JP2007077226A - Flavor and fragrance composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new flavor and fragrance composition imparted with an unconventional natural feeling by solving difficulty in conventional technologies, and also a product having improved fragrance and flavor. <P>SOLUTION: This flavor and fragrance composition comprises a component selected from (R)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one and (S)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one as an active ingredient. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to a flavor and fragrance composition comprising optically active 4- (2,6,6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one as an active ingredient And a product containing the optically active substance as an active ingredient.

  Conventionally, many of the compounds used as flavor components and fragrance components in cosmetics and foods and drinks are racemic, for example, 4- (2,6,6-trimethyl-2-cyclohexen-1-yl)- A racemate of 3-buten-2-one (hereinafter sometimes referred to as “α-ionone”) has a violet-like fragrance and has been used for a long time as a flavor component and a fragrance component. On the other hand, (R) -α-yonone and (S) -α-yonone, which are optically active, are found from, for example, Black tea (Solvent extract), Boronia megastigma Nees (absolute), Raspberry fruit juice concentrate, Tobacco extract and the like. (R) -α-yonon has a violet-like, fruity, raspberry-like, floral-like strong aroma and flavor, and (S) -α-yonone is woody, cedarwood-like, raspberry-like, It is known to have a β-ionon-like aroma and flavor (Non-patent Document 1).

  However, all of these reports merely evaluate the aroma and flavor of the compound alone. There have been no reports on the evaluation of aroma using optically active α-ionone in cosmetics, and there has been no report on the flavors and odors. There has been no report of any evaluation of the above.

Lebensmittel-Untersuchung und-Forshung, (1991), 192: 111-115

  An object of the present invention is to provide an excellent flavor and fragrance composition with high palatability that can satisfy the demands of diversifying cosmetics and foods and drinks.

  Under such circumstances, the present inventors have conducted intensive research and found that racemic 4- (2,6,6-trimethyl-2-cyclohexen-1-yl) -3-butene is widely used in the market. Unlike 2-one (hereinafter sometimes referred to as “α-ionone”), it is a flavor containing optically active α-yonone as an active ingredient, which was extremely difficult to take in large amounts from natural sources. The present inventors have found that the fragrance composition has an excellent aroma and flavor with high palatability and can impart a natural feeling that is insufficient with a racemate, thereby completing the present invention.

  That is, the present invention is as follows.

(1) (R) -4- (2,6,6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one and (S) -4- (2,6,6-trimethyl- A flavor and fragrance composition comprising one or more compounds selected from 2-cyclohexen-1-yl) -3-buten-2-one as an active ingredient.

(2) The flavor and fragrance composition according to item 1, which is a fragrance composition.

(3) The fragrance composition according to item 2, wherein the content of the compound defined in item 1 is 20 ppm to 20% by mass.

(4) The optical purity of the compound defined in item 1 is 10% e.e. e. The fragrance composition according to item 2 or 3, which is as described above.

(5) (R) -4- (2,6,6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one and (S) -4- (2,6,6-trimethyl- Fragranced product characterized in that it contains one or more compounds selected from 2-cyclohexen-1-yl) -3-buten-2-one as active ingredients.

(6) (R) -4- (2,6,6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one and (S) -4- (2,6,6-trimethyl- A component selected from 2-cyclohexen-1-yl) -3-buten-2-one is contained as an active ingredient in an amount of 2 ppb to 20% by mass with respect to 1 part by mass of the fragranced product. 5. A fragranced product according to item 5.

(7) The optical purity of the compound defined in item 5 is 10% e.e. e. The fragrance-attached product according to item 5 or 6, characterized by the above.

(8) The flavor and fragrance composition according to item 1, which is a flavor composition.

(9) The flavor composition according to claim 8, wherein the content of the compound defined in item 1 is 0.2 ppm to 20% by mass.

(10) The optical purity of the compound defined in item 1 is 10% e.e. e. The flavor composition according to Item 8 or 9, which is as described above.

(11) (R) -4- (2,6,6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one and (S) -4- (2,6,6-trimethyl- A flavored product comprising one or more compounds selected from 2-cyclohexen-1-yl) -3-buten-2-one as an active ingredient.

(12) (R) -4- (2,6,6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one and (S) -4- (2,6,6-trimethyl- 2 or more compounds selected from 2-cyclohexen-1-yl) -3-buten-2-one as an active ingredient, contained in 0.02 ppb to 0.2 mass per 1 mass part of flavored product The flavored food and drink according to item 11, characterized in that:

(13) The optical purity of the compound defined in item 11 is 10% e.e. e. 13. A flavored product according to item 11 or 12, characterized by the above.

(14) (R) -4- (2,6,6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one and (S) -4- (2,6,6-trimethyl- A method for enhancing, improving or modulating aroma and flavor, comprising adding one or more compounds selected from 2-cyclohexen-1-yl) -3-buten-2-one.

  According to the present invention, (R) -4- (2,6,6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one, which was extremely difficult to take in large amounts from natural sources, and (S) -4- (2,6,6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one selected from at least one compound selected from optical purity and mixing ratio as desired The flavor and fragrance composition having a natural taste with high palatability can be obtained.

  The present invention is described in detail below.

  In the present invention, (R) -4- (2,6,6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one (hereinafter referred to as “(R) -α-ionone”) And (S) -4- (2,6,6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one (hereinafter referred to as “(S) -α-ionone”) In addition, at least one compound selected from (1) is used as an essential component.

  (R) -α-ionone and (S) -α-yonone used in the present invention can be those obtained by isolation and purification from natural products, or racemic α-ionone can be used. Those obtained by optical resolution can be used, and those obtained by a chemical synthesis method can also be used.

  In order to obtain a large amount of (R) -α-ionone and (S) -α-yonone of the present invention, it is preferable to use those obtained by using a chemical synthesis method.

