Citrus oil extract

Abstract

The present invention relates to a citrus oil extract having reduced levels of oxidation by-product compounds, wherein the level of oxidation by-product compounds is less than 2500 ppm. Preferably, the oxidation by-product compounds are selected from the group consisting of p-cymene, t-menth-2-en-1-ol, t-menth-2,8-dienol, t-limonene oxide, camphor, p-cymen-8-ol, t-limonene 8,9-epoxide, c-limonene 8,9-epoxide, and t-carveol. The present invention also relates to a method for preparing the citrus oil extract and to flavored or perfumed consumer products containing the citrus oil extract of the present invention.

Description

Technical Field

[0001] The present invention relates to a citrus oil extract in which the amount of oxidized by-product compounds is reduced, wherein the amount of oxidized by-product compounds is less than 2500 ppm, a flavoring composition comprising said extract, and a method for preparing said extract. The invention further relates to the use of said extract as a taste or flavor ingredient in consumer products, and to a method for enhancing, improving or modifying the taste or flavor of consumer products using said extract.

[0002] background Citrus oil extracts are widely used in the food, beverage, flavor and pharmaceutical industries. Citrus oil extracts are popular because they provide attractive tastes and aromas to consumers, and are a key ingredient when considering consumer acceptance as a standard for product development. In recent years, consumer awareness has increasingly been directed towards the quality of citrus oil extracts and the manufacturing methods used for their preparation. Natural products prepared without going through chemical synthesis processes have become increasingly popular due to the recognized preservation of the nutritional value of fruits, including flavor, color, taste, pigments and the like.

[0003] An important criterion in the preparation of citrus oil extracts is to minimize the amount of oxidized by-products generated during the extraction process. This is because such by-products impart undesirable notes to the extract, which is undesirable from the consumer's perspective.

[0004] Conventional methods for producing citrus oil extracts use equipment that heats citrus oil at temperatures above 100°C for long periods of time, typically more than 10 hours. Under such conditions, compounds such as terpenes, which are universally present in all citrus oils, undergo dehydrogenation, epoxidation, double bond cleavage, allylic oxidation and / or rearrangement in the presence of heat to form oxidized by-products. As mentioned above, the presence of such products in citrus oil extracts is undesirable from the consumer's perspective.

[0005] Therefore, the inventors aimed to prepare a citrus oil extract, also known as a "clean label" extract, that is more natural while reducing the amount of oxidative by-products, using an extraction method that replaces currently used methods. [Brief explanation of the drawing]

[0006] [Figure 1] This figure shows the composition of the oxidative by-product compounds of the citrus oil extract of the present invention obtained from lime.

[0007] Detailed explanation A first aspect of the present invention provides a citrus oil extract in which the amount of oxidative by-compounds is reduced, and the amount of oxidative by-compounds is less than 2500 ppm.

[0008] Citrus oil is a well-known flavoring and aromating composition. Citrus oil is prepared from citrus fruits using extraction methods well known in the art. In a typical process, the endocarp of the fruit is mechanically crushed to break down the tissue, releasing oil from the endocarp. The oil is then washed away from the tissue to obtain a citrus oil / water mixture. The oil is then isolated from the mixture to obtain citrus oil.

[0009] However, when such citrus oils are used in the manufacture of food and flavoring products, the important note-granting compounds can be overdiluted, and the high concentrations of terpenes can cause solubility problems, making them difficult to use in industrial applications. Therefore, extracts are prepared from citrus oils that concentrate the note-granting compounds while reducing the amount of terpenes.

[0010] Conventional methods for producing citrus oil extracts involve using equipment that heats citrus oil at temperatures exceeding 100°C for extended periods (typically more than 10 hours). Under such conditions, compounds such as terpenes (universally present in all citrus oils) undergo dehydrogenation, epoxidation, double bond cleavage, allyl oxidation in the presence of heat, and / or rearrangement to form oxidative byproducts. Certain compounds formed by excessively prolonged exposure to high temperatures during the citrus oil extraction process are well known in the art and are well understood by those skilled in the art. The oxidation of citrus compounds has been shown to be affected by temperature. Prior art has shown, for example, the formation of off-odors, limonene oxides, p-cymene, and carveols due to the oxidation of terpenes such as d-limonene.

[0011] However, when such oxidative by-compounds are present in citrus oil extracts, they impart undesirable notes. For example, p-cymene imparts rancid, oxidized citrus notes; limonene oxide imparts minty, spearmint herb notes; camphor imparts medicinal, camphor, menthol, and woody notes; tp-mentha-2-en-1-ol imparts herb notes; tp-mentha-2,8-dienol imparts mint notes; and p-cymene-8-ol imparts spicy, celery, herb, and black pepper notes.

[0012] As shown below, the inventors have invented a novel and innovative method for significantly reducing the amount of oxidative by-compounds in citrus oil extracts. This results in a bright, fresh, and true-to-the-original citrus oil extract compared to citrus oil extracts prepared using existing extraction protocols, which tend to be flat, lacking in body, and appear distilled (see the examples below for details of this evaluation). The reason for this improvement in consumer performance is that the amount of oxidative by-compounds is reduced, in particular, to less than 2500 ppm.

[0013] International Publication No. 2001 / 039610 discloses the treatment of citrus oil with cysteine ​​or a salt or ester thereof. However, the invention described in the claims of this application does not use such additives. Furthermore, the extraction method disclosed in that document differs significantly from the extraction method used for the preparation of the citrus oil extract of the present invention; for example, the extraction method used in that document does not involve distillation. Therefore, the citrus oil extract claimed herein cannot be produced by the method described in that document.

[0014] U.S. Patent No. 5,558,893 relates to the removal of pesticides from citrus peel oil, which is quite different from the problem addressed in this invention. Furthermore, the extraction method disclosed in that document is also quite different from the extraction method used to prepare the citrus oil extract in this invention; for example, the extraction method used in that document employs thin-film distillation.

[0015] International Publication No. 2016 / 121186 relates to a method for producing refined citrus oil. This method uses thin-film distillation to remove volatile substances from non-volatile substances, and then vacuum distillation to remove monoterpenes while retaining oxygen-containing compounds. Heating the citrus oil for a longer period during vacuum distillation generates more oxidized compounds. On the other hand, the citrus oil extract claimed herein is prepared using an improved method that employs hybrid thin-film technology, which enables fractionation within a thin film. Consequently, the method described in this document does not prepare the citrus oil extract claimed herein.

[0016] Korean Patent Publication No. 10-1921193 relates to a method for producing citrus oil from fruit peel by adding sugar to an emulsion of cold-pressed oil using a combination of cold pressing and thin-film evaporation. Since this method differs significantly from the hybrid thin-film distillation method used in the present invention, the method described in this document does not prepare the citrus oil extract claimed herein.

[0017] International Publication No. 2008 / 138083 relates to a method for clarifying and concentrating oils obtained from citrus fruits using molecular distillation. However, this document only discloses a method using thin-film distillation, which does not prepare the citrus oil extract claimed herein.

[0018] This invention relates to a citrus oil extract. The citrus oil extract is prepared from the above-mentioned citrus oil. Therefore, the terpenes contained in the citrus oil extract of this invention are less than the terpenes contained in citrus oil extracted from fruit, preferably less than 50% of the total composition, and more preferably less than 5%.

[0019] The citrus oil extract of the present invention can be obtained from oils obtained from any citrus fruit of the Rutaceae family. This family, also known as the rue family, generally includes flowering plants that have a strong fragrance. Citrus fruits include, but are not limited to, lemons, limes, oranges, grapefruits, Satsuma mandarins, as well as tangerines, mandarins, yuzu, bergamots, and pomelos. Preferably, the citrus oil extract is not orange. More preferably, the citrus oil extract is lemon or lime.

