluding the following component (B1), and one or more kinds selected from the group consisting of the component (B1) gallic acid and its ester; (condition 2) the total amount of contents of Na+ and NH4+ is 100 ppm or more and 5,000 ppm or less based on the cyclic carboxylic acid;(condition 3) a total inorganic ion content (excluding hydrogen ion and hydroxy group ion) is 300 ppm or more and 5,000 ppm or less based on the cyclic carboxylic acid; and (condition 4) the component (A) cyclic carboxylic acid excluding the following component (B2), and the component (B2) of amino acid are included.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a water-soluble additive composition.

[0002] Patent Documents 6 and 7 disclose techniques relating to compositions containing cyclic carboxylic acids. Patent Document 6 (JP 2014-31347 A) describes a composition containing a cyclic hydroxy acid or a derivative thereof having a specific structure and a sterol ester. According to this document, such a composition can provide a composition that has an excellent free radical scavenging effect and is also excellent in terms of irritation, usability, odor, and storage stability, and is therefore capable of preventing or improving aging phenomena such as wrinkle formation, loss of skin elasticity, and hair loss.

[0003] Patent Document 7 (WO 2016 / 039407) describes a composition containing an acylproline or a salt thereof having a specific structure and a zinc salt of pyrrolidone carboxylate, as a technique for providing a composition in which the peculiar odor of acylproline or a salt thereof is reduced, which has a moist feeling and is highly stable, and also describes that such a composition may contain a hydroxycarboxylic acid. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] JP 2004-35440 A [Patent Document 2] JP 2013-155158 A [Patent Document 3] JP 2009-215266 A [Patent Document 4] Japanese Patent Application Publication No. 7-126135 [Patent Document 5] JP 2018-150288 A [Patent Document 6] JP 2014-31347 A [Patent Document 7] International Publication No. 2016 / 039407 [Patent Document 8] JP 2007-238469 A [Patent Document 9] Japanese Patent Application Publication No. 8-92589 Summary of the Invention [Problem to be solved by the invention]

[0005] The present invention provides novel compositions comprising cyclic carboxylic acids. [Means for solving the problem]

[0006] According to the present invention, There is provided a water-soluble additive composition that contains a cyclic carboxylic acid and satisfies at least one of the following conditions 1 to 4. (Condition 1) Contains the following components (A) and (B1). (A) The cyclic carboxylic acid is other than the following component (B1): (B1) One or more selected from the group consisting of gallic acid and its esters (Condition 2) Na + and NH4 + The total content of the above is 100 ppm or more and 5000 ppm or less based on the cyclic carboxylic acid. (Condition 3) The total inorganic ion content (excluding hydrogen ions and hydroxyl ions) is 300 ppm or more and 5000 ppm or less based on the cyclic carboxylic acid. (Condition 4) Contains the following components (A) and (B2). (A) The cyclic carboxylic acid is other than the following component (B2): (B2) Amino acids

[0007] According to the present invention, A food or flavoring containing a plant-derived sugar and at least one of a cyclic compound and its derivative derived from a microorganism is provided.

[0008] According to the present invention, A food additive is provided which contains a plant-derived sugar and at least one of a cyclic compound derived from a microorganism and a derivative thereof.

[0009] According to the present invention, A method for producing a cyclic compound or a derivative thereof for use as a food, a food additive, or a flavoring, comprising the steps of: preparing a culture solution containing plant-derived sugars and a microorganism so as to produce at least one of the cyclic compound and its derivatives; Concentrating the culture solution to obtain a concentrate; recovering at least one of the cyclic compound and its derivative from the concentrated solution by crystallization, precipitation, extraction, sublimation purification, or distillation; The present invention provides a method for producing a cyclic compound or a derivative thereof, comprising: Effect of the Invention

[0010] According to the present invention, a novel composition containing a cyclic carboxylic acid can be provided. [Brief description of the drawings]

[0011] [Figure 1] FIG. 1 is a diagram showing evaluation results of antibacterial compositions. [Diagram 2] FIG. 1 is a diagram showing evaluation results of antibacterial compositions. [Diagram 3] FIG. 1 is a diagram showing evaluation results of antibacterial compositions. [Figure 4] FIG. 1 is a diagram showing evaluation results of antibacterial compositions. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] Hereinafter, the embodiments of the present invention will be described with specific examples. In the embodiments, the composition may contain each component alone or in combination of two or more. In addition, the symbol "to" indicating a numerical range indicates a range from above to below, and both ends of the range are included.

[0013] (First embodiment) The present embodiment relates to an antibacterial composition.

[0014] Patent Documents 1 to 3 describe techniques relating to compositions containing antibacterial components. Patent Document 1 (JP Patent Publication No. 2004-35440) describes a dullness-inhibiting agent that contains a specific melanin production inhibitor, a specific fibroblast proliferation promoter, and a specific blood circulation promoter, and also describes that such an agent may be used in combination with an antibacterial agent such as shikimic acid as an additional additive.

[0015] Patent Document 2 (JP Patent Publication No. 2013-155158) describes an antibacterial composition containing an onion skin extract and acting against one or more bacteria selected from the group consisting of bacteria causing acne vulgaris and bacteria causing dental caries, and specifically describes the obtaining of an antibacterial composition containing specific amounts of quercetin, quercetin-4' glucoside, and protocatechuic acid.

[0016] Patent Document 3 (JP Patent Publication No. 2009-215266) describes a melanin production inhibitor containing one or more compounds selected from shikimic acid and its salts as an active ingredient, and describes that the use of such an agent does not include use as a chelating agent or antibacterial agent, or for use on hair.

[0017] Although in a different technical field, a composition containing polyphenols is described in Patent Document 4. Patent Document 4 (JP Patent Publication 7-126135 A) describes an external preparation for the skin in which at least one type of alcohol and / or polyphenol is added to an external preparation containing kojic acid and / or its derivatives and an ultraviolet absorber, and lists a large number of examples of polyphenols including gallic acid, gallic acid esters, and shikimic acid.

[0018] As a result of the inventors' investigation of the techniques described in the above-mentioned patent documents, it became clear that there was room for improvement in terms of improving antibacterial properties. Therefore, the present embodiment provides a composition having excellent antibacterial properties.

[0019] According to this embodiment, Components (A) and (B1) below: (A) Cyclic carboxylic acids (excluding component (B1) below) (B1) One or more selected from the group consisting of gallic acid and its esters An antimicrobial composition is provided comprising:

[0020] Furthermore, according to this embodiment, for example, daily necessities or cosmetics containing the antibacterial composition of this embodiment can also be obtained.

[0021] According to this embodiment, a composition having excellent antibacterial properties can be provided.

[0022] The embodiment will be described in more detail below. In the embodiment, the composition may contain each component alone or in combination of two or more kinds.

[0023] In this embodiment, the antibacterial composition contains the following components (A) and (B1). (A) Cyclic carboxylic acids (excluding component (B1) below) (B1) One or more selected from the group consisting of gallic acid and its esters

[0024] (Component (A)) Component (A) is a cyclic carboxylic acid and is a component other than component (B1) described below. Specific examples of component (A) include cyclic carboxylic acids having one or more hydroxy groups, and cyclic carboxylic acids having one or more amino groups, and preferably cyclic polyhydroxycarboxylic acids having two or more hydroxy groups.

[0025] Cyclic carboxylic acids include, for example, benzoic acid. Examples of cyclic carboxylic acids having a hydroxy group include aromatic hydroxycarboxylic acids and alicyclic hydroxycarboxylic acids. Examples of aromatic hydroxycarboxylic acids include hydroxybenzoic acids such as salicylic acid and 4-hydroxybenzoic acid, monohydroxybenzoic acids such as hydroxy(methyl)benzoic acid and hydroxy(methoxy)benzoic acid, and derivatives thereof; dihydroxybenzoic acids such as protocatechuic acid, gentisic acid, etc., dihydroxybenzoic acids such as orselliic acid, etc., and dihydroxy(methyl)benzoic acids and their derivatives; Included are monohydroxycinnamic acids such as ferulic acid and its derivatives. Examples of the alicyclic hydroxycarboxylic acid include shikimic acid and quinic acid. The cyclic carboxylic acid having a hydroxy group preferably has two or more hydroxy groups.

[0026] In addition, examples of cyclic carboxylic acids having an amino group include monoaminobenzoic acids such as 4-aminobenzoic acid and derivatives thereof, and other aromatic aminocarboxylic acids; and Alicyclic aminocarboxylic acids are included.

[0027] From the viewpoint of improving the antibacterial properties of the antibacterial composition, component (A) is preferably one or more selected from the group consisting of protocatechuic acid, shikimic acid, 4-hydroxybenzoic acid, 4-aminobenzoic acid, and ferulic acid, and more preferably one or more selected from the group consisting of protocatechuic acid and shikimic acid.

[0028] From the viewpoint of improving antibacterial properties, the content of component (A) in the antibacterial composition may be, for example, 50 mass% or more, preferably 80 mass% or more, more preferably 90 mass% or more, even more preferably 95 mass% or more, and still more preferably 98 mass% or more, based on the total amount of the antibacterial composition. From the same viewpoint, the content of component (A) in the antibacterial composition is less than 100 mass%, preferably 99.999 mass% or less, more preferably 99.990 mass% or less, even more preferably 99 mass% or less, and even more preferably 98 mass% or less, based on the total antibacterial composition.

[0029] (Component (B1)) Component (B1) is one or more selected from the group consisting of gallic acid and its esters. Examples of gallic acid esters include esters of linear alkyl groups having 1 to 20 carbon atoms, such as methyl gallate, ethyl gallate, propyl gallate, butyl gallate, pentyl gallate, hexyl gallate, heptyl gallate, octyl gallate, nonyl gallate, decyl gallate, lauryl gallate, and stearyl gallate.

[0030] From the viewpoint of improving the antibacterial properties of the antibacterial composition, the component (B1) is preferably gallic acid.

[0031] From the viewpoint of improving antibacterial properties, the content of component (B1) in the antibacterial composition may be, for example, 0.001 mass % or more, preferably 0.005 mass % or more, more preferably 0.01 mass % or more, even more preferably 0.1 mass % or more, and even more preferably 1 mass % or more, based on the total amount of the antibacterial composition. From a similar viewpoint, the content of component (B1) in the antibacterial composition may be, for example, 10 mass % or less, preferably 5 mass % or less, more preferably 4 mass % or less, and even more preferably 3 mass % or less, based on the total antibacterial composition.

[0032] From the viewpoint of improving the antibacterial properties of the antibacterial composition, the content of component (B1) relative to the content of component (A) in the antibacterial composition ((B1) / (A)) is preferably a mass ratio of 0.01 or more, more preferably 0.015 or more, and even more preferably 0.02 or more. From the same viewpoint, the mass ratio ((B1) / (A)) is preferably 5 or less, more preferably 1 or less, even more preferably 0.5 or less, and even more preferably 0.1 or less.

[0033] The antibacterial composition may contain components other than the above-mentioned components (A) and (B1). In this embodiment, the antibacterial composition can be obtained, for example, by preparing the above-mentioned components (A) and (B1) and other components as appropriate, and blending and mixing these in predetermined ratios.

[0034] Another method for preparing the antibacterial composition includes, for example, obtaining a culture solution containing a cyclic carboxylic acid by a bioprocess, and then concentrating and purifying the culture solution to obtain a composition containing components (A) and (B1). The method for obtaining a culture solution containing components (A) and (B1) by a bioprocess will be described below. In the bioprocess, the recovery rate of cyclic carboxylic acids and their derivatives can be improved by appropriately selecting the microorganism, culture medium, culture equipment, and culture conditions. The method for obtaining a culture solution containing the components (A) and (B1) by a bioprocess includes a raw material liquid preparation step S01, an activated carbon treatment step S02, a crystallization step S03, and a solid-liquid separation step S04.

[0035] (Raw material liquid preparation process S01) First, prepare biomass. Here, biomass refers to organic resources derived from plants. Specifically, biomass includes those that have been converted and stored in the form of starch or cellulose, the bodies of animals that grow by eating plants, and products made by processing plant or animal bodies.

[0036] More specifically, examples of biomass include cellulosic crops (pulp, kenaf, wheat straw, rice straw, waste paper, papermaking residues, etc.), wood, charcoal, compost, natural rubber, cotton, sugarcane, soybean pulp, oils and fats (rapeseed oil, cottonseed oil, soybean oil, coconut oil, castor oil, etc.), carbohydrate crops (corn, potatoes, wheat, rice, rice husks, rice bran, old rice, cassava, sago palm, etc.), bagasse, buckwheat, soybeans, essential oils (pine oil, orange oil, eucalyptus oil, etc.), black pulp liquor, food waste, vegetable oil residue, fishery residue, livestock waste, food waste, wastewater sludge, etc. More specifically, examples of biomass include sugarcane pomace.

[0037] -Pretreatment- The biomass is then pretreated to obtain a mixed sugar. Such pretreatments include, for example, physical treatments, chemical treatments, physicochemical treatments, biological treatments, etc., and one or a combination of two or more of these treatments may be used.

[0038] Of these, examples of the physical treatment include pulverization using a disk mill or grinder, compression, electromagnetic wave irradiation, and electron beam irradiation.

[0039] Examples of chemical treatments include treatment with ionic liquids such as sulfuric acid, nitric acid, hydrochloric acid, phosphoric acid, and alkali, hydrothermal treatment, subcritical water treatment, supercritical fluid treatment, treatment with a catalyst, treatment with an oxidizing agent, treatment to impart thermal energy, and treatment to impart light energy.

[0040] Examples of physicochemical treatments include steam explosion treatment and ammonia explosion treatment. Biological treatments include, for example, treatments using fungi, bacteria, and the like.

[0041] In this manner, a sugar mixture is obtained. Examples of the resulting sugar mixture include oligosaccharides or polysaccharides having glucose units. Specific examples include monosaccharides such as glucose, fructose, mannose, arabinose, xylose, and galactose, disaccharides such as cellobiose, sucrose, lactose, maltose, trehalose, cellobiose, and xylobiose, and polysaccharides such as dextrin or soluble starch.

[0042] In addition to the above, mixed sugars may also be those containing saccharified liquid obtained by saccharifying materials such as straw (rice straw, barley straw, wheat straw, rye straw, oat straw, etc.), inedible agricultural waste such as bagasse, energy crops such as switchgrass, napier grass, and myscanthus, wood chips, and waste paper using saccharifying enzymes, or molasses.

[0043] -Preparation of raw liquid- Next, a raw material liquid is prepared by culturing or reacting a microorganism or a transformant thereof in a reaction liquid containing the sugar mixture.

[0044] Microorganisms or transformants thereof The microorganism or its transformant is preferably grown in culture in a medium prior to reaction with the sugar mixture.

[0045] Culture medium The medium to be used may be a natural medium or a synthetic medium containing a carbon source, a nitrogen source, inorganic salts, other nutrients, etc. A specific example of the medium is LB medium.

[0046] The concentration of the nitrogen source in the medium varies depending on the nitrogen source used, but is, for example, 0.1 to 10 (mass / v%).

[0047] The concentration of inorganic salts in the medium varies depending on the inorganic salts used, but is, for example, 0.01 to 1 (mass / v%).

[0048] The concentration of nutrients in the medium varies depending on the nutrients used, but is, for example, 0.1 to 10 (mass / v%).

[0049] Furthermore, vitamins can be added as needed.

[0050] The pH of the medium is preferably 6-8.

[0051] Reaction solution The reaction liquid may be a natural or synthetic reaction liquid containing a carbon source, a nitrogen source, inorganic salts, etc.

[0052] Among these, the above-mentioned mixed sugar is used as the carbon source. The concentration of the mixed sugar in the reaction solution is preferably 1 to 20 (mass / v%), more preferably 2 to 10 (mass / v%), and even more preferably 2 to 5 (mass / v%).

[0053] In addition, other carbon sources may be appropriately selected from the above-mentioned carbon sources. The concentration of the total carbon source including the mixed sugar is preferably 2 to 5 (mass / v%).

[0054] The nitrogen source is selected from the above-mentioned nitrogen sources. The concentration of the nitrogen source in the reaction solution varies depending on the concentration of the nitrogen source used, but is, for example, 0.01 to 1 (mass / v%).

[0055] The inorganic salt is selected from the inorganic salts described above. The concentration of the nutrient in the reaction solution varies depending on the concentration of the nutrient used, but is, for example, 0.1 to 10 (mass / v%). Furthermore, if necessary, vitamins appropriately selected from those mentioned above may be used.

[0056] Reaction conditions The reaction temperature between the sugar mixture and the microorganism or its transformant, ie, the survival temperature of the microorganism or its transformant, is preferably 20 to 50°C, more preferably 25 to 47°C, from the viewpoint of efficient production of a cyclic carboxylic acid.

[0057] The reaction time is preferably 1 to 7 days, and more preferably 1 to 3 days.

[0058] The culture may be performed in any of a batch, fed-batch, or continuous manner, with the batch culture being preferred. The reaction may be carried out under aerobic or reducing conditions.

[0059] The reaction solution under reducing conditions can be prepared by any known method without any restrictions. For example, a reaction solution under reducing conditions can be obtained by removing dissolved gases through heating or reduced pressure treatment. In this case, the reaction solution under reducing conditions can be prepared by removing dissolved gases (more specifically, dissolved oxygen) by treating under reduced pressure of preferably 10 mmHg or less, more preferably 5 mmHg or less, and even more preferably 3 mmHg or less for about 1 to 60 minutes, more preferably 5 to 40 minutes.

[0060] Alternatively, an appropriate reducing agent (for example, thioglycolic acid, ascorbic acid, cysteine ​​hydrochloride, mercaptoacetic acid, thiolacetic acid, glutathione, sodium sulfide) may be added to prepare an aqueous solution for the reaction liquid under reducing conditions. Furthermore, these methods may be combined as appropriate.

[0061] When the reaction is carried out under reducing conditions, it is preferable to maintain the reaction solution under reducing conditions during the reaction. In order to maintain the reducing conditions during the reaction, it is preferable to prevent the inclusion of oxygen from outside the reaction system as much as possible. Specifically, the reaction system can be sealed under an inert gas such as nitrogen gas or carbon dioxide gas. As a method for more effectively preventing the inclusion of oxygen, it may be necessary to add a pH maintaining adjustment solution to the reaction system or various nutrient dissolving solutions appropriately in order to efficiently function the metabolic functions in the cells of the aerobic bacteria during the reaction. In such cases, it is preferable to remove oxygen from the solution to be added in advance.

[0062] After the preparation of the raw material liquid, the microorganism or its transformant is separated and removed. Examples of the separation and removal method include a sedimentation method, a centrifugation method, a filtration method, etc. A combination of two or more of these methods may also be used.

[0063] This step may be provided as necessary, and may be replaced with, for example, a step of preparing a liquid containing a cyclic carboxylic acid produced by recycling or the like.

[0064] -Concentration treatment- The obtained raw material liquid may be concentrated as necessary. Concentration methods include, for example, distillation, adsorption, extraction, membrane separation, dialysis, reverse osmosis, etc., and one or more of these may be used in combination.

[0065] Among these, the concentration process is a process in which the raw liquid is brought into contact with a heated heat transfer surface to evaporate the solvent contained in the raw liquid, and is preferably a process in which the raw liquid is repeatedly brought into contact with the heat transfer surface. According to such a process, the heat transfer surface can be constantly wetted with the raw liquid when evaporating the solvent contained in the raw liquid, so that the occurrence of scorching can be suppressed.

