Water soluble crocetin-containing composition

Abstract

To provide a water-soluble crocetin-containing composition that contains crocetin and gentiobiose, and further to provide a method for stabilizing crocetin and gentiobiose.SOLUTION: It was found that, by including a step of saponifying a crocetin glycoside, a step of blending an anionic polysaccharide, and a step of adjusting the pH to 2.0-8.0 with an acidic compound, a water-soluble crocetin-containing composition can be obtained and crocetin and gentiobiose can be further stabilized, thereby completing the present invention.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a water-soluble crocetin-containing composition and the like. [Background technology]

[0002] Crocetin is a type of carotenoid that is known to be obtained by saponifying crocetin glycosides such as crocin, which are found in gardenia fruit, saffron, and crocus pistils, thereby removing two ester-bonded gentiobiose molecules. Crocetin has been reported to have various functional properties, such as improving eye fatigue and sleep quality, but due to its lipid solubility, there is a need to improve its water solubility.

[0003] Disclosed methods for increasing the water solubility of crocetin include a carotenoid pigment solubilization method (Patent Document 1), which involves first making the pH alkaline, mixing cyclodextrins with the dissolved carotenoid pigment, and then returning the pH to neutral; a crocetin preparation production method (Patent Document 2), which involves dispersing crocetin in an aqueous solution containing gum arabic to prepare a dispersion, with the median particle size of the crocetin in the dispersion being less than 0.4 μm (Patent Document 3); and a transparent liquid preparation consisting of a) at least one carotenoid, b) at least one food-grade modified starch that is OSA starch, c) at least one saccharide, d) water, e) a water-soluble antioxidant, and f) a fat-soluble antioxidant.

[0004] Gentiobiose is a type of disaccharide in which two glucose molecules are linked by a β1-6 bond, and is a rare sugar with a bitter taste. It is known to have the effect of promoting the growth of bifidobacteria, and also to improve the taste of food and beverages when added to them (Patent Document 4), and various methods for producing it have been disclosed (Patent Document 5). [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Publication No. 07-23736 [Patent Document 2] Patent No. 5600513 [Patent Document 3] Patent No. 6492335 [Patent Document 4] Patent No. 3100139 [Patent Document 5] Japanese Patent Application Laid-Open No. 2018-61494 Summary of the Invention [Problem to be solved by the invention]

[0006] An object of the present invention is to provide a water-soluble crocetin-containing composition containing crocetin and gentiobiose, and further to provide a method for stabilizing crocetin and gentiobiose. [Means for solving the problem]

[0007] The inventors conducted extensive research to solve these problems and discovered that a water-soluble crocetin-containing composition can be obtained and crocetin and gentiobiose can be stabilized by including the steps of saponifying crocetin glycoside, blending an anionic polysaccharide, and adjusting the pH to 2.0 to 8.0 with an acidic compound, thereby completing the present invention.

[0008] That is, the present invention has been completed based on the above findings, and comprises the following [1] to

[10] . [1] A water-soluble crocetin-containing composition comprising crocetin, gentiobiose, an anionic polysaccharide, an acid, and a monovalent base. [2] The crocetin-containing composition according to [1], which contains 0.1 to 60 parts by weight of an anionic polysaccharide per 1 part by weight of crocetin. [3] The crocetin-containing composition according to [1] or [2], which contains 1 to 60 moles of a monovalent base per mole of crocetin. [4] A method for producing a water-soluble crocetin-containing composition containing crocetin, gentiobiose, an anionic polysaccharide, an acid, and a monovalent base, comprising: i) a step of saponifying crocetin glycoside with a monovalent basic compound; ii) a step of blending an anionic polysaccharide; and iii) a step of adjusting the pH after saponification to 2.0 to 8.0 with an acidic compound. [5] The method for producing a crocetin-containing composition according to [4], wherein 0.1 to 60 parts by weight of an anionic polysaccharide is blended with 1 part by weight of crocetin. [6] A method for producing a crocetin-containing composition according to [4] or [5], wherein 1 to 60 moles of a monovalent basic compound are combined with 1 mole of crocetin. [7] A method for stabilizing crocetin and gentiobiose in a water-soluble crocetin-containing composition containing crocetin, gentiobiose, an anionic polysaccharide, an acid, and a monovalent base, the method comprising: i) a step of saponifying crocetin glycoside with a monovalent basic compound; ii) a step of blending an anionic polysaccharide; and iii) a step of adjusting the pH after saponification to 2.0 to 8.0 with an acidic compound. [8] The stabilization method according to [7], wherein 0.1 to 60 parts by weight of an anionic polysaccharide is blended with 1 part by weight of crocetin. [9] The stabilization method according to [7] or [8], wherein 1 to 60 moles of a monovalent basic compound are combined per mole of crocetin.