[0020] The citrus oil extract of the present invention contains a reduced amount of oxidative by-product compounds. The amount of oxidative by-product compounds is preferably less than 2500 ppm, more preferably less than 2300 ppm, more preferably less than 2100 ppm, more preferably less than 1900 ppm, more preferably less than 1800 ppm, more preferably less than 1700 ppm, preferably less than 1600 ppm, preferably less than 1500 ppm, and preferably less than 1400 ppm.

[0021] "Oxidative by-products" are compounds that are formed, for example, in the citrus oil extraction process when the product is subjected to excessively high temperatures for an extended period. As mentioned above, such compounds impart undesirable notes to the extract and are therefore undesirable from a consumer's perspective.

[0022] In preferred embodiments, the oxidation by-product compound is selected from the group consisting of p-cymene, tp-mentha-2-en-1-ol, tp-mentha-2,8-dienol, t-limonene oxide, camphor, p-cymene-8-ol, t-limonene 8,9-epoxide, c-limonene 8,9-epoxide, and t-carbeol.

[0023] The structures and CAS numbers of the compounds are very well known in the art, and those skilled in the art will understand what each oxidative by-product compound is.

[0024] The citrus oil extract is preferably lemon or lime. In a preferred embodiment, the citrus fruit is lemon, and the amount of oxidative by-compounds is less than 1500 ppm, preferably 1400 ppm, more preferably less than 1320 ppm, and more preferably 1311 ppm. Preferably, the amount of oxidative by-compounds is 1385 ppm. In a further preferred embodiment, the citrus fruit is lime, and the amount of oxidative by-compounds is less than 1900 ppm, preferably less than 1800 ppm, more preferably less than 1700 ppm, more preferably less than 1650 ppm, and more preferably 1649 ppm. Preferably, the amount of oxidative by-compounds is 1453 ppm.

[0025] In a preferred embodiment of the present invention, the oxidation by-products are (i) p-cymene in an amount of 230 ppm or less, (ii) tp-mentha-2-en-1-ol in an amount of 110 ppm or less, (iii) tp-mentha-2,8-dienol in an amount of 125 ppm or less, (iv) t-limonene oxide in an amount of 10 ppm or less, (v) camphor in an amount of 185 ppm or less, (vi) p-cymene-8-ol in an amount of 220 ppm or less, (vii) t-limonene 8,9-epoxide in an amount of 290 ppm or less, (viii) c-limonene 8,9-epoxide in an amount of 350 ppm or less, and / or (ix) t-carbeol in an amount of 420 ppm or less.

[0026] In another preferred embodiment of the present invention, the citrus oil extract is lemon oil, and the extract comprises: (i) p-cymene in an amount of 100 ppm or less, (ii) trans-p-menth-2-en-1-ol in an amount of 5 ppm or less, (iii) trans-p-mentha-2,8-dienol in an amount of 75 ppm or less, (iv) trans-limonene oxide in an amount of 5 ppm or less, (v) camphor in an amount of 180 ppm or less, (vi) p-cymene-8-ol in an amount of 120 ppm or less, (vii) trans-limonene 8,9-epoxide in an amount of 290 ppm or less, (viii) cis-limonene 8,9-epoxide in an amount of 150 ppm or less, and / or (ix) trans-carveol in an amount of 420 ppm or less.

[0027] Preferably, the citrus oil extract is lemon oil, and the extract comprises: (i) p-cymene in an amount of 100 ppm, (ii) trans-p-menth-2-en-1-ol in an amount of 0 ppm, (iii) trans-p-mentha-2,8-dienol in an amount of 75 ppm or less, (iv) trans-limonene oxide in an amount of 0 ppm, (v) camphor in an amount of 178 ppm, (vi) p-cymene-8-ol in an amount of 116 ppm, (vii) trans-limonene 8,9-epoxide in an amount of 282 ppm, (viii) cis-limonene 8,9-epoxide in an amount of 147 ppm, and (ix) trans-carveol in an amount of 413 ppm.

[0028] In another preferred embodiment of the present invention, the citrus oil extract is lime oil, and the extract comprises: (i) p-cymene in an amount of 230 ppm or less, (ii) trans-p-menth-2-en-1-ol in an amount of 110 ppm or less, (iii) trans-p-mentha-2,8-dienol in an amount of 125 ppm or less, (iv) trans-limonene oxide in an amount of 5 ppm or less, (v) camphor in an amount of 150 ppm or less, (vi) p-cymene-8-ol in an amount of 200 ppm or less, (vii) trans-limonene 8,9-epoxide in an amount of 220 ppm or less, (viii) cis-limonene 8,9-epoxide in an amount of 350 ppm or less, and / or (ix) trans-carveol in an amount of 300 ppm or less.

[0029] Preferably, the citrus oil extract is lime, and the extract comprises (i) p-cymene in an amount of 229 ppm, (ii) t-p-mentha-2-en-1-ol in an amount of 0 ppm, (iii) t-p-mentha-2,8-dienol in an amount of 123 ppm, (iv) t-limonene oxide in an amount of 0 ppm, (v) camphor in an amount of 145 ppm, (vi) p-cymene-8-ol in an amount of 195 ppm, (vii) t-limonene 8,9-epoxide in an amount of 214 ppm, (viii) c-limonene 8,9-epoxide in an amount of 345 ppm, and (ix) t-carveol in an amount of 292 ppm.

[0030] In a further aspect of the present invention, there is provided an orange citrus oil extract having a reduced amount of oxidative by-product compounds, wherein the amount of the oxidative by-product compounds is less than 15000 ppm.

[0031] The orange citrus oil extract preferably comprises (i) p-cymene in an amount of 100 ppm or less, (ii) t-p-mentha-2-en-1-ol in an amount of 100 ppm or less, (iii) t-p-mentha-2,8-dienol in an amount of 1500 ppm or less, (iv) t-limonene oxide in an amount of 2500 ppm or less, (v) camphor in an amount of 100 ppm or less, (vi) p-cymene-8-ol in an amount of 500 ppm or less, (vii) t-limonene 8,9-epoxide in an amount of 100 ppm or less, (viii) c-limonene 8,9-epoxide in an amount of 1000 ppm or less, and / or (ix) t-carveol in an amount of 8000 ppm or less.

[0032] Preferably, the orange citrus oil comprises t-p-mentha-2,8-dienol in an amount of 1269 ppm, t-limonene oxide in an amount of 2183 ppm, p-cymene-8-ol in an amount of 388 ppm, c-limonene 8,9-epoxide in an amount of 900 ppm, and t-carveol in an amount of 7712 ppm.

[0033] As used herein, the "ppm" value indicates the amount of a specified compound in a citrus oil extract. Methods for determining the ppm value of a compound in a sample are well known in the art, and include, for example, methods using gas chromatography. An example of the use of such a measurement system is described herein in the examples below.

[0034] Another object of the present invention is to use the citrus oil extract of the present invention as a flavoring or scenting composition. In other words, the present invention relates to a method or process for imparting, enhancing, improving or altering the olfactory properties of a flavoring or scenting composition, or a flavored or scented article or surface, the method comprising adding an effective amount of the citrus oil extract of the present invention to the composition or article, for example, to impart its characteristic note.

[0035] In this specification, “use of the citrus oil extract of the present invention” should also be understood as the use of any composition containing the citrus oil extract of the present invention that can be advantageously used in the fragrance or flavor industry.

[0036] Furthermore, the citrus oil extract of the present invention can be used in all areas of flavoring to advantageously impart or alter the taste of consumer products to which the composition is added. Accordingly, the present invention relates to flavored consumer products comprising the citrus oil extract of the present invention as defined above.