  With respect to the synthesis method, for example, (1) α-cyclogeranic acid is optically resolved to obtain (R) -α-cyclogeranic acid and (S) -α-cyclogeranic acid (Non-patent Document 2), and this is used as a raw material A method of synthesizing (R) -α-ionone and (S) -α-ionone (Non-patent Document 3), (2) using optically active 2,4,4-trimethyl-2-cyclohexen-1-ol as a raw material, There is a method of synthesizing optically active α-ionone in 4 steps (Patent Document 1).

Japanese Patent Application Laid-Open No. 10-8489 Agric. Biol. Chem., 1987, 51, p1271-75 Helv. Chem. Acta., 1969, 52, p1729-31

  The present invention contains a compound selected from (R) -α-yonone and (S) -α-yonone thus obtained as an active ingredient in a flavor and fragrance composition. It was revealed that flavors and fragrance compositions with enhanced and improved flavor and flavor imparted with an unprecedented natural feeling that could not be recalled from the flavor were obtained.

That is, by blending a compound selected from (R) -α-ionone and (S) -α-yonone into a fragrance composition, the fragrance composition has a natural fresh and gorgeous floral feeling and a fresh green feeling. In addition, in the flavor composition, a fruity flavor composition such as strawberry, peach, raspberry and blueberry and a green flavored tea composition such as green tea are given a natural fresh sensation. In addition, fruit juice feeling (fruity feeling) can be enhanced and improved.
At least one compound selected from the group consisting of (R) -α-ionone and (S) -α-ionone used in the present invention has an optical purity of 10% e.e. e. It can be used from the above compounds. Preferably, 30% to 95% e.e. e. And more preferably 50% to 80% e.e. e. Range.

(R) -α-ionone and (S) -α-yonone synthesized according to the above method have an optical purity of 99% e.e. e. Although it was obtained with the above high purity, the optical purity of the optically active substance was tested to determine the optical purity, and in the present invention, approximately 10% e.e. e. It was found that the effect of optical purity began to appear at a degree. Also, approximately 30% to 95% e.e. e. If it is within the range, the effect of optical purity becomes remarkable, and further, approximately 50% to 80% e.e. e. It has been found that the optical purity effect becomes more noticeable within a range of about.
Accordingly, it has been found that, if the optical purity is within the range, it can be used as it is without purification, and the effects of fragrance, flavor and odor of cosmetics and foods can be reliably expected.

The present invention has a natural taste with high palatability by blending one or more compounds selected from (R) -α-ionone and (S) -α-yonone into commonly used flavor and fragrance compositions. The present invention provides a flavor and fragrance composition having an enhanced and improved aroma and flavor.
The present invention also uses a flavor component and a fragrance component obtained by further adding one or more compounds selected from (R) -α-ionone and (S) -α-yonone to a commonly used flavor component and fragrance component. it can. Other flavor components and fragrance components that can be added and used include various synthetic flavors, natural essential oils, synthetic essential oils, citrus oils, animal flavors, etc., especially floral, green and fruit flavor components. For example, a wide range of flavor components and fragrance components as described in Non-Patent Document 4 can be used. Typical examples include α-pinene, limonene, cis-3-hexenol, phenylethyl alcohol, styryl acetate, eugenol, rose oxide, linalool, benzaldehyde, γ-undecalactone, and ethyl butyrate.

Arctander S. "Perfume and Flavor Chemicals", published by the author, Montclair, N .; J. et al. (U.S.A.) 1969

Specifically, in the present invention, one or more compounds selected from (R) -α-ionone and (S) -α-yonone are used, for example, bergamot oil, galvanum oil, lemon oil, geranium oil, lavender oil, When added to natural essential oils such as mandarin oil, the flavor and flavor inherent in natural essential oils are mild and rich, and are fresh, highly palatable, and have a new flavor with enhanced diffusibility, retention and durability. -A fragrance composition can be prepared.
Further, for example, prepared from various synthetic fragrances, natural fragrances, natural essential oils, citrus oils, tea extracts, animal fragrances, etc., for example, strawberry, lemon, orange, grapefruit, apple, pineapple, banana, melon, green tea, oolong tea, When added to flavors and fragrance compositions such as tea, it gives a mild, rich, natural fruity-like, green-like, tropical-like fragrance and flavor, and also provides a fresh, highly-flavored fragrance and flavor. A flavor and fragrance composition can be prepared that imparts and enhances diffusibility, retention and durability.

In the present invention, the blending amount of one or more compounds selected from (R) -α-ionone and (S) -α-yonone into the flavor and fragrance composition varies depending on the type and purpose of the flavor and fragrance composition. However, in general, in the fragrance composition, for example, a blending amount of 2 ppm to 20% by mass, particularly 20 ppm to 20% by mass in the composition is preferable, and in the flavor composition, for example, the composition A blending amount of 0.02 ppm to 2 mass%, particularly 0.02 ppm to 20 mass%, more preferably 0.2 ppm to 20 mass% is suitable.
Moreover, you may mix | blend the 1 type (s) or 2 or more types of the retention agent normally used for a flavor and a fragrance composition, for example, ethylene glycol, propylene glycol, dipropylene glycol, glycerin, hexyl glycol, benzyl benzoate, triethylcyto It can also be used in combination with rate, diethyl phthalate, hercoline, medium chain fatty acid triglyceride, medium chain fatty acid diglyceride and the like.

  In the present invention, a compound selected from (R) -α-ionone and (S) -α-yonone alone, or a flavor and fragrance composition containing the compound, for example, fragrance products, basic cosmetics, finished cosmetics, hair Cosmetics, tanning cosmetics, medicinal cosmetics, hair care products, soap, body cleaning agents, bath preparations, detergents, softeners, cleaning agents, kitchen detergents, bleaching agents, aerosols, deodorants and fragrances, miscellaneous goods; or eating and drinking Fragranced products and flavored products can be provided in which products, oral compositions, and pharmaceuticals are blended with appropriate amounts capable of imparting the unique aroma and flavor.