[0066] Specifically, the raw liquid is placed in a mixing tank whose inner wall surface is a heat transfer surface, and the raw liquid that has accumulated at the bottom is pumped up and concentrated using a device that stirs the raw liquid while spraying it on the inner wall surface. This makes it possible to maximize the effective area of ​​the heat transfer surface and increase the concentration efficiency. In addition, the occurrence of scorching due to drying of the heat transfer surface is suppressed, and coloring of the precipitated solid can be suppressed.

[0067] The heating temperature in the concentration treatment is not limited, but is preferably about 15 to 120° C., and more preferably about 20 to 90° C. This can increase the efficiency of concentration while suppressing the occurrence of scorching and denaturation of solutes.

[0068] The raw solution in the concentration process may be placed under reduced pressure. This promotes the evaporation of the solvent and increases the concentration efficiency. The pressure of the environment in which the raw solution is placed is not limited, but is preferably 80 kPa or less, and more preferably 0.1 to 50 kPa.

[0069] For the concentration, a salt of a cyclic carboxylic acid may be prepared using a basic substance and then dissolved in an aqueous medium. Furthermore, the concentration treatment may be carried out as necessary and may be omitted.

[0070] In addition, by concentrating the raw liquid, the ratio (yield) of the amount of solids that can be recovered from a unit amount of raw liquid can be increased, which can reduce the time and energy required for the steps described below and increase the production efficiency of solids (production capacity of solids per unit time).

[0071] (Activated carbon treatment process S02) Next, the raw liquid is treated with activated carbon. Specifically, activated carbon is added to the raw liquid and the mixture is stirred. This makes it possible to decolorize the solutes in the raw liquid.

[0072] Examples of activated carbon include, but are not limited to, powdered activated carbon, granular activated carbon, fibrous activated carbon, sheet-like activated carbon, and honeycomb-like activated carbon.

[0073] The temperature for the activated carbon treatment is preferably about 10 to 150° C. The time for the activated carbon treatment is not limited, but is preferably about 10 minutes to 40 hours.

[0074] In addition, the amount of activated carbon added per 100 g of raw liquid is not limited, but from the viewpoint of obtaining sufficient decolorization effect while suppressing the solute from being adsorbed by the activated carbon, it is preferably 0.01 to 10 g, and more preferably 0.1 to 5 g.

[0075] The activated carbon treatment may be performed as necessary and may be omitted. The order of the activated carbon treatment step is not limited to that in this embodiment, and may be after the elution step, for example. After the treatment, the activated carbon is removed by solid-liquid separation such as filtration.

[0076] (Crystallization process S03) Next, the raw liquid is subjected to a crystallization process to precipitate the solute of the raw liquid as a solid. This crystallization process involves a process in which the solubility of the solute in the solution is reduced to precipitate a solid, and a solid substance with high purity can be recovered by a subsequent solid-liquid separation process. This makes it possible to easily produce a cyclic carboxylic acid that is useful as a raw material for daily necessities, cosmetics, pharmaceuticals, foods, etc.

[0077] The crystallization process may be any process that causes a solute to precipitate as a solid from a raw material liquid. Specifically, examples of such processes include a process in which the temperature of the raw liquid is changed to utilize the temperature dependency of solubility for crystallization, a process in which the solvent is evaporated from the raw liquid by heating or reducing pressure or the like to cause crystallization, a process in which a solvent in which the solute has low solubility is added to utilize the solvent-type dependency of solubility for crystallization, and a process in which the pH of the raw solution is changed to utilize the pH-responsiveness of solubility for crystallization, and the like. One or a combination of these processes can be used.

[0078] For example, when using a crystallization process that utilizes pH responsiveness, the solubility of the cyclic carboxylic acid contained in the solute in water generally decreases at low pH levels. Therefore, by lowering the pH to, for example, about 1 to 4 in the crystallization process, the solubility can be reduced and the solute can be precipitated.

[0079] The temperature at this time is not limited, but is preferably, for example, about 15 to 80° C., and more preferably about 20 to 60° C. This makes it possible to achieve both the capacity and yield of the crystallization treatment.

[0080] The crystallization process may be a batch process or a continuous process. For the crystallization operation, a known stirring tank is used.

[0081] In order to promote crystallization, seed crystals containing the solid components to be precipitated may be added as necessary. This promotes crystallization with the seed crystals acting as nuclei, thereby increasing the crystallization efficiency and facilitating high purity.

[0082] (Solid-liquid separation process S04) Next, solid cyclic carboxylic acids are recovered from the feed liquid. Examples of solid-liquid separation include filtration, sedimentation, dehydration under reduced pressure, and dehydration under pressure, among which filtration is preferably used from the viewpoints of ease of operation and accuracy of separation. Specifically, a centrifugal filter can be used. The solid-liquid separation operation may be a batch operation or a continuous operation.

[0083] Thereafter, washing is carried out using a poor solvent as appropriate, and then drying is carried out as appropriate. In this manner, a solid or other antibacterial composition containing the components (A) and (B1) can be recovered.

[0084] The obtained antibacterial composition may be used to obtain an antibacterial composition blend liquid containing a medium such as water, ethanol, etc. In this case, the content of the medium in the blend liquid may be, for example, the remainder after excluding components other than the medium in the blend liquid. The concentration of component (A) in the above blended liquid may be, for example, 0.01% by mass or more, preferably 0.05% by mass or more, more preferably 0.15% by mass or more, even more preferably 0.25% by mass or more, and even more preferably 0.4% by mass or more, and may be, for example, 10% by mass or less, preferably 5% by mass or less, more preferably 3% by mass or less, even more preferably 2% by mass or less, and even more preferably 1% by mass or less.

[0085] The antibacterial composition obtained in this embodiment is not limited in its form, and may be in a solid form such as powder or granules, or in a liquid form. Furthermore, the antibacterial composition obtained in this embodiment can be used in daily necessities, cosmetics, medicines, foods, etc., and is particularly suitable for use in daily necessities and cosmetics. Specific examples of daily necessities include antibacterial agents, antifungal agents, deodorants, detergents, hygiene products, bath products, household chemical products, and oral care products. Further, examples of cosmetics include milk lotions, creams, foundations, eye shadows, lipsticks, blushers, hair cosmetics, emollient creams, emollient lotions, cream rinses, cold creams, vanishing creams, lotions, packs, gels, face packs, soaps, body soaps, shampoos, conditioners, rinses, bath additives, bath additives, facial cleansers, shaving creams, hair creams, hair lotions, hair treatments, hair packs, glosses, and lip balms.

[0086] In addition, the antibacterial composition of the present embodiment can be suitably used to inhibit the proliferation of one or more species selected from the group consisting of bacteria such as Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa, yeasts such as Candida, and molds such as Aspergillus niger.

[0087] The present embodiment includes the following aspects. I-1. Components (A) and (B1) below: (A) Cyclic carboxylic acids (excluding component (B1) below) (B1) One or more selected from the group consisting of gallic acid and its esters 1. An antibacterial composition comprising: I-2. The antibacterial composition according to I-1, wherein the component (A) is one or more selected from the group consisting of protocatechuic acid, shikimic acid, 4-hydroxybenzoic acid, 4-aminobenzoic acid and ferulic acid. I-3. The antibacterial composition according to I-1 or I-2, wherein the content of component (B1) relative to the content of component (A) in the antibacterial composition ((B1) / (A)) is 0.01 or more and 5 or less in terms of mass ratio.

[0088] Second Embodiment The present embodiment relates to a water-soluble additive composition.

[0089] A technology for improving the solubility of cyclic carboxylic acids is described in Patent Document 5 (JP Patent Publication No. 2018-150288 A). The document describes a technology for providing crystals of protocatechuic acid (PCA) cationic salt that are excellent in solubility and stable under high humidity conditions, and a method for producing the same, including a step of precipitating crystals of PCA cationic salt by dropping or adding an alcohol solution or a nitrile solution to an alcohol solution of PCA in which a cation-containing compound is dissolved, and a step of collecting crystals of PCA cationic salt from the solution.

[0090] As a result of the inventors' investigation of the technology described in the aforementioned Patent Document 5, it became clear that there is still room for improvement in terms of obtaining a composition having a high purity of a cyclic carboxylic acid and excellent water solubility of the cyclic carboxylic acid.

[0091] According to this embodiment, A water-soluble additive composition comprising a cyclic carboxylic acid, Na +and NH4 + The total content of the above is 100 ppm or more and 5000 ppm or less based on the cyclic carboxylic acid.

[0092] Further, according to this embodiment, A water-soluble additive composition comprising a cyclic carboxylic acid, A water-soluble additive composition is provided having a total inorganic ion content (excluding hydrogen ions and hydroxyl ions) of 300 ppm or more and 5000 ppm or less relative to the cyclic carboxylic acid.

[0093] Furthermore, according to this embodiment, for example, daily necessities or cosmetics containing the water-soluble additive composition of this embodiment can also be obtained.

[0094] According to the present embodiment, a composition containing a cyclic carboxylic acid with high purity and excellent water solubility can be provided.

[0095] The embodiment will be described in more detail below. In the embodiment, the composition may contain each component alone or in combination of two or more kinds.

[0096] (Embodiment 2-1) In this embodiment, the water-soluble additive composition includes a cyclic carboxylic acid. + and NH4 + The total content of the above is 100 ppm or more and 5000 ppm or less based on the cyclic carboxylic acid.

[0097] (Embodiment 2-2) In this embodiment, the water-soluble additive composition contains a cyclic carboxylic acid, and the total inorganic ion content (excluding hydrogen ions and hydroxyl ions) in the water-soluble additive composition is 300 ppm or more and 5000 ppm or less relative to the cyclic carboxylic acid.

[0098] The components of the water-soluble additive composition will be described in more detail below. The following components can be used in each of the above-mentioned embodiments. In addition, the components described in each of the above-mentioned embodiments can be used in combination with other embodiments.

[0099] (Cyclic Carboxylic Acid) Specific examples of the cyclic carboxylic acid include cyclic carboxylic acids having one or more hydroxy groups and cyclic carboxylic acids having one or more amino groups.

[0100] Examples of cyclic carboxylic acids having a hydroxy group include aromatic hydroxycarboxylic acids and alicyclic hydroxycarboxylic acids. Examples of aromatic hydroxycarboxylic acids include hydroxybenzoic acids such as salicylic acid and 4-hydroxybenzoic acid, monohydroxybenzoic acids such as hydroxy(methyl)benzoic acid and hydroxy(methoxy)benzoic acid, and derivatives thereof; dihydroxybenzoic acids such as protocatechuic acid, gentisic acid, etc., dihydroxybenzoic acids such as orselliic acid, etc., and dihydroxy(methyl)benzoic acids and their derivatives; Included are monohydroxycinnamic acids such as ferulic acid and its derivatives. Examples of the alicyclic hydroxycarboxylic acid include shikimic acid and quinic acid.

[0101] In addition, examples of cyclic carboxylic acids having an amino group include monoaminobenzoic acids such as 4-aminobenzoic acid and derivatives thereof, and other aromatic aminocarboxylic acids; and Alicyclic aminocarboxylic acids are included.

[0102] From the viewpoint of stably improving the water solubility of the water-soluble additive composition, the cyclic carboxylic acid is preferably one or more selected from the group consisting of protocatechuic acid, shikimic acid, 4-hydroxybenzoic acid, 4-aminobenzoic acid, and ferulic acid, and more preferably one or more selected from the group consisting of protocatechuic acid and shikimic acid.

[0103] From the viewpoint of obtaining a composition with a higher concentration, the content of the cyclic carboxylic acid in the water-soluble additive composition is preferably 95 mass% or more, more preferably 95.3 mass% or more, and even more preferably 95.6 mass% or more, based on the entire water-soluble additive composition. Furthermore, from the viewpoint of improving the water solubility of the water-soluble additive composition, the content of the cyclic carboxylic acid in the water-soluble additive composition is less than 100 mass% based on the entire water-soluble additive composition, and may be, for example, 99.97 mass% or less, preferably 99.9 mass% or less, more preferably 99.5 mass% or less, and even more preferably 99 mass% or less.

[0104] Na in the water-soluble additive composition + and NH4 + From the viewpoint of stably improving the water solubility of the cyclic carboxylic acid in the water-soluble additive composition, the total content of is preferably 100 ppm or more, more preferably 200 ppm or more, and even more preferably 300 ppm or more, relative to the cyclic carboxylic acid. From the same viewpoint, Na in the water-soluble additive composition + and NH4 + The total content of is preferably 5000 ppm or less, more preferably 2000 ppm or less, further preferably 1000 ppm or less, and further more preferably 500 ppm or less, based on the cyclic carboxylic acid.

[0105] Na in the water-soluble additive composition + From the viewpoint of stably improving the water solubility of the cyclic carboxylic acid in the water-soluble additive composition, the content of may be, for example, 10 ppm or more, or, for example, 90 ppm or more, preferably 100 ppm or more, more preferably 200 ppm or more, and even more preferably 300 ppm or more, relative to the cyclic carboxylic acid. From the same viewpoint, Na in the water-soluble additive composition +The content of is preferably 5000 ppm or less, more preferably 4500 ppm or less, even more preferably 4000 ppm or less, even more preferably 3000 ppm or less, still more preferably 1000 ppm or less, and even more preferably 500 ppm or less, based on the cyclic carboxylic acid.

[0106] Water-soluble additive composition NH4 + From the viewpoint of stably improving the water solubility of the cyclic carboxylic acid in the water-soluble additive composition, the content of may be, for example, 10 ppm or more, preferably 100 ppm or more, more preferably 200 ppm or more, and even more preferably 300 ppm or more, relative to the cyclic carboxylic acid. From the same viewpoint, the NH4 + The content of is preferably 5000 ppm or less, more preferably 2000 ppm or less, further preferably 1000 ppm or less, and further more preferably 500 ppm or less, based on the cyclic carboxylic acid.

[0107] Here, Na in the water-soluble additive composition + and NH4 + The content of and K + , SO4 2- , PO4 3- , NO2 - , NO3 - and Cl - The contents of each of the above are measured by ion chromatography or capillary electrophoresis.

[0108] The total inorganic ion content (excluding hydrogen ions and hydroxyl ions) of the water-soluble additive composition is, from the viewpoint of stably improving the water solubility of the cyclic carboxylic acid in the water-soluble additive composition, preferably 300 ppm or more, more preferably 500 ppm or more, even more preferably 800 ppm or more, and still more preferably 1500 ppm or more, based on the cyclic carboxylic acid. From the same viewpoint, the total inorganic ion content (excluding hydrogen ions and hydroxyl ions) of the water-soluble additive composition is preferably 5000 ppm or less, more preferably 4000 ppm or less, even more preferably 3000 ppm or less, and even more preferably 2000 ppm or less, relative to the cyclic carboxylic acid.

[0109] Here, among the inorganic ions (excluding hydrogen ions and hydroxyl ions) contained in the water-soluble additive composition, the above-mentioned Na + and NH4 + Other than that, for example, K + etc.;SO4 2- , PO4 3- , NO2 - , NO3 - , Cl - Examples of anions include:

[0110] K of the water-soluble additive composition + The content of is 0 ppm or more relative to the cyclic carboxylic acid. In addition, the water-soluble additive composition is + When the water-soluble additive composition contains the cyclic carboxylic acid, the content thereof may be, for example, 10 ppm or more, and preferably 50 ppm or more, based on the cyclic carboxylic acid, from the viewpoint of stably improving the water solubility of the cyclic carboxylic acid in the water-soluble additive composition. From the same viewpoint, the K + The content of is preferably 200 ppm or less, more preferably 100 ppm or less, based on the cyclic carboxylic acid.

[0111] Water-soluble additive composition SO4 2- The content of is 0 ppm or more relative to the cyclic carboxylic acid. In addition, the water-soluble additive composition is SO4 2- When it contains, its content is preferably 1000 ppm or less, more preferably 500 ppm or less, and further preferably 100 ppm or less, based on the cyclic carboxylic acid. Also, SO4 2- The content may be, for example, 10 ppm or more relative to the cyclic carboxylic acid.

[0112] Water-soluble additive composition PO4 3- The content of may be 0 ppm or more, for example 10 ppm or more, based on the cyclic carboxylic acid. In addition, the water-soluble additive composition is PO4 3- When it contains, its content is preferably 500 ppm or less, more preferably 300 ppm or less, and further preferably 200 ppm or less, based on the cyclic carboxylic acid.

[0113] Water-soluble additive composition NO2 - The content of may be 0 ppm or more, for example 1 ppm or more, relative to the cyclic carboxylic acid. In addition, the water-soluble additive composition is NO2 - When it contains, its content is preferably 100 ppm or less, more preferably 50 ppm or less, and further preferably 30 ppm or less, based on the cyclic carboxylic acid.

[0114] Water-soluble additive composition NO3 - The content of may be 0 ppm or more, for example 10 ppm or more, based on the cyclic carboxylic acid. In addition, the water-soluble additive composition is NO3 - When it contains, its content is preferably 100 ppm or less, more preferably 50 ppm or less, and further preferably 30 ppm or less, based on the cyclic carboxylic acid.

[0115] Cl of the water-soluble additive composition - The content of may be 0 ppm or more, for example 5 ppm or more, based on the cyclic carboxylic acid. In addition, the water-soluble additive composition contains Cl - When it contains, its content is preferably 100 ppm or less, more preferably 50 ppm or less, and further preferably 30 ppm or less, based on the cyclic carboxylic acid.

[0116] The water-soluble additive composition may contain components other than the cyclic carboxylic acids described above. For example, the water-soluble additive composition may contain a medium such as water, ethanol, etc. In this case, the content of the medium in the composition may be, for example, the remainder excluding components other than the medium in the composition.

[0117] Next, a method for producing the water-soluble additive composition will be described. An example of a method for preparing the water-soluble additive composition is a method in which a culture solution containing a cyclic carboxylic acid is obtained by a bioprocess as described below, and then the culture solution is concentrated and purified to obtain a composition containing the cyclic carboxylic acid. Where Na + and N.H. 4+ In order to control the total inorganic ion content or the total inorganic ion content to be within the above-mentioned specific range, it is important to appropriately select the conditions for producing the cyclic carboxylic acid in the bioprocess and the conditions for purification. For example, the conditions for concentration and filtration and the number of washings are appropriately selected as the purification conditions.

[0118] The water-soluble additive composition obtained in this embodiment is Na + and NH4 + Since the total content of the above or the total inorganic ion content is within a specific range, the purity of the cyclic carboxylic acid is high and the water solubility of the cyclic carboxylic acid is excellent.

[0119] A method for obtaining a culture solution containing a cyclic carboxylic acid by a bioprocess will be described below. The method for obtaining a culture solution containing a cyclic carboxylic acid by a bioprocess includes a raw material liquid preparation step S01, an activated carbon treatment step S02, a crystallization step S03, and a solid-liquid separation step S04.

[0120] (Raw material liquid preparation process S01) The raw material liquid preparation step S01 can be carried out, for example, in accordance with the raw material liquid preparation step S01 described in the first embodiment. For example, the materials, procedures, methods, conditions, etc. used in the raw material liquid preparation step S01 can be those described in the first embodiment.

[0121] (Activated carbon treatment process S02) The activated carbon treatment step S02 can be appropriately performed, for example, in accordance with the activated carbon treatment step S02 described in the first embodiment. For example, the materials, procedures, methods, conditions, etc. used in the activated carbon treatment step S02 can be those described in the first embodiment.