[0037] For clarification, “flavored consumer products” means edible products or oral compositions such as pharmaceutical compositions, edible gel mixtures and compositions, dental compositions, food and beverages, and beverage products. Flavored consumer products may take many forms. A non-exclusive list of suitable forms of consumer products includes fried, frozen, marinated, coated and deep-fried, chilled, dehydrated, powdered blends, canned, rehydrated, retorted, baked, cooked, fermented, microfiltered, sterilized, blended, or preserved forms. Thus, a flavored consumer product according to the present invention also contains the compositions of the present invention, as well as any beneficial agents corresponding to the taste and flavor profile of a desired edible product, such as a cream dessert.

[0038] Accordingly, further embodiments of the present invention are flavored consumer products comprising the citrus oil extract of the present invention, selected from the group consisting of baked products, dairy products, dairy product analogues, fat and oil or emulsion-based products thereof, dairy products, confectionery products, desserts, chocolate and compound coatings, cereal products, non-alcoholic beverages including flavored carbonated water and non-carbonated mineral water and table water, alcoholic beverages, or instant or ready-to-drink beverages.

[0039] The properties and types of ingredients in food or beverages do not need to be described in more detail herein; those skilled in the art can select them based on their general knowledge and according to the properties of the product.

[0040] Typical examples of the aforementioned flavored consumer products include: • Baked products (e.g., bread, dry biscuits, cakes, mochi, rice crackers, cookies, crackers, donuts, muffins, pastries, premixes, and other baked goods) Non-alcoholic beverages (e.g., water-based beverages, fortified water / low-sugar water, flavored carbonated beverages and non-carbonated mineral water and table water, carbonated soft drinks, non-carbonated beverages, carbonated water, non-carbonated water, soft drinks, bottled water, sports / energy drinks, juice drinks, vegetable juices, vegetable juice preparations, broth drinks), • Alcoholic beverages (e.g., beer and malt beverages, distilled beverages, wine, liqueurs), • Instant or ready-to-drink beverages (e.g., instant vegetable drinks, powdered soft drinks, instant coffee and tea, black tea, green tea, oolong tea, herbal infused beverages, (e.g., water-based) cocoa, tea-based beverages, coffee-based beverages, cocoa-based beverages, infused beverages, syrups, frozen fruit, frozen fruit juice, water-based ice, fruit ice, sherbet), • Cereal products (e.g., breakfast cereals, cereal bars, energy bars / nutrition bars, granola, pre-cooked rice products, rice flour products, grain and sorghum products, raw or cooked noodles, and pasta products), • Dairy products (e.g., fruit yogurt or flavored yogurt, ice cream, fruit ice cream, frozen desserts, fresh cheese, soft cheese, hard cheese, milk beverages, whey, butter, partially or completely hydrolyzed milk protein products, fermented dairy products, condensed milk and similar products), • Dairy product imitations (dairy product imitations) containing ingredients that are not dairy products (plant-based proteins, plant-based fats), • Confectionery products (e.g., fillings, toppings, chewing gum, hard and soft candies), • Chocolate and compound coatings (e.g., chocolate, spreads), • Fats and oils or emulsion-based products (e.g., mayonnaise, spreads, regular or low-fat margarine, butter / margarine blends, flavored oils, shortening, remoulade, dressings, salad dressings, spice preparations, peanut butter), • Eggs or egg products (dried eggs, egg whites, egg yolks, custard), • Desserts (e.g., gelatin, pudding, dessert cream), • Products made from soy protein or other soy fractions (e.g., soy milk and products made from soy milk, soy lecithin-containing preparations, fermented products such as tofu or tempeh, or products manufactured therefrom, soy sauce) • Vegetable preparations (e.g., ketchup, sauces, processed and rehydrated vegetables, dried vegetables, flash-frozen vegetables, cooked vegetables, pickled vegetables, vegetable concentrates or pastes, cooked vegetables, potato preparations) • Fruit preparations (e.g., jam, marmalade, canned fruit) • Vegetarian meat substitutes or meat alternatives, vegetarian burgers Spices or spice preparations (e.g., mustard preparations, horseradish preparations, pickles), mixed spices, and seasonings used in particular, for example, in the field of snacks. • Snack products (e.g., baked or fried potato chips or potato dough products, bread dough products, corn, rice or ground nut-based extruded products), • Prepared foods (e.g., instant noodles, rice, pasta, pizza, tortillas, wraps) as well as soups and broths (e.g., stocks, flavor cubes, dried soups, instant soups, prepared soups, retort soups), sauces (instant sauces, dried sauces, ready-made sauces, gravy, sweet sauces, herb sauces, sour sauces), • Oral care products, such as toothpaste, mouthwash, dental care products (e.g., denture adhesive), dental rinses, mouth sprays, dental powders, dental gels, or dental floss. • Pet or animal food These are some examples.

[0041] Preferably, the flavored consumer product may be a baked product, dairy product, dairy product imitation, fat and oil or emulsion-based product thereof, dairy products, confectionery products, desserts, chocolate and compound coatings, cereal products, non-alcoholic beverages, alcoholic beverages, or instant or ready-to-drink beverages.

[0042] Preferably, flavored consumer products may be crusts and fillings, sugar-based products, bread, dry biscuits, cakes, mochi, rice crackers, cookies, crackers, donuts, muffins, pastries, premixes, fillings, toppings, fruit or flavored yogurt, ice cream, fruit ice cream, frozen desserts, spreads, regular or low-fat margarine, butter / margarine blends, flavored oils, shortening, dressings, spice preparations, peanut butter, fresh cheese, soft cheese, milk beverages, whey, butter, partially or fully hydrolyzed milk protein-containing products, fermented dairy products, condensed milk and similar products, gelatin, pudding, dessert cream, chocolate, spreads, water beverages, fortified water beverages / low-sugar water beverages, flavored carbonated beverages, and This may include non-carbonated mineral water and table water, carbonated soft drinks, non-carbonated beverages, sparkling water, non-carbonated water, soft drinks, bottled water, sports / energy drinks, juice drinks, vegetable juices, vegetable juice preparations, beer and malt beverages, distilled beverages, wine, liqueurs, instant vegetable drinks, powdered soft drinks, instant coffee and tea, black tea, green tea, oolong tea, herbal infusions, cocoa, tea-based beverages, coffee-based beverages, cocoa-based beverages, infusions, syrups, chewing gum, hard and soft candies, frozen fruit, frozen fruit juices, water-based ice, fruit ice, sherbet, breakfast cereals, cereal bars, energy bars / nutrition bars, granola, cooked ready-made rice products, rice flour products, grain and sorghum products, fresh or cooked noodles, and pasta products.

[0043] Some of the above-mentioned flavored consumer products may exhibit aggressive media toward the citrus oil extract of the present invention; therefore, it may be necessary to protect the citrus oil extract from premature degradation, for example, by encapsulation.

[0044] The proportion of the citrus oil extract of the present invention that can be incorporated into the various products described above varies over a wide range. These values ​​depend on the nature of the consumer product being flavored and the desired sensory effect, as well as on the properties of auxiliary components in a given base when the citrus oil extract of the present invention is mixed with flavoring or aromatic components, solvents, or additives commonly used in the art.

[0045] A typical effective amount of the extract of the present invention is 0.001 ppm to 1000 ppm, more preferably 0.1 ppm to 500 ppm, even more preferably 0.5 ppm to 350 ppm, most preferably 1 ppm to 250 ppm, most preferably 1 ppm to 150 ppm, most preferably 1 ppm to 100 ppm, most preferably 1 ppm to 50 ppm, most preferably 1 ppm to 30 ppm, most preferably 1 ppm to 20 ppm, and most preferably 1 ppm to 10 ppm, relative to the weight of the composition or the weight of the article in which the extract of the present invention is incorporated.