Examples of fragranced products include the following.
Fragrance products include perfume, eau de parfum, eau de toilette, eau de cologne, etc .; basic cosmetics include face wash cream, burnishing cream, cleansing cream, cold cream, massage cream, milky lotion, skin lotion, cosmetic liquid, pack, makeup remover, etc .; Finished cosmetics include foundation, powdery, solid, talcum powder, lipstick, lip balm, blusher, eyeliner, mascara, eyeshadow, eyebrow, eye pack, nail enamel, enamel rim bar, etc .; , Brilliant, set lotion, hair stick, hair solid, hair oil, hair treatment, hair cream, hair nick, hair liquid, hair spray, bundling, hair restoration , Hair dye, and the like;

Suntan products, suntan products, sunscreen products, etc .; medicinal cosmetics, antiperspirants, after shaving lotions and gels, permanent wave agents, medicated soaps, medicated shampoos, medicated skin cosmetics, etc .; hair care products Is a shampoo, rinse, rinse-in shampoo, conditioner, treatment, hair pack, etc .; soap is cosmetic soap, bath soap, perfume soap, clear soap, synthetic soap, etc .; body cleanser is body soap, body shampoo , Hand soap, etc .; bathing agents include bath salt (bath salt, bath tablet, bath liquid, etc.), foam bath (bubble bath, etc.), bath oil (bath perfume, bath capsule, etc.), milk bath, Bath jelly, bath cube, etc .;
As detergents, heavy detergents for clothing, light detergents for clothing, liquid detergents, laundry soaps, compact detergents, powdered soaps, etc .; softeners, softeners, furniture cares, etc .; cleansers, cleansers, House cleaner, toilet cleaner, bathroom cleaner, glass cleaner, mold remover, drainpipe cleaner, etc .; kitchen detergent, kitchen soap, kitchen synthetic soap, dishwasher, etc .; bleaching agent Oxidation bleach (chlorine bleach, oxygen bleach, etc.), reduction bleach (sulfur bleach, etc.), optical bleach, etc .; As aerosols, spray type, powder spray Deodorant / fragrance as solid type, gel type, liquid type, etc. As miscellaneous goods, various forms such as tissue paper, toilet paper, etc. It can be mentioned.

Examples of the flavored product include the following.
Beverages such as fruit juices, fruit liquors, milk beverages, carbonated drinks, soft drinks, drinks; frozen confections such as ice creams, sorbets, ice candy; Japanese / Western confectionery, jam , Candies, jellies, gums, breads, coffees, cocoa, teas, oolong teas, green teas and other favorite beverages; Japanese soups, western soups, Chinese soups, flavor seasonings , Various instant beverages or foods, various snack foods, etc .; oral compositions include, for example, toothpaste, oral cleansing agents, mouthwashes, troches, chewing gums; and pharmaceuticals such as haps and ointments Various forms such as external preparations for skin and internal preparations can be mentioned.

In the present invention, fragrance products, basic cosmetics, finishing cosmetics, hair cosmetics, tanning cosmetics, medicated cosmetics, hair care products, soap, body cleaning agents, bath preparations, detergents, softeners, cleaning agents, kitchen detergents, bleaching agents, Aerosols, deodorants and fragrances, miscellaneous goods; or compounds selected from (R) -α-ionone and (S) -α-yonone for foods and drinks, oral compositions, pharmaceuticals, etc. When using flavors and fragrance compositions containing the above, as they are, or in the form of liquids in which these are dissolved in polyhydric alcohols such as alcohols, propylene glycol and glycerin; natural gums such as gum arabic and tragacanth Emulsified with emulsifier such as glycerin fatty acid ester and sucrose fatty acid ester; natural gum such as gum arabic Powder, coated with excipients such as gelatin, dextrin, etc .; solubilized with surfactants such as nonionic surfactants, anionic surfactants, cationic surfactants, amphoteric surfactants Alternatively, dispersed solubilized or dispersed forms; or microcapsules obtained by treatment with an encapsulating agent; any shape is selected and used depending on the purpose.
Further, the flavor and flavor composition / flavor composition may be stabilized and sustained-released by inclusion in a clathrate such as cyclodextrin. These are appropriately selected and used in the form of the final product, for example, liquid, solid, powder, gel, mist, aerosol and the like.

In addition, fragrance products that are fragranced, basic cosmetics, finishing cosmetics, hair cosmetics, tanning cosmetics, medicated cosmetics, hair care products, soap, body cleaning agents, bath preparations, detergents, softeners, cleaning agents, kitchen use The amount of the compound selected from (R) -α-ionone and (S) -α-yonone to detergents, bleaches, aerosols, deodorants and fragrances, sundries, etc. is the expected effect depending on the case. Although it is arbitrarily adjusted depending on the action, it is generally about 2 ppb to 20% by mass.
Moreover, the addition amount of the compound chosen from (R) -α-ionone and (S) -α-yonone to foods and beverages, oral compositions, pharmaceuticals, and the like, which are flavored products, depends on the case. Although it is arbitrarily adjusted according to the expected effect and action, it is generally about 0.02 ppb to 0.2 mass%.

  Hereinafter, the present invention will be specifically described with reference to examples. However, the present invention is not limited to these examples, and may be changed without departing from the scope of the present invention. In the examples and comparative examples, the unit of prescription shown in the table was expressed in parts by mass.

[Synthesis Example] (R) -α-ionone and (S) -α-yonone were prepared according to the synthesis methods described in Non-Patent Documents 2 and 3.
As a result of analyzing the obtained (R) -α-ionone by gas chromatography, the chemical purity was 100% and the optical purity was 99.9% e.e. e. That was all. As a result of analyzing gas of (S) -α-ionone by gas chromatography, the chemical purity was 100% and the optical purity was 99.9% e.e. e. That was all.
In addition, the obtained optical activity of 99.9% e.e. e. By mixing the above-mentioned (R) -α-yonone and (S) -α-yonone with racemic α-yonone (manufactured by SIGMA-ALDRICH) at an arbitrary ratio, (R) having any optical purity -Α-ionone and (S) -α-yonone were prepared.