[0122] (Crystallization process S03) The crystallization step S03 can be carried out, for example, in accordance with the crystallization step S03 described in the first embodiment. For example, the materials, procedures, methods, conditions, etc. used in the crystallization step S03 can be those described in the first embodiment.

[0123] (Solid-liquid separation process S04) The solid-liquid separation step S04 can be carried out, for example, in accordance with the solid-liquid separation step S04 described in the first embodiment. For example, the materials, procedures, methods, conditions, etc. used in the solid-liquid separation step S04 can be those described in the first embodiment.

[0124] Thereafter, washing is carried out using a poor solvent as appropriate, and then drying is carried out as appropriate. In the above, for example, by appropriately selecting purification conditions, a water-soluble additive composition in a solid state or the like having an ion content within a specific range can be recovered.

[0125] The form of the water-soluble additive composition obtained in this embodiment is not limited, and it may be, for example, a solid form such as powder or granules, or a liquid. Furthermore, the water-soluble additive composition obtained in this embodiment can be used in daily necessities, cosmetics, medicines, foods, etc., and is particularly suitable for use in daily necessities and cosmetics. Examples of daily necessities include antibacterial agents, antifungal agents, deodorants, detergents, hygiene products, bath products, household chemical products, and oral care products. Further, examples of cosmetics include milk lotions, creams, foundations, eye shadows, lipsticks, blushers, hair cosmetics, emollient creams, emollient lotions, cream rinses, cold creams, vanishing creams, lotions, packs, gels, face packs, soaps, body soaps, shampoos, conditioners, rinses, bath additives, bath additives, facial cleansers, shaving creams, hair creams, hair lotions, hair treatments, hair packs, glosses, lip balms, and the like. In addition, in this embodiment, the water-soluble additive composition can be used, for example, as an antibacterial agent or a taste enhancer.

[0126] The present embodiment includes the following aspects. II-1. A water-soluble additive composition comprising a cyclic carboxylic acid, Na + and NH4 + The water-soluble additive composition, wherein the total content of the above is 100 ppm or more and 5000 ppm or less relative to the cyclic carboxylic acid. II-2. A water-soluble additive composition containing a cyclic carboxylic acid, A water-soluble additive composition having a total inorganic ion content (excluding hydrogen ions and hydroxyl ions) of 300 ppm or more and 5000 ppm or less based on the cyclic carboxylic acid. II-3. The water-soluble additive composition according to II-1. or II-2., wherein the cyclic carboxylic acid is one or more selected from the group consisting of protocatechuic acid, shikimic acid, 4-hydroxybenzoic acid, 4-aminobenzoic acid and ferulic acid. II-4. The water-soluble additive composition according to any one of II-1 to II-3, wherein the content of the cyclic carboxylic acid in the water-soluble additive composition is 95% by mass or more and 99.9% by mass or less based on the entire water-soluble additive composition.

[0127] (Third embodiment) The present embodiment relates to a water-soluble additive composition.

[0128] Techniques relating to compositions containing cyclic carboxylic acids include those described in Patent Document 6 (JP 2014-31347 A) and Patent Document 7 (WO 2016 / 039407 A) mentioned in the Background Art section.

[0129] The present inventors have examined the techniques described in the above-mentioned Patent Documents 6 and 7 and have found that there is room for improvement in terms of improving the moisturizing properties and antibacterial properties. Therefore, the present embodiment provides a composition that has excellent moisturizing properties and antibacterial properties.

[0130] According to this embodiment, Components (A) and (B2) below: (A) Cyclic carboxylic acids (excluding component (B2) below) (B2) Amino acids A water soluble additive composition is provided comprising:

[0131] Furthermore, according to this embodiment, for example, daily necessities or cosmetics containing the water-soluble additive composition of this embodiment can also be obtained.

[0132] According to this embodiment, a composition having excellent moisturizing properties and antibacterial properties can be provided.

[0133] The embodiment will be described in more detail below. In the embodiment, the composition may contain each component alone or in combination of two or more kinds.

[0134] In this embodiment, the water-soluble additive composition comprises the following components (A) and (B2). (A) Cyclic carboxylic acids (excluding component (B2) below) (B2) Amino acids

[0135] (Component (A)) Component (A) is a cyclic carboxylic acid and is a component other than component (B2) described below. Specific examples of component (A) include cyclic carboxylic acids having one or more hydroxy groups, and cyclic carboxylic acids having one or more amino groups.

[0136] Examples of cyclic carboxylic acids having a hydroxy group include aromatic hydroxycarboxylic acids and alicyclic hydroxycarboxylic acids. Examples of aromatic hydroxycarboxylic acids include hydroxybenzoic acids such as salicylic acid and 4-hydroxybenzoic acid, monohydroxybenzoic acids such as hydroxy(methyl)benzoic acid and hydroxy(methoxy)benzoic acid, and derivatives thereof; dihydroxybenzoic acids such as protocatechuic acid, gentisic acid, etc., dihydroxybenzoic acids such as orselliic acid, etc., and dihydroxy(methyl)benzoic acids and their derivatives; Included are monohydroxycinnamic acids such as ferulic acid and its derivatives. Examples of the alicyclic hydroxycarboxylic acid include shikimic acid and quinic acid.

[0137] In addition, examples of cyclic carboxylic acids having an amino group include monoaminobenzoic acids such as 4-aminobenzoic acid and derivatives thereof, and other aromatic aminocarboxylic acids; and Alicyclic aminocarboxylic acids are included.

[0138] From the viewpoint of improving the moisturizing properties and antibacterial properties of the water-soluble additive composition, component (A) is preferably one or more selected from the group consisting of protocatechuic acid, shikimic acid, 4-hydroxybenzoic acid, 4-aminobenzoic acid, and ferulic acid, and more preferably one or more selected from the group consisting of protocatechuic acid and shikimic acid.

[0139] From the viewpoint of improving moisturizing properties and antibacterial properties, the content of component (A) in the water-soluble additive composition is preferably 95 mass% or more, more preferably 97 mass% or more, and even more preferably 98 mass% or more, based on the entire water-soluble additive composition. From a similar viewpoint, the content of component (A) in the water-soluble additive composition is less than 100 mass% based on the entire water-soluble additive composition, and may be, for example, 99.999 mass% or less or, for example, 99.98 mass% or less, preferably 99.9 mass% or less, more preferably 99.5 mass% or less, and even more preferably 99 mass% or less.

[0140] (Component (B2)) Component (B2) is an amino acid. Examples of component (B2) include neutral amino acids, acidic amino acids, and basic amino acids. Neutral amino acids, for example, aliphatic amino acids such as glycine, alanine, valine, leucine, and isoleucine; oxyamino acids such as serine and threonine; Sulfur-containing amino acids such as cysteine, cystine, and methionine; Aromatic amino acids such as phenylalanine, tyrosine, and tryptophan; imino acids, such as proline; and Examples include acetic acid amino acid amides such as asparagine and glutamine. Examples of acidic amino acids include aspartic acid and glutamic acid. Basic amino acids include, for example, lysine, histidine, and arginine.

[0141] From the viewpoint of improving the moisturizing properties and antibacterial properties of the water-soluble additive composition, component (B2) is preferably one or more amino acids selected from the group consisting of glutamic acid, alanine, valine, glycine, aspartic acid, serine, histidine, threonine, arginine, tyrosine, cystine, methionine, phenylalanine, isoleucine, leucine, lysine and proline, more preferably one or more amino acids selected from the group consisting of aspartic acid, glutamic acid, glycine, alanine, valine, isoleucine, lysine and proline, and even more preferably glutamic acid.

[0142] From the viewpoint of improving moisturizing properties and antibacterial properties, the content of component (B2) in the water-soluble additive composition may be, for example, 0.001 mass% or more, preferably 0.005 mass% or more, more preferably 0.01 mass% or more, even more preferably 0.1 mass% or more, and even more preferably 1 mass% or more, based on the entire water-soluble additive composition. From the same viewpoint, the content of component (B2) in the water-soluble additive composition may be, for example, 5 mass% or less, preferably 4 mass% or less, more preferably 3 mass% or less, and even more preferably 2 mass% or less, based on the entire water-soluble additive composition.

[0143] Moreover, the water-soluble additive composition preferably contains glutamic acid, and the content of glutamic acid in the water-soluble additive composition is preferably 0.001% by mass or more, more preferably 0.01% by mass or more, and even more preferably 0.1% by mass or more, based on the entire water-soluble additive composition, from the viewpoint of improving the moisturizing properties and antibacterial properties of the water-soluble additive composition. From a similar viewpoint, when the water-soluble additive composition contains glutamic acid, the content of glutamic acid in the water-soluble additive composition is preferably 5 mass % or less, more preferably 1 mass % or less, even more preferably 0.5 mass % or less, and even more preferably 0.2 mass % or less, based on the entire water-soluble additive composition.

[0144] When the water-soluble additive composition contains aspartic acid, the content of aspartic acid in the water-soluble additive composition is preferably 1 ppm or more, more preferably 10 ppm or more, and is preferably 200 ppm or less, more preferably 50 ppm or less, based on the entire water-soluble additive composition, from the viewpoint of improving the moisturizing properties and antibacterial properties of the water-soluble additive composition.

[0145] When the water-soluble additive composition contains glycine, the content of glycine in the water-soluble additive composition is, from the viewpoint of improving the moisturizing properties and antibacterial properties of the water-soluble additive composition, preferably 1 ppm or more, more preferably 10 ppm or more, and also preferably 200 ppm or less, more preferably 100 ppm or less, based on the entire water-soluble additive composition.

[0146] When the water-soluble additive composition contains alanine, the content of alanine in the water-soluble additive composition is preferably 10 ppm or more, more preferably 50 ppm or more, and is preferably 3000 ppm or less, more preferably 1000 ppm or less, based on the entire water-soluble additive composition, from the viewpoint of improving the moisturizing properties and antibacterial properties of the water-soluble additive composition.

[0147] When the water-soluble additive composition contains valine, the content of valine in the water-soluble additive composition is, from the viewpoint of improving the moisturizing properties and antibacterial properties of the water-soluble additive composition, preferably 1 ppm or more, more preferably 10 ppm or more, and also preferably 500 ppm or less, more preferably 200 ppm or less, based on the entire water-soluble additive composition.

[0148] When the water-soluble additive composition contains isoleucine, the content of isoleucine in the water-soluble additive composition is preferably 1 ppm or more, more preferably 2 ppm or more, and preferably 20 ppm or less, more preferably 10 ppm or less, based on the entire water-soluble additive composition, from the viewpoint of improving the moisturizing properties and antibacterial properties of the water-soluble additive composition.

[0149] When the water-soluble additive composition contains proline, the content of proline in the water-soluble additive composition is, from the viewpoint of improving the moisturizing properties and antibacterial properties of the water-soluble additive composition, preferably 5 ppm or more, more preferably 50 ppm or more, and also preferably 1000 ppm or less, more preferably 500 ppm or less, based on the entire water-soluble additive composition.

[0150] The water-soluble additive composition may contain components other than the above-mentioned components (A) and (B2). For example, the water-soluble additive composition may contain a medium such as water, ethanol, etc. In this case, the content of the medium in the composition may be, for example, the remainder excluding components other than the medium in the composition.

[0151] Next, a method for producing the water-soluble additive composition will be described. In this embodiment, the water-soluble additive composition can be obtained, for example, by preparing the above-mentioned components (A) and (B2) and other components as appropriate, and blending and mixing these in predetermined ratios.

[0152] Another method for preparing the water-soluble additive composition includes, for example, obtaining a culture solution containing the components (A) and (B2) by a bioprocess, and then concentrating and purifying the culture solution to obtain a composition containing the components (A) and (B2). The method for obtaining a culture solution containing a cyclic carboxylic acid by a bioprocess is described below. The method for obtaining a culture solution containing the components (A) and (B2) by a bioprocess includes a raw material liquid preparation step S01, an activated carbon treatment step S02, a crystallization step S03, and a solid-liquid separation step S04.

[0153] (Raw material liquid preparation process S01) The raw material liquid preparation step S01 can be carried out, for example, in accordance with the raw material liquid preparation step S01 described in the first embodiment. For example, the materials, procedures, methods, conditions, etc. used in the raw material liquid preparation step S01 can be those described in the first embodiment.

[0154] (Activated carbon treatment process S02) The activated carbon treatment step S02 can be appropriately performed, for example, in accordance with the activated carbon treatment step S02 described in the first embodiment. For example, the materials, procedures, methods, conditions, etc. used in the activated carbon treatment step S02 can be those described in the first embodiment.

[0155] (Crystallization process S03) The crystallization step S03 can be carried out, for example, in accordance with the crystallization step S03 described in the first embodiment. For example, the materials, procedures, methods, conditions, etc. used in the crystallization step S03 can be those described in the first embodiment.

[0156] (Solid-liquid separation process S04) The solid-liquid separation step S04 can be carried out, for example, in accordance with the solid-liquid separation step S04 described in the first embodiment. For example, the materials, procedures, methods, conditions, etc. used in the solid-liquid separation step S04 can be those described in the first embodiment.

[0157] Thereafter, washing is carried out using a poor solvent as appropriate, and then drying is carried out as appropriate. In this manner, a water-soluble additive composition in a solid form or the like containing the components (A) and (B2) can be recovered.

[0158] The form of the water-soluble additive composition obtained in this embodiment is not limited, and it may be, for example, a solid form such as powder or granules, or a liquid. Furthermore, the water-soluble additive composition obtained in this embodiment can be used in daily necessities, cosmetics, medicines, foods, etc., and is particularly suitable for use in daily necessities and cosmetics. Specific examples of daily necessities include antibacterial agents, antifungal agents, deodorants, detergents, hygiene products, bath products, household chemical products, and oral care products. Further, examples of cosmetics include milk lotions, creams, foundations, eye shadows, lipsticks, blushers, hair cosmetics, emollient creams, emollient lotions, cream rinses, cold creams, vanishing creams, lotions, packs, gels, face packs, soaps, body soaps, shampoos, conditioners, rinses, bath additives, bath additives, facial cleansers, shaving creams, hair creams, hair lotions, hair treatments, hair packs, glosses, and lip balms. In the present embodiment, the water-soluble additive composition can be used, for example, as a moisturizer or an antibacterial agent. Furthermore, according to this embodiment, for example, it is also possible to obtain a water-soluble additive composition that is less irritating to the skin.

[0159] The present embodiment includes the following aspects. III-1. Components (A) and (B2) below: (A) Cyclic carboxylic acids (excluding component (B2) below) (B) Amino acids 1. A water-soluble additive composition comprising: III-2. The water-soluble additive composition according to III-1, wherein the component (A) is one or more selected from the group consisting of protocatechuic acid, shikimic acid, 4-hydroxybenzoic acid, 4-aminobenzoic acid and ferulic acid. III-3. The water-soluble additive composition according to III-1. or III-2., wherein the component (B2) contains one or more amino acids selected from the group consisting of glutamic acid, alanine, valine, glycine, aspartic acid, serine, histidine, threonine, arginine, tyrosine, cystine, methionine, phenylalanine, isoleucine, leucine, lysine, and proline. III-4. The water-soluble additive composition according to any one of III-1. to III-3., wherein the content of the component (A) in the water-soluble additive composition is 95% by mass or more and 99.9% by mass or less. III-5. The water-soluble additive composition according to any one of III-1. to III-4., wherein the content of the component (B2) in the water-soluble additive composition is 0.001% by mass or more and 5% by mass or less. III-6. The water-soluble additive composition according to any one of III-1. to III-5., wherein the component (B2) contains glutamic acid, and the content of the glutamic acid in the water-soluble additive composition is 0.001% by mass or more and 1% by mass or less.

[0160] (Fourth embodiment) The present embodiment relates to a method for producing a food, a food additive, and a cyclic compound or a derivative thereof.

[0161] It is known that cyclic compounds having a specific structure are used as food additives. For example, Patent Document 8 (JP Patent Publication 2007-238469 A) describes that aromatic hydroxycarboxylic acids are important as food preservatives.

[0162] However, such cyclic compounds are usually obtained from petroleum. In such cases, the petroleum-derived cyclic compounds (chemical products) that can be recovered by fractional distillation and refining of petroleum are so-called backbone compounds with simple chemical structures. On the other hand, high-value-added compounds with more complex chemical structures must be derived from these backbone compounds through a synthesis process. In this case, unless petroleum is fractionally refined to a high degree, regardless of production costs, various isomers derived from the raw materials and synthesis process, trace components derived from catalysts, ionic components, mineral components, etc. may remain in the petroleum-derived chemical products. These impurities contained in petroleum-derived chemical products cannot be said to be desirable from the viewpoint of safety for the human body.

[0163] The object of the present embodiment is to provide safer foods and food additives that do not contain petroleum-derived impurities, and to provide a method for producing a cyclic compound or a derivative thereof that can be used as a food or a food additive.

[0164] Such an object can be achieved by the present embodiment described in (VI-1) to (VI-10) below. (VI-1) Foods containing plant-derived sugars and at least one of cyclic compounds and their derivatives derived from microorganisms.

[0165] (VI-2) The food according to the above (VI-1), wherein the cyclic compound is a compound represented by the following general formula (1): [ka] [In the above general formula (1), ring A is a five-membered saturated ring, partially saturated ring, or aromatic ring, or a six-membered saturated ring, partially saturated ring, or aromatic ring; X is a single bond or a bond containing one or more carbon atoms; Y is a hydrogen atom or an alkyl group; R 2~R 6 (When ring A is a 5-membered ring, R 2 ~R 5 ) are independently a hydrogen atom, a hydroxyl group, an amino group, an alkoxy group, a carboxyl group, or a carbonyl group.

[0166] (VI-3) The food according to (VI-2) above, wherein the cyclic compound is at least one selected from the group consisting of 2-hydroxybenzoic acid, 3-hydroxybenzoic acid, 4-hydroxybenzoic acid, 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 2,5-dihydroxybenzoic acid, 2,6-dihydroxybenzoic acid, 3,4-dihydroxybenzoic acid, and 3,5-dihydroxybenzoic acid.

[0167] (VI-4) When ring A of the cyclic compound is a five-membered saturated or partially saturated ring in which all of the ring constituent atoms are carbon atoms, R 2 ~R 5 and when one or more of the carbon atoms of ring A to which X is bonded is an asymmetric carbon atom, and ring A of the cyclic compound is a 6-membered saturated or partially saturated ring in which all of the ring constituent atoms are carbon atoms, R 2 ~R 6 And the food according to the above (VI-2), wherein one or more of the carbon atoms of ring A to which X is bonded are asymmetric carbon atoms.

[0168] (VI-5) In the above cyclic compound, the carbon atom of ring A to which X is bonded is C 1 Let R 2 The carbon atom of ring A to which is bonded is C 2 Let R 3 The carbon atom of ring A to which is bonded is C 3 Let R 4 The carbon atom of ring A to which is bonded is C 4 Let R 5 The carbon atom of ring A to which is bonded is C 5 Let R 6 The carbon atom of ring A to which is bonded is C 6 The food according to the above (VI-4), wherein the combination of asymmetric carbon atoms is one selected from the group consisting of the following (a) to (h): (a)C1 (b)C 2 (c)C 3 (d) C 4 (e)C 1 and C 4 (f)C 3 and C 4 (g) C 1 , C 3 and C 4 (h)C 3 , C 4 and C 5

[0169] (VI-6) The food according to the above (VI-1), wherein the cyclic compound or a derivative thereof is 3-dehydroquinate, 3-dehydroshikimic acid, shikimic acid, chorismic acid or prephenic acid.