[0046] The citrus oil extract of the present invention can also be advantageously used in all fields of modern fragrances, i.e., perfumes or functional fragrances, to positively impart or alter the scent of consumer products to which the composition is added. Therefore, another object of the present invention is a scented consumer product containing the citrus oil extract of the present invention as defined above.

[0047] For clarity, “fragrance-enhanced consumer product” means a consumer product that provides at least a pleasant fragrance effect to the surface or space to which it is applied (e.g., skin, hair, textiles, air, or dwelling surfaces). In other words, a fragrance-enhanced consumer product according to the present invention is a fragrance-enhanced consumer product comprising a functional formulation corresponding to a desired consumer product, as well as optionally additional beneficial agents and an olfactory effective amount of the citrus oil extract of the present invention. For clarity, the fragrance-enhanced consumer product is a non-edible product.

[0048] Accordingly, a further aspect of the present invention provides a scented article comprising a citrus oil extract of the present invention, the scented article being selected from the group consisting of aromatic perfumes, perfumes, colognes, bath gels, shower gels, shampoos, hair care products, cosmetics, deodorants, air fresheners, detergents, fabric softeners, and household cleaning agents.

[0049] The properties and types of ingredients in scented consumer products are not exhaustive and do not need to be described in further detail herein, but those skilled in the art can select them based on their general knowledge and in accordance with the properties of the product and the desired effect.

[0050] Appropriately scented consumer products include, but are not limited to, fragrances such as perfumes, splashes or eau de parfums, colognes, or shave or aftershave lotions; fabric care products such as liquid or solid detergents, fabric softeners, liquid or solid fragrance enhancers, fabric refreshers, ironing water, paper, bleach, carpet cleaners, and curtain care products; body care products such as hair care products (shampoos, coloring preparations or hairsprays, color care products, hair styling products, dental care products, etc.), disinfectants, and intimate care products; cosmetic preparations (skin creams or lotions, vanishing creams or deodorants or antiperspirants (sprays or roll-ons, etc.), hair removal products, tanning products, etc.) Examples include sunscreens or after-sun products, nail products, skin cleansers, makeup, etc.; or skincare products (soaps, shower or bath mousses, oils or gels, or hygiene products, or foot / hand care products); air care products, e.g., air fresheners or "ready-to-use" powdered air fresheners for use in residential spaces (rooms, refrigerators, cupboards, shoes or cars) and / or public spaces (halls, hotels, malls, etc.); or home care products, e.g., mold removers, furniture care products, wipes, dish soap or hard surface cleaners (e.g., floors, bathtubs, sanitary or window cleaners); leather care products; and car care products, e.g., polishes, waxes or plastic cleaners.

[0051] Since some of the above-mentioned scented consumer products may exhibit aggressive media toward the compositions of the present invention, it may be necessary to protect the compositions of the present invention from premature degradation, for example, by encapsulation or by chemically bonding them to other chemicals suitable for releasing component portions of the compositions of the present invention in response to appropriate external stimuli such as enzymes, light, heat, or changes in pH.

[0052] According to any one of the embodiments described above, the citrus oil extract of the present invention may be combined with one or more flavoring or aroma-enhancing components.

[0053] In this specification, “flavoring or aromating auxiliary component” means a compound used in a flavoring or aromating preparation or composition to impart a pleasurable effect. In other words, for such a component to be considered a flavoring or aromating component, it must not merely have a taste or smell, but be recognized by those skilled in the art as being able to impart or alter the taste or smell of a composition in an active or pleasant way.

[0054] The properties and types of flavoring or aromatic auxiliary components present in a composition do not need to be described in further detail herein; those skilled in the art can select them based on their general knowledge, the intended use or application, and the desired sensory effect. Broadly speaking, these flavoring or aromatic auxiliary components belong to a class of chemicals such as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogen or sulfur heterocyclic compounds, and essential oils, and may be of natural or synthetic origin. Many of these auxiliary components are, in any case, listed in reference to the book S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA or its latest edition, or other similar publications, as well as in numerous patent documents in the field of flavors and fragrances. It is also understood that the auxiliary components may be compounds known to release various types of flavoring or aromatic compounds in a controlled manner.

[0055] A non-limiting list of suitable flavoring adjuncts available includes: phenol, 2-methoxyphenol, 2-methoxy-4-vinylphenol, 4-methylphenol, 2-methoxy-4-(2-propen-1-yl)phenol, 2-methoxy-4-(1-propen-1-yl)phenol, 2-methoxy-4-methylphenol, 2,6-dimethoxyphenol, 2-ethoxy-5-(1-propenyl)phenol, 4-ethenylphenol, 2-methylphenol, 4-hydroxybenzenemethanol, (4- Methyl methoxyphenyl formate, 4-methoxybenzaldehyde, 3-ethoxy-4-hydroxybenzaldehyde, benzaldehyde, 3,4-dimethoxybenzaldehyde, 4-methoxybenzoic acid, 1,3-benzodioxol-5-carbaldehyde, 4-methoxybenzenemethanol, 3-hydroxy-2-methyl-4H-pyran-4-one, 4-(4-methoxyphenyl)-2-butanone, 4-methoxybenzyl acetate, 4-hydroxy-2,5-dimethyl-3-furanone, 4-methoxybenzenemethanol Luacetate, ethyl 3-phenyl-2-propenoate, methyl-3-phenyl-2-propenoate, ethyl benzoate, 1,4-dimethoxybenzene, 2-ethyl-3-hydroxy-4H-pyran-4-one, 3-phenyl-2-propenal, phenylacetaldehyde, 5,6-dihydro-6-pentyl-2H-pyran-2-one, decanoic acid, butanoic acid; 2-methylpropanoic acid, dihydro-5-pentyl-2(3H)-furanone, methyl 2-hydroxybenzoic acid, methyl 2-hydroxybenzoic acid, 6-methyl-2H- 1-Benzopyrran-2-one, 3,4-dihydro-2H-1-benzopyran-2-one, 1-benzopyran-2-one, hexahydro-3,6-dimethyl-2(3H)-benzofuranone, tetrahydro-6-propyl-2H-pyran-2-one, 6-butyltetrahydro-2H-pyran-2-one, 6-heptyltetrahydro-2H-pyran-2-one, 3-phenyl-2-propen-1-ol, 2-furanmethanol, 3-phenyl-2-propenoic acid, 2-furancarboxyaldehyde, 3-hydroxy-2-butanone, 2,This includes 3-pentanedione, 2-hydroxybenzaldehyde, 5-pentylfuran-2(5H)-one, methyl 2-hydroxy-4-methoxybenzoate, 5-allyl-1,2,3-trimethoxybenzene, (-)-(1R,4E,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undeca-4-ene, tetrahydro-6-pentyl-2H-pyran-2-one, 3-methylbutanal, 1-(2-hydroxy-4-methoxyphenyl)ethanone, cocoa extract, vanilla extract, benzoin extract, Peruvian balsam extract, true balsam extract, guaiac wood oil, and combinations thereof. Preferably, the flavoring auxiliary ingredients are phenol, 2-methoxyphenol, 2-methoxy-4-vinylphenol, 4-methylphenol, 2-methoxy-4-(2-propen-1-yl)phenol, 2-methoxy-4-(1-propen-1-yl)phenol, 2-methoxy-4-methylphenol, 2,6-dimethoxyphenol, 2-ethoxy-5-(1-propenyl)phenol, 4-ethenylphenol, 2-methylphenol, 4-hydroxybenzenemethanol, methyl (4-methoxyphenyl)formate, 4-methoxybenzaldehyde, 3-ethoxy-4-hydroxybenzaldehyde Dimethyl, benzaldehyde, 3,4-dimethoxy-benzaldehyde, 4-methoxybenzoic acid, 1,3-benzodioxol-5-carbaldehyde, 4-methoxybenzenemethanol, 3-hydroxy-2-methyl-4H-pyran-4-one, 4-(4-methoxyphenyl)-2-butanone, 4-methoxybenzylacetate, 4-hydroxy-2,5-dimethyl-3-furanone, 4-methoxybenzenemethanolacetate, 3-phenyl-2-propenylol, 2-furanmethanol, 3-phenyl-2-propenoic acid, 2-furancarboxyaldehyde, 3-hydroxy-2-butanone, 2,Selected from the group consisting of 3-pentanedione, tetrahydro-6-pentyl-2H-pyran-2-one, 3-methylbutanal, 1-(2-hydroxy-4-methoxyphenyl)ethanone, cocoa extract, vanilla extract, benzoin extract, Peruvian balsam extract, true balsam extract, guaiac wood oil, and combinations thereof. More preferably, the flavoring auxiliary component is selected from the group consisting of phenol, 2-methoxyphenol, 2-methoxy-4-vinylphenol, 2-methoxy-4-(2-propen-1-yl)phenol, 2-methoxy-4-(1-propen-1-yl)phenol, 2-methoxy-4-(1-propen-1-yl)phenol, 2-methoxy-4-methylphenol, 2-ethoxy-5-(1-propenyl)phenol, 4-ethenylphenol, 4-methoxybenzaldehyde, benzaldehyde, 4-methoxybenzoic acid; 1,3-benzodioxol-5-carbaldehyde, 3-hydroxy-2-methyl-4H-pyran-4-one, 4-hydroxy-2,5-dimethyl-3-furanone, 1-(2-hydroxy-4-methoxyphenyl)ethanone, and combinations thereof.