Examples 1 and 2, Comparative Example 1 Rose-like fragrance composition In the rose-like fragrance composition shown in Table 1 below, an optical activity of 70% e.e. e. Of (R) -α-yonone (Example 1) and (S) -α-yonone (Example 2) and containing α-ionone at a concentration of 4% by mass. A product was prepared. A racemic α-ionone (manufactured by SIGMA-ALDRICH) was added as Comparative Example 1. Each fragrance composition was subjected to sensory evaluation by five perfumers having 5 years of experience.

  As a result, Example 1 to which (R) -α-ionone was added had a scent that emphasized a fresh and gorgeous floral feeling, and Example 2 to which (S) -α-yonone was added was used. The panelist said that the fresh and fresh green feeling had an emphasized scent, while the comparative example 1 to which the racemic body was added was a natural scent but lacked strength and had some miscellaneous feeling. All pointed out.

[Test Example 1] (R) -α-ionone and (S) -α-yonone synthesized by the method of Synthesis Example have an optical purity of 99.9% e.e. e. Although it was above, it was tested by what optical purity the effect of (R) -α-ionone and (S) -α-yonone was manifested. Racemic α-ionone (manufactured by SIGMA-ALDRICH) was mixed at an arbitrary ratio to prepare (R) -α-yonone and (S) -α-yonone of any optical purity. The rose-like fragrance composition shown in Table 1 above was prepared using (R) -α-yonone and (S) -α-yonone of any optical purity obtained.
Optical purity that can clearly discriminate the effect of the optically active substance is presented to the panel as a 2: 2 point identification method (samples A and B are first shown as light samples to identify two samples A and B). Then, after memorizing the characteristics, A and B are presented as blind samples, the sample different from A is pointed out, and the difference between the two samples from the number of correct answers obtained in several iterations. A method for determining whether or not there is: Measurement by applying Shin Sato, “Introduction to Sensory Test”, page 54 (October 16, 1978, published by Nikka Girenren Publishing Co., Ltd.).
As a result, an optical purity of 10% e.e. was obtained using either (R) -α-ionone or (S) -α-yonone. e. It was found that the effects of optical purity began to appear with the above. Also, optical purity 30% -95% e.e. e. If it is within the range, the effect of the optical purity becomes remarkable, and the optical purity is approximately 50% to 80% e.e. e. It has been found that the optical purity effect becomes more noticeable within a range of about.

[Test Example 2] In Examples 1 and 2, it was 4% by mass of (R) -α-ionone and (S) -α-yonone, but (R) -α-yonone and (S) -α. -It was tested at what compounding amount the effect of Yonon was clearly exhibited. In Table 1 above, an optical purity of 70% e. e. A rose-like fragrance composition containing (R) -α-yonone and (S) -α-yonone was prepared.
As a result, any of (R) -α-yonone and (S) -α-yonone may be used in the range of 20 ppm to 20% by mass. It was found that the amount of the fragrance composition itself was unbalanced when the amount of the fragrance composition itself was over 20% by mass.

[Examples 3-4, Comparative Example 2] Gardenia-like fragrance composition The gardenia-like fragrance composition shown in Table 2 below has an optical purity of 70% e.e. e. Of (R) -α-ionone (Example 3) and (S) -α-yonone (Example 4) and containing α-ionone at a concentration of 10% by mass. A product was prepared. Further, Comparative Example 2 was obtained by adding racemic α-ionone (manufactured by SIGMA-ALDRICH). Each fragrance composition was subjected to sensory evaluation by five perfumers having 5 years of experience.

  As a result, Example 3 to which (R) -α-ionone was added had a fragrance that emphasized a fresh and gorgeous floral feeling, and Example 4 to which (S) -α-yonone was added was used. The panelists said that the fresh and fresh green feeling had an emphasized scent, while the comparative example 2 to which the racemic body was added had a natural scent but lacked strength and had some miscellaneous feeling. All pointed out.

[Examples 5 to 6, Comparative Example 3] Carnation-like fragrance composition In the carnation-like fragrance composition shown in Table 3 below, an optical purity of 60% e.e. e. (R) -α-ionone (Example 5) and (S) -α-yonone (Example 6), and containing α-ionone at a concentration of 2% by mass, the fragrance compositions of Examples 5 and 6 A product was prepared. A racemic α-ionone (manufactured by SIGMA-ALDRICH) was added as Comparative Example 3. Each fragrance composition was subjected to sensory evaluation by five perfumers having 5 years of experience.

  As a result, Example 5 to which (R) -α-ionone was added had a fragrance that emphasized a fresh and gorgeous floral feeling, and Example 6 to which (S) -α-yonone was added was used. The panelists said that the fresh and fresh green feeling had an emphasized scent, while the comparative example 2 to which the racemic body was added had a natural scent but lacked strength and had some miscellaneous feeling. All pointed out.

Examples 7 to 8 and Comparative Example 4 Ottomanth-like fragrance composition In the Ottomanth-like fragrance composition shown in Table 4 below, an optical purity of 80% e.e. e. Of (R) -α-ionone (Example 7) and (S) -α-yonone (Example 8) and containing α-ionone at a concentration of 5% by mass. A product was prepared. A racemic α-ionone (manufactured by SIGMA-ALDRICH) was added as Comparative Example 4. Each fragrance composition was subjected to sensory evaluation by five perfumers having 5 years of experience.

  As a result, Example 7 to which (R) -α-yonone was added had a scent with a fresh and gorgeous floral feeling, and in Example 8 to which (S) -α-yonone was added. The panelists said that the fresh and fresh green sensation had an emphasized scent, while the comparative example 4 to which the racemic body was added had a natural scent but lacked strength and had some miscellaneous sensation. All pointed out.