[0170] (VI-7) The food according to any one of (VI-1) to (VI-6) above, wherein the microorganism is Escherichia coli, Bacillus subtilis, Staphylococcus aureus, Corynebacterium, Actinomycete, Cyanobacterium, Methanogen, Halophile, Thermotolerant Acidophile, Acid-fast Bacteria, Mold, Yeast, or a transformant thereof.

[0171] (VI-8) The food according to any one of (VI-1) to (VI-7) above, wherein the raw material for the plant-derived sugars is a non-edible biomass resource.

[0172] (VI-9) Food additives containing at least one of plant-derived sugars and cyclic compounds and their derivatives derived from microorganisms.

[0173] (VI-10) A method for producing a cyclic compound or a derivative thereof for use as a food or a food additive, comprising the steps of: preparing a culture solution containing plant-derived sugars and a microorganism so as to produce at least one of the cyclic compound and its derivatives; Concentrating the culture solution to obtain a concentrate; recovering at least one of the cyclic compound and its derivative from the concentrated solution by crystallization, precipitation, extraction, sublimation purification, or distillation; A method for producing a cyclic compound or a derivative thereof, comprising:

[0174] According to the present embodiment, safer foods and food additives that do not contain petroleum-derived impurities can be provided.

[0175] Furthermore, according to the present embodiment, safer foods or food additives that do not contain petroleum-derived impurities can be efficiently produced.

[0176] Hereinafter, the method for producing the food, food additive, and cyclic compound or derivative thereof of the present embodiment will be described in detail based on preferred embodiments.

[0177] <Food and food additives> As a result of intensive research, the present inventors have found that by including at least one of a cyclic compound and its derivative derived from a microorganism and a plant-derived saccharide, a food or food additive free of petroleum-derived impurities can be provided. In this case, they have found that it is preferable to produce the cyclic compound or its derivative by a bioprocess using a plant-derived saccharide (raw material) and a microorganism.

[0178] That is, the food of the present embodiment contains at least one of a cyclic compound and its derivative derived from a plant-derived sugar and a microorganism. In other words, the food of the present embodiment contains at least one of a cyclic compound and its derivative produced by a reaction (bioprocess) between a plant-derived sugar and a microorganism.

[0179] This makes it possible to provide food that is free of petroleum-derived impurities, and such food is safer than food that contains petroleum-derived impurities.

[0180] In addition, at least one of the plant-derived saccharides and the cyclic compounds and their derivatives derived from microorganisms can be used as food additives.

[0181] This makes it possible to provide a food additive that contains at least one of a cyclic compound and its derivative and does not contain petroleum-derived impurities. Such a food additive is safer than food additives that contain petroleum-derived impurities.

[0182] Examples of cyclic compounds contained in foods or food additives include compounds whose ring-constituting atoms are carbon atoms, nitrogen atoms, oxygen atoms, sulfur atoms, etc., and whose ring members are about 3 to 12. The bond between the atoms constituting the ring may be a single bond or a double bond.

[0183] Such a cyclic compound is preferably, but not limited to, a compound represented by the following general formula (1).

[0184] [ka]

[0185] [In the above general formula (1), ring A is a five-membered saturated ring, partially saturated ring, or aromatic ring, or a six-membered saturated ring, partially saturated ring, or aromatic ring; X is a single bond or a bond containing one or more carbon atoms; Y is a hydrogen atom or an alkyl group; R 2 ~R 6 (When ring A is a 5-membered ring, R 2 ~R 5 ) are independently a hydrogen atom, a hydroxyl group, an amino group, an alkoxy group, a carboxyl group, or a carbonyl group.

[0186] Examples of the five-membered saturated ring, partially saturated ring, or aromatic ring include a furan structure, a thiophene structure, a pyrrole structure, a pyrrolidine structure, a tetrahydrofuran structure, a 2,3-dihydrofuran structure, a pyrazole structure, an imidazole structure, an oxazole structure, an isoxazole structure, a thiazole structure, and an isothiazole structure.

[0187] Examples of the six-membered saturated ring include a hydrocarbon saturated ring such as a cyclohexane structure, a nitrogen-containing saturated ring such as a piperidine structure, a piperazine structure, a triazinane structure, a tetrazinane structure, a pentazinane structure, or a quinuclidine structure, an oxygen-containing saturated ring such as a tetrahydropyran structure or a morpholine structure, or a sulfur-containing saturated ring such as a tetrahydrothiopyran structure.

[0188] Examples of the six-membered partially saturated ring include a hydrocarbon partially saturated ring such as a cyclohexene structure or a cyclohexadiene structure, a nitrogen-containing partially saturated ring such as a piperidine structure, an oxygen-containing partially saturated ring such as a pyran structure, and a sulfur-containing partially saturated ring such as a thiazine structure.

[0189] Examples of the six-membered aromatic ring include a hydrocarbon aromatic ring such as a benzene structure, and a nitrogen-containing aromatic ring (nitrogen-containing unsaturated ring) such as a pyridine structure, a pyridazine structure, a pyrimidine structure, a pyrazine structure, a triazine structure, a tetrazine structure, and a pentazine structure.

[0190] X is a single bond or a bond containing one or more carbons (having one or more carbon atoms). When X is a single bond, the oxygen atom is directly bonded to a ring-constituting atom of ring A.

[0191] On the other hand, examples of bonds containing one or more carbon atoms include hydrocarbon groups having 1 to 4 carbon atoms, ether bonds, ester bonds, amide bonds, carbonyl groups, vinylidene groups, and the like, and include one or a combination of two or more of these.

[0192] Among these, the hydrocarbon group having 1 to 4 carbon atoms may be either linear or branched, and may be either saturated or unsaturated. The hydrogen atom of the hydrocarbon group may be substituted with a substituent such as an alkyl group having 1 to 2 carbon atoms, a hydroxyl group, an amino group, a carboxyl group, or a halogen atom.

[0193] In addition to the above-mentioned bond, X may contain any atom or atomic group. For example, X may be an atomic group containing a carbonyl group and a bond containing one or more carbons.

[0194] Y is a hydrogen atom or an alkyl group, the alkyl group preferably having 1 to 12 carbon atoms, more preferably 1 to 4 carbon atoms.

[0195] When ring A is a 6-membered ring, R 2 ~R 6 are independently a hydrogen atom, a hydroxyl group, an amino group, an alkoxy group, a carboxyl group, or a carbonyl group. When ring A is a 5-membered ring, R 2 ~R 5 are independently a hydrogen atom, a hydroxyl group, an amino group, an alkoxy group, a carboxyl group, or a carbonyl group.

[0196] In addition, when ring A is a 6-membered ring, R 2 ~R 6 or R when ring A is a 5-membered ring. 2 ~R 5 When either of the above is a carbonyl group, the ring-constituting atom of ring A is a carbon atom, and the ring-constituting atom is connected to an oxygen atom via a double bond, which is called a carbonyl group. When ring A is a 6-membered ring, the carbon atoms constituting ring A are independently bonded to one carbon atom by R 2 ~R 6 In addition, when ring A is a 5-membered ring, the carbon atoms constituting ring A may be independently bonded to one carbon atom constituting ring A by R 2 ~R 5 Any one of them may be bonded, or any two of them may be bonded.

[0197] Specific examples of cyclic compounds include benzoic acid, phthalic acid, isophthalic acid, terephthalic acid, hemimellitic acid, trimellitic acid, trimesic acid, mellophanic acid, prenitic acid, pyromellitic acid, phenylacetic acid, hydroxyphenylacetic acid, phenylbutyric acid (phenyllactate), hydroxyphenylbutyric acid, phenylpyruvic acid, hydroxyphenylpyruvic acid, phenyllactic acid, hydroxyphenyllactic acid, anthranilic acid, hydroatropic acid, atropic acid, hydrophenyllactic acid, phenylacetate ... Cinnamic acid (coumaric acid), cinnamic acid, salicylic acid (2-hydroxybenzoic acid), m-salicylic acid (3-hydroxybenzoic acid), p-salicylic acid (4-hydroxybenzoic acid), methoxybenzoic acid, aminobenzoic acid, hydroxybenzoic acid, pyrocatechuic acid (2,3-dihydroxybenzoic acid), β-resorcylic acid (2,4-dihydroxybenzoic acid), gentisic acid (2,5-dihydroxybenzoic acid), γ-resorcylic acid (2,6-dihydroxybenzoic acid), protocatechuic acid (3,4-dihydroxybenzoic acid), α-resorcylic acid (3,5-dihydroxybenzoic acid), trihydroxybenzoic acid, vanillic acid (4-hydroxy-3-methoxybenzoic acid), isovanillic acid (3-hydroxy-4-methoxybenzoic acid), veratric acid, gallic acid, syringic acid, asaronic acid, mandelic acid, vanillylmandelic acid, anisic acid, homoprotocatechuic acid, homovanillic acid, homoisovanillic acid, homoveratric acid, homophthalic acid, homoiso ... Examples of these include moterephthalic acid, phthalonic acid, isophthalonic acid, terephthalonic acid, atrolactic acid, tropic acid, mellitic acid, phloretic acid, dihydrocaffeic acid, hydroferulic acid, hydroisoferulic acid, umbellic acid, caffeic acid (caffeic acid), ferulic acid, isoferulic acid, sinapic acid, syringic acid, dehydroquinic acid, dehydroshikimic acid, shikimic acid, chorismic acid, L-tryptophan, L-tyrosine, prephenic acid, arogenic acid, and L-phenylalanine.

[0198] Other specific examples of cyclic compounds include polyphenols such as flavonoids, lignans, chalcones, stilbenoids, alkaloids, curcuminoids, terpenoids, saponins, various glycosides, and various polyphenol-based aromatic compounds, as well as amino acids and vitamins.

[0199] Among these, examples of flavonoids include anthocyanidins such as aurantidin, cyanidin, delphinidin, europinidin, luteolinidin, pelargonidin, malvidin, peonidin, petunidin, and rosinidin, anthocyanins such as procyanidin, flavanones such as naringenin, eriocitrin, pinocembrin, and eriodictyol, flavans such as catechin, flavones such as apigenin, luteolin, baicalein, and chrysin, flavonols such as quercetin and kaempferol, isoflavones, isoflavones, isoflavanes, isoflavandiols, and isoflavonoids such as genistein, as well as neoflavonoids, biflavonoids, aurones, prenylated flavonoids, and O-methylated flavonoids.

[0200] Examples of lignans include pinoresinol, lariciresinol, secoisolariciresinol, matairesinol, hydroxymatairesinol, syringaresinol, sesamin, arctigenin, sesaminol, podophyllotoxin, and steganacin.

[0201] Further examples of stilbenoids include aglycones such as piceatannol, pinosylvin, pterostilbene, resveratrol, 4'-methoxyresveratrol, pinostilbene, and piciatannol, and oligomers such as α-viniferin, ampelopsin A, ampelopsin E, diptoindonesin C-kawane, diptoindonesin F-dammarbua, ε-viniferin, flexosol A, gnetin H, hemsleyanol D, hopeaphenol, diptoindonesin B, and vaticanol B.

[0202] Examples of curcuminoids include curcumin and shogaol.

[0203] Further, examples of terpenoids include carotenoids such as lutein, vitamin A, vitamin E, and β-carotene, as well as steroids such as sitosterol.

[0204] Examples of various glycosides include phenolic glycosides such as salicin, β-glucogallin, salicylic acid glucoside, salidroside, gastrodin, poplin, phloridzin, and arbutin, coumarin glycosides such as esculin, flavonoid glycosides such as hesperidin and rutin, and stilbenoid glycosides such as astringin, piceid, and diptoindonesin A.

[0205] Furthermore, examples of various polyphenol aromatic compounds include tyrosol, hydroxytyrosol, esculetin, phloretin, rosmarinic acid, salvianic acid A, reticuline, paracoumaryl alcohol, coniferyl alcohol, and caffeyl alcohol.

[0206] Furthermore, examples of amino acids include phenylalanine and tyrosine. Furthermore, vitamins include, for example, vitamin A, vitamin D, vitamin E, etc.

[0207] Further specific examples of the cyclic compound include aromatic compounds, alicyclic compounds, aliphatic compounds, and heterocyclic compounds.

[0208] Among these, examples of aromatic compounds include vanillin, 2-phenylethanol, phenylacetic acid, cinnamic alcohol, isoeugenol, ferulic acid, 4-aminobenzoic acid, anethole, estragole, methyl anthranilate, methyl cinnamate, ethyl cinnamate, phenylacetaldehyde, cinnamic aldehyde, cinnamyl acetate, resorcin, 4-vinylphenol, 4-vinyl-2-methoxyphenol, 3,4-dihydroxystyrene, dopamine, levodopa, hydroquinone, coumarin, 7-hydroxycoumarin, 4-hydroxycoumarin, and xiamenmycin A.

[0209] Examples of alicyclic compounds include carveol, perilla alcohol, borneol, methyl jasmonate, 1,8-cineole, L-menthone, valencene, nootkatone, α-pinene, camphene, L-carvone, perilla aldehyde, myrtenal, L-menthyl acetate, and β-ionone.

[0210] Furthermore, examples of aliphatic compounds include cis-3-hexenol, cis-3-hexenyl acetate, acetoin, nerol, farnesol, arginine, and muconic acid.

[0211] Examples of heterocyclic compounds include niacin, niacinamide, maltol, and indole.

[0212] On the other hand, examples of derivatives of cyclic compounds include esters, acid anhydrides, amides, acid halides, salts, etc. of the above-mentioned compounds, or all compounds derived from cyclic compounds.

[0213] Among the above cyclic compounds, the cyclic compound represented by the above general formula (1) is preferably at least one selected from the group consisting of 2-hydroxybenzoic acid, 3-hydroxybenzoic acid, 4-hydroxybenzoic acid, 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 2,5-dihydroxybenzoic acid, 2,6-dihydroxybenzoic acid, 3,4-dihydroxybenzoic acid, and 3,5-dihydroxybenzoic acid. By using these, it is possible to realize foods or food additives that have various efficacies and are safer.

[0214] The molecular weight of the cyclic compound or its derivative is not limited, but is preferably 120-1,000, and more preferably 130-800.

[0215] In addition, when ring A of the cyclic compound represented by the above general formula (1) is a five-membered saturated or partially saturated ring in which all of the ring constituent atoms are carbon atoms, R 2 ~R 5It is preferable that one or more of the carbon atoms of ring A to which X is bonded is an asymmetric carbon atom. In addition, when ring A of the cyclic compound represented by the above general formula (1) is a 6-membered saturated or partially saturated ring in which all of the ring constituent atoms are carbon atoms, R 2 ~R 6 And, among the carbon atoms of ring A to which X is bonded, one or more are preferably asymmetric carbon atoms.

[0216] In such a case, the cyclic compound becomes a stereoisomer, which allows a meaningful food or food additive to be realized. In addition, by producing such a cyclic compound from a plant-derived sugar, a food or food additive containing a specific stereoisomer in high purity can be obtained. That is, a food or food additive containing a specific stereoisomer in high purity and having a low content of other stereoisomers can be obtained. Such a food or food additive is useful from the viewpoint of realizing a food or food additive with excellent safety and efficacy. In addition, since a complicated production process associated with the removal of unnecessary stereoisomers is not required, the production cost can be reduced.

[0217] In addition, in the cyclic compound represented by the above general formula (1), the carbon atom of ring A to which X is bonded is C 1 Let R 2 The carbon atom of ring A to which is bonded is C 2 Let R 3 The carbon atom of ring A to which is bonded is C 3 Let R 4 The carbon atom of ring A to which is bonded is C 4 Let R 5 The carbon atom of ring A to which is bonded is C 5 Let R 6 The carbon atom of ring A to which is bonded is C 6 In this case, it is preferable that the combination of these asymmetric carbon atoms is one selected from the group consisting of the following (a) to (h): C 1 ~C 6 may be different carbon atoms, or C 1 ~C 6 Any two of the carbon atoms may be the same.

[0218] (a)C 1 (b)C 2 (c)C 3 (d) C 4 (e)C 1 and C 4 (f)C 3 and C 4 (g) C 1 , C 3 and C 4 (h)C 3 , C 4 and C 5

[0219] The following general formula (2) is a compound represented by the general formula (1) above. 1 ~C 6 This is an equation with the notation added.

[0220] [ka]

[0221] [In the above general formula (2), ring A is a five-membered saturated ring, partially saturated ring, or aromatic ring, or a six-membered saturated ring, partially saturated ring, or aromatic ring; X is a single bond or a bond containing one or more carbon atoms; Y is a hydrogen atom or an alkyl group; R 2 ~R 6 (When ring A is a 5-membered ring, R 2 ~R 5 ) are independently a hydrogen atom, a hydroxyl group, an amino group, an alkoxy group, a carboxyl group, or a carbonyl group. 1 ~C 6 are carbon atoms constituting the ring A.

[0222] In such a case, the cyclic compound becomes a stereoisomer, which allows the realization of a more significant food or food additive. In addition, by producing such a cyclic compound from a plant-derived sugar, a food or food additive containing a specific stereoisomer selected from the group consisting of (a) to (h) above in high purity can be obtained. That is, a food or food additive containing a specific stereoisomer in high purity and having a low content of other stereoisomers can be obtained. Such a food or food additive is useful from the viewpoint of realizing a food or food additive with excellent safety and efficacy. In addition, the complicated production process associated with the removal of unnecessary stereoisomers can be reduced, thereby reducing the production cost.

[0223] The cyclic compound and its derivative according to this embodiment are preferably compounds represented by the above general formula (2), and further preferably 3-dehydroquinate, 3-dehydroshikimic acid, shikimic acid, chorismic acid, or prephenic acid. All of these compounds can be produced from plant-derived sugars, and are useful as foods or food additives. Therefore, by using these compounds produced from plant-derived sugars, it is possible to realize foods or food additives that have better efficacy and are safer. The structures of these cyclic compounds are represented by the following formulas.

[0224] 3-Dehydroquinate

[0225] [ka]

[0226] 3-Dehydroshikimic acid

[0227] [ka]

[0228] Shikimic acid

[0229] [ka]

[0230] Chorismic acid

[0231] [ka]

[0232] Prephenic acid

[0233] [ka]

[0234] Foods containing at least one of the above-mentioned cyclic compounds and their derivatives are not limited as long as they are commonly eaten foods and drinks. Examples include oral compositions such as gums and candies, fish paste products such as kamaboko and chikuwa, livestock products such as sausages and hams, Western confectioneries, Japanese confectioneries, noodles such as Chinese noodles, udon and soba, seasonings such as sauces, soy sauces and sauces, side dishes, juices, soups, etc.

[0235] In addition, when it is used as a supplement or health food, it may be provided in the form of capsules or tablets like medicines, or it may be provided in the form of being added to various foods such as beverages, seasonings, confectioneries, etc. Functions of the supplement or health food include, for example, antioxidant effect, anti-arteriosclerosis, anti-hypertension, radical scavenging activity, enzyme inhibitory effect, health of cellular tissue inside the skin, regeneration of capillaries, strengthening of resistance to bacteria, regeneration of red blood cells, regulation of blood pressure, immune enhancement, anti-cancer, anti-virus, suppression of blood sugar level rise, improvement of liver function, improvement of intestinal flora, improvement of bowel movements, improvement of lipid metabolism, enhancement of antioxidant function, enhancement of physical strength, promotion of beautiful skin, hair growth, and function of preventing or improving at least one of vascular-related diseases (arteriosclerosis, hypertension, heart disease), neurodegenerative diseases, ischemic cerebrovascular disorders, ischemic heart disease, inflammatory bowel disease, and eye diseases.

