JP7027677B2 - A citrus fragrance that imparts a pericarp feeling or enhances the pericarp feeling - Google Patents

Description

The present invention provides a perfume material for imparting or enhancing an aroma reminiscent of citrus peel.

Citrus fruits (lemon, orange, grapefruit, etc.) are used in a wide range of foods due to their refreshing aroma. Citrus fruits have oil vesicles on the peel and the essential oil is stored there, and the citrus essential oil used as a natural fragrance is mainly obtained by collecting the peel oil. Most of the oils used as citrus essential oils are cold pressed oils that are physically squeezed from the pericarp, so the image of citrus aroma is mostly derived from the pericarp oil. The aroma component of peel oil is mostly hydrocarbons represented by terpenes, and they play an important role in the sensation of citrus peel. However, since hydrocarbons are hydrophobic, water-soluble food flavors such as beverages have a problem of solubility. Therefore, in order to suppress the separation of essential oils, citrus essential oil is extracted with hydrous ethanol to stably disperse it in beverages. The method of causing is generally used. According to this method, since the hydrophobic aroma component is remarkably reduced, there is a problem that it becomes difficult to reproduce the target aroma because the overall aroma is weakened or the aroma balance is changed. Therefore, a method has been adopted in which micelles containing hydrophobic components are formed using an emulsifier and stably dispersed in water. However, the stability varies greatly depending on the particle size of the micelles and the conditions after dispersion. However, the reality is that considerable trial and error is unavoidable in order to achieve stable emulsification and dispersion.

On the other hand, although it is known that sulfur-containing compounds are used as fragrances, sulfur-containing compounds are generally used because they have a low threshold value and have a unique odor that is unpleasant at least at the concentration at which other fragrance compounds are used. The range is not wide. Among them, thiols have a particularly low threshold value and a strong unique aroma even at a low concentration, so that even if they are detected by component analysis, they often cannot be expected to contribute to the aroma (Non-Patent Document 1). In addition, thiols are relatively easy to assume as a kind of heat-generated aroma such as roasted coffee aroma and other cooking aromas, but in other foods, they are regarded as unfavorable aromas such as deteriorated odor of beer. (Non-Patent Document 2). On the other hand, there is a description in Patent Document 1 that the sulfur-containing compound can be widely applied and can be used for citrus beverages, but since it merely gives an example of the use in which the sulfur-containing compound can be used. The specific type, use, and usage of the sulfur-containing compound are not described, and it is not clear which of the many compound groups in which thioethers and thioesters are presumed to be used can be used. Further, Non-Patent Document 3 analyzes the aroma component of trifoliate orange peel, which is a kind of citrus, focusing on sulfur-containing compounds, and many sulfur-containing compounds have been found. Although trifoliate orange is a type of citrus, its aroma is jasmine-like and has a ripe or rotten mango-like sulfur-like aroma, which is significantly different from other citrus fruits such as lemon and orange. It is stated that. Among them, regarding the aroma of 3-mercapto-3-methylbutylacetate, it is stated that it has tomato leaf, grapefruit, and mango tones when 1 ppm is added to water, but what kind of aroma contribution is made in the essential oil? No suggestion is made as to.

International Publication No. 02/77096

”Identification, Synthesis, and characterization of Novel Sulfur-Containing Volatile Compounds from the In-Depth Analysis of Lisbon Lemon Peels (Citrus limon L. Burm. F. Cv. Lisbon)”, Journal of Agricultural and Food Chemistry, 2015, No. No. 63, pp. 1915-1931 "Food Science Research on Beverage Flavors", Journal of Japan Society for Food Science and Technology, 2011, Vol. 58, No. 3, pp. 81-87 "Volatile Organic Sulfur-Containing Constituents in Poncirus trifoliata (L.) Raf. (Rutaceae)", Journal of Food Chemistry, 2007, Vol. 55, pp. 4511-4517

An object of the present invention is to provide a perfume material for imparting or enhancing an aroma reminiscent of citrus peel.

As a result of various studies to identify a component that improves the citrus-like pericarp feeling in order to solve the above-mentioned problems, the present inventors have found that some sulfur-containing compound groups contribute to the citrus-like pericarp feeling. I found it. Furthermore, the present invention was completed by repeating the addition test of these compounds to the fragrance.

That is, the present invention is a citrus aroma consisting of one or more selected from 3-methyl-2-butene-1-thiol, 3-mercapto-3-methylbutylformate, and 3-mercapto-3-methylbutylacetate. It is a fruit skin sensation-imparting or enhancing agent, and is a citrus flavor, a food or drink, or a cosmetic product obtained by adding a specific amount of one or more selected from the above compound group.

According to the present invention, it is possible to produce a food or drink having a citrus flavor that is more palatable than that reminiscent of the aroma of the peel of a natural fruit. Furthermore, it is also possible to apply a citrus fragrance using the pericarp sensation improving agent of the citrus fragrance of the present invention to a fragrance for cosmetics, and the citrus fragrance with higher palatability can be added by adding the fragrance for cosmetics. It is also possible to produce fragrant cosmetics.

