JP7377341B2 - Flavoring agent consisting of 10-hydroxy-4,8-dimethyl-4-decenal - Google Patents

Description

The present invention relates to a flavoring agent comprising 10-hydroxy-4,8-dimethyl-4-decenal, and further relates to a flavoring composition containing the flavoring agent, and a consumable product containing the flavoring agent or flavoring composition. Concerning wealth.

In recent years, consumer demands for food, drink, and cosmetics have become more sophisticated and diversified, and in particular, attention has been focused on fragrance, and the characteristics of fragrance have become an important factor in the appeal of products. For example, there is an increasing demand for flavoring compounds that can be formulated to improve flavor, for example to impart or enhance aroma and taste, such as persistence, naturalness, and volume, and to impart better flavor to consumer products. There continues to be hope for the development of new flavor compounds that can differentiate the flavors of existing products.

Regarding 10-hydroxy-4,8-dimethyl-4-decenal, according to JP-A-52-91815, 10-hydroxy-4,8-dimethyl-4-decenal synthesized by the method described in the document is It is described as a compound reminiscent of a ripe, sweet cyclamen, and the compound is specifically used for the fragrance of flowers characterized by sweetness and richness, such as cyclamen, jasmine, ylang-ylang, and gardenia. has been proposed for use.

An object of the present invention is to provide a new flavoring agent that can impart various flavors to various articles.

The present inventors conducted intensive research to solve the above problem and found that, to their surprise, 10-hydroxy-10-hydroxy- Regarding 4,8-dimethyl-4-decenal, it has been discovered that by setting a specific isomer ratio, it has excellent effects such as various flavor imparting effects and improved odor persistence. Regarding 10-hydroxy-4,8-dimethyl-4-decenal, for uses other than those described in JP-A-52-91815, usefulness of geometric isomers and mixtures thereof, etc., please refer to JP-A-52-91815. The discovery by the present inventors was completely unexpected, as there have been no research reports for more than 30 years since 1978, the year Publication No. 91815 was published.

Thus, the present invention provides the following aspects.
[1] A flavor imparting agent consisting of 10-hydroxy-4,8-dimethyl-4-decenal represented by the following formula (1).

[In the formula, the wavy line represents a mixture of E-form and Z-form, and represents that the content x of Z-form in the mixture is 0%≦x≦50%. ]
[2] The flavor imparting agent according to [1], wherein the flavor is a lily of the valley or a citrus flavor.
[3] A fragrance composition containing the flavor imparting agent according to [1] or [2].
[4] A consumer product containing the flavor imparting agent according to [1] or [2], or the flavor composition according to [3].
[5] A method for imparting flavor to a flavor composition, which comprises blending the flavor imparting agent according to [1] or [2] into the flavor composition.
[6] A method for imparting flavor to consumer goods, comprising blending the flavor imparting agent according to [1] or [2] or the flavor composition according to [3] into consumer goods.

Hereinafter, the present invention will be explained in more detail by giving specific examples. In this specification, "~" indicating a range means a range that includes the lower limit and the upper limit, concentration and % represent mass concentration and mass %, respectively, unless otherwise specified, and ratios refer to the range unless otherwise specified. As far as mass ratio is concerned. Further, unless otherwise specified, