JPH0132879B2 - - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to perfume compositions, and particularly to perfume compositions containing ω-alkenyl methyl ketones. BACKGROUND ART In recent years, as tastes have diversified and become more sophisticated, demand for fragrances having fruit-like aromas, particularly tropical fruit-like aromas, has been increasing in the fields of foods, cosmetics, and the like. In view of these circumstances, the present inventors conducted intensive studies to develop a new synthetic fragrance having a tropical fruit-like aroma, and as a result, they arrived at the highly effective present invention. That is, the present invention provides an ω-alkenyl methyl ketone represented by the general formula () CH ₂ =CH (CH ₂ ) _o CH ₂ COCH ₃ ………() (in the formula, n represents an integer from 5 to 10). The present invention provides a fragrance composition characterized by containing the following. The ω-alkenyl methyl ketone represented by the general formula () has a fresh, gentle green note and mild sweetness reminiscent of tropical fruits such as mango and guava, and the pulpy texture of melon. It also has a flower-like fragrance, and is characterized by being long-lasting.
A fragrance composition containing this as an active ingredient exhibits extremely excellent aroma or flavor characteristics and is also excellent in persistence, so it can be used as a fragrance for many purposes. As a compound represented by the general formula (), 9-
Decen-2-one, 10-undecen-2-one,
11-dodecen-2-one, 12-tridecen-2-
13-tetradecen-2-one and 14-pentadecen-2-one. Many of these compounds are described, for example, in Bull.Soc.Chim.Fr., (3), 1072
(1972), they are known, but of course, there are no prior examples in which their aroma or flavor properties suggest their use in perfumery applications. Of the compounds relatively similar to the compound represented by the general formula (), it is already known that 8-nonen-2-one imparts a dairy-like flavor to foods; It has a limited flavor similar to dairy products and has insufficient sustainability, ie, retention, which poses a practical problem. In the present invention, ω- represented by the general formula ()
One or more alkenyl methyl ketones are used by adding them to various fragrance compositions. For example, food flavoring compositions used in shade products, frozen desserts, desserts, confectionery, milk oil products, etc., perfumes, colognes, pomades, hair tonics, lotions, creams, milky lotions, soaps, shampoos, conditioners, detergents, etc. Fragrance compositions for cosmetics, indoor aromatic agents, deodorizers, aerosols, industrial fragrance compositions used in cleaners, fragrance compositions for health, hygiene, and medicine, fragrance compositions for toothpaste, fragrance compositions for tobacco,
It can be added to feed flavoring compositions and the like to significantly improve their organoleptic properties. When adding and blending the compound into a fragrance composition,
In order to obtain an effective sensory effect, it is generally preferable to add it in an amount ranging from 0.001 to 20% by weight, depending on the purpose and the type of perfume composition to be added. Even in small amounts added in this way, the organoleptic properties of the perfume compositions to which they are added can be significantly improved, strengthened and modulated. When the compound is added to a flavor composition for food, it is possible to emphasize the mellow and rich flavor. For example, when used in fruit flavor compositions such as mango, guava, melon, etc., the mild sweetness and fresh blue color are brought out, the natural freshness is doubled, and favorable results can be obtained.