[0056] The concentrations (unit: ppm RTC) of these compounds are: phenol (0.0001~0.3); 2-methoxyphenol (0.0001~0.5); 2-methoxy-4-vinylphenol (0.0001~0.3); 2-methoxy-4-(2-propen-1-yl)phenol; 2-methoxy-4-(1-propen-1-yl)phenol (0.0001~0.1); 2-methoxy-4-methylphenol (0.0001~0.5); 2-ethoxy-5-(1-propenyl)phenol (0 These include 0.0001~5); 4-ethenylphenol (0.0001~0.3); 4-methoxybenzaldehyde (0.0005~5); benzaldehyde (0.0001~5); 4-methoxybenzoic acid (0.1~200); 1,3-benzodioxol-5-carbaldehyde (0.01~50); 3-hydroxy-2-methyl-4H-pyran-4-one (0.05~200); and 4-hydroxy-2,5-dimethyl-3-furanone (0.05~100).

[0057] According to any one of the embodiments described above, the citrus oil extract of the present invention can be combined with at least one flavor or aroma carrier. The term "flavor or aroma carrier" refers to a material that is substantially neutral in terms of flavoring or aroma, as long as it does not significantly alter the sensory properties of the flavoring or aroma-adding component. The carrier may be liquid or solid.

[0058] Suitable liquid carriers include, for example, emulsions, i.e., solvent and surfactant systems, or solvents commonly used in flavors or fragrances. It is not possible to comprehensively describe in detail the properties and types of solvents commonly used in flavors or fragrances. Suitable solvents used in flavors include, for example, propylene glycol, triacetin, caprylic / capric triglyceride (neobee®), triethyl citrate, benzyl alcohol, ethanol, vegetable oils such as linseed oil, sunflower oil, or coconut oil, and glycerol. Non-limiting examples of fragrance solvents include butylene or propylene glycol, glycerol, dipropylene glycol and its monoethers, 1,2,3-propanetriyltriacetate, dimethyl glutarate, dimethyl adipate, 1,3-diacetyloxypropane-2-yl acetate, diethyl phthalate, isopropyl myristate, benzyl benzoate, benzyl alcohol, 2-(2-ethoxyethoxy)-1-ethanol, triethyl citrate, ethanol, water / ethanol mixtures, limonene or other terpenes, isoparaffins such as those known by the trademark Isopar® (manufactured by Exxon Chemical), or glycol ethers and glycol ether esters such as those known by the trademark Dowanol® (manufactured by Dow Chemical Company), or hydrogenated castor oil such as those known by the trademark Cremophor® RH40 (manufactured by BASF), or mixtures thereof.

[0059] Suitable solid carriers include, for example, absorbent gums or polymers, and even encapsulating materials. Examples of such materials include wall-forming and plasticizing materials, such as monosaccharides, disaccharides, polysaccharides, natural or modified starches, hydrophilic colloids, cellulose derivatives, polyvinyl acetate, polyvinyl alcohol, xanthan gum, gum arabic, acacia gum, or materials cited in reference, for example, H. Scherz, Hydrokolloid: Stabilisatoren, Dickungs- und Geliermittel in Lebensmitteln, Band 2 der Schriftenreihe Lebensmittelchemie, Lebensmittelqualitaet, Behr's Verlag GmbH & Co., Hamburg, 1996. Encapsulation is a method well known to those skilled in the art and may be carried out using techniques such as spray drying, agglomeration, extrusion, coating, plating, and coacervation.

[0060] The citrus oil extract of the present invention may contain at least one flavor enhancer. In this specification, “flavor enhancer” means an ingredient that can impart further additional advantages such as color (e.g., caramel) and chemical stability. It is impossible to comprehensively describe in detail the properties and types of enhancers commonly used in flavoring compositions. Nevertheless, such enhancers are well known to those skilled in the art, and they can be selected based on their general knowledge and according to the intended use or application. Non-limiting specific examples include viscosities (e.g., emulsifiers, thickeners, gelling and / or rheological modifiers, e.g., pectin or agar gum), stabilizers (e.g., antioxidants, heat / light stabilizers and / or buffers, e.g., citric acid), colorants (e.g., natural or synthetic colorants, or natural extracts for coloring), preservatives (e.g., antibacterial or antimicrobial or antifungal agents, e.g., benzoic acid), vitamins, and mixtures thereof.

[0061] The citrus oil extract of the present invention may be combined with at least one fragrance additive. In this specification, “fragrance additive” means an ingredient that can impart further additional advantages such as color, specific lightfastness, and chemical stability. It is impossible to comprehensively describe in detail the properties and types of additives commonly used in fragranced compositions, but it should be noted that these ingredients are well known to those skilled in the art. Non-limiting specific examples include viscosity agents (e.g., surfactants, thickeners, gelling and / or rheological modifiers), stabilizers (e.g., preservatives, antioxidants, heat / light stabilizers and / or buffers, or chelating agents such as BHT), colorants (e.g., dyes and / or pigments), preservatives (e.g., antibacterial or antimicrobial or antifungal or anti-irritant agents), abrasives, skin coolants, fixatives, insecticides, ointments, vitamins, and mixtures thereof.

[0062] According to any one of the embodiments described above, the citrus oil extract of the present invention may be combined with a sweetener. Not limited examples of suitable sweeteners include common sugar sweeteners, e.g., sucrose, fructose (such as D-fructose), glucose (such as D-glucose); sweetener compositions containing natural sugars, e.g., stevia (all types and grades), corn syrup (including high-fructose corn syrup) or other syrups, or sweetener concentrates derived from natural fruits and vegetables; semi-synthetic "sugar alcohol" sweeteners, e.g., erythritol, isomalt, lactitol, mannitol. Sweeteners such as sorbitol, xylitol, maltodextrin, glycerol, slateitol, arabitol, ribitol, and dulciitol; artificial sweeteners such as miraculin, aspartame, super aspartame, saccharin, saccharin sodium salt, acesulfame K, cyclamate, cyclamate sodium, and alitame; other sweeteners such as trehalose, melibitose, melibiose, raffinose, palatinose, lactulose, cyclamic acid, mo Mogroside, tagatose (D-tagatose, etc.), maltose, galactose (D-galactose, etc.), L-rhamnose, D-sorbose, maunose (D-maunose, etc.), lactose, L-arabinose, D-ribose, D-glyceraldehyde, curculin, blazein, mogroside, neohesperidin dihydrochalcone (NHDC), neotame and other aspartame derivatives, D-tryptophan, D-leucine, D-threonine, glycine, D-asparagine, D- Examples include phenylalanine, L-proline, maltitol, hydrogenated glucose syrup (HGS), magap, sucralose, ragdune, sukurononate, sukurooctate, monatin, phyllodulcin, hydrogenated starch hydrolysate (HSH), stevioside, rebaudioside A, rebaudioside D, rebaudioside M, and other sweeteners, stevia-based glycosides, monk fruit, thaumatin, monelin, carrelameand, and other guanidine-based sweeteners.