[10] A food or drink comprising the water-soluble crocetin-containing composition according to any one of [1] to [3]. [Effects of the Invention]

[0009] According to the present invention, a crocetin-containing composition in which crocetin and gentiobiose are stabilized can be provided. DETAILED DESCRIPTION OF THE INVENTION

[0010] The present invention provides a water-soluble crocetin-containing composition by comprising: i) a step of saponifying crocetin glycoside with a monovalent basic compound; ii) a step of blending an anionic polysaccharide; and iii) a step of adjusting the pH after saponification to 2.0 to 8.0 with an acidic compound. The crocetin-containing composition is a water-soluble crocetin-containing composition that contains crocetin, gentiobiose, an anionic polysaccharide, an acid, and a monovalent base.

[0011] The crocetin glycoside described in the present invention can be crocin, and is not particularly limited as long as it contains a crocetin glycoside whose sugar moiety is gentiobiose. Extracts obtained by extracting gardenia fruit, saffron, crocus pistils, or the like with water, alcohol, or aqueous alcohol can be used, but gardenia fruit extract is preferred, and commercially available gardenia fruit extracts can be used. Crocetin and gentiobiose are produced by hydrolyzing a crocetin glycoside whose sugar moiety is gentiobiose by saponification or the like.

[0012] The crocetin described in the present invention is a naturally occurring carotenoid carboxylic acid. It is found in small amounts in extracts obtained by extracting gardenia fruit, saffron, or crocus pistils with water, alcohol, or aqueous alcohol, and is also produced by saponifying crocetin glycoside. While cis-trans isomers are acceptable, it is preferable to have a higher trans-crocetin content than cis-crocetin. The crocetin content of the water-soluble crocetin-containing composition is preferably 1 to 50 wt. % of the solid content of the composition, more preferably 2 to 45 wt. % and even more preferably 5 to 40 wt.

[0013] Gentiobiose, a disaccharide formed by the β1-6 bond between two glucose molecules, is produced by saponifying crocetin glycoside. The gentiobiose content in the water-soluble crocetin-containing composition is preferably 0.01 to 2 mol, more preferably 0.02 to 1 mol, and even more preferably 0.05 to 0.5 mol, per mol of crocetin.

[0014] The anionic polysaccharide described in the present invention may be any polysaccharide having a negative charge, and is preferably a polysaccharide having a carboxy group, such as gum arabic, gum ghatti, starch sodium octenyl succinate, xanthan gum, alginic acid, gellan gum, carrageenan, pectin, etc. The content of the anionic polysaccharide in the water-soluble crocetin-containing composition is preferably 0.1 to 60 parts by weight, more preferably 0.2 to 50 parts by weight, and even more preferably 0.5 to 40 parts by weight, per part by weight of crocetin.

[0015] The monovalent base described in the present invention may be any substance that dissociates in water to generate hydroxide ions, and refers to the base present after adjusting a solution containing a monovalent basic compound such as sodium hydroxide, potassium hydroxide, sodium carbonate, or potassium carbonate to pH 2.0 to 8.0 with an acidic compound. The content of the base is preferably 1 to 60 mol, more preferably 1.5 to 50 mol, and even more preferably 2 to 45 mol, per mol of crocetin in the crocetin glycoside.