The present invention is a citrus fragrance or citrus consisting of one or more selected from 3-methyl-2-butene-1-thiol, 3-mercapto-3-methylbutylformate, and 3-mercapto-3-methylbutylacetate. It is an agent for imparting or enhancing the skin feeling of flavored foods and drinks, and further is a citrus flavor containing them, a food or drink having a citrus flavor, or a cosmetic product having a citrus flavor. The active ingredients of the present invention, 3-methyl-2-butene-1-thiol, 3-mercapto-3-methylbutylformate, and 3-mercapto-3-methylbutylacetate, should be added to the fragrance at the following concentrations. Improves the citrus-like pericarp feeling. The following numerical range is a general range, with the upper limit being the case where no solvent is added and the lower limit being the case of diluting to 10% by mass with a solvent, and the dilution rate is less than 10%. The overall aroma can be adjusted by reducing the addition amount according to the above.

(a) 3-Methyl-2-butene-1-thiol: 1ppt-10ppb
(b) 3-Mercapto-3-methylbutylformate: 1ptt-10ppb
(c) 3-Mercapto-3-methylbutylacetate: 1ptt-100ppb

Since the aroma of the active ingredient of the present invention is different from that of citrus, the citrus aroma is not formed only by the pericarp-imparting or enhancing agent of the present invention. Therefore, the pericarp-imparting or enhancing agent of the present invention must coexist with at least one of citrus juice, citrus peel oil, and citrus flavor at the stage of the product to be finally consumed. Further, if the compound is added in excess of the above numerical range, the aroma of each compound itself can be felt, which may impair the flavor of the food or drink as a whole. Further, when the value falls below the lower limit of the above numerical range, the citrus peel feeling is not sufficiently improved, and there is no difference in palatability from the non-added one.

The agent for imparting or enhancing the pericarp feeling of the present invention is one or more of 3-methyl-2-butene-1-thiol, 3-mercapto-3-methylbutylformate, and 3-mercapto-3-methylbutylacetate. Although it is effective, it is preferable to combine two or more of them because the aroma characteristics closer to those of natural citrus fruits can be obtained. When two or more compounds of the present invention are combined, the ratio is determined in consideration of the amount added to the finally consumed product.

The active ingredients of the present invention, 3-methyl-2-butene-1-thiol, 3-mercapto-3-methylbutylformate, and 3-mercapto-3-methylbutylacetate, are all known compounds and are therefore known. It can be manufactured by the method of.

The pericarp-imparting or enhancing agent of the present invention or the flavor containing the agent can be used as long as it is a food or drink having a citrus flavor. For example, fruit beverages, beverages containing fruit juice, vegetable juices, effervescent beverages, concentrated juices, frozen juices, sports drinks, nutritional drinks, other functional drinks, flavored teas, dairy beverages, lactic acid bacteria beverages, soymilk and other beverages in general. , Yogurt, jelly, mousse, desserts, ice cream, lacto ice, ice milk, sherbet and other cold confectionery, and baked confectionery and steamed confectionery including Western and Japanese confectionery such as frozen confectionery, cakes, cookies, biscuits, pies, roasted rice cakes, and other rice confectionery. Confectionery such as confectionery, bread, snacks, chewing gum, hard candy, soft candy, jelly beans, gummy, general sugar confectionery including tablet confectionery, cream, fruit flavor sauce, jam and marmalade, sweetener, syrup, canned, frozen Examples of oral hygiene products include foods and the like, and examples of oral hygiene products include non-medicinal products such as oral refreshing agents, mouthwashes and toothpastes, and pharmaceuticals such as syrups.

Further, the fragrance of the present invention can be applied to fragrances for cosmetics, and any fragrance having a citrus aroma can be used. Specific uses include, for example, perfumes, colons, eau de toilette, lotions, basic cosmetics, shampoos, rinses, hair treatments, hair styling products, facial cleansers, body cleaners, dish detergents, laundry detergents, and softeners. , Cleaning products, air fresheners, deodorants, incense, incense, external skin agents, inks, stationery with odors, toys, etc.

The fragrance containing the pericarp feeling-imparting or enhancing agent of the present invention may be appropriately diluted with a solvent or the like for convenience in use. The solvent used for dilution is not particularly limited as long as it is commonly used in fragrance compositions. Further, a composition may be prepared by adding other additives commonly used as ingredients other than fragrances as long as the aroma or flavor is not adversely affected. Further, in the fragrance of the present invention, a formulation technique generally applied to fragrances can be applied, and it can be adjusted to a desired form by information such as powdering and encapsulation.

Add 3-methyl-2-butene-1-thiol, 3-mercapto-3-methylbutylformate, and 3-mercapto-3-methylbutylacetate to citrus flavors and change the flavor by sensory evaluation by a specialized panel. confirmed.