[0063] According to any one of the embodiments described above, the citrus oil extract of the present invention may be combined with at least one coolant. Non-limiting examples of suitable coolants include WS-23 (2-isopropyl-N,2,3-trimethylbutylamide), FEMA 3804; WS-3 (N-ethyl-p-menthane-3-carboxamide), FEMA 3455; WS-5 [ethyl 3-(p-menthane-3-carboxamide) acetate], FEMA 4309; WS-12 (1R,2S,5R)-N-(4-methoxyphenyl)-p-menthanecarboxamide, FEMA 4681; WS-27 (N-ethyl-2,2-diisopropylbutanamide), FEMA 4557; N-cyclopropyl-5-methyl-2-isopropylcyclohexanecarboxamide, FEMA 4693, WS-116 (N-(1,1-dimethyl-2-hydroxyethyl)-2,2-diethylbutanamide), N-(1,1-dimethyl-2-hydroxyethyl)2,2-diethylbutanamide, FEMA 4603, menthoxyethanol, FEMA 4154, N-(4-cyanomethylphenyl)-p-menthanecarboxamide, FEMA 4496; N-(2-(pyridine-2-yl)ethyl)-3-p-menthanecarboxamide, FEMA 4549; N-(2-hydroxyethyl)-2-isopropyl-2,3-dimethylbutanamide, FEMA 4602 and (also N-(4-(carbamoylmethyl)phenyl)-menthylcarboxamide, FEMA 4684; (1R,2S,5R)-N-(4-methoxyphenyl)-p-menthanecarboxamide (WS-12), FEMA 4681; (2S,5R)-N-[4-(2-amino-2-oxoethyl)phenyl]-p-menthanecarboxamide, FEMA 4684; and N-cyclopropyl-5-methyl-2-isopropylcyclohexanecarbonecarboxamide, FEMA 4693; 2-[(2-p-menthoxy)ethoxy]ethanol, FEMA 4718; (2,6-diethyl-5-isopropyl-2-methyltetrahydropyran, FEMA 4680); trans-4-tert-butylcyclohexanol, FEMA 4724; 2-(p-tolyloxy)-N-(1H-pyrazole-5-yl)-N-((thiophen-2-yl)methyl)acetamide, FEMA 4809;Menthong glycosyl ketal, FEMA 3807; Menthong glycosyl ketal (FEMA GRAS 3808); (-)-menthoxypropane-1,2-diol; 3-(1-menthoxy)-2-methylpropane-1,2-diol, FEMA 3849; isopuregol; (+)-cis & (-)-trans p-menthane-3,8-diol, ratio ~62:38, FEMA 4053; 2,3-dihydroxy-p-menthane; 3,3,5-trimethylcyclohexanone glycerol ketal; menthylpyrrolidone carboxylate; (1R,3R,4S)-3-menthyl-3,6-dioxaheptanoate; (1R,2S,5R)-3-menthyl methoxyacetate; (1R,2S,5R)-3-menthyl 3,6,9-trioxadecanoate; (1R,2S,5R)-3-menthyl 3,6,9-trioxadecanoate; (1R,2S,5R)-3-menthyl (2-hydroxyethoxy)acetate; (1R,2S,5R)-menthyl 11-hydroxy-3,6,9-trioxaundecanoate; cubebol, FEMA 4497; N-(4-cyanomethylphenyl)p-menthanecarboxamide, FEMA 4496; 2-Isopropyl-5-methylcyclohexyl 4-(dimethylamino)-4-oxobutanoate, FEMA 4230; N-(4-cyanomethylphenyl)p-menthanecarboxamide, FEMA 4496; N-(2-pyridine-2-ylethyl); p-menthanecarboxamide, FEMA 4549, Menthyl lactate, FEMA 3748; 6-Isopropyl-3,9-dimethyl-1,4-dioxaspiro[4.5]decan-2-one, FEMA 4285; N-benzo[1,3]dioxol-5-yl-3-p-menthanecarboxamide; N-(1-isopropyl-1,2-dimethylpropyl)-1,3-benzodioxol-5-carboxamide; N-(R)-2-oxotetrahydrofuran-3-yl-(1R,2S,5R)-p-menthane-3-carboxamide; a mixture of 2,2,5,6,6-pentamethyl-2,3,6,6a-tetrahydropentalen-3a(1H)-ol and 5-(2-hydroxy-2-methylpropyl)-3,4,4-trimethylcyclopenta-2-en-1-one;(1R,2S,5R)-2-isopropyl-5-methyl-N-(2-(pyridine-2-yl)ethyl)cyclohexanecarboxamide, FEMA 4549; (2S,5R)-2-isopropyl-5-methyl-N-(2-(pyridine-4-yl)ethyl)cyclohexanecarboxamide; N-(4-cyanomethylphenyl)p-menthanecarboxamide, FEMA 4496; (1S,2S,5R)-N-(4-(cyanomethyl)phenyl)-2-isopropyl-5-methylcyclohexanecarboxamide; 1 / 7-isopropyl-4 / 5-methyl-bicyclo[2.2.2]octa-5-ene derivative; 4-methoxy-N-phenyl-N-[2-(pyridine-2-yl)ethyl]benzamide; 4-methoxy-N-phenyl-N-[2-(pyridine-2-yl)ethyl]benzenesulfonamide; 4-chloro-N-phenyl-N-[ 2-(pyridine-2-yl)ethyl]benzenesulfonamide; 4-cyano-N-phenyl-N-[2-(pyridine-2-yl)ethyl]benzenesulfonamide; 4-((benzhydrylamino)methyl)-2-methoxyphenol; 4-((bis(4-methoxyphenyl)-methylamino)-methyl)-2-methoxyphenol; 4-((1,2-diphenylethylamino)methyl)-2-methoxyphenol; 4-((benzhydryloxy)methyl)-2- Methoxyphenol, 4-((9H-fluoren-9-ylamino)methyl)-2-methoxyphenol; 4-((benzhydrylamino)methyl)-2-ethoxyphenol; 1-(4-methoxyphenyl)-2-(1-methyl-1H-benzo[d]imidazole-2-yl)vinyl 4-methoxybenzoate; 2-(1-isopropyl-6-methyl-1H-benzo[d]imidazole-2-yl)-1-(4-methoxyphenyl)vinyl 4-methoxybenzoate (Z)-2-(1-isopropyl-5-methyl-1H-benzo[d]imidazole-2-yl)-1-(4-methoxyphenyl)vinyl-4-methoxybenzoate; 3-alkyl-p-methane-3-ol derivatives; derivatives of phentyl, D-bornyl, L-bornyl, exonorbornyl, 2-methylisobornyl, 2-ethylphentyl, 2-methylbornyl, cis-pinan-2-yl, berbanyl, and isobornyl; menthyl oxamate derivatives;Examples include menthyl 3-oxocarboxylic acid esters; N α-(menthanecarbonyl) amino acid amides; p-menthanecarboxamide and WS-23 analogues; (-)-(1R,2R,4S)-dihydroumbellol; p-menthanealkyloxyamides; cyclohexane derivatives; butone derivatives; mixtures of 3-menthoxy-1-propanol and 1-menthoxy-2-propanol; 1-[2-hydroxyphenyl]-4-[2-nitrophenyl-]-1,2,3,6-tetrahydropyrimidine-2-one; 4-methyl-3-(1-pyrrolidinyl)-2[5H]-furanone; and combinations thereof. Preferably, the coolant is menthol, menthol methyl ether, menthol glycoside acetal (FEMA GRAS 3807), menthol glycoside ketal (FEMA GRAS 3808), menthyl lactate (FEMA GRAS 3748), menthyl acetate, menthol ethylene glycol carbonate (FEMA GRAS 3805), menthol propylene glycol carbonate (FEMA GRAS 3806), menthyl-N-ethyl oxamate, monomethyl succinate (FEMA GRAS 3810), monomentyl glutamate (FEMA GRAS 4006), menthoxy-1,2-propanediol (FEMA GRAS 3784), menthoxy-2-methyl-1,2-propanediol (FEMA GRAS Selected from the group consisting of (1R,2S,5R)-N-(4-(cyanomethyl)phenyl)menthylcarboxamide (FEMA GRAS 4496), (1R,2S,5R)-N-(2-(pyridine-2-yl)ethyl)menthylcarboxamide (FEMA GRAS 4549), their menthane carboxylic acid esters and amides WS-3, WS-4, WS-5, WS-12, WS-14, WS-30, and mixtures.