[0016] The acid described in this invention may be any substance that dissociates in water to generate hydrogen ions, and refers to the acid present after adjusting a solution containing a monovalent basic compound to pH 2.0 to 8.0 with an acidic compound, such as an organic acid (e.g., citric acid, lactic acid, acetic acid, tartaric acid), or an inorganic acid (e.g., hydrochloric acid, phosphoric acid, sulfuric acid). The content of the acid is preferably 0.2 to 15 mol, more preferably 0.3 to 12 mol, and even more preferably 0.4 to 10 mol, per mol of crocetin in the crocetin glycoside.

[0017] The water-soluble crocetin-containing composition of the present invention is not particularly limited as long as it contains crocetin and is soluble in water, and may be in a liquid form or a dried form such as a powder. The drying method is not particularly limited, and drying can be performed using known means, such as a spray dryer, drum dryer, freeze dryer, or air dryer. Furthermore, the dried product may be pulverized and used, or, if necessary, granulated using a granulator or the like. Drying is preferably performed with the addition of an excipient. Common excipients can be used, such as disaccharides (e.g., lactose, trehalose), polysaccharides (e.g., dextrin, starch, modified starch), and sugar alcohols, and two or more types may be used in combination. The content of the excipient is preferably 1 to 90 wt. % of the total solid content, more preferably 5 to 80 wt. % and even more preferably 10 to 70 wt. %.

[0018] The water-soluble crocetin-containing composition of the present invention may be formed into tablets and may contain a lubricant. Conventional lubricants can be used, such as magnesium stearate, calcium stearate, sodium stearyl fumarate, sucrose fatty acid esters, sodium lauryl sulfate, talc, light anhydrous silicic acid, hydrous silicon dioxide, and hydrogenated oils, and two or more types may be used in combination. The content of the lubricant is preferably 0.01 to 30 wt. % of the total solid content, more preferably 0.05 to 20 wt. %, and even more preferably 0.1 to 10 wt. %.

[0019] The production of the water-soluble crocetin-containing composition of the present invention uses crocetin glycoside, anionic polysaccharide, acidic compound, monovalent basic compound, and water as production raw materials, and includes the steps of i) saponifying the crocetin glycoside with a monovalent basic compound, ii) blending the anionic polysaccharide, and iii) adjusting the pH after saponification to 2.0 to 8.0 with an acidic compound. This process allows for the production of a water-soluble crocetin-containing composition and stabilizes crocetin and gentiobiose in the water-soluble crocetin-containing composition. Step ii) may be performed before step i) and then step iii), or step i) may be performed after step i) and then step iii), or step ii) may be performed simultaneously with step i) and then step iii), or step i) may be performed after step i) and then step ii). However, from the viewpoint of solubilization, it is preferable to perform step iii) after steps i) and ii). The raw materials for producing the water-soluble crocetin-containing composition preferably contain water in an amount of 30 to 99.5 wt %, more preferably 40 to 99 wt %.

[0020] i) The step of saponifying crocetin glycoside with a monovalent basic compound involves blending the monovalent basic compound in the presence of crocetin glycoside. The saponification conditions can be appropriately set so that crocetin and gentiobiose are produced. For example, the monovalent basic compound, such as sodium hydroxide, potassium hydroxide, sodium carbonate, or potassium carbonate, is blended in an amount of preferably 1 to 60 moles, more preferably 1.5 to 50 moles, and even more preferably 2 to 45 moles, per mole of crocetin in the crocetin glycoside. The pH after blending is preferably 10 to 14, more preferably 10.5 to 13. The temperature is, for example, 10 to 100°C, and preferably 30 to 70°C. The time is, for example, 10 to 360 minutes, and preferably 30 to 180 minutes. Stirring may be performed. The crocetin glycoside is preferably blended in the raw materials for producing the water-soluble crocetin-containing composition at 0.01 to 20% by weight, more preferably 0.02 to 10% by weight, and even more preferably 0.05 to 5% by weight.