[Examples 9 to 10, Comparative Example 5] Violet-like fragrance composition In the violet-like fragrance composition shown in Table 5 below, an optical purity of 50% e.e. e. Of (R) -α-ionone (Example 9) and (S) -α-yonone (Example 10), and containing α-ionone at a concentration of 15% by mass. A product was prepared. Further, Comparative Example 5 was obtained by adding racemic α-ionone (manufactured by SIGMA-ALDRICH). Each fragrance composition was subjected to sensory evaluation by five perfumers having 5 years of experience.

  As a result, Example 9 to which (R) -α-ionone was added had a scent with a fresh and gorgeous floral feeling, and Example 10 to which (S) -α-yonone was added. The panelists said that the fresh and fresh green sensation had an emphasized scent, while the comparative example 5 to which the racemic body was added had a natural scent but lacked strength and had some miscellaneous sensation. All pointed out.

[Examples 11 to 12, Comparative Example 6] Heliotrope-like fragrance composition In the heliotrope-like fragrance composition shown in Table 6 below, an optical purity of 65% e.e. e. Of (R) -α-ionone (Example 11) and (S) -α-yonone (Example 12) and containing α-ionone at a concentration of 8% by mass. A product was prepared. A racemic α-ionone (manufactured by SIGMA-ALDRICH) was added as Comparative Example 6. Each fragrance composition was subjected to sensory evaluation by five perfumers having 5 years of experience.

  As a result, Example 11 to which (R) -α-ionone was added had a fragrance that emphasized a fresh and gorgeous floral feeling, and in Example 12 to which (S) -α-yonone was added. The panelist said that the fresh and fresh green feeling had an emphasized scent, while the comparative example 6 to which the racemic body was added was a natural scent but lacked strength and had some miscellaneous feeling. All pointed out.

[Examples 13-14, Comparative Example 7] Lilac-like fragrance composition In the lilac-like fragrance composition shown in Table 7 below, an optical purity of 60% e.e. e. Of (R) -α-ionone (Example 13) and (S) -α-yonone (Example 14) and containing α-ionone at a concentration of 2% by weight. A product was prepared. Further, Comparative Example 7 was obtained by adding racemic α-ionone (manufactured by SIGMA-ALDRICH). Each fragrance composition was subjected to sensory evaluation by five perfumers having 5 years of experience.

  As a result, Example 13 to which (R) -α-ionone was added had a scent that emphasized a fresh and gorgeous floral feeling, and Example 14 to which (S) -α-yonone was added. It was a panelist that the fresh and fresh green feeling had an emphasized scent, while the comparative example 7 to which the racemic body was added was a natural scent, but lacked strength and had some miscellaneous feeling. All pointed out.

[Examples 15 to 16, Comparative Example 8] Lilac-like fragrance composition In the lilac-like fragrance composition shown in Table 8 below, an optical purity of 70% e.e. e. Of (R) -α-ionone (Example 15) and (S) -α-yonone (Example 16), and containing α-ionone at a concentration of 7.5% by mass. A fragrance composition was prepared. Further, Comparative Example 8 was obtained by adding racemic α-ionone (manufactured by SIGMA-ALDRICH). Each fragrance composition was subjected to sensory evaluation by five perfumers having 5 years of experience.

  As a result, in Example 15 to which (R) -α-yonone was added, it had a fragrance that emphasized a fresh and gorgeous floral feeling, and in Example 16 to which (S) -α-yonone was added. The panelist said that the fresh and fresh green feeling had an emphasized scent, while the comparative example 8 to which the racemic body was added was a natural scent but lacked strength and had some miscellaneous feeling. All pointed out.

[Examples 17-18, Comparative Example 9] Manufacture of shampoo Using the rose-like fragrance composition prepared in Examples 1-2 and Comparative Example 1, the following ingredients were heated and stirred at 80 ° C until uniform, and then A shampoo was prepared by cooling to 35 ° C. Each shampoo composition was subjected to sensory evaluation by five perfumers having 5 years of experience.

[Shampoo composition] (% by mass)
Sodium lauryl sulfate 40.00
N-coconut oil fatty acid acyl-N-
Carboxymethoxyethyl-
N-carboxymethyl
Ethylenediamine disodium 10.00
Palm oil fatty acid diethanolamide (2) 2.00
Butylene glycol 2.00
Citric acid 0.35
Sodium chloride 0.10
Methylparaben 0.20
Propylparaben 0.10
Edetate tetrasodium 0.10
Rose-like fragrance composition 0.50
Purified water balance
Total 100.00

[Evaluation results of Examples 17 to 18 and Comparative Example 9]
As a result of evaluating the fragrances of the shampoos of Examples 17 to 18 and Comparative Example 9, Example 17 to which a fragrance composition containing (R) -α-ionone was added had a fragrance that emphasized a fresh and gorgeous floral feeling. In addition, Example 18 to which the fragrance composition containing (S) -α-ionone was added had a scent that emphasized a fresh, fresh green feeling, while racemic α-ionone. All of the panelists pointed out that Comparative Example 9 to which a fragrance composition containing odor was added had a natural fragrance, but lacked strength and had some miscellaneous feeling.
Moreover, all the panelists pointed out that the shampoo based on optically active α-ionone was excellent in diffusibility and had a fresh and natural feeling.

[Examples 19 to 20, Comparative Example 10] Production of body shampoo Using the gardenia-like fragrance compositions prepared in Examples 3 to 4 and Comparative Example 2, body shampoos were prepared. Each body shampoo composition was subjected to sensory evaluation by five perfumers having 5 years experience.