When used in dairy-based flavor compositions, it provides a soft and rich flavor. In addition, the compound is
When used not only in food flavoring compositions but also in cosmetic flavoring compositions, it imparts soft sweetness and a unique green note, creating a mellow and rich aroma. This effect is particularly noticeable in perfume compositions having diasmine and tuberose-like aromas. Furthermore, when the compound is used in a flavor composition for cigarettes, it promotes a cigarette-like flavor, and in particular, the texture of the smoke becomes finer during smoking, resulting in a mild, sweet flavor. ω represented by the general formula () used in the present invention
-Alkenyl methyl ketone can be produced by any known method. The inventors are the Tettrahedron
Letters (1), 129 (1966), the compound ω-alkenyl methyl ketone was prepared using the 1,4-addition reaction of methyl vinyl ketone and α-halogenated ω-alkene with a Grignard reagent. Obtained. For example, 9-decen-2-one was obtained by reacting methyl vinyl ketone with 5-hexenylmagnesium bromide in a THF solvent under a cuprous chloride catalyst at -10°C to obtain a pure product in a yield of 57%. The present invention will be explained in detail below with reference to Examples, but the present invention is not limited thereto. Example 1 A melon fragrance was prepared according to the composition shown below. Parts by weight Ethyl butyrate 7 Isoamyl acetate 18 2-Methylbutyric acid 2 Hexyl acetate 2 Ethyl acetate 10 Methyl phenyl glycidate 4 Ethyl maltol 15 Heliotropine 2 Vanillin 5 Methyl 2-nonenoate 11 Propyl acetate 4 Methylheptenone 10% (in propylene glycol) 2 Ethyl propionate 3 Ethyl levulinate 14 Lemon oil 1 Propylene glycol 895 995 To 995 parts of the above composition, 5 parts of 9-decene-2
- When a panel of 10 experts conducted a sensory test on the additive and non-additive products, all agreed that the additive product brought out the mild sweetness and fresh, juicy melon-specific blue color, It was considered a good thing because it improved the quality of the product. Example 2 A mango fragrance was prepared according to the composition shown below. Part by weight Hexanol 6 Ethyl 2-methylbutyrate 2 Ethyl caproate 5 Cis-3-hexenol 18 Geranyl acetate 1 γ-decalactone 4 Nerol 4 Allyl caproate 8 Ethyl levulinate 7 Acetoin 2 Caproic acid 5 Methyl β-methylthio Propionate 5 Styralyl acetate 20 Ethyl butyrate 3 Hexyl acetate 3 Cis-3-hexenyl acetate 6 Vanillin 1 Propylene glycol 885 985 To 985 parts of the above composition, add 15 parts of 14-pentadecen-2-one, When a 10-person expert panel conducted a sensory test on the additive and non-additive products, 9 people found the additive product to be good, saying it was less harsh than a chemically synthesized product and had a better mango pulp feel. And so. Example 3 A butter flavor was prepared according to the composition shown below. Parts by weight Acetoin 15 2-nonanone 10 2-Undecanone 4 2-Heptanone 4 Diacetyl 7 Butyric acid 40 Caproic acid 18 Dimethyl sulfide 10% (in refined vegetable oil) 2 δ-Decalactone 10 δ-Undecalactone 5 δ-Dodecalactone 35 “Milklactone” 5 Caprylic acid 25 Capric acid 6 Isovaleraldehyde 1 Refined vegetable oil 806 993 To 993 parts of the above composition, 7 parts of 12-tridecen-2-one was added, and for the additive and non-additive products, 10 When a sensory test was conducted by a panel of experts, 9 people found the additive to be good, saying that it had a strong mellow and rich flavor, and that the flavor was long lasting. Example 4 A diasmine fragrance was prepared according to the composition shown below. Parts by weight Linalool 80 Benzyl acetate 300 Benzyl alcohol 50 Hexyl benzoate 70 Hedeion 150 Isophytol 50 Hexylcinnamic aldehyde 70 Indole 10% (in triethyl citrate) 30 Benzyl benzoate 50 Benzyl salicylate 30 Ylang-ylang oil 30 Benzyl salicylate 80 990 Above composition 990 parts of the substance, 10 parts of 11-dodecene-
2-one is added, and for additive and non-additive products,
A sensory test was conducted by a panel of 10 experts, and all agreed that the additive was better, saying it was softer and had a natural character and strength. Example 5 A tuberose base was prepared with the composition shown below. Parts by weight Linalool 70 Linalyl acetate 10 Methyl benzoate 50 Benzyl acetate 100 Methyl anthranilate 40 Benzyl benzoate 100 Benzyl salicylate 100 Methyl salicylate 10 Diasminal 100 γ-nonalactone 50 Eugenol 20 Triethyl citrate 330 980 980 parts of the above composition 20 copies When 10-undecen-2-one was added to the product, a panel of 10 experts conducted a sensory test on the additive and non-additive products, and all agreed that the additive product had a softer, rougher feel. It was rated as good because it has an increased mild creamy sweetness and a more natural and attractive fragrance tone. Example 6 A tobacco flavoring agent was prepared using the composition shown below. Parts by weight Rum (50゜) 450 Ethyl oleate 10 Ethyl stearate 10 Maltol 5 Anisole 3 Coffee extract 30 Black tea extract 20 St. John's Bread alcoholic extract 210 Veratraldehyde 10 Fennel oil 1 δ-decalactone 0.1 95% Ethanol 100 Water 150.4 999.5 Add 0.5 parts of 13-tetradecen-2-one to 999.5 parts of the above composition, and inject 0.01 to 1.0% by weight of the additive and non-additive into commercially available tobacco shreds or filters, respectively. A sensory test was conducted by 10 expert panelists, and all of them agreed that the additive was good because it promoted a tobacco-like aroma, especially when smoking, and produced a finer smoke, resulting in a milder, sweeter aroma. did. The aroma characteristics of ω-alkenyl methyl ketones in various applications were evaluated depending on the number of carbon atoms, and the results are shown in Table 1. The evaluation was carried out as follows. Tropical fruit flavor: A composition obtained by adding 15 parts of ω-alkenyl methyl ketone (n = 3 to 10) to 985 parts of the mango flavor composition shown in Example 2.