[0021] ii) The step of blending an anionic polysaccharide can be carried out before, after, or simultaneously with saponification. The anionic polysaccharide is preferably blended in an amount of 0.05 to 10% by weight, more preferably 0.08 to 8% by weight, and even more preferably 0.1 to 5% by weight, of the raw materials for producing the water-soluble crocetin-containing composition and stirred. Preferably, 0.1 to 60 parts by weight of the anionic polysaccharide is blended per 1 part by weight of crocetin in the crocetin glycoside, more preferably 0.2 to 50 parts by weight, and even more preferably 0.5 to 40 parts by weight.

[0022] The step iii) of adjusting the pH after saponification to 2.0 to 8.0 with an acidic compound may be performed after saponification, but is preferably performed after steps i) and ii) from the viewpoint of solubilization. The pH of the solution can be adjusted to 2.0 to 8.0 by adding an acidic compound, such as an organic acid (e.g., citric acid, lactic acid, acetic acid, or tartaric acid) or an inorganic acid (e.g., hydrochloric acid, phosphoric acid, or sulfuric acid), followed by stirring, with the pH adjusted to 2.0 to 8.0, preferably 2.5 to 7.5, and more preferably 3 to 7. The amount of the acidic compound added is preferably 0.2 to 15 mol, more preferably 0.3 to 12 mol, and even more preferably 0.4 to 10 mol, per mol of crocetin in the crocetin glycoside.

[0023] The crocetin-containing composition of the present invention has solubilized crocetin and stabilized crocetin and gentiobiose, making it highly versatile and suitable for a wide range of foods and beverages, including functional foods, supplements, and beverages. Furthermore, because the crocetin-containing composition of the present invention contains gentiobiose, its addition to foods and beverages can impart a bitter taste or improve the flavor. The crocetin content of the crocetin-containing composition is not particularly limited, but is preferably 0.1 to 60 wt%, more preferably 0.15 to 50 wt%, and even more preferably 0.2 to 40 wt%. The amount of the crocetin-containing composition added to foods and beverages is not particularly limited, but is preferably 0.01 to 50 wt%, more preferably 0.05 to 30 wt%, and even more preferably 0.1 to 10 wt%. [Example]

[0024] The present invention will be specifically described below with reference to examples, but the present invention is not limited to the following examples. In the present invention, all % is by weight unless otherwise specified.

[0025] [Example 1] Gardenia extract powder containing crocetin glycosides (Gardenia jasmine fruit extract, Tokyo Chemical Industry Co., Ltd., crocetin content less than 1%), the anionic polysaccharide gum arabic (Instant Gum AA, Nexira Inc.), 20% potassium hydroxide aqueous solution, and tap water were mixed and dissolved according to the formulation shown in Table 1. The mixture was then saponified at 50°C for 60 minutes and neutralized to pH 6.0 with 20% phosphoric acid aqueous solution to obtain a crocetin-containing composition (Product 1). The pH of the blended solution before the addition of the 20% potassium hydroxide aqueous solution was 6.0, and the pH of the solution after the addition of the 20% potassium hydroxide aqueous solution was 10.5. The proportions of each ingredient are shown in Table 1, with the total ingredients used being 100%.

[0026] [Comparative Example 1] Crocetin-containing compositions (pH 6.0) designated as Comparative Products 1-1 to 1-4 were obtained in the same manner as in Example 1, except that no anionic polysaccharide was used (Comparative Example 1-1), or trehalose (Treha, Hayashibara Co., Ltd.) (Comparative Example 1-2), dextrin (Sandec (registered trademark) #30, Sanwa Starch Industry Co., Ltd.), an uncharged polysaccharide, or guar gum enzymatic hydrolysate (Sunfiber (registered trademark) HG, Taiyo Kagaku Co., Ltd.), an uncharged polysaccharide, was used in place of gum arabic in the proportions shown in Table 1.

[0027] [Evaluation Test 1] For the evaluation of the solubility of crocetin in an acidic aqueous solution, the crocetin-containing compositions (pH 6.0) of Product 1 and Comparative Products 1-1 to 1-4 were each diluted 10-fold with 50 mM sodium citrate buffer (pH 3.5) to obtain an acidic aqueous solution. After centrifugation (10,000 rpm, 5 minutes) to remove the insoluble crocetin and recover the supernatant, the water-soluble crocetin concentration was measured under the following HPLC conditions. After multiplying the numerical value by 10, it was compared as water-soluble crocetin. The results are shown in Table 1. The water-soluble crocetin content at pH 6.0 before dilution was approximately 0.2% for all samples.