[0236] Furthermore, food additives containing at least one of a cyclic compound and its derivatives include additives designated under the Food Sanitation Law. Examples include preservatives, sweeteners, colorants, food flavors, etc. Among these, for example, protocatechuic acid is used as a sweetness enhancer. By using such a sweetness enhancer, the sweetness intensity of food can be increased, so the amount of added sugar can be relatively reduced. As a result, it is possible to realize a food that has added value in terms of low sugar and is safe. Furthermore, functions of food flavors include, for example, flavoring, aromatization, flavor correction, sweetness enhancement, sourness and bitterness reduction, appetite enhancement, etc.

[0237] The food additive may be in the form of, for example, a water-soluble liquid, an oil-soluble liquid, an emulsion, a powder, or the like.

[0238] <Method for producing cyclic compound or derivative thereof> The above-mentioned cyclic compound or derivative thereof is produced by a bioprocess using a microorganism and a plant-derived sugar as a raw material. That is, the above-mentioned cyclic compound or derivative thereof is derived from a plant-derived sugar and a microorganism.

[0239] Plant-derived sugars include, but are not limited to, monosaccharides, polysaccharides, and mixtures thereof.

[0240] The monosaccharide is not limited, and examples thereof include sugars that can be processed by the transformant of the microorganism described below. From the viewpoint of improving the phenol productivity of the transformant, examples of such sugars (monosaccharides) include tetrose (C4 sugar), pentose (C5 sugar), hexose (C6 sugar), and heptose (C7 sugar). Among these, the monosaccharide is preferably at least one selected from the group consisting of arabinose, xylose, glucose, mannitol, fructose, mannose, galactose, and sucrose. Moreover, such sugars may be used alone or in combination as a sugar mixture.

[0241] Polysaccharides are polymers of monosaccharides. The average degree of polymerization of polysaccharides is not limited, but is preferably 2 to 100, more preferably 2 to 50, from the viewpoint of improving productivity in a bioprocess using a microorganism. Moreover, the polysaccharides may be used alone or in combination. Examples of polysaccharides include maltose, lactose, cellobiose, xylobiose, trehalose, acarbose, stachyose, fructooligosaccharides, galactooligosaccharides, and mannanoligosaccharides.

[0242] The plant-derived sugars are preferably produced from non-edible biomass resources, in other words, the raw material for the plant-derived sugars is preferably a non-edible biomass resource.

[0243] As the biomass resource, various materials can be used as long as they contain at least monosaccharides or polysaccharides, from the viewpoint of obtaining the above-mentioned sugars. Examples of the biomass resource include vegetation resources such as weeds that occur in urban areas or cultivated land and thinning materials in forestry production areas, as well as waste cellulose, waste starch, and blackstrap molasses that are recovered as process residues or waste materials in the general food industry, or sugarcane pomace in the sugar manufacturing industry, and sake lees and shochu lees in the sake brewing industry, and these can be used alone or in combination. Processed products can also be used as the biomass resource.

[0244] The plant-derived sugars can be obtained by saccharifying such biomass resources. As such plant-derived sugars, cellulose-derived sugars obtained by saccharifying waste cellulose are preferred, and cellulose-derived mixed sugars are more preferred. Hereinafter, a process for producing a cyclic compound or a derivative thereof using a microorganism and using plant-derived sugars as a raw material will be described in detail.

[0245] The process using microorganisms using plant-derived sugars as a raw material includes the steps of obtaining a culture solution containing at least one of the cyclic compound and its derivatives produced by microorganisms using the plant-derived sugars as a raw material (produced by the microorganisms converting the plant-derived sugars), concentrating the culture solution to obtain a concentrated solution, and recovering at least one of the cyclic compound and its derivatives from the concentrated solution by crystallization, precipitation, extraction, sublimation purification, or distillation. Through such a process, at least one of the cyclic compound and its derivatives can be obtained efficiently. In addition, according to such a process using microorganisms, a cyclic compound or its derivative is produced as a result of the reaction between the raw material and the microorganism. Therefore, by limiting the type of raw material and the microorganism (for example, limiting the raw material to plant-derived sugars and limiting the type of the microorganism to bacteria), the cyclic compound or its derivative can be obtained efficiently. Such an effect can be exhibited remarkably by further limiting the type of raw material and the microorganism (for example, limiting the raw material to a cellulose-derived sugar mixture and limiting the type of the bacteria). In this respect, it is different from processes that do not use microorganisms (for example, processes that use extracts from plants). From this perspective, plant-derived sugars and cyclic compounds and derivatives thereof derived from microorganisms can be referred to as cyclic compounds and derivatives thereof (excluding those derived from plant extracts).

[0246] In the bioprocess, the recovery rate of the cyclic compound and its derivatives can be improved by appropriately selecting the microorganism, medium, culture equipment and culture conditions.

[0247] <Step of preparing culture medium> First, a culture solution is prepared containing raw materials, microorganisms, a medium, etc. In this culture solution, the microorganisms are cultured and the raw materials, etc. are reacted with the microorganisms (by a bioprocess) to produce at least one of a cyclic compound and its derivatives.

[0248] The microorganism may be of any type as long as it can produce the cyclic compound and its derivatives with high efficiency. In general, bacteria such as Escherichia coli, Bacillus subtilis, Staphylococcus aureus, and Corynebacterium glutamicum, actinomycetes such as Streptomyces griseus, cyanobacteria such as Microcystis aeruginosa, archaea such as Methanogens (Methanobacterium thermoautotrophicum), halophiles (Halobacterium salinarum), thermoacidophiles (Sulfolobus acidocaldarius), thermotolerant acidophiles (Alicyclobacillus acidoterrestris), and acid-fast bacteria, molds such as Aspergillus oryzae, and yeasts such as Saccharomyces cerevisiae. A yeast such as yeast Saccharomyces cerevisiae is selected according to the purpose, and a transformant obtained by a known method is used as necessary.

[0249] As the medium, a medium that is usually used for culturing microorganisms may be applied. The medium contains medium components to prepare an environment necessary for the growth of the microorganism. The medium components preferably contain a carbon source, a nitrogen source, inorganic salts or other nutrients in appropriate amounts depending on the type of microorganism to be used. Therefore, the culture solution before the bioprocess preferably contains the raw material, the microorganism and the medium components.

[0250] Examples of carbon sources include carbohydrates or sugar alcohols such as glucose, fructose, sucrose, mannose, maltose, mannitol, xylose, arabinose, galactose, starch, molasses, sorbitol, glycerin, etc., organic acids such as acetic acid, citric acid, lactic acid, fumaric acid, maleic acid, gluconic acid, etc., and alcohols such as ethanol, propanol, etc. As the carbon source, one of these may be used alone, or two or more may be used in combination.

[0251] Examples of the nitrogen source include inorganic or organic ammonium compounds such as ammonium chloride, ammonium sulfate, ammonium nitrate, and ammonium acetate, urea, aqueous ammonia, sodium nitrate, and potassium nitrate. In addition, nitrogen-containing organic compounds such as corn steep liquor, meat extract, peptone, NZ-amine, protein hydrolysates, and amino acids can also be used. As the nitrogen source, one of these may be used alone, or two or more may be used in combination.

[0252] Examples of inorganic salts include monopotassium phosphate, dipotassium phosphate, magnesium sulfate, sodium chloride, ferrous nitrate, manganese sulfate, zinc sulfate, cobalt sulfate, calcium carbonate, etc. As the inorganic salt, one of these may be used alone, or two or more of them may be used in combination.

[0253] Examples of nutrients include meat extract, peptone, polypeptone, yeast extract, dry yeast, corn steep liquor, skimmed milk powder, hydrolyzed skimmed soybeans with hydrochloric acid, or extracts of animals, plants, or microbial cells or their decomposition products. Furthermore, vitamins can be added to the medium as needed. Examples of vitamins include biotin, thiamine (vitamin B1), pyridoxine (vitamin B6), pantothenic acid, inositol, nicotinic acid, etc.

[0254] The culture equipment may be any of batch, fed-batch, and continuous types, but the batch type is preferred when multiple types of production are envisaged. In addition, a seed culture method is generally adopted in which the culture is expanded stepwise from a flask-scale culture, and a group of culture vessels with several different sizes depending on the production scale is used as a set. As culture conditions, the medium temperature is preferably about 15 to 45°C, and the pH of the medium is preferably about 6 to 8. Other parameters such as the aeration method and aeration amount to the culture tank, the stirring method and rotation speed, the shape of the stirring blade, and the culture time are appropriately set according to the scale and specifications of the culture equipment, the type and concentration of the microorganisms used, and the culture process is appropriately adjusted by real-time monitoring.

[0255] <Concentration process and isolation and purification process> The culture solution obtained by the bioprocess can be prepared in a state containing the cyclic compound or its derivative at a suitable concentration if the microbial growth environment is appropriately selected. In order to selectively and efficiently recover the cyclic compound or its derivative from the culture solution thus prepared, a recovery process including a culture solution concentration step and an isolation and purification step is applied. According to such a method, the cyclic compound or its derivative can be efficiently produced.

[0256] The concentration step is carried out for the purpose of increasing the concentration of at least one of the cyclic compound and its derivative in the culture solution obtained after the bioprocess, and recovering the target compound in high yield and high purity in the subsequent isolation and purification step. The concentration step will be described below.

[0257] The culture solution after the bioprocess contains at least one of the cyclic compound and its derivative produced by the bioprocess, as well as a carbon source, a nitrogen source, inorganic salts, nutrients, etc. as medium components, and also contains organic acids, amino acids, and their salts that are by-produced during the bioprocess. Note that 70 to 99% of the total weight of the culture solution after the bioprocess is usually water. Therefore, in the concentration process, it is desirable to efficiently remove water without altering or depleting the cyclic compound or its derivative, and without further increasing the amount of by-products associated with concentration. To achieve this purpose, chemical engineering techniques such as heat concentration, reduced pressure distillation, solvent extraction, solid extraction, and membrane separation can be applied, but reduced pressure concentration is more preferably used to avoid alteration and depletion of the cyclic compound or its derivative due to heat or oxidation during the concentration process and to reduce the amount of thermal energy input associated with water removal.

[0258] The isolation and purification step is carried out for the purpose of selectively recovering at least one of the cyclic compound and its derivative from the concentrate obtained in the concentration step.

[0259] In the isolation and purification process, various chemical engineering techniques can be applied, such as steam distillation, precision fractionation, temperature crystallization, acid crystallization, salting out, reprecipitation, sublimation, column purification, extraction, membrane separation, etc. A suitable technique is selected taking into consideration the properties of the target compound and the properties of the impurities and by-products to be removed. The properties of cyclic compounds vary depending on the type and number of substituents, but when the cyclic compound or its derivative is solid at room temperature and the impurities and by-products are relatively highly soluble in water, a crystallization method (temperature crystallization or acid crystallization) is preferably used.

[0260] <Processing into food or food additives> The cyclic compound or its derivative produced as described above can be processed as necessary to obtain a food or food additive. One example of such processing is the addition of any component. The food or food additive of this embodiment may contain any other component within a range that does not impair the effect of this embodiment.

[0261] Other ingredients include, for example, sugar, condensed milk, wheat flour, shortening, salt, glucose, eggs, butter, margarine, starch syrup, calcium, iron, seasonings, spices and oils (animal and vegetable oils, mineral oils, ester oils, wax oils, silicone oils, higher alcohols, phospholipids, fatty acids, etc.), surfactants (anionic, cationic, amphoteric or nonionic surfactants), vitamins (vitamin A group, vitamin B group, folic acid, nicotinic acid, pantothenic acid, biotin, vitamin C group, vitamin D group, vitamin E group, ferulic acid, γ-oryzanol, etc.), ultraviolet absorbing agents (p-aminobenzoic acid, anthranilic acid, salicylic acid, coumarin, benzotriazole, tetrazole, imidazoline, pyrimidine, dioxane, furan, pyrone, camphor, nucleic acid, allantoin or derivatives thereof, amino acid compounds, shikonin, baicalin, baicalein, berberine, etc.). , antioxidants (stearic acid esters, nordihydroguarthenic acid, dibutyl hydroxytoluene, butyl hydroxyanisole, parahydroxyanisole, propyl gallate, sesamol, sesamolin, gossypol, etc.), thickeners (hydroxyethyl cellulose, ethyl cellulose, carboxyethyl cellulose, methyl cellulose, carboxymethyl cellulose, sodium carboxymethyl cellulose, hydroxypropyl cellulose, nitrocellulose, polyvinyl alcohol, polyvinyl methyl ether, polyvinylpyrrolidone, polyvinyl methacrylate, polyacrylates, carboxyvinyl polymers, gum arabic, gum tragacanth, agar, casein, dextrin, gelatin, pectin, starch, alginic acid or its salts, etc.), moisturizers (propylene glycol, 1,3-butylene glycol, polyethylene glycol, glycerin, 1,2-pentanediol, hexylene glycol, octylene glycol, chondroitin sulfate or its salt, hyaluronic acid or its salt, sodium lactate, etc.), lower alcohols, polyhydric alcohols, water-soluble polymers, pH adjusters, preservatives and antifungal agents, colorants, fragrances, refreshing agents, stabilizers, animal and plant extracts, animal and plant proteins or their decomposition products, animal and plant polysaccharides or their decomposition products, animal and plant glycoproteins or their decomposition products, microbial culture metabolic components, blood flow promoters, anti-inflammatory agents, anti-inflammatory agents, anti-allergic agents, cell activators, amino acids or their salts, keratolytic agents, astringents, wound healing agents, foaming agents, oral agents, deodorants and deodorants, emulsifiers, etc. These may be used alone or in combination of two or more.

[0262] The form of the food product in this embodiment is arbitrary and is not limited. Although the food or food additive of this embodiment has been described above, specific examples of the food or food additive are not limited to those described above and may be any.

[0263] Fifth embodiment The present embodiment relates to a method for producing a fragrance, and a cyclic compound or a derivative thereof.

[0264] It is known that cyclic compounds having a specific structure are used as fragrances. For example, Patent Document 9 (JP Patent Publication 8-92589 A) discloses a fragrance composition containing alcohols and aromatic aldehydes.

[0265] However, cyclic compounds such as the aromatic aldehydes are usually obtained from petroleum. In such cases, the petroleum-derived cyclic compounds (chemical products) that can be recovered by fractional distillation and refining of petroleum are so-called backbone compounds with simple chemical structures. On the other hand, high-value-added compounds with more complex chemical structures must be derived from these backbone compounds through a synthesis process. In this case, unless petroleum is fractionally refined to a high degree, regardless of production costs, various isomers derived from the raw materials and synthesis process, trace components derived from catalysts, ionic components, mineral components, etc. may remain in the petroleum-derived chemical products. These impurities contained in petroleum-derived chemical products cannot be said to be preferable from the viewpoint of safety for the human body.

[0266] The object of the present embodiment is to provide a safer fragrance that does not contain petroleum-derived impurities, and to provide a method for producing a cyclic compound or a derivative thereof that can be used as a fragrance.

[0267] Such an object can be achieved by the present embodiment described in (V-1) to (V-9) below. (V-1) A fragrance containing at least one of a plant-derived sugar and a cyclic compound or a derivative thereof derived from a microorganism.

[0268] (V-2) The fragrance according to the above (V-1), wherein the cyclic compound is a compound represented by the following general formula (1): [ka] [In the above general formula (1), ring A is a five-membered saturated ring, partially saturated ring, or aromatic ring, or a six-membered saturated ring, partially saturated ring, or aromatic ring; X is a single bond or a bond containing one or more carbon atoms; Y is a hydrogen atom or an alkyl group; R 2 ~R 6 (When ring A is a 5-membered ring, R 2 ~R 5 ) are independently a hydrogen atom, a hydroxyl group, an amino group, an alkoxy group, a carboxyl group, or a carbonyl group.

[0269] (V-3) The fragrance according to (V-2) above, wherein the cyclic compound is at least one selected from the group consisting of 2-hydroxybenzoic acid, 3-hydroxybenzoic acid, 4-hydroxybenzoic acid, 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 2,5-dihydroxybenzoic acid, 2,6-dihydroxybenzoic acid, 3,4-dihydroxybenzoic acid, and 3,5-dihydroxybenzoic acid.

[0270] (V-4) When ring A of the cyclic compound is a five-membered saturated or partially saturated ring in which all of the ring constituent atoms are carbon atoms, R 2 ~R 5 and when one or more of the carbon atoms of ring A to which X is bonded is an asymmetric carbon atom, and ring A of the cyclic compound is a 6-membered saturated or partially saturated ring in which all of the ring constituent atoms are carbon atoms, R 2 ~R 6 and the fragrance according to the above (V-2), wherein one or more of the carbon atoms of ring A to which X is bonded is an asymmetric carbon atom.

[0271] (V-5) In the cyclic compound, the carbon atom of ring A to which X is bonded is C 1 Let R 2 The carbon atom of ring A to which is bonded is C 2 Let R 3 The carbon atom of ring A to which is bonded is C 3 Let R 4 The carbon atom of ring A to which is bonded is C 4 Let R 5 The carbon atom of ring A to which is bonded is C 5 Let R 6 The carbon atom of ring A to which is bonded is C 6 The fragrance according to the above (V-4), wherein the combination of asymmetric carbon atoms is one selected from the group consisting of the following (a) to (h): (a)C 1 (b)C 2 (c)C 3 (d) C 4 (e)C 1 and C 4 (f)C 3 and C 4 (g) C 1 , C 3 and C 4 (h)C 3 , C 4 and C 5

[0272] (V-6) The fragrance according to the above (V-1), wherein the cyclic compound or a derivative thereof is 3-dehydroquinate, 3-dehydroshikimic acid, shikimic acid, chorismic acid or prephenic acid.

[0273] (V-7) The fragrance according to any one of (V-1) to (V-6) above, wherein the microorganism is Escherichia coli, Bacillus subtilis, Staphylococcus aureus, Corynebacterium, Actinomycete, Cyanobacterium, Methanogen, Halophile, Thermotolerant Acidophile, Acid-fast Bacteria, Mold, Yeast, or a transformant thereof.

[0274] (V-8) The flavoring according to any one of (V-1) to (V-7) above, wherein the raw material of the plant-derived sugar is a non-edible biomass resource.

[0275] (V-9) A method for producing a cyclic compound or a derivative thereof for use as a fragrance, comprising the steps of: preparing a culture solution containing plant-derived sugars and a microorganism so as to produce at least one of the cyclic compound and its derivatives; Concentrating the culture solution to obtain a concentrate; recovering at least one of the cyclic compound and its derivative from the concentrated solution by crystallization, precipitation, extraction, sublimation purification, or distillation; A method for producing a cyclic compound or a derivative thereof, comprising:

[0276] According to the present embodiment, it is possible to provide a safer fragrance that does not contain petroleum-derived impurities.

[0277] Furthermore, according to the present embodiment, safer flavorings that do not contain petroleum-derived impurities can be efficiently produced.

[0278] Hereinafter, the flavoring material of the present embodiment and the method for producing the cyclic compound or its derivative will be described in detail based on preferred embodiments.

[0279] ≪Fragrance≫ As a result of intensive research, the present inventors have found that by including at least one of a cyclic compound and its derivative derived from a plant-derived sugar and a microorganism, a flavoring agent free from petroleum-derived impurities can be provided. In this case, they have found that it is preferable to produce the cyclic compound or its derivative by a bioprocess using a plant-derived sugar (raw material) and a microorganism.