(Addition test to lemon-flavored beverage)
The lemon fragrance was prepared by blending at the following mass ratio and standing at -3 ° C for 18 hours, and then filtered. Lemon fragrance was added to a sugar acid solution containing 7% by mass of granulated sugar and 0.12% by mass of citric acid. A lemon-flavored beverage was prepared by adding 1% by mass. The compound of the present invention was added thereto and its effect was confirmed. In the addition test, sensory evaluation was performed by four trained specialized panels, and the strength of the pericarp feeling was evaluated on a five-point scale from 1 to 5 with the additive-free product as 1. The results are shown in Table 1.

Lemon fragrance ――――――――――――――――
Lemon oil 10.0
95 vol% ethanol 67.6
Water 32.4
―――――――――――――――
110.0

(Addition test to grapefruit flavored beverage)
Grapefruit fragrance was prepared by blending in the following mass ratio and allowing to stand at -3 ° C for 18 hours to obtain a grapefruit fragrance. A grapefruit-flavored beverage was prepared by adding 1% by mass. The compound of the present invention was added thereto and its effect was confirmed. In the addition test, sensory evaluation was performed by four trained specialized panels, and the strength of the pericarp feeling was evaluated on a five-point scale from 1 to 5 with the additive-free product as 1. The results are shown in Table 2.

Grapefruit fragrance ――――――――――――――――
Grapefruit oil 10.0
95 vol% ethanol 67.6
Water 32.4
―――――――――――――――
110.0

(Addition test to yuzu flavored beverage)
The citric acid solution containing 9% by mass of granulated sugar and 0.12% by mass of citric acid was mixed with the following mass ratio and filtered after standing at -3 ° C for 18 hours, and the yuzu fragrance was 0. A citric acid-flavored beverage was prepared by adding 1% by mass. The compound of the present invention was added thereto and its effect was confirmed. In the addition test, sensory evaluation was performed by four trained specialized panels, and the strength of the pericarp feeling was evaluated on a five-point scale from 1 to 5 with the additive-free product as 1. The results are shown in Table 3.

Yuzu fragrance ――――――――――――――――
Yuzu oil 5.0
95 vol% ethanol 67.6
Water 32.4
―――――――――――――――
105.0

From the test results shown in Tables 1 to 3, 3-methyl-2-butene-1-thiol, 3-mercapto-3-methylbutylformate, and 3-mercapto-3-methylbutylacetate of the present invention are citrus flavors. When added to, the feeling of pericarp was increased in all cases. Furthermore, at a certain concentration, it reminded me of the feeling of freshly squeezed pericarp. That is, the active ingredients in the present invention, 3-methyl-2-butene-1-thiol, 3-mercapto-3-methylbutylformate, and 3-mercapto-3-methylbutylacetate, are all types of citrus fruits. It was confirmed that it has the effect of improving the feeling of pericarp regardless of the type.

Claims (5)

Citrus flavored foods and drinks containing one or more selected from citrus juice, citrus peel oil, and citrus flavors, citrus flavored cosmetics or citrus flavors that impart or enhance the citrus peel sensation, 3-methyl- A citrus peeling agent or a citrus peel enhancing agent consisting of one or more selected from 2-butene-1-thiol, 3-mercapto-3-methylbutylformate, and 3-mercapto-3-methylbutylacetate. Agent. By adding the citrus-based pericarp sensation-imparting agent or the citrus-based pericarp sensation enhancer according to claim 1, one or more of the compounds (a) to (c) are contained, and (a) to (c) A citrus fragrance that imparts or enhances a citrus peel sensation , each adjusted to have the following concentrations.
(a) 3-Methyl-2-butene-1-thiol: 1ppb-10ppm
(b) 3-Mercapto-3-methylbutylformate: 1ppb-10ppm
(c) 3-Mercapto-3-methylbutylacetate: 1ppb-100ppm A food or drink having a citrus flavor or a cosmetic having a citrus aroma, which is obtained by adding the citrus flavor according to claim 2, and has a citrus flavor that imparts or enhances a citrus peel feeling . By adding the citrus-based pericarp sensation-imparting agent or the citrus-based pericarp sensation enhancer according to claim 1, one or more of the compounds (a) to (c) are contained, and (a) to (c) Citrus-flavored foods and drinks with or enhanced citrus peel sensation , each adjusted to have the following concentrations.
(a) 3-Methyl-2-butene-1-thiol: 1ppt-1ppb
(b) 3-Mercapto-3-methylbutylformate: 1ppt-1ppb
(c) 3-Mercapto-3-methylbutylacetate: 1ptt-10ppb A method for imparting or enhancing a citrus-like pericarp feeling to any of a citrus flavor, a citrus-flavored food and drink, and a cosmetic having a citrus aroma, to which the pericarp feeling-imparting or enhancing agent according to claim 1 is added.