[0028] <HPLC measurement conditions> · Detector: VIS detector (435 nm) · Column: InertSustain C18 (inner diameter 4.6 mm, length 250 mm) · Mobile phase: Acetonitrile gradient from 20% aqueous acetonitrile solution · Flow rate: 1.0 ml / min · Column temperature: 40 °C · Standard: Crocin (manufactured by FUJIFILM Wako Pure Chemical Corporation) was dissolved in acetonitrile to prepare a calibration curve.

[0029]

Table 1

[0030] In the crocetin-containing composition of Product 1 prepared by blending gum arabic, an anionic polysaccharide, there was almost no change in the water-soluble crocetin content whether it was neutral or acidic. In contrast, in the crocetin-containing compositions of Comparative Product 1-1 without anionic polysaccharide, Comparative Product 1-2 blended with trehalose, or Comparative Product 1-3 or Comparative Product 1-4 blended with dextrin or enzymatically decomposed guar gum, which are polysaccharides without charge, it was found that when made into an acidic aqueous solution (50 mM sodium citrate buffer (pH 3.5)), the water-soluble crocetin content became less than about one-third and two-thirds or more of the crocetin was insolubilized.

[0031] It was confirmed that the incorporation of gum arabic, an anionic polysaccharide, prevents crocetin from becoming insoluble even in an acidic aqueous solution, thereby improving the water solubility of crocetin. The amount of potassium hydroxide per mole of crocetin calculated from the water-soluble crocetin content obtained in Example 1 and the amount of potassium hydroxide solution added was 8.3 moles. Similarly, the amount of phosphoric acid per mole of crocetin calculated from the amount of phosphoric acid solution added was 1.4 moles. Furthermore, the amount of gum arabic per part by weight of crocetin calculated from the measured water-soluble crocetin content and the amount of gum arabic added was 4.8 parts by weight.

[0032] [Example 2] Gardenia extract powder containing crocetin glycosides (gardenia fruit extract, crocetin content less than 1%), the anionic polysaccharide gum ghatti (Gaticol SS, San-ei Pharmaceutical Trading Co., Ltd.) at various concentrations (Examples 2-1 to 2-5), 20% aqueous sodium hydroxide, and tap water were mixed and dissolved in the proportions shown in Table 2. The mixture was then saponified at 50°C for 60 minutes and neutralized to pH 6.0 with 50% aqueous citric acid to obtain crocetin-containing compositions (Examples 2-1 to 2-5). The pH of the blended solutions in Examples 2-1 to 2-5 before blending with the 20% aqueous sodium hydroxide solution was 6.0, and the pH of the blended solutions after blending was 11.5, 11.4, 11.3, 11.3, and 11.3, respectively. The proportions of each ingredient are shown in Table 2, with the total ingredients used being 100%.

[0033] To evaluate the solubility of crocetin in acidic solutions, the concentrations of water-soluble crocetin in the crocetin-containing compositions (pH 6.0) of Examples 2-1 to 2-5 were measured according to Evaluation Test 1, and the values ​​were then multiplied by 10 to compare the water-soluble crocetin values. The results are shown in Table 2. The amount of gum ghatti blended per part by weight of crocetin was calculated from the measured water-soluble crocetin content and the content of gum ghatti blended, and is shown in Table 2.

[0034] [Table 2]

[0035] The crocetin-containing compositions of Examples 2-1 to 2-5, which were prepared by blending gum ghatti, an anionic polysaccharide, at various concentrations, all contained a high amount of water-soluble crocetin at 0.2 to 5% gum ghatti blends.It was confirmed that by blending gum ghatti, an anionic polysaccharide, crocetin does not become insoluble even in an acidic aqueous solution, and the water solubility of crocetin can be improved. Furthermore, based on the water-soluble crocetin content obtained in Example 2-1 and the content of the sodium hydroxide solution added, the amount of sodium hydroxide added per mole of crocetin was calculated to be 7.6 moles.Similarly, based on the content of the citric acid solution added, the amount of citric acid added per mole of crocetin was calculated to be 0.79 moles.