[0280] That is, the fragrance of the present embodiment contains at least one of a cyclic compound and its derivative derived from a plant-derived saccharide and a microorganism. In other words, the fragrance of the present embodiment contains at least one of a cyclic compound and its derivative produced by a reaction (bioprocess) between a plant-derived saccharide and a microorganism.

[0281] This makes it possible to provide a fragrance that is free of petroleum-derived impurities, and such a fragrance is safer than a fragrance that contains petroleum-derived impurities.

[0282] Examples of cyclic compounds contained in such fragrances include compounds whose ring-constituting atoms are carbon atoms, nitrogen atoms, oxygen atoms, sulfur atoms, etc., and whose ring members are about 3 to 12. The bond between the atoms constituting the ring may be a single bond or a double bond.

[0283] Although such a cyclic compound is not limited, it is preferable that the compound is represented by the general formula (1) described above in the fourth embodiment. The specific structure of the compound represented by the general formula (1) can be the structure described above in the fourth embodiment.

[0284] Specific examples of cyclic compounds include benzoic acid, phthalic acid, isophthalic acid, terephthalic acid, hemimellitic acid, trimellitic acid, trimesic acid, mellophanic acid, prenitic acid, pyromellitic acid, phenylacetic acid, hydroxyphenylacetic acid, phenylbutyric acid (phenyllactate), hydroxyphenylbutyric acid, phenylpyruvic acid, hydroxyphenylpyruvic acid, phenyllactic acid, hydroxyphenyllactic acid, anthranilic acid, hydroatropic acid, atropic acid, hydrophenyllactic acid, phenylacetate ... Cinnamic acid (coumaric acid), cinnamic acid, salicylic acid (2-hydroxybenzoic acid), m-salicylic acid (3-hydroxybenzoic acid), p-salicylic acid (4-hydroxybenzoic acid), methoxybenzoic acid, aminobenzoic acid, hydroxybenzoic acid, pyrocatechuic acid (2,3-dihydroxybenzoic acid), β-resorcylic acid (2,4-dihydroxybenzoic acid), gentisic acid (2,5-dihydroxybenzoic acid), γ-resorcylic acid (2,6-dihydroxybenzoic acid), protocatechuic acid (3,4-dihydroxybenzoic acid), α-resorcylic acid (3,5-dihydroxybenzoic acid), trihydroxybenzoic acid, vanillic acid (4-hydroxy-3-methoxybenzoic acid), isovanillic acid (3-hydroxy-4-methoxybenzoic acid), veratric acid, gallic acid, syringic acid, asaronic acid, mandelic acid, vanillylmandelic acid, anisic acid, homoprotocatechuic acid, homovanillic acid, homoisovanillic acid, homoveratric acid, homophthalic acid, homoiso ... Examples of these include moterephthalic acid, phthalonic acid, isophthalonic acid, terephthalonic acid, atrolactic acid, tropic acid, mellitic acid, phloretic acid, dihydrocaffeic acid, hydroferulic acid, hydroisoferulic acid, umbellic acid, caffeic acid (caffeic acid), ferulic acid, isoferulic acid, sinapic acid, syringic acid, dehydroquinic acid, dehydroshikimic acid, shikimic acid, chorismic acid, L-tryptophan, L-tyrosine, prephenic acid, arogenic acid, and L-phenylalanine.

[0285] Other specific examples of cyclic compounds include polyphenols such as flavonoids, lignans, chalcones, stilbenoids, alkaloids, curcuminoids, terpenoids, saponins, various glycosides, and various polyphenol-based aromatic compounds, as well as amino acids and vitamins.

[0286] Among these, examples of flavonoids include anthocyanidins such as aurantidin, cyanidin, delphinidin, europinidin, luteolinidin, pelargonidin, malvidin, peonidin, petunidin, and rosinidin, anthocyanins such as procyanidin, flavanones such as naringenin, eriocitrin, pinocembrin, and eriodictyol, flavans such as catechin, flavones such as apigenin, luteolin, baicalein, and chrysin, flavonols such as quercetin and kaempferol, isoflavones, isoflavones, isoflavanes, isoflavandiols, and isoflavonoids such as genistein, as well as neoflavonoids, biflavonoids, aurones, prenylated flavonoids, and O-methylated flavonoids.

[0287] Examples of lignans include pinoresinol, lariciresinol, secoisolariciresinol, matairesinol, hydroxymatairesinol, syringaresinol, sesamin, arctigenin, sesaminol, podophyllotoxin, and steganacin.

[0288] Further examples of stilbenoids include aglycones such as piceatannol, pinosylvin, pterostilbene, resveratrol, 4'-methoxyresveratrol, pinostilbene, and piciatannol, and oligomers such as α-viniferin, ampelopsin A, ampelopsin E, diptoindonesin C-kawane, diptoindonesin F-dammarbua, ε-viniferin, flexosol A, gnetin H, hemsleyanol D, hopeaphenol, diptoindonesin B, and vaticanol B.

[0289] Examples of curcuminoids include curcumin and shogaol.

[0290] Further, examples of terpenoids include carotenoids such as lutein, vitamin A, vitamin E, and β-carotene, as well as steroids such as sitosterol.

[0291] Examples of various glycosides include phenolic glycosides such as salicin, β-glucogallin, salicylic acid glucoside, salidroside, gastrodin, poplin, phloridzin, and arbutin, coumarin glycosides such as esculin, flavonoid glycosides such as hesperidin and rutin, and stilbenoid glycosides such as astringin, piceid, and diptoindonesin A.

[0292] Furthermore, examples of various polyphenol aromatic compounds include tyrosol, hydroxytyrosol, esculetin, phloretin, rosmarinic acid, salvianic acid A, reticuline, paracoumaryl alcohol, coniferyl alcohol, and caffeyl alcohol.

[0293] Furthermore, examples of amino acids include phenylalanine and tyrosine. Furthermore, vitamins include, for example, vitamin A, vitamin D, vitamin E, etc.

[0294] Further specific examples of the cyclic compound include aromatic compounds, alicyclic compounds, aliphatic compounds, and heterocyclic compounds.

[0295] Among these, examples of aromatic compounds include vanillin, 2-phenylethanol, phenylacetic acid, cinnamic alcohol, isoeugenol, ferulic acid, 4-aminobenzoic acid, anethole, estragole, methyl anthranilate, methyl cinnamate, ethyl cinnamate, phenylacetaldehyde, cinnamic aldehyde, cinnamyl acetate, resorcin, 4-vinylphenol, 4-vinyl-2-methoxyphenol, 3,4-dihydroxystyrene, dopamine, levodopa, hydroquinone, coumarin, 7-hydroxycoumarin, 4-hydroxycoumarin, and xiamenmycin A.

[0296] Examples of alicyclic compounds include carveol, perilla alcohol, borneol, methyl jasmonate, 1,8-cineole, L-menthone, valencene, nootkatone, α-pinene, camphene, L-carvone, perilla aldehyde, myrtenal, L-menthyl acetate, and β-ionone.

[0297] Furthermore, examples of aliphatic compounds include cis-3-hexenol, cis-3-hexenyl acetate, acetoin, nerol, farnesol, arginine, and muconic acid.

[0298] Examples of heterocyclic compounds include niacin, niacinamide, maltol, and indole.

[0299] On the other hand, examples of derivatives of cyclic compounds include esters, acid anhydrides, amides, acid halides, salts, etc. of the above-mentioned compounds, or all compounds derived from cyclic compounds.

[0300] Among the above-mentioned cyclic compounds, the cyclic compound represented by the above general formula (1) is preferably at least one selected from the group consisting of 2-hydroxybenzoic acid, 3-hydroxybenzoic acid, 4-hydroxybenzoic acid, 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 2,5-dihydroxybenzoic acid, 2,6-dihydroxybenzoic acid, 3,4-dihydroxybenzoic acid, and 3,5-dihydroxybenzoic acid. By using these, it is possible to realize a fragrance having various efficacies and being safer.

[0301] The molecular weight of the cyclic compound or its derivative is not limited, but is preferably 120-1,000, and more preferably 130-800.

[0302] In addition, when ring A of the cyclic compound represented by the above general formula (1) is a five-membered saturated or partially saturated ring in which all of the ring constituent atoms are carbon atoms, R 2 ~R 5It is preferable that one or more of the carbon atoms of ring A to which X is bonded is an asymmetric carbon atom. In addition, when ring A of the cyclic compound represented by the above general formula (1) is a 6-membered saturated or partially saturated ring in which all of the ring constituent atoms are carbon atoms, R 2 ~R 6 And, among the carbon atoms of ring A to which X is bonded, one or more are preferably asymmetric carbon atoms.

[0303] In such a case, the cyclic compound becomes a stereoisomer, which allows a meaningful fragrance to be realized. In addition, by producing such a cyclic compound from a plant-derived sugar, a fragrance containing a specific stereoisomer in high purity can be obtained. That is, a fragrance containing a specific stereoisomer in high purity and having a low content of other stereoisomers can be obtained. Such a fragrance is useful from the viewpoint of realizing a fragrance with excellent safety and efficacy. In addition, since a complicated production process associated with the removal of unnecessary stereoisomers is not required, the production cost can be reduced.

[0304] In addition, in the cyclic compound represented by the above general formula (1), the carbon atom of ring A to which X is bonded is C 1 Let R 2 The carbon atom of ring A to which is bonded is C 2 Let R 3 The carbon atom of ring A to which is bonded is C 3 Let R 4 The carbon atom of ring A to which is bonded is C 4 Let R 5 The carbon atom of ring A to which is bonded is C 5 Let R 6 The carbon atom of ring A to which is bonded is C 6 In this case, it is preferable that the combination of these asymmetric carbon atoms is one selected from the group consisting of the following (a) to (h):

[0305] (a)C 1 (b)C 2 (c)C 3 (d) C 4 (e)C 1 and C 4 (f)C 3 and C 4 (g) C 1 , C 3 and C 4 (h)C 3 , C 4 and C 5

[0306] The general formula (2) described in the fourth embodiment is a cyclic compound represented by the general formula (1) above. 1 ~C 6 This is an equation with the notation added.

[0307] In such a case, the cyclic compound becomes a stereoisomer, which allows a more significant fragrance to be realized. In addition, by producing such a cyclic compound from a plant-derived saccharide, a fragrance containing a specific stereoisomer selected from the group consisting of (a) to (h) above in high purity can be obtained. That is, a fragrance containing a specific stereoisomer in high purity and having a low content of other stereoisomers can be obtained. Such a fragrance is useful from the viewpoint of realizing a fragrance with excellent safety and efficacy. In addition, the complicated manufacturing process associated with the removal of unnecessary stereoisomers can be reduced, thereby reducing the manufacturing cost.

[0308] The cyclic compound and its derivative according to this embodiment are preferably compounds represented by the above general formula (2), and further preferably 3-dehydroquinate, 3-dehydroshikimic acid, shikimic acid, chorismic acid, or prephenic acid. All of these compounds can be produced from plant-derived sugars, and are useful as fragrances. Therefore, by using these compounds produced from plant-derived sugars, it is possible to realize fragrances that have better efficacy and are safer. The structures of these cyclic compounds are represented by the following formulas.

[0309] 3-Dehydroquinate

[0310] [ka]

[0311] 3-Dehydroshikimic acid

[0312] [ka]

[0313] Shikimic acid

[0314] [ka]

[0315] Chorismic acid

[0316] [ka]

[0317] Prephenic acid

[0318] [ka]

[0319] Examples of flavors containing at least one of the above-mentioned cyclic compounds and their derivatives include food flavors (flavors), cosmetic flavors (fragrances), etc. Among these, functions of food flavors include, for example, flavoring, aromatization, flavor correction, sweetness enhancement, sourness / bitterness reduction, appetite enhancement, etc. Furthermore, applications of cosmetic flavors include, for example, perfumes, colognes, toiletry products, household products, air fresheners, etc.

[0320] The form of the fragrance may be, for example, a water-soluble liquid, an oil-soluble liquid, an emulsion, a powder, or the like.

[0321] <Method for producing cyclic compound or derivative thereof> The above-mentioned cyclic compound or derivative thereof is produced by a bioprocess using a microorganism and a plant-derived sugar as a raw material. That is, the above-mentioned cyclic compound or derivative thereof is derived from a plant-derived sugar and a microorganism. Specific examples of the materials, raw materials, materials used, etc. from which the cyclic compound or its derivatives are derived and the production method can be, for example, the method described in the fourth embodiment. More specifically, the step of preparing a culture solution, as well as the concentration step and the isolation and purification step can be carried out in accordance with the fourth embodiment.

[0322] <Processing into fragrances> The cyclic compound or its derivative produced as described above can be processed as necessary to obtain a fragrance. One example of such processing is the addition of any component. The fragrance of the present embodiment may contain any other component within a range that does not impair the effect of the present embodiment.

[0323] Other ingredients include, for example, sugar, condensed milk, wheat flour, shortening, salt, glucose, eggs, butter, margarine, starch syrup, calcium, iron, seasonings, spices and oils (animal and vegetable oils, mineral oils, ester oils, wax oils, silicone oils, higher alcohols, phospholipids, fatty acids, etc.), surfactants (anionic, cationic, amphoteric or nonionic surfactants), vitamins (vitamin A group, vitamin B group, folic acid, nicotinic acid, pantothenic acid, biotin, vitamin C group, vitamin D group, vitamin E group, ferulic acid, γ-oryzanol, etc.), ultraviolet absorbers (p-aminobenzoic acid, anthranilic acid, salicylic acid, salicylic acid glucoside, benzotriazole, tetrazole, imidazoline, pyrimidine, dioxane, furan, pyrone, camphor, nucleic acid, allantoin or derivatives thereof, amino acid compounds, shikonin, baicalin, baicalein, berberi , etc.), antioxidants (stearic acid esters, nordihydroguarthenic acid, dibutyl hydroxytoluene, butyl hydroxyanisole, parahydroxyanisole, propyl gallate, sesamol, sesamolin, gossypol, etc.), thickeners (hydroxyethyl cellulose, ethyl cellulose, carboxyethyl cellulose, methyl cellulose, carboxymethyl cellulose, sodium carboxymethyl cellulose, hydroxypropyl cellulose, nitrocellulose, polyvinyl alcohol, polyvinyl methyl ether, polyvinylpyrrolidone, polyvinyl methacrylate, polyacrylates, carboxyvinyl polymers, gum arabic, gum tragacanth, agar, casein, dextrin, gelatin, pectin, starch, alginic acid or its salts, etc.), moisturizers (propylene glycol, 1,3-butylene glycol, polyethylene glycol, glycerin, 1,2-pentanediol, hexylene glycol, octylene glycol, chondroitin sulfate or its salt, hyaluronic acid or its salt, sodium lactate, etc.), lower alcohols, polyhydric alcohols, water-soluble polymers, pH adjusters, preservatives and antifungal agents, colorants, fragrances, refreshing agents, stabilizers, animal and plant extracts, animal and plant proteins or their decomposition products, animal and plant polysaccharides or their decomposition products, animal and plant glycoproteins or their decomposition products, microbial culture metabolic components, blood flow promoters, anti-inflammatory agents, anti-inflammatory agents, anti-allergic agents, cell activators, amino acids or their salts, keratolytic agents, astringents, wound healing agents, foaming agents, oral agents, deodorants and deodorants, emulsifiers, etc. These may be used alone or in combination of two or more.

[0324] Although the fragrance of this embodiment has been described above, specific examples of the fragrance are not limited to those described above and may be any fragrance.

[0325] Although the embodiments of the present invention have been described above, these are merely examples of the present invention, and various configurations other than those described above can be adopted. EXAMPLES

[0326] Example I (Examples I-1 to I-4, Comparative Examples I-1 to I-4) In this example, the antimicrobial properties of the composition were evaluated. The components were mixed according to the formulations shown in Tables 1 to 4 to obtain a water-soluble additive composition for each example, specifically an antibacterial composition. That is, in each example, 98% by mass of protocatechuic acid (a reagent, manufactured by Tokyo Chemical Industry Co., Ltd.) and 2% by mass of gallic acid were mixed to obtain an antibacterial composition. On the other hand, in each comparative example, the above-mentioned protocatechuic acid was used as it is.

[0327] For each example, the obtained composition was used to obtain aqueous solutions (antibacterial composition blended solutions) having antibacterial composition concentrations of 0.1 mass %, 0.2 mass %, 0.3 mass % and 0.5 mass %. The antibacterial properties of the obtained compositions were evaluated by the following method.

[0328] (Evaluation method) For each example, the test solution adjusted to each of the above concentrations and the test bacteria were mixed in a bacterial medium containing 1% polyoxyethylene polyoxypropylene alkyl ether. After stirring, the absorbance at 650 nm was measured and used as the initial value. The mixture was cultured for 24 hours under aerobic conditions at 37°C, and the absorbance at 650 nm was measured again, from which the initial value was subtracted to determine the turbidity derived from the bacteria. The test results were expressed as a percentage (%), with the absorbance of 0% test sample taken as 100. In addition, Staphylococcus aureus (Staphylococcus aureus, Example I-1 and Comparative Example I-1), Escherichia coli (Escherichia coli, Example I-2 and Comparative Example I-2), Pseudomonas aeruginosa (Pseudomonas aeruginosa, Example I-3 and Comparative Example I-3), and Candida albicans (yeast, Example I-4 and Comparative Example I-4) were used as test bacteria. The evaluation results are shown in Tables 1 to 4 and are also shown in Figures 1 to 4. Figures 1 to 4 are diagrams showing the evaluation results of the antibacterial compositions.

[0329] [Table 1]

[0330] [Table 2]

[0331] [Table 3]

[0332] [Table 4]

[0333] As can be seen from Tables 1 to 4 and Figs. 1 to 4, the compositions obtained in the examples tended to have lower absorbance than those in the comparative examples, and were excellent in antibacterial properties.

[0334] (Examples I-5 to I-7, Comparative Examples I-5 to I-7) The components were mixed according to the formulations shown in Tables 5 to 7, and water-soluble additive compositions containing a cyclic carboxylic acid were obtained in accordance with Example I-1 or Comparative Example I-1. Here, in Example I-5 and Comparative Example I-5, shikimic acid (reagent, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was used. In Example I-6 and Comparative Example I-6, 4-hydroxybenzoic acid (reagent, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was used. In Example I-7 and Comparative Example I-7, 4-aminobenzoic acid (reagent, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was used.

[0335] For each example, the obtained composition was used to obtain aqueous solutions (antibacterial composition blended solutions) having antibacterial composition concentrations of 0.1 mass %, 0.2 mass %, 0.3 mass % and 0.5 mass %. The antibacterial properties of the obtained composition were evaluated in accordance with Example I-1 or Comparative Example I-1 using Staphylococcus aureus as the test bacteria. The evaluation results are shown in Tables 5 to 7.

[0336] [Table 5]

[0337] [Table 6]

[0338] [Table 7]

[0339] Example II (Examples II-1 to II-4, Comparative Examples II-1 and II-2) In this example, a water-soluble additive composition was prepared and its solubility characteristics were evaluated, as well as the purity of the cyclic carboxylic acid in the composition.

[0340] (Example II-1) <Production of protocatechuic acid by bioprocess> Protocatechuic acid was produced by bioprocessing in a 10 L jar fermenter. The medium used was LB medium, in which 10% of refined sugar from sugarcane pomace was dissolved.