An aqueous solution containing 1 ppm was prepared and a flavor test was performed by applying it privately to evaluate the aroma dynamic characteristics other than persistence. Regarding the sustainability test, the above composition to which ω-alkenyl methyl ketone was added was applied up to 1 cm of the tip of a piece of paper (width 5 mm x length 10 cm), and after being left in an open system at room temperature for one day, the aroma intensity was evaluated. . The evaluation results were conducted by 10 expert panelists. If each aroma characteristic is well expressed, mark it with an ○.
In addition, if it cannot be said to be well expressed, it is indicated by a △ mark. Persistence is indicated by a mark ◯ if the fragrance is almost unchanged from the original, and a mark △ if a decrease is observed. For other evaluation items, ○ marks indicate that the characteristics are well expressed, and △ marks indicate that they are not. Butter flavor: Butter flavor composition shown in Example 3
7 parts of ω-alkenyl methyl ketone (n
An aqueous solution containing 1 ppm of the composition containing 3 to 10) was prepared and a flavor test was conducted by drinking. The meanings of the symbols indicating the evaluation results are the same as those for the tropical fruit flavor. Diasmine fragrance: An aqueous solution containing 1 ppm of a composition obtained by adding 10 parts of ω-alkenyl methyl ketone (n = 3 to 10) to 990 parts of the diasmine fragrance composition shown in Example 4 was prepared, and a flavor test was conducted by drinking. The aroma characteristics were evaluated. The meanings of the symbols indicating the evaluation results are the same as those for the tropical fruit flavor and butter flavor. Tuberose fragrance: A composition prepared by adding 10 parts of ω-alkenyl methyl ketone (n=3 to 10) to 980 parts of the tuberose-based fragrance composition shown in Example 5.
An aqueous solution containing 1 ppm was prepared and a drinking flavor test was conducted to evaluate the aroma characteristics. The meanings of the symbols indicating the evaluation results are the same as those for the tropical fruit flavor and butter flavor. Tobacco flavoring: Tobacco flavoring composition shown in Example 6
Add 0.5 parts of ω-alkenyl methyl ketone to 999.5 parts and add 1.0 parts to commercially available tobacco shreds or filters.
% by weight was injected, and 10 expert panelists conducted an aroma and taste test while smoking, and conducted a sensory evaluation. The meanings of the symbols indicating the evaluation results are the same as those for the tropical fruit flavor and butter flavor. 【table】

Claims (1)

[Claims] 1 ω-Alkenylmethyl represented by the general formula () CH ₂ =CH (CH ₂ ) _o CH ₂ COCH ₃ ...... () (in the formula, n represents an integer from 5 to 10) A fragrance composition characterized by containing a ketone. 2 The content of the ω-alkenyl ketone is from 0.001 to
20% by weight of the fragrance composition according to claim 1. 3 Claim 1 used for cosmetics applications
The fragrance composition according to item 1 or 2. 4. The flavor composition according to claim 1 or 2, which is used for food applications.