[0036] [Example 3] Gardenia extract powder containing crocetin glycoside (gardenia fruit extract, crocetin content less than 1%), the anionic polysaccharide gum ghatti (Gaticol SS), 20% aqueous sodium hydroxide solution, and tap water were used in the formulation shown in Table 3. Specifically, in Example 3-1, gum ghatti was mixed with the raw materials and dissolved, followed by saponification at 50°C for 60 minutes, and then adjusted to pH 4.0 with 50% citric acid to obtain Product 3-1 (a crocetin-containing composition). In Example 3-2, the raw materials other than gum ghatti were mixed and dissolved, followed by saponification at 50°C for 60 minutes, followed by dissolution of gum ghatti, and then adjusted to pH 4.0 with 50% citric acid to obtain Product 3-2 (a crocetin-containing composition). In Example 3-3, the raw materials other than gum ghatti were mixed and dissolved, followed by saponification at 50°C for 60 minutes, followed by adjustment to pH 4.0 with 50% citric acid, followed by dissolution of gum ghatti, and then obtained Product 3-3 (a crocetin-containing composition). The pH values ​​of the solutions after addition of 20% sodium hydroxide in Examples 3-1 to 3-3 were 11.3, 11.4, and 11.6, respectively. The proportion of each raw material is shown in Table 3, with the total raw materials used being 100%.

[0037] To evaluate the solubility of crocetin in acidic aqueous solutions, the crocetin concentrations of the crocetin-containing compositions (pH 4.0) of Examples 3-1 to 3-3 were measured according to Evaluation Test 1 (except that the 10-fold dilution was not performed), and the raw values ​​were converted into water-soluble crocetin for comparison. The results are shown in Table 3. The amount of gum ghatti blended per part by weight of crocetin was calculated from the measured water-soluble crocetin content and the content of gum ghatti blended, and is shown in Table 3.

[0038] [Table 3]

[0039] The crocetin-containing compositions of Examples 3-1 to 3-3, which were prepared by incorporating the anionic polysaccharide gum ghatti, all contained water-soluble crocetin. Furthermore, the water-soluble crocetin content of Examples 3-1 and 3-2, which were prepared by incorporating gum ghatti before saponification or before pH adjustment after saponification, was 1.5 times higher than the water-soluble crocetin content of Example 3-3, which was prepared by incorporating gum ghatti after pH adjustment. These results suggest that incorporating the anionic polysaccharide before saponification or before pH adjustment after saponification is preferable, as this makes crocetin less likely to become insoluble even under acidic conditions and further improves the water solubility of crocetin. Furthermore, based on the water-soluble crocetin content obtained in Example 3-1 and the content of the sodium hydroxide solution added, the amount of sodium hydroxide added per mole of crocetin was calculated to be 7.7 moles.Similarly, based on the content of the citric acid solution added, the amount of citric acid added per mole of crocetin was calculated to be 1.8 moles.

[0040] [Example 4] Gardenia extract powder containing crocetin glycoside (50% Gardenia extract, Vidia Japan Co., Ltd., crocetin content less than 1%), 20% aqueous sodium hydroxide, and tap water were mixed and dissolved according to the ratio shown in Table 4. The mixture was saponified at 50°C for 60 minutes, after which the anionic polysaccharide starch sodium octenyl succinate (Emulstar® 500A, Matsutani Chemical Industry Co., Ltd.) was added and dissolved, and the pH was adjusted to 6.0 with 50% aqueous lactic acid to obtain a crocetin-containing composition. The pH of the solution after the addition of 20% aqueous sodium hydroxide was 12.4. The proportions of each ingredient are shown in Table 4, with the total ingredients used being 100%.

[0041] Furthermore, starch sodium octenyl succinate and an equal amount of dextrin (Pinedex (registered trademark) #2, Matsutani Chemical Industry Co., Ltd.) were mixed and dissolved as an excipient, and the mixture was heated at 90°C for 10 minutes, after which it was dried using a spray dryer to obtain a crocetin-containing powder (Product 4).