[Body shampoo composition] (mass%)
Dibutylhydroxytoluene 0.05
Methylparaben 0.10
Propylparaben 0.10
Edetate tetrasodium 0.10
Potassium chloride 0.20
Glycerin 5.00
Coconut oil fatty acid diethanolamide (2) 3.00
Polyoxyethylene lauryl
Sodium ether acetate (3EO) (30%) 10.00
Palm oil fatty acid amidopropyl betaine solution (34%) 25.00
Potassium myristate (40%) 25.00
Gardenia-like fragrance composition 0.50
Purified water balance
Total 100.00

[Evaluation results of Examples 19 to 20 and Comparative Example 10]
As a result of evaluating the fragrances of the body shampoos of Examples 19 to 20 and Comparative Example 10, in Example 19 to which the fragrance composition containing (R) -α-ionone was added, a fresh gorgeous floral scent was emphasized. Example 20 to which the fragrance composition containing (S) -α-ionone was added had a scent with a fresh and fresh green feeling, while the racemic α- All the panelists pointed out that Comparative Example 10 to which a fragrance composition containing yonon was added had a natural scent, but lacked strength and had some miscellaneous feeling.
Moreover, all the panelists pointed out that the body shampoo based on optically active α-ionone was excellent in diffusibility and had a fresh and natural feeling.

[Examples 21-22, Comparative Example 11] Production of Cosmetic Cream Cosmetic creams were prepared using the lilac-like fragrance compositions prepared in Examples 13-14 and Comparative Example 7. Each cosmetic cream composition was subjected to sensory evaluation by five perfumers having 5 years of experience.

[Cosmetic cream] (mass%)
Stearyl alcohol 6.0
Stearic acid 2.0
Hydrogenated lanolin 4.0
Squalane 9.0
Octyldecanol 10.0
Glycerin 6.0
Polyethylene glycol 1500 4.0
Polyoxyethylene (25) cetyl ether 3.0
Glucerin monostearate 2.0
Methyl paraben Appropriate amount Ethyl paraben Appropriate amount Lilac-like fragrance composition 0.1
Purified water balance
Total 100.0

[Evaluation results of Examples 21 to 22 and Comparative Example 11]
As a result of evaluating the fragrances of the cosmetic creams of Examples 21 to 22 and Comparative Example 11, in Example 21 to which the fragrance composition containing (R) -α-ionone was added, the fresh gorgeous floral scent was emphasized. Example 22 to which the fragrance composition containing (S) -α-ionone was added had a scent with a fresh, fresh green feeling emphasized, while the racemic α- All the panelists pointed out that Comparative Example 11 to which a fragrance composition containing yonon was added had a natural scent, but lacked strength and had some miscellaneous feeling.
Moreover, all the panelists pointed out that the cosmetic cream based on optically active α-ionone was excellent in diffusibility and powdery feeling and had a fresh luxury feeling.

[Examples 23 to 24, Comparative Example 12] Manufacture of powder detergents Using the lilac-like fragrance compositions prepared in Examples 15 to 16 and Comparative Example 8, powder detergents were prepared. Each powder detergent composition was subjected to sensory evaluation by five perfumers having 5 years of experience.

[Powder detergent] (mass%)
C14-15 alkyl ethoxy sulfonic acid 5.5
C12-13 linear alkyl sulfonic acid 12.7
C12-13 alkyl ethoxylate 0.5
Aluminosilicate (76%) 25.4
Soap 3.0
Zeolite 23.0
Sodium silicate 1.0
Sodium carbonate Balanced sodium sulfate 4.0
Sodium sulfite 1.0
Enzyme 1.0
Acrylic acid maleic acid copolymer 2.5
Fluorescent dye 0.3
Silicone 0.3
Lilac-like fragrance composition 0.3
Purified water 3.0
Total 100.0

[Evaluation results of Examples 23 to 24 and Comparative Example 12]
As a result of evaluating the fragrances of the powder detergents of Examples 23 to 24 and Comparative Example 12, in Example 23 to which the fragrance composition containing (R) -α-ionone was added, the fresh gorgeous floral scent was emphasized. In Example 24 to which the fragrance composition containing (S) -α-ionone was added, the fresh and fresh green feeling had a scent emphasized, while the racemic α- All the panelists pointed out that Comparative Example 12 to which a fragrance composition containing yonon was added had a natural scent, but lacked strength and had some miscellaneous feeling.
Moreover, all the panelists pointed out that the powder detergent based on optically active α-ionone was excellent in diffusibility and had a fresh and natural feeling.

[Examples 25-26, Comparative Example 13] Manufacture of a softener for clothing A softener for clothing was prepared using the heliotrope-like fragrance composition prepared in Examples 11-12 and Comparative Example 6. About each softener composition for clothing, sensory evaluation was performed by five perfumers who have more than 5 years experience.

[Clothing softener] (% by mass)
Dialkyldimethylammonium chloride 15.0
POE (30) lauryl ether 3.0
Fatty acid 1.0
Dimethylpolysiloxane 0.5
Ethylene glycol 5.0
Preservative Appropriate amount sequestering agent Appropriate amount Heliotrope-like fragrance composition 0.3
Purified water balance
Total 100.0

[Evaluation results of Examples 25 to 26 and Comparative Example 13]
As a result of evaluating the aromas of the softeners for clothing of Examples 25 to 26 and Comparative Example 13, fresh gorgeous floral feeling was emphasized in Example 25 to which the fragrance composition containing (R) -α-ionone was added. It had a scent, and in Example 26 to which the fragrance composition containing (S) -α-ionone was added, it had a scent that emphasized a fresh, fresh green feeling, All of the panelists pointed out that Comparative Example 13 to which the fragrance composition containing α-ionone was added had a natural fragrance but lacked strength and had some miscellaneous feeling.
Moreover, all the panelists pointed out that the soft material based on optically active α-ionone had excellent diffusibility and a fresh refreshing feeling.

Examples 27 to 28, Comparative Example 14 Peach Flavor Composition In the peach flavor composition shown in Table 9 below, an optical purity of 70% e.e. e. Of (R) -α-ionone (Example 27) and (S) -α-yonone (Example 28), and containing α-ionone at a concentration of 0.05% by mass. A flavor composition was prepared. Further, Comparative Example 14 was obtained by adding racemic α-ionone (manufactured by SIGMA-ALDRICH). Each flavor composition was subjected to sensory evaluation by five flavorists who had more than 5 years of experience.