[0341] <Recovery of protocatechuic acid composition from culture medium through a concentration and purification process> The culture liquid obtained by the bioprocess was concentrated by vacuum concentration to a total solid content of 15 to 30% by mass. The degree of vacuum was set to 100 to 5000 Pa, the liquid temperature was set to 30 to 80°C, and the concentration treatment was performed using a vacuum distillation apparatus. Although the degree of concentration depends on the treatment time, a concentrated liquid with a total solid content of 15 to 30% by mass was recovered by a concentration treatment for 6 to 8 hours. Hydrochloric acid was added to this concentrated liquid to adjust the pH to 4 or less, and the liquid was further cooled to 0°C to room temperature. The crystallized product was collected by filtration, washed three times with pure water in an amount 20 times the mass of the precipitate, and then dried under reduced pressure to recover a powdery water-soluble additive composition containing protocatechuic acid.

[0342] (Example II-2) After concentrating the culture solution, a composition containing protocatechuic acid was recovered in the same manner as in Example II-1, except that the filtered precipitate was washed four times with 20 times the mass of pure water.

[0343] (Example II-3) After concentrating the culture solution, a composition containing protocatechuic acid was recovered in the same manner as in Example II-1, except that the filtered precipitate was washed twice with 20 times the mass of pure water.

[0344] (Example II-4) After concentrating the culture solution, a composition containing protocatechuic acid was recovered in the same manner as in Example II-1, except that the filtered precipitate was washed once with 20 times the mass of pure water.

[0345] (Comparative Example II-1) A commercially available protocatechuic acid reagent (Tokyo Chemical Industry Co., Ltd.) was prepared.

[0346] (Comparative Example II-2) After concentrating the culture solution, a composition containing protocatechuic acid was recovered in the same manner as in Example II-1, except that the precipitate obtained by filtration was not washed.

[0347] (Evaluation method) (cyclic carboxylic acid concentration) The concentration of the cyclic carboxylic acid in each composition was measured by high performance liquid chromatography (HPLC) under the following conditions: Column: COSMOSIL 5C18-AR-II (φ4.6mm×250mm) manufactured by Nacalai Tesque Mobile phase: Water / methanol / perchloric acid = 4 / 1 / 0.0075 (vol / vol / vol) isocratic elution Flow rate: 1mL / mmin Column temperature: 40℃ Detection method: Photodiode array (PDA) detector (210 nm)

[0348] (Ion concentration) The compositions obtained in each example were subjected to ion chromatography to determine Na + , NH4 + , K + , SO4 2- , PO4 3- , NO2 - , NO3 - and Cl - The concentration of each ion and the total inorganic ion concentration (ppm, excluding hydrogen ions and hydroxyl ions) were measured under the following conditions. Column: (cation) Shim-pack IC-C4 (Shimadzu Corporation), (anion) Shim-pack IC-SA2 (Shimadzu Corporation) Mobile phase: (cation) water / oxalic acid dihydrate = 1000 / 0.315 (mass / mass), (anion) water / sodium bicarbonate / sodium carbonate = 1000 / 1.008 / 0.0636 (mass / mass / mass), isocratic elution for both anion and cation Flow rate: (both cation and anion) 1mL / mm Column temperature: (cation) 40°C, (anion) 30°C Detection method: Electrical conductivity detector The concentration of each ion was calculated as the ratio (ppm) of the concentration (ppm) of each ion to the concentration (ppm) of the cyclic carboxylic acid in the composition measured by HPLC. The measurement results are shown in Table 8.

[0349] (purity) The purity of the cyclic carboxylic acid in the composition was judged based on the total inorganic ion concentration (excluding hydrogen ions and hydroxyl ions) from the above-mentioned ion concentration measurement results, according to the following criteria, and those with the following "◎" and "○" were deemed to have passed. The results are shown in Table 8. ◎: Total inorganic ion amount is 0 to less than 1000 ○: Total inorganic ion amount is less than 1000-5000 ×: Total inorganic ion amount is 5000ppm or more

[0350] (Solubility) For the compositions obtained in each example, 50 g of the composition was added to 1 L of pure water adjusted to a liquid temperature of 25°C, and the mixture was stirred with a stirrer for one day. The cyclic carboxylic acid concentration of the supernatant was then measured by HPLC to calculate the solubility. Solubility of 12 g / L or more was deemed to be acceptable. The measurement results are shown in Table 8.

[0351] [Table 8]

[0352] As can be seen from Table 8, the compositions obtained in the respective Examples had high purity of protocatechuic acid and excellent water solubility of protocatechuic acid.

[0353] (Examples II-5 to II-8, Comparative Examples II-3 and II-4) A water-soluble additive composition containing shikimic acid instead of protocatechuic acid was prepared and its solubility characteristics were evaluated, as well as the purity of the cyclic carboxylic acid in the composition.

[0354] (Example II-5) <Production of shikimic acid using bioprocesses> Shikimic acid was produced by bioprocessing in a 10 L jar fermenter. The medium used was LB medium, in which 10% of refined sugar from sugarcane pomace was dissolved.

[0355] <Recovery of shikimic acid composition from culture medium through a concentration and purification process> The culture liquid obtained by the bioprocess was concentrated by vacuum concentration to a total solid content of 15 to 30% by mass. The degree of vacuum was set to 100 to 5000 Pa, the liquid temperature was set to 30 to 80°C, and the concentration treatment was performed using a vacuum distillation apparatus. Although the degree of concentration depends on the treatment time, a concentrated liquid with a total solid content of 15 to 30% by mass was recovered by a concentration treatment for 6 to 8 hours. Hydrochloric acid was added to this concentrated liquid to adjust the pH to 4 or less, and the liquid was further cooled to 0°C to room temperature. The crystallized product was collected by filtration, washed three times with pure water in an amount 20 times the mass of the precipitate, and then dried under reduced pressure to recover a powdered water-soluble additive composition containing shikimic acid.

[0356] (Example II-6) After concentrating the culture solution, a composition containing shikimic acid was recovered in the same manner as in Example II-5, except that the filtered precipitate was washed four times with 20 times the mass of pure water.

[0357] (Example II-7) After concentrating the culture solution, a composition containing shikimic acid was recovered in the same manner as in Example II-5, except that the filtered precipitate was washed twice with 20 times the mass of pure water.

[0358] (Example II-8) After concentrating the culture solution, a composition containing shikimic acid was recovered in the same manner as in Example II-5, except that the filtered precipitate was washed once with 20 times the mass of pure water.

[0359] (Comparative Example II-3) A commercially available shikimic acid reagent (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was prepared.

[0360] (Comparative Example II-4) After concentrating the culture solution, a composition containing shikimic acid was recovered in the same manner as in Example II-5, except that the filtered precipitate was not washed.

[0361] (Evaluation method) The compositions obtained in each example were evaluated for cyclic carboxylic acid concentration, ion concentration, purity, and solubility in accordance with the above-mentioned Examples II-1 to II-4 and Comparative Examples II-1 and II-2. The results are shown in Table 9.

[0362] [Table 9]

[0363] (Examples II-9 to II-12, Comparative Examples II-5 and II-6) A water-soluble additive composition containing 4-hydroxybenzoic acid instead of protocatechuic acid was prepared and its solubility characteristics were evaluated, as well as the purity of the cyclic carboxylic acid in the composition.

[0364] (Example II-9) <Production of 4-hydroxybenzoic acid using bioprocess> 4-Hydroxybenzoic acid was produced by bioprocessing in a 10L jar fermenter. The medium used was LB medium, in which 10% of refined sugar from sugarcane pomace was dissolved.

[0365] <Recovery of 4-hydroxybenzoic acid composition from culture medium through concentration and purification process> The culture liquid obtained by the bioprocess was concentrated by vacuum concentration to a total solid content of 15 to 30% by mass. The degree of vacuum was set to 100 to 5000 Pa, the liquid temperature was set to 30 to 80°C, and the concentration treatment was performed using a vacuum distillation apparatus. Although the degree of concentration depends on the treatment time, a concentrated liquid with a total solid content of 15 to 30% by mass was recovered by a concentration treatment for 6 to 8 hours. Hydrochloric acid was added to this concentrated liquid to adjust the pH to 4 or less, and the liquid was further cooled to 0°C to room temperature. The crystallized product was collected by filtration, washed three times with pure water in an amount 20 times the mass of the precipitate, and then dried under reduced pressure to recover a powdery water-soluble additive composition containing 4-hydroxybenzoic acid.

[0366] (Example II-10) After concentrating the culture solution, a composition containing 4-hydroxybenzoic acid was recovered in the same manner as in Example II-9, except that the filtered precipitate was washed four times with pure water in an amount 20 times by mass.

[0367] (Example II-11) After concentrating the culture liquid, a composition containing 4-hydroxybenzoic acid was recovered in the same manner as in Example II-9, except that the filtered precipitate was washed twice with 20 times the mass of pure water.

[0368] (Example II-12) After concentrating the culture liquid, a composition containing 4-hydroxybenzoic acid was recovered in the same manner as in Example II-9, except that the filtered precipitate was washed once with 20 times the mass of pure water.

[0369] (Comparative Example II-5) A commercially available 4-hydroxybenzoic acid reagent (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was prepared.

[0370] (Comparative Example II-6) After concentrating the culture solution, a composition containing 4-hydroxybenzoic acid was recovered in the same manner as in Example II-9, except that the precipitate obtained by filtration was not washed.

[0371] (Evaluation method) The compositions obtained in each example were evaluated for cyclic carboxylic acid concentration, ion concentration, purity, and solubility in accordance with the above-mentioned Examples II-1 to II-4 and Comparative Examples II-1 and II-2. The results are shown in Table 10.

[0372] [Table 10]

[0373] (Examples II-13 to II-16, Comparative Examples II-7 and II-8) A water-soluble additive composition containing 4-aminobenzoic acid instead of protocatechuic acid was prepared and its solubility characteristics were evaluated, as well as the purity of the cyclic carboxylic acid in the composition.

[0374] (Example II-13) <Production of 4-aminobenzoic acid by bioprocess> 4-Aminobenzoic acid was produced by bioprocessing in a 10 L jar fermenter. The medium used was LB medium, in which 10% of refined sugar from sugarcane pomace was dissolved.

[0375] <Recovery of 4-aminobenzoic acid composition from culture medium through concentration and purification process> The culture liquid obtained by the bioprocess was concentrated by vacuum concentration to a total solid content of 15 to 30% by mass. The degree of vacuum was set to 100 to 5000 Pa, the liquid temperature was set to 30 to 80°C, and the concentration treatment was performed using a vacuum distillation apparatus. Although the degree of concentration depends on the treatment time, a concentrated liquid with a total solid content of 15 to 30% by mass was recovered by a concentration treatment for 6 to 8 hours. Hydrochloric acid was added to this concentrated liquid to adjust the pH to 4 or less, and the liquid was further cooled to 0°C to room temperature. The crystallized product was collected by filtration, washed three times with pure water in an amount 20 times the mass of the precipitate, and then dried under reduced pressure to recover a powdery water-soluble additive composition containing 4-aminobenzoic acid.

[0376] (Example II-14) After concentrating the culture solution, a composition containing 4-aminobenzoic acid was recovered in the same manner as in Example II-13, except that the filtered precipitate was washed four times with pure water in an amount 20 times by mass.

[0377] (Example II-15) After concentrating the culture solution, a composition containing 4-aminobenzoic acid was recovered in the same manner as in Example II-13, except that the filtered precipitate was washed twice with 20 times the mass of pure water.

[0378] (Example II-16) After concentrating the culture solution, a composition containing 4-aminobenzoic acid was recovered in the same manner as in Example II-13, except that the filtered precipitate was washed once with 20 times the mass of pure water.

[0379] (Comparative Example II-7) A commercially available 4-aminobenzoic acid reagent (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was prepared.

[0380] (Comparative Example II-8) After concentrating the culture solution, a composition containing 4-aminobenzoic acid was recovered in the same manner as in Example II-13, except that the filtered precipitate was not washed.

[0381] (Evaluation method) The compositions obtained in each example were evaluated for cyclic carboxylic acid concentration, ion concentration, purity, and solubility in accordance with the above-mentioned Examples II-1 to II-4 and Comparative Examples II-1 and II-2. The results are shown in Table 11.

[0382] [Table 11]

[0383] Example III (Examples III-1 to III-4, Comparative Example III-1) In the present examples, compositions were prepared and evaluated for their moisturizing and antibacterial properties. The methods for producing and evaluating the compositions of each example are as follows.

[0384] (Example III-1) Washing 1 <Production of protocatechuic acid by bioprocess> Protocatechuic acid was produced by bioprocessing in a 10 L jar fermenter. The medium used was LB medium, in which 10% of refined sugar from sugarcane pomace was dissolved.

[0385] <Recovery of protocatechuic acid composition from culture medium through a concentration and purification process> The culture liquid obtained by the bioprocess was concentrated by vacuum concentration to a total solid content of 30 to 50% by mass. The degree of vacuum was set to 100 to 5000 Pa, the liquid temperature was set to 30 to 80°C, and the concentration treatment was performed using a vacuum distillation apparatus. Although the degree of concentration depends on the treatment time, a concentrated liquid with a total solid content of 30 to 50% by mass was recovered by a concentration treatment for 6 to 8 hours. Hydrochloric acid was added to this concentrated liquid to adjust the pH to 4 or less, and the liquid was further cooled to 0°C to room temperature. The crystallized product was collected by filtration, washed once with pure water in an amount 20 times the mass of the precipitate, and then dried under reduced pressure to recover a powdery water-soluble additive composition containing protocatechuic acid.

[0386] (Example III-2) Washing 2 After concentrating the culture solution, a composition containing protocatechuic acid was recovered in the same manner as in Example III-1, except that the filtered precipitate was washed twice with 20 times the mass of pure water.

[0387] (Example III-3) Washing 3 After concentrating the culture solution, a composition containing protocatechuic acid was recovered in the same manner as in Example III-1, except that the filtered precipitate was washed three times with 20 times the mass of pure water.

[0388] (Example III-4) Washing 4 After concentrating the culture solution, a composition containing protocatechuic acid was recovered in the same manner as in Example III-1, except that the filtered precipitate was washed four times with 20 times the mass of pure water.

[0389] (Comparative Example III-1) Reagents A commercially available protocatechuic acid reagent (Tokyo Chemical Industry Co., Ltd.) was prepared.

[0390] (Amino acid concentration) The concentration of each amino acid in the composition obtained in each example was measured by high performance liquid chromatography (HPLC, post-column fluorescence detection using ortho-phthalaldehyde as a reaction reagent, column: Shimadzu Shim-pack Amino-Na). The results are shown in Table 12.

[0391] (PCA purity) For the composition obtained in each example, the purity of the cyclic carboxylic acid in the composition was measured. First, the concentration of the cyclic carboxylic acid in each composition obtained in each example was measured by high performance liquid chromatography (HPLC) under the following measurement conditions. Column: COSMOSIL 5C18-AR-II (φ4.6mm×250mm) manufactured by Nacalai Tesque Mobile phase: Water / methanol / perchloric acid = 4 / 1 / 0.0075 (vol / vol / vol) isocratic elution Flow rate: 1mL / mmin Column temperature: 40℃ Detection method: Photodiode array (PDA) detector (210 nm) In addition, the total inorganic ion concentration (ppm) was measured by ion chromatography, where the concentration of each ion was calculated as the ratio (ppm) of the concentration of each ion (ppm) to the concentration (ppm) of the cyclic carboxylic acid in the composition measured by HPLC. Based on the measured total inorganic ion concentration, the purity of the cyclic carboxylic acid in the composition was determined according to the following criteria. The results are shown in Table 12. ◎: Total inorganic ion amount is 0 to less than 1000 ○: Total inorganic ion amount is less than 1000-5000 ×: Total inorganic ion amount is 5000ppm or more

[0392] (moisturizing) A 2.0% by mass aqueous solution of the water-soluble additive composition obtained in each example was prepared and used as a test solution. The moisture content of the stratum corneum was measured immediately after application of the test solution to the skin and 15 minutes later. The test results were expressed as a percentage, with the moisture content of the stratum corneum immediately after application taken as 100. The evaluation criteria are shown below. Evaluation results of "◎" and "○" were deemed to be acceptable. ◎: The decrease in stratum corneum moisture content is less than 10% 〇: The reduction in stratum corneum moisture is between 10% and 50% ×: The reduction in stratum corneum moisture is 50% or more. The evaluation results are also shown in Table 12.

[0393] (Antibacterial) A 2.0% by mass aqueous solution of the water-soluble additive composition obtained in each example was prepared as a test solution. The test solution and test bacteria of each example were mixed in a bacterial medium containing 1% polyoxyethylene polyoxypropylene alkyl ether. After stirring, the absorbance at 650 nm was measured and used as the initial value. The mixture was cultured for 24 hours under aerobic conditions at 37°C, and the absorbance at 650 nm was measured again, from which the initial value was subtracted to determine the turbidity derived from the bacteria. The test results were expressed as a percentage, with the absorbance of 0% test sample taken as 100. Four types of test bacteria were used: Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, and Candida albicans. The evaluation criteria are as follows. Evaluation results of "A" and "B" were deemed to be acceptable. ◎: Absorbance is less than 10% ○: Absorbance is 10% or more but less than 50% ×: absorbance is 50% or more The evaluation results are also shown in Table 12.

[0394] [Table 12]

[0395] As can be seen from Table 12, the compositions obtained in each Example had excellent moisturizing properties and antibacterial properties.

[0396] (Examples III-5 to III-8, Comparative Example III-2) In this example, compositions containing shikimic acid instead of protocatechuic acid were prepared and evaluated for their moisturizing and antibacterial properties. The production method and evaluation method for each example composition are as follows.

[0397] (Example III-5) Washing 1 <Production of shikimic acid using bioprocesses> Shikimic acid was produced by bioprocessing in a 10 L jar fermenter. The medium used was LB medium, in which 10% of refined sugar from sugarcane pomace was dissolved.

[0398] <Recovery of shikimic acid composition from culture medium through a concentration and purification process> The culture liquid obtained by the bioprocess was concentrated by vacuum concentration to a total solid content of 30 to 50% by mass. The degree of vacuum was set to 100 to 5000 Pa, the liquid temperature was set to 30 to 80°C, and the concentration treatment was performed using a vacuum distillation apparatus. Although the degree of concentration depends on the treatment time, a concentrated liquid with a total solid content of 30 to 50% by mass was recovered by a concentration treatment for 6 to 8 hours. Hydrochloric acid was added to this concentrated liquid to adjust the pH to 4 or less, and the liquid was further cooled to 0°C to room temperature. The crystallized product was collected by filtration, washed once with pure water in an amount 20 times the mass of the precipitate, and then dried under reduced pressure to recover a powdery water-soluble additive composition containing shikimic acid.

[0399] (Example III-6) Washing 2 After concentrating the culture solution, a composition containing shikimic acid was recovered in the same manner as in Example III-5, except that the filtered precipitate was washed twice with 20 times the mass of pure water.

[0400] (Example III-7) Washing 3 After concentrating the culture solution, a composition containing shikimic acid was recovered in the same manner as in Example III-5, except that the filtered precipitate was washed three times with 20 times the mass of pure water.

[0401] (Example III-8) Washing 4 After concentrating the culture solution, a composition containing shikimic acid was recovered in the same manner as in Example III-5, except that the filtered precipitate was washed four times with 20 times the mass of pure water.

[0402] (Comparative Example III-2) Reagents A commercially available shikimic acid reagent (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was prepared.