[0064] According to any one of the embodiments described above, the citrus oil extract of the present invention may be further combined with ingredients that impart a warming effect, a tingling sensation, a saliva-stimulating effect, a cleansing effect, or an alcohol-enhancing effect, such as chili pepper extract, spice extracts (all types of pepper including ginger, guinea ginger, and sansho pepper, piperine, capsaicin, jambu extract, spiranthol, etc.).

[0065] Those skilled in the art will understand that, not only through trial and error, but simply by applying standard knowledge in the art, the optimal formulation for achieving the desired effect can be perfectly designed by mixing the components of the above-mentioned flavoring or aromating composition.

[0066] For clarification, it is also understood that any mixture obtained directly from chemical synthesis, such as a reaction medium that is not sufficiently purified and in which the compounds of the present invention may be included as a starting material, intermediate product, or final product, cannot be considered a flavoring or aromatic composition of the present invention unless such a mixture provides the compounds of the present invention in a form suitable for fragrance or aroma. Therefore, unless otherwise specified, unpurified reaction mixtures are generally excluded from the present invention.

[0067] Further embodiments of the present invention include: A) A step of subjecting citrus oil to hybrid thin-film distillation to evaporate volatile substances, B) A step in which the volatile substances evaporated from step A) are placed in a cooling condenser and the vapor is converted into a liquid. C) A step of collecting the liquid from step B) as the citrus oil extract of the present invention. The present invention provides a method for preparing a citrus oil extract, which includes [a specific ingredient / method].

[0068] In one embodiment of the present invention, the vapor extract from step A) is passed through a fractionation column before step B). Preferably, the fractionation column is integrated with a hybrid thin-film distillation apparatus.

[0069] In embodiments of the method of the present invention, the process is preferably repeated two, three, four, five, or more times to further concentrate the citrus oil extract.

[0070] Examples of the method of the present invention are described in the following examples.

[0071] Step A) of the method of the present invention requires subjecting the citrus oil to hybrid thin-film distillation to evaporate volatile substances. As described above, the citrus oil can be obtained from, but is not limited to, any citrus fruit of the Rutaceae family, preferably lemon, lime, orange, grapefruit, Satsuma mandarin and tangerine, mandarin, yuzu, bergamot, and pomelo. The citrus oil may be prepared using generally known methods or may be commercially obtained from the many existing suppliers of citrus oil.

[0072] The first step of the method of the present invention is to subject citrus oil to hybrid thin-film distillation to evaporate volatile substances. "Hybrid thin-film distillation" is an extraction method known in the art and readily available to those skilled in the art. Essentially, this method is a distillation method in which citrus oil is heated for a short time under high vacuum conditions where there are few opportunities for intermolecular collisions and at a temperature where there are few opportunities for conversion of compounds into oxidative by-products.

[0073] Apparatus for performing hybrid thin-film distillation is well known and readily available to those skilled in the art. Examples of such apparatus and protocols for their use are described in the following examples.

[0074] In a preferred embodiment, the hybrid thin-film distillation is carried out using (i) a vacuum of 1.33 Pa to 13333 Pa, (ii) a temperature of 30 to 160°C, and (iii) the citrus oil is subjected to hybrid thin-film distillation for 3 to 15 minutes, preferably less than 1 minute, more preferably 3 to 15 seconds.

[0075] In a preferred embodiment of the present invention, step A) is repeated two or more times, and in the second or final step A), the temperature is higher and the pressure is lower than in the first step A).

[0076] Preferably, the vacuum is 1.33 Pa to 13333 Pa, more preferably 13.3 Pa to 1333 Pa, 66.6 Pa to 666 Pa, and preferably 100 Pa to 400 Pa.

[0077] Preferably, the temperature is 30°C to 160°C, more preferably 50°C to 130°C, 75°C to 125°C, 80°C to 120°C, or 90°C to 110°C.

[0078] Preferably, the citrus oil is subjected to hybrid thin-film distillation for 3-15 minutes, 4-10 minutes, 4-8 minutes, and 5-6 minutes. More preferably, the citrus oil is subjected to hybrid thin-film distillation for 3-15 seconds, 4-10 seconds, 4-8 seconds, and 5-6 seconds.

[0079] Step B) of the method of the present invention requires passing the evaporated volatile substance from step A) through a cooling condenser to convert the vapor into a liquid.

[0080] A refrigerated condenser is a standard experimental apparatus well known in the art and can be easily combined with a fractionation column apparatus. They are connected so that the vapor extract from step B) enters directly into the refrigerated condenser. An example of such an apparatus and a protocol for its use are described in the following example.

[0081] Step C) of the method of the present invention requires that the liquid from step B) be collected as the citrus oil extract of the present invention. Again, examples of such apparatus and protocols for their use are described in the following examples.

[0082] In any step of the method of the present invention, the steam extract from A) is passed through a fractionation column before step B). This optional step can remove more terpenes and other oils from the extract and thus increase the solubility of the citrus oil extract of the present invention.

[0083] A fractionation column is a standard experimental apparatus well known in the art and can be easily combined with a hybrid thin-film distillation apparatus. The fractionation column is connected so that the vapor extract from step A) enters the fractionation column directly. Examples of such apparatus and protocols for their use are described in the following examples.

[0084] The present invention will now be described in more detail by the following examples illustrating its effects and advantages.

[0085] Examples Example 1: Preparation of the citrus oil extract composition of the present invention The method for preparing the citrus oil extract of the present invention is shown below. The starting material was commercially available citrus oil.

[0086] Process 1 Set the inner surface of the wiped film evaporator equipped with a fractionation column to 80°C to 120°C, reduce the pressure to 2000 Pa to 3000 Pa, and begin supplying citrus oil to the evaporator. The supply rate should be sufficient to optimize the available evaporation capacity of the system and should not overload the condenser. Set the initial reflux ratio and adjust it as needed so that the aldehyde concentration in the distillate is 0.5% or less. Adjust the supply rate and / or pressure to achieve the desired residue-to-distillate ratio.

[0087] This step of the present invention removes unwanted components present in the citrus oil used as the starting material.