  As a result, Example 27 to which (R) -α-yonone was added had a savory flavor with an emphasis on fresh aging, and Example 28 to which (S) -α-yonone was added. Had a flavor that gave a fresh and fresh green feeling and emphasized the fruit juice feeling, while Comparative Example 14 to which a racemic body was added had a natural flavor, but lacked strength and had a slight miscellaneous feeling. All the panelists pointed out.

[Test Example 3] (R) -α-ionone and (S) -α-yonone synthesized by the method of Synthesis Example have an optical purity of 99.9% e.e. e. Although it was above, it was tested by what optical purity the effect of (R) -α-ionone and (S) -α-yonone was manifested. Racemic α-ionone (manufactured by SIGMA-ALDRICH) was mixed at an arbitrary ratio to prepare (R) -α-yonone and (S) -α-yonone of any optical purity. Using the obtained optical purity (R) -α-yonone and (S) -α-yonone, peach flavor compositions shown in Table 9 above were prepared.
Optical purity that can clearly discriminate the effect of the optically active substance is presented to the panel as a 2: 2 point identification method (samples A and B are first shown as light samples to identify two samples A and B). Then, after memorizing the characteristics, A and B are presented as blind samples, the sample different from A is pointed out, and the difference between the two samples from the number of correct answers obtained in several iterations. A method for determining whether or not there is: Measurement by applying Shin Sato, “Introduction to Sensory Test”, page 54 (October 16, 1978, published by Nikka Girenren Publishing Co., Ltd.).
As a result, an optical purity of 10% e.e. was obtained using either (R) -α-ionone or (S) -α-yonone. e. It was found that the effects of optical purity began to appear with the above. Also, optical purity 30% -95% e.e. e. If it is within the range, the effect of the optical purity becomes remarkable, and the optical purity is approximately 50% to 85% e.e. e. It has been found that the optical purity effect becomes more noticeable within a range of about.

[Test Example 4] In Examples 27 to 28, (R) -α-yonone and (S) -α-yonone were mixed at 0.05% by mass, but (R) -α-yonone and (S). It was tested at what compounding amount the effect of -α-yonone was manifested. The optical purity of 70% e. e. A peach flavor composition containing (R) -α-ionone and (S) -α-yonone was prepared.
As a result, any of (R) -α-yonone and (S) -α-yonone may be used in the range of 0.2 ppm to 20% by mass, and in a small amount of less than 0.2 ppm, It has been found that the effect of blending is not clearly observed, and that the flavor balance and flavor of the flavor composition itself are impaired when the amount exceeds 20% by mass.

[Examples 29 to 30, Comparative Example 15] Strawberry flavor composition In the strawberry flavor composition shown in Table 10 below, an optical purity of 75% e.e. e. Of (R) -α-yonone (Example 29) and (S) -α-yonone (Example 30), and containing α-ionone at a concentration of 0.01% by mass. A flavor composition was prepared. A racemic α-ionone (manufactured by SIGMA-ALDRICH) was added as Comparative Example 15. Each flavor composition was subjected to sensory evaluation by five flavorists who had more than 5 years of experience.

  As a result, Example 29 to which (R) -α-yonone was added had a savory flavor with an emphasis on fresh aging, and Example 30 to which (S) -α-yonone was added. Had a flavor that gave a fresh and fresh green feeling and emphasized the fruit juice feeling, while Comparative Example 15 to which the racemic body was added had a natural flavor but lacked strength and had a slight miscellaneous feeling. All the panelists pointed out.

[Examples 31 to 32, Comparative Example 16] Raspberry flavor composition In the raspberry flavor composition shown in Table 11 below, the optical activity was 55% e.e. e. Of (R) -α-ionone (Example 31) and (S) -α-yonone (Example 32) and containing α-ionone at a concentration of 1.5% by mass. A flavor composition was prepared. Further, Comparative Example 16 was obtained by adding racemic α-ionone (manufactured by SIGMA-ALDRICH). Each flavor composition was subjected to sensory evaluation by five flavorists who had more than 5 years of experience.

  As a result, Example 31 to which (R) -α-yonone was added had a savory flavor with an emphasis on fresh aging, and Example 32 to which (S) -α-yonone was added. Had a flavor that gave a fresh and fresh green feeling and emphasized the fruit juice feeling, while Comparative Example 16 to which the racemic body was added had a natural flavor but lacked strength and had a slight miscellaneous feeling. All the panelists pointed out.

[Examples 33 to 34, Comparative Example 17] Blueberry flavor composition In the blueberry flavor composition shown in Table 12 below, an optical activity of 75% e.e. e. Examples (33) and (34) containing (R) -α-yonone (Example 33) and (S) -α-yonone (Example 34) of e and containing α-ionone at a concentration of 0.2% by mass. A flavor composition was prepared. Further, Comparative Example 17 was obtained by adding racemic α-ionone (manufactured by SIGMA-ALDRICH). Each flavor composition was subjected to sensory evaluation by five flavorists who had more than 5 years of experience.

  As a result, Example 33 to which (R) -α-ionone was added had a savory flavor with an emphasis on fresh aging, and Example 34 to which (S) -α-yonone was added. Had a flavor that gave a fresh and fresh green feeling and emphasized the fruit juice feeling, while Comparative Example 17 to which the racemic body was added had a natural flavor but lacked strength and had a slight miscellaneous feeling. All the panelists pointed out.

[Examples 35 to 36, Comparative Example 18] Green Tea Flavor Composition (R) -α-Yonone (Example 35) and (S) obtained in Synthesis Example in the green tea flavor composition shown in Table 13 below. Flavor compositions of Examples 35 and 36 containing α-ionone at a concentration of 0.01% by weight were prepared by adding -α-yonone (Example 36). Further, Comparative Example 18 was obtained by adding racemic α-ionone (manufactured by SIGMA-ALDRICH). Each flavor composition was subjected to sensory evaluation by five flavorists who had more than 5 years of experience.