[0403] (Evaluation method) The compositions obtained in each example were evaluated for amino acid concentration, purity, moisturizing property, and antibacterial property in accordance with the above-mentioned Examples III-1 to III-4 and Comparative Example III-1. The results are shown in Table 13.

[0404] [Table 13]

[0405] (Examples III-9 to III-12, Comparative Example III-3) In this example, compositions containing 4-hydroxybenzoic acid instead of protocatechuic acid were prepared and evaluated for their moisturizing and antibacterial properties. The methods for producing and evaluating the compositions of each example are as follows.

[0406] (Example III-9) Washing 1 <Production of 4-hydroxybenzoic acid using bioprocess> 4-Hydroxybenzoic acid was produced by bioprocessing in a 10L jar fermenter. The medium used was LB medium, in which 10% of refined sugar from sugarcane pomace was dissolved.

[0407] <Recovery of 4-hydroxybenzoic acid composition from culture medium through concentration and purification process> The culture liquid obtained by the bioprocess was concentrated by vacuum concentration to a total solid content of 30 to 50% by mass. The degree of vacuum was set to 100 to 5000 Pa, the liquid temperature to 30 to 80°C, and the concentration treatment was performed using a vacuum distillation apparatus. Although the degree of concentration depends on the treatment time, a concentrated liquid with a total solid content of 30 to 50% by mass was recovered by a concentration treatment for 6 to 8 hours. Hydrochloric acid was added to this concentrated liquid to adjust the pH to 4 or less, and the liquid was further cooled to 0°C to room temperature. The crystallized product was collected by filtration, washed once with pure water in an amount 20 times the mass of the precipitate, and then dried under reduced pressure to recover a powdery water-soluble additive composition containing 4-hydroxybenzoic acid.

[0408] (Example III-10) Washing 2 After concentrating the culture liquid, a composition containing 4-hydroxybenzoic acid was recovered in the same manner as in Example III-9, except that the filtered precipitate was washed twice with 20 times the mass of pure water.

[0409] (Example III-11) Washing 3 After concentrating the culture solution, a composition containing 4-hydroxybenzoic acid was recovered in the same manner as in Example III-9, except that the filtered precipitate was washed three times with 20 times the mass of pure water.

[0410] (Example III-12) Washing 4 After concentrating the culture liquid, a composition containing 4-hydroxybenzoic acid was recovered in the same manner as in Example III-9, except that the filtered precipitate was washed four times with 20 times the mass of pure water.

[0411] (Comparative Example III-3) Reagents A commercially available 4-hydroxybenzoic acid reagent (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was prepared.

[0412] (Evaluation method) The compositions obtained in each example were evaluated for amino acid concentration, purity, moisturizing property, and antibacterial property in accordance with the above-mentioned Examples III-1 to III-4 and Comparative Example III-1. The results are shown in Table 14.

[0413] [Table 14]

[0414] (Examples III-13 to III-16, Comparative Example III-4) In this example, compositions containing 4-aminobenzoic acid instead of protocatechuic acid were prepared and evaluated for their moisturizing and antibacterial properties. The methods for producing and evaluating the compositions of each example are as follows.

[0415] (Example III-13) Washing 1 <Production of 4-aminobenzoic acid by bioprocess> 4-Aminobenzoic acid was produced by bioprocessing in a 10 L jar fermenter. The medium used was LB medium, in which 10% of refined sugar from sugarcane pomace was dissolved.

[0416] <Recovery of 4-aminobenzoic acid composition from culture medium through concentration and purification process> The culture liquid obtained by the bioprocess was concentrated by vacuum concentration to a total solid content of 30 to 50% by mass. The degree of vacuum was set to 100 to 5000 Pa, the liquid temperature was set to 30 to 80°C, and the concentration treatment was performed using a vacuum distillation apparatus. Although the degree of concentration depends on the treatment time, a concentrated liquid with a total solid content of 30 to 50% by mass was recovered by a concentration treatment for 6 to 8 hours. Hydrochloric acid was added to this concentrated liquid to adjust the pH to 4 or less, and the liquid was further cooled to 0°C to room temperature. The crystallized product was collected by filtration, washed once with pure water in an amount 20 times the mass of the precipitate, and then dried under reduced pressure to recover a powdery water-soluble additive composition containing 4-aminobenzoic acid.

[0417] (Example III-14) Washing 2 After concentrating the culture solution, a composition containing 4-aminobenzoic acid was recovered in the same manner as in Example III-13, except that the filtered precipitate was washed twice with 20 times the mass of pure water.

[0418] (Example III-15) Washing 3 After concentrating the culture solution, a composition containing 4-aminobenzoic acid was recovered in the same manner as in Example III-13, except that the filtered precipitate was washed three times with 20 times the mass of pure water.

[0419] (Example III-16) Washing 4 After concentrating the culture solution, a composition containing 4-aminobenzoic acid was recovered in the same manner as in Example III-13, except that the filtered precipitate was washed four times with 20 times the mass of pure water.

[0420] (Comparative Example III-4) Reagents A commercially available 4-aminobenzoic acid reagent (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was prepared.

[0421] (Evaluation method) The compositions obtained in each example were evaluated for amino acid concentration, purity, moisturizing property, and antibacterial property in accordance with the above-mentioned Examples III-1 to III-4 and Comparative Example III-1. The results are shown in Table 15.

[0422] [Table 15]

[0423] Example VI (Example VI-1) <Production of 3,4-dihydroxybenzoic acid by bioprocess> The culture liquid obtained by the bioprocess using plant-derived sugar and microorganisms was concentrated by vacuum concentration to a total solid content of 15 to 30% by mass. The degree of vacuum was set to 100 to 5000 Pa, the liquid temperature to 30 to 80°C, and the concentration treatment was performed using a vacuum distillation apparatus. Although the degree of concentration depends on the treatment time, a concentrated liquid with a total solid content of 15 to 30% by mass was recovered by concentration treatment for 6 to 8 hours. Hydrochloric acid was added to this concentrated liquid to adjust the pH to 4 or less, and it was further cooled to 0°C to room temperature. The crystallized product was collected by filtration, washed appropriately, and then dried under reduced pressure to recover high-purity 3,4-dihydroxybenzoic acid with a purity of 99% or more.

[0424] The recovered high-purity 3,4-dihydroxybenzoic acid, i.e., cyclic compound, was free of petroleum-derived impurities.

[0425] (Example VI-2) <Production of shikimic acid using bioprocesses> Activated carbon was added to the culture liquid obtained by a bioprocess using plant-derived sugars and microorganisms, and activated carbon treatment was performed. Next, a column packed with ion exchange resin was prepared and treated with 2 mol / L sodium hydroxide aqueous solution. The ion exchange resin used was a strongly basic anion exchange resin. Pure water was passed through the column until the effluent water became neutral, and then the raw liquid treated with activated carbon was passed through the column, and then pure water was passed through. Then, 2 mol / L acetic acid aqueous solution was passed as an eluent, and acidic fractions were recovered. The concentration of shikimic acid in each recovered fraction was measured, and the eluent was passed through until the elution of shikimic acid was completed. A solid was precipitated from the eluent by concentration crystallization to obtain solid shikimic acid. The concentration crystallization refers to a process in which a concentration process and a cooling crystallization process are performed in sequence to precipitate solid shikimic acid.

[0426] The recovered high-purity shikimic acid, i.e., cyclic compound, was free of petroleum-derived impurities.

[0427] Example V (Example V-1) <Production of 3,4-dihydroxybenzoic acid by bioprocess> The culture liquid obtained by the bioprocess using plant-derived sugar and microorganisms was concentrated by vacuum concentration to a total solid content of 15 to 30% by mass. The degree of vacuum was set to 100 to 5000 Pa, the liquid temperature to 30 to 80°C, and the concentration treatment was performed using a vacuum distillation apparatus. Although the degree of concentration depends on the treatment time, a concentrated liquid with a total solid content of 15 to 30% by mass was recovered by concentration treatment for 6 to 8 hours. Hydrochloric acid was added to this concentrated liquid to adjust the pH to 4 or less, and it was further cooled to 0°C to room temperature. The crystallized product was collected by filtration, washed appropriately, and then dried under reduced pressure to recover high-purity 3,4-dihydroxybenzoic acid with a purity of 99% or more.

[0428] The recovered high-purity 3,4-dihydroxybenzoic acid, i.e., cyclic compound, was free of petroleum-derived impurities.

[0429] (Example V-2) <Production of shikimic acid using bioprocesses> Activated carbon was added to the culture liquid obtained by a bioprocess using plant-derived sugars and microorganisms, and activated carbon treatment was performed. Next, a column packed with ion exchange resin was prepared and treated with 2 mol / L sodium hydroxide aqueous solution. The ion exchange resin used was a strongly basic anion exchange resin. Pure water was passed through the column until the effluent water became neutral, and then the raw liquid treated with activated carbon was passed through the column, and then pure water was passed through. Then, 2 mol / L acetic acid aqueous solution was passed as an eluent, and acidic fractions were recovered. The concentration of shikimic acid in each recovered fraction was measured, and the eluent was passed through until the elution of shikimic acid was completed. A solid was precipitated from the eluent by concentration crystallization to obtain solid shikimic acid. The concentration crystallization refers to a process in which a concentration process and a cooling crystallization process are performed in sequence to precipitate solid shikimic acid.

[0430] The recovered high-purity shikimic acid, i.e., cyclic compound, was free of petroleum-derived impurities.

Claims

1. A water-soluble additive composition comprising a cyclic carboxylic acid, the water-soluble additive composition satisfying at least one of the following conditions 1 to 4: (Condition 1) The composition contains the following components (A) and (B1). (A) The cyclic carboxylic acid is other than the following component (B1). (B1) One or more selected from the group consisting of gallic acid and its esters (Condition 2) Na + and N.H. 4 + The total content of the above is 100 ppm or more and 5000 ppm or less based on the cyclic carboxylic acid. (Condition 3) Total inorganic ion content (excluding hydrogen ions and hydroxyl ions. ) is 300 ppm or more and 5000 ppm or less relative to the cyclic carboxylic acid. (Condition 4) The composition contains the following components (A) and (B2). (A) The cyclic carboxylic acid is other than the following component (B2). (B2) Amino acid

2. The water-soluble additive composition according to claim 1, which satisfies the above condition 1 and is an antibacterial composition.

3. The water-soluble additive composition according to claim 2, wherein the component (A) is one or more selected from the group consisting of protocatechuic acid, shikimic acid, 4-hydroxybenzoic acid, 4-aminobenzoic acid, and ferulic acid.

4. 4. The water-soluble additive composition according to claim 2 or 3, wherein the content of the component (B1) relative to the content of the component (A) in the antibacterial composition ((B1) / (A)) is in a mass ratio of 0.01 or more and 5 or less.

5. The water-soluble additive composition according to claim 1 , wherein the water-soluble additive composition satisfies the condition 2.

6. The water-soluble additive composition according to claim 1 , wherein the water-soluble additive composition satisfies condition 3.

7. The water-soluble additive composition according to claim 5 or 6, wherein the cyclic carboxylic acid is at least one selected from the group consisting of protocatechuic acid, shikimic acid, 4-hydroxybenzoic acid, 4-aminobenzoic acid and ferulic acid.

8. 8. The water-soluble additive composition according to claim 5, wherein the content of the cyclic carboxylic acid in the water-soluble additive composition is 95% by mass or more and 99.9% by mass or less based on the entire water-soluble additive composition.

9. The water-soluble additive composition according to claim 1 , wherein the water-soluble additive composition satisfies condition 4.

10. The water-soluble additive composition according to claim 9, wherein the component (A) is one or more selected from the group consisting of protocatechuic acid, shikimic acid, 4-hydroxybenzoic acid, 4-aminobenzoic acid, and ferulic acid.

11. The water-soluble additive composition according to claim 9 or 10, wherein the component (B2) comprises one or more amino acids selected from the group consisting of glutamic acid, alanine, valine, glycine, aspartic acid, serine, histidine, threonine, arginine, tyrosine, cystine, methionine, phenylalanine, isoleucine, leucine, lysine and proline.

12. The water-soluble additive composition according to any one of claims 9 to 11, wherein the content of the component (A) in the water-soluble additive composition is 95 mass % or more and 99.9 mass % or less.

13. 13. The water-soluble additive composition according to claim 9, wherein the content of the component (B2) in the water-soluble additive composition is 0.001% by mass or more and 5% by mass or less.

14. 14. The water-soluble additive composition according to claim 9, wherein the component (B2) contains glutamic acid, and the content of the glutamic acid in the water-soluble additive composition is 0.001% by mass or more and 1% by mass or less.

15. A food product comprising at least one of a plant-derived sugar and a cyclic compound derived from a microorganism and its derivative.

16. The food according to claim 15, wherein the cyclic compound is a compound represented by the following general formula (1): 【Chemistry 1】 [In the above general formula (1), ring A is a five-membered saturated ring, partially saturated ring, or aromatic ring, or a six-membered saturated ring, partially saturated ring, or aromatic ring; X is a single bond or a bond containing one or more carbon atoms; Y is a hydrogen atom or an alkyl group; R ２ ~R ６ (When ring A is a 5-membered ring, R ２ ~R ５ ) are independently a hydrogen atom, a hydroxyl group, an amino group, an alkoxy group, a carboxyl group, or a carbonyl group.

17. The food according to claim 16, wherein the cyclic compound is at least one selected from the group consisting of 2-hydroxybenzoic acid, 3-hydroxybenzoic acid, 4-hydroxybenzoic acid, 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 2,5-dihydroxybenzoic acid, 2,6-dihydroxybenzoic acid, 3,4-dihydroxybenzoic acid, and 3,5-dihydroxybenzoic acid.

18. When ring A of the cyclic compound is a saturated or partially saturated 5-membered ring in which all of the ring constituent atoms are carbon atoms, R ２ ~R ５ and when one or more of the carbon atoms of ring A to which X is bonded are asymmetric carbon atoms, and ring A of the cyclic compound is a 6-membered saturated or partially saturated ring in which all of the ring constituent atoms are carbon atoms, R ２ ~R ６ and one or more of the carbon atoms of ring A to which X is bonded are asymmetric carbon atoms.

19. In the cyclic compound, the carbon atom of ring A to which X is bonded is C １ Let R ２ The carbon atom of ring A to which is bonded is C ２ Let R ３ The carbon atom of ring A to which is bonded is C ３ Let R ４ The carbon atom of ring A to which is bonded is C ４ Let R ５ The carbon atom of ring A to which is bonded is C ５ Let R ６ The carbon atom of ring A to which is bonded is C ６ The food according to claim 18, wherein the combination of the carbon atoms in the asymmetric carbon atom is one selected from the group consisting of the following (a) to (h): (a)C １ (b)C ２ (c)C ３ (d)C ４ (e) C １ and C ４ (f) C ３ and C ４ (g) C １ , C ３ and C ４ (h) C ３ , C ４ and C ５

20. The food according to claim 15, wherein the cyclic compound or a derivative thereof is 3-dehydroquinate, 3-dehydroshikimic acid, shikimic acid, chorismic acid or prephenic acid.

21. 21. The food according to any one of claims 15 to 20, wherein the microorganism is Escherichia coli, Bacillus subtilis, Staphylococcus aureus, Corynebacterium, Actinomycete, Cyanobacterium, Methanogen, Halobacterium, Thermotolerant Acidophilic Bacteria, Acid-Fast Bacteria, Mold, Yeast, or a transformant thereof.

22. 22. The food product according to claim 15, wherein the source of the plant-derived sugar is a non-edible biomass resource.

23. A food additive comprising at least one of a plant-derived sugar and a cyclic compound derived from a microorganism and its derivative.

24. A method for producing a cyclic compound or a derivative thereof for use as a food or a food additive, comprising the steps of: preparing a culture solution containing plant-derived sugars and a microorganism so as to produce at least one of the cyclic compound and its derivatives; Concentrating the culture solution to obtain a concentrate; recovering at least one of the cyclic compound and its derivative from the concentrated solution by crystallization, precipitation, extraction, sublimation purification, or distillation; A method for producing a cyclic compound or a derivative thereof, comprising:

25. A fragrance containing at least one of a plant-derived sugar and a cyclic compound derived from a microorganism and its derivative.

26. The fragrance according to claim 25, wherein the cyclic compound is a compound represented by the following general formula (1): 【Chemistry 2】 [In the above general formula (1), ring A is a five-membered saturated ring, partially saturated ring, or aromatic ring, or a six-membered saturated ring, partially saturated ring, or aromatic ring; X is a single bond or a bond containing one or more carbon atoms; Y is a hydrogen atom or an alkyl group; R ２ ~R ６ (When ring A is a 5-membered ring, R ２ ~R ５ ) are independently a hydrogen atom, a hydroxyl group, an amino group, an alkoxy group, a carboxyl group, or a carbonyl group.

27. The fragrance according to claim 26, wherein the cyclic compound is at least one selected from the group consisting of 2-hydroxybenzoic acid, 3-hydroxybenzoic acid, 4-hydroxybenzoic acid, 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 2,5-dihydroxybenzoic acid, 2,6-dihydroxybenzoic acid, 3,4-dihydroxybenzoic acid, and 3,5-dihydroxybenzoic acid.

28. When ring A of the cyclic compound is a saturated or partially saturated 5-membered ring in which all of the ring constituent atoms are carbon atoms, R ２ ~R ５ and when one or more of the carbon atoms of ring A to which X is bonded are asymmetric carbon atoms, and ring A of the cyclic compound is a 6-membered saturated or partially saturated ring in which all of the ring constituent atoms are carbon atoms, R ２ ~R ６ and one or more of the carbon atoms of ring A to which X is bonded are asymmetric carbon atoms.

29. In the cyclic compound, the carbon atom of ring A to which X is bonded is C １ Let R ２ The carbon atom of ring A to which is bonded is C ２ Let R ３ The carbon atom of ring A to which is bonded is C ３ Let R ４ The carbon atom of ring A to which is bonded is C ４ Let R ５ The carbon atom of ring A to which is bonded is C ５ Let R ６ The carbon atom of ring A to which is bonded is C ６ The fragrance according to claim 28, wherein the combination of asymmetric carbon atoms is one selected from the group consisting of the following (a) to (h): (a)C １ (b)C ２ (c)C ３ (d)C ４ (e) C １ and C ４ (f) C ３ and C ４ (g) C １ , C ３ and C ４ (h) C ３ , C ４ and C ５

30. The fragrance according to claim 25, wherein the cyclic compound or a derivative thereof is 3-dehydroquinate, 3-dehydroshikimic acid, shikimic acid, chorismic acid or prephenic acid.

31. The fragrance according to any one of claims 25 to 30, wherein the microorganism is Escherichia coli, Bacillus subtilis, Staphylococcus aureus, Corynebacterium, Actinomycete, Cyanobacterium, Methanogen, Halobacterium, Thermotolerant Acidophilic Bacteria, Acid-Fast Bacteria, Mold, Yeast or a transformant thereof.

32. The flavoring according to any one of claims 25 to 31, wherein the raw material of the plant-derived sugar is a non-edible biomass resource.

33. A method for producing a cyclic compound or a derivative thereof for use as a fragrance, comprising the steps of: preparing a culture solution containing plant-derived sugars and a microorganism so as to produce at least one of the cyclic compound and its derivatives; Concentrating the culture solution to obtain a concentrate; recovering at least one of the cyclic compound and its derivative from the concentrated solution by crystallization, precipitation, extraction, sublimation purification, or distillation; A method for producing a cyclic compound or a derivative thereof, comprising:

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