[0088] Process 2 The inner surface of a short-pass distiller equipped with an internal condenser is set to a higher temperature than in step 1, for example, 100°C to 120°C, and the pressure is reduced to a lower temperature than in step 1, for example, less than 150 Pa, and the feed of the residue from step 1 is started. The feed rate should be sufficient to optimize the available evaporation capacity of the system and should not overload the condenser. The distillate and residue are collected separately as distinct products, and their ratio is determined by the composition of the feed.

[0089] Example 2: Analysis of the composition of the citrus oil extract of the present invention The inventors investigated the components of the oxidative by-product compounds of the citrus oil extract of the present invention and compared them with the composition of citrus oil extract prepared by conventional vacuum distillation. The results are shown below.

[0090] Sample analysis was performed using an Agilent 6890N GC system (Agilent Technologies, Santa Clara, California). The inlet temperature was set to 250°C, and the oven temperature program consisted of a linear gradient of 5°C / min from 40°C to 360°C. The injection volume was 0.2 μL (100:1 split ratio).

[0091] Identification analysis was performed using an Agilent 5975 quadrupole mass spectrometer with Masshunter software (Agilent Technologies, Santa Clara, California) and a ZB-5MSi capillary column measuring 30 m × 0.25 mm with an id of 0.25 μm (Phenomenex, Torrance, California). Helium was used as the carrier gas in constant flow mode at 0.8 mL / min. The source was maintained at 230°C and the quadrupole at 150°C. The transfer line and injector were maintained at 300°C. Electron impulse ionization in cation mode was used, scanning the mass range from 15–300 m / z for 0–2.4 minutes, followed by scanning from 33–450 m / z. Mass spectral matching was performed by comparison with the NIST 2008 version 2.0 standard spectrum (NIST, Gaithersburg, Maryland) and the in-house MS library. MS deconvolution was performed using AMDIS version 2.69 (NIST, Gaithersburg, Maryland).

[0092] Quantitative analysis was performed using the GC system's built-in FID. Helium was used as the carrier gas in constant flow mode at 1.4 mL / min. The FID temperature was set to 300°C, the hydrogen fuel gas flow rate to 40.0 mL / min, and the utility compressed air to 400.0 mL / min. Makeup gas was turned off, and the lit offset was set to 1.

[0093] Using the analytical method described above, the composition of four samples was analyzed: a conventional lemon oil extract obtained by vacuum distillation, the lemon oil extract of the present invention, a conventional lime oil extract obtained by vacuum distillation, and the lime oil extract of the present invention. The data is shown below, and the lime extract is also shown in Figure 1.

[0094] [Table 1]

[0095] [Table 2]

[0096] Herein, it is clear that the citrus oil extract of the present invention has far fewer oxidative by-products than extracts prepared using conventional vacuum distillation methods. As mentioned above, oxidative by-products give the extract an undesirable note, so this is preferable for consumers.

[0097] Example 3: Sensory analysis of the citrus oil extract of the present invention Sensory analysis was performed using a descriptive analysis on a hedonic scale from 0 to 5. Samples prepared with a standard taste solution (7% sucrose and 0.1% citric acid) were presented blindly to trained panelists, who were asked to rate the freshness of each sample on a scale of 0 to 5. The data are shown in Table 3 below.

[0098] [Table 3]

Claims

1. A citrus oil extract obtained from citrus fruits, wherein the amount of oxidative by-compounds is reduced, the total amount of oxidative by-compounds contained in the citrus oil extract is less than 2500 ppm, and the oxidative by-compounds are selected from the group consisting of p-cymene, t-p-mentha-2-en-1-ol, t-p-mentha-2,8-dienol, t-limonene oxide, camphor, p-cymene-8-ol, t-limonene 8,9-epoxide, c-limonene 8,9-epoxide, and t-carbeol. Citrus oil extract, wherein the citrus fruit is selected from the group including lemon, lime, grapefruit, Satsuma mandarin, and tangerine.

2. The citrus oil extract according to claim 1, wherein the citrus fruit is lime, and the total amount of the oxidative by-product compound contained in the citrus oil extract is less than 1900 ppm.

3. The citrus oil extract according to claim 1, wherein the citrus fruit is lemon, and the total amount of the oxidative by-product compound contained in the citrus oil extract is less than 1500 ppm.

4. The citrus oil extract according to any one of claims 1 to 3, wherein the oxidative by-product compound is (i) p-cymene in an amount of 230 ppm or less, (ii) t-p-mentha-2-en-1-ol in an amount of 110 ppm or less, (iii) t-p-mentha-2,8-dienol in an amount of 125 ppm or less, (iv) t-limonene oxide in an amount of 10 ppm or less, (v) camphor in an amount of 185 ppm or less, (vi) p-cymene-8-ol in an amount of 220 ppm or less, (vii) t-limonene 8,9-epoxide in an amount of 290 ppm or less, (viiii) c-limonene 8,9-epoxide in an amount of 350 ppm or less, and / or (ix) t-carveol in an amount of 420 ppm or less.

5. The citrus oil extract according to any one of claims 1, 3, and 4, wherein the citrus oil extract is lemon, and the extract comprises (i) p-cymene in an amount of 100 ppm or less, (ii) t-p-mentha-2-en-1-ol in an amount of 5 ppm or less, (iii) t-p-mentha-2,8-dienol in an amount of 75 ppm or less, (iv) t-limonene oxide in an amount of 5 ppm or less, (v) camphor in an amount of 180 ppm or less, (vi) p-cymene-8-ol in an amount of 120 ppm or less, (vii) t-limonene 8,9-epoxide in an amount of 290 ppm or less, (viiii) c-limonene 8,9-epoxide in an amount of 150 ppm or less, and / or (ix) t-carveol in an amount of 420 ppm or less.

6. The citrus oil extract according to any one of claims 1, 2, and 4, wherein the citrus oil extract is lime, and the extract comprises (i) p-cymene in an amount of 230 ppm or less, (ii) t-p-mentha-2-en-1-ol in an amount of 110 ppm or less, (iii) t-p-mentha-2,8-dienol in an amount of 125 ppm or less, (iv) t-limonene oxide in an amount of 5 ppm or less, (v) camphor in an amount of 150 ppm or less, (vi) p-cymene-8-ol in an amount of 200 ppm or less, (vii) t-limonene 8,9-epoxide in an amount of 220 ppm or less, (viiii) c-limonene 8,9-epoxide in an amount of 350 ppm or less, and / or (ix) t-carveol in an amount of 300 ppm or less.

7. A flavoring composition or fragrance composition comprising a citrus oil extract according to any one of claims 1 to 6.

8. A flavored consumer product comprising a citrus oil extract according to any one of claims 1 to 6, the flavored consumer product being selected from the group consisting of baked products, dairy products, dairy product analogues, fats and oils or emulsion-based products thereof, dairy products, confectionery products, desserts, chocolates and compound coatings, cereal products, non-alcoholic beverages including flavored carbonated water and non-carbonated mineral water and table water, alcoholic beverages, or instant or ready-to-drink beverages.

9. A scented article comprising a citrus oil extract according to any one of claims 1 to 6, the scented article being selected from the group consisting of aromatic perfumes, perfumes, colognes, bath gels, shower gels, shampoos, hair care products, cosmetics, deodorants, air fresheners, detergents, fabric softeners, and household cleaning agents.

10. A) A process of evaporating volatile substances by subjecting citrus oil to hybrid thin-film distillation. B) A step of placing the volatile substance evaporated from step A) into a cooling condenser and converting the vapor into a liquid. C) A step of collecting the liquid from step B) as the citrus oil extract of the present invention. Includes, A method for preparing a citrus oil extract, wherein the steam extract from A) is passed through a fractionation column before step B).

11. The method according to claim 10, wherein the hybrid thin-film distillation is carried out using (i) a vacuum of 1.33 Pa to 13333 Pa, (ii) a temperature of 30 to 160°C, and (iii) the citrus oil.

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