As a result, all of the panelists pointed out that the added Examples 35 and 36 were given a natural deep freshness not found in Comparative Example 18. As a result, Example 35 to which (R) -α-ionone was added was added. In Example 30, to which (S) -α-ionone was added, a fresh, fresh green feeling was imparted, and there was a high-class flavor. On the other hand, all the panelists pointed out that Comparative Example 18 to which the racemic body was added had a natural flavor but lacked strength and had some miscellaneous feeling.

[Examples 37 to 38, Comparative Example 19] Production of Peach-like Carbonated Beverage Using the peach flavor composition prepared in Examples 27 to 28 and Comparative Example 14, 60 parts by mass of purified water was added to the following prescription ingredients and mixed. A carbonated beverage was prepared by adding 4 parts of carbonated water to 6 parts by mass of this syrup prepared by dissolving and preparing peach fruit juice syrup. About each carbonated beverage composition, sensory evaluation was performed by five flavorists who have more than 5 years of experience.

[Prescription] (mass%)
Maltitol syrup 8.0
Aspartame 0.01
Polydextrins syrup 6.3
Peach 5 times concentrated fruit juice 0.7
Citric acid (crystal) 0.1
Peach-like fragrance 0.2
Menthol 0.0002
Menthoxypropanediol 0.00002

[Evaluation results of Examples 37 to 38 and Comparative Example 19]
As a result of evaluating the flavors of the carbonated beverages of Examples 37 to 38 and Comparative Example 19, Example 37 to which the flavor composition containing (R) -α-ionone was added had a fresh and refreshing flavor. In addition, in Example 38 to which the flavor composition containing (S) -α-ionone was added, it had a fresh and fruity flavor, while the flavor containing racemic α-yonone. All the panelists pointed out that Comparative Example 19 to which the composition was added had a natural flavor but lacked strength and had a slight miscellaneous feeling.
Moreover, all the panelists pointed out that the carbonated drink based on optically active α-ionone had excellent diffusibility and had a fresh smell.

[Examples 39 to 40, Comparative Example 20] Production of Raspberry Jam Using the raspberry flavor compositions prepared in Examples 39 to 40 and Comparative Example 20, the raspberries were heated in a low heat according to the following recipe, and boiled. Add granulated sugar, lemon juice, and brandy, and boil for about 10 minutes to avoid scorching while removing acupuncture over medium heat. After cooling to room temperature, raspberry flavor was added to prepare raspberry jam. For each jam composition, sensory evaluation was performed by five flavorists who had more than 5 years of experience.

[Prescription] (mass%)
Raspberry 250g
175 g of granulated sugar
Lemon juice 1/4 for brandy 5g
Raspberry flavor 0.1g

[Evaluation results of Examples 39 to 40 and Comparative Example 20]
As a result of evaluating the flavors of the jams of Examples 39 to 40 and Comparative Example 20, Example 39 to which the flavor composition containing (R) -α-ionone was added had a fresh and refreshing flavor. In addition, in Example 40 to which the flavor composition containing (S) -α-ionone was added, it had a fresh and savory flavor, while the flavor composition containing racemic α-yonone. All the panelists pointed out that Comparative Example 20 to which the product was added had a natural flavor but lacked strength and had a slight miscellaneous feeling.
Moreover, all the panelists pointed out that the jam based on optically active α-ionon was excellent in diffusibility and had a fresh smell.

[Examples 41-42, Comparative Example 21] Production of Strawberry Sauce Using the strawberry flavor composition prepared in Examples 29-30 and Comparative Example 15, while removing strawberries and granulated sugar over medium heat according to the following formulation: When heated and boiled, lemon juice was added and mixed, cooled to room temperature, and then a strawberry flavor was added to prepare a strawberry sauce. For each source composition, sensory evaluation was performed by five flavorists with more than 5 years of experience.

[Prescription] (mass%)
Strawberry 250g
175 g of granulated sugar
Strawberry flavor 0.1g for 1/4 lemon juice

[Evaluation results of Examples 41 to 42 and Comparative Example 21]
As a result of evaluating the flavors of the strawberry sauces of Examples 41 to 42 and Comparative Example 21, Example 41 to which the flavor composition containing (R) -α-ionone was added had a fresh and refreshing flavor. Further, in Example 42 to which the flavor composition containing (S) -α-ionone was added, it had a fresh and fruity flavor, while the flavor containing racemic α-yonone. All the panelists pointed out that Comparative Example 21 to which the composition was added had a natural flavor but lacked strength and had a slight miscellaneous feeling.
In addition, all the panelists pointed out that the strawberry sauce based on optically active α-ionon had excellent diffusibility and had a fresh smell.

Claims (6)

(R) -4- (2,6,6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one and (S) -4- (2,6,6-trimethyl-2-cyclohexene) A flavor and fragrance composition comprising one or more compounds selected from -1-yl) -3-buten-2-one as an active ingredient. The flavor and fragrance composition according to claim 1, which is a fragrance composition. (R) -4- (2,6,6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one and (S) -4- (2,6,6-trimethyl-2-cyclohexene) A fragranced product comprising one or more compounds selected from -1-yl) -3-buten-2-one as an active ingredient. A flavor and fragrance composition according to claim 1, which is a flavor composition. (R) -4- (2,6,6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one and (S) -4- (2,6,6-trimethyl-2-cyclohexene) A flavored product comprising as an active ingredient one or more compounds selected from -1-yl) -3-buten-2-one. (R) -4- (2,6,6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one and (S) -4- (2,6,6-trimethyl-2-cyclohexene) -1-yl) A method for enhancing, improving or modulating aroma and flavor, which comprises adding one or more compounds selected from 3-buten-2-one.