[0042] [Table 4]

[0043] After dissolving 1 g of the resulting crocetin-containing powder of Example 4 in 99 g of distilled water, the water-soluble crocetin content was measured under the above HPLC conditions and found to be 0.246% (24.6% per powder). The amount of starch sodium octenyl succinate blended with 1 part by weight of crocetin was calculated from the measured content of starch sodium octenyl succinate blended with 1 part by weight of water-soluble crocetin, resulting in 1.2 parts by weight. The excipient content in the water-soluble crocetin-containing powder was 29%. Furthermore, based on the obtained water-soluble crocetin content and the content of the blended sodium hydroxide solution, the amount of sodium hydroxide blended per 1 mole of crocetin was calculated to be 40 moles.Similarly, based on the content of the blended lactic acid solution, the amount of lactic acid blended per 1 mole of crocetin was calculated to be 1.2 moles.

[0044] [Example 5] Regarding the stability of the crocetin-containing powder obtained in Example 4, the crocetin content and the gentiobiose content were measured before and after storage at 50°C for 60 days, and the residual ratio was calculated. The crocetin content was measured under the HPLC conditions of Evaluation Test 1, and the gentiobiose content was measured under the following HPLC conditions. The results are shown in Table 5.

[0045] <HPLC Measurement Conditions> · Detector: Differential refractive index detector · Column: InertSustain NH2 (inner diameter 4.6 mm, length 250 mm) · Mobile phase: 80% acetonitrile aqueous solution · Flow rate: 0.7 ml / min · Column temperature: 40°C · Standard: Gentiobiose (>96%, manufactured by Tokyo Chemical Industry Co., Ltd.) was dissolved in distilled water to prepare a calibration curve.

[0046]

Table 5

[0047] It was found that for both crocetin and gentiobiose, the residual ratio after storage at 50°C for 60 days was 96% or more, and there was almost no decrease in the content after storage, indicating that crocetin and gentiobiose can be stably maintained.

Claims

1. A water-soluble crocetin-containing composition comprising crocetin, gentiobiose, an anionic polysaccharide, an acid, and a monovalent base.

2. 2. The crocetin-containing composition according to claim 1, comprising 0.1 to 60 parts by weight of an anionic polysaccharide per 1 part by weight of crocetin.

3. 3. The crocetin-containing composition according to claim 1, which comprises 1 to 60 moles of a monovalent base per mole of crocetin.

4. A method for producing a water-soluble crocetin-containing composition comprising crocetin, gentiobiose, an anionic polysaccharide, an acid, and a monovalent base, the method comprising: i) saponifying crocetin glycoside with a monovalent basic compound; ii) incorporating an anionic polysaccharide; and iii) adjusting the pH after saponification to 2.0 to 8.0 with an acidic compound; A method for producing a water-soluble crocetin-containing composition.

5. 5. The method for producing a crocetin-containing composition according to claim 4, wherein 0.1 to 60 parts by weight of an anionic polysaccharide is blended with 1 part by weight of crocetin.

6. 6. The method for producing a crocetin-containing composition according to claim 4, wherein 1 to 60 moles of a monovalent basic compound are combined with 1 mole of crocetin.

7. A method for stabilizing crocetin and gentiobiose in a water-soluble crocetin-containing composition comprising crocetin, gentiobiose, an anionic polysaccharide, an acid, and a monovalent base, comprising: i) saponifying crocetin glycoside with a monovalent basic compound; ii) incorporating an anionic polysaccharide; and iii) adjusting the pH after saponification to 2.0 to 8.0 with an acidic compound; Stabilization method.

8. 8. The method for stabilization according to claim 7, wherein 0.1 to 60 parts by weight of an anionic polysaccharide is blended with 1 part by weight of crocetin.

9. 9. The method for stabilization according to claim 7 or 8, wherein 1 to 60 moles of the monovalent basic compound are combined per mole of crocetin.

10. A food or drink comprising the water-soluble crocetin-containing composition according to claim 1 or 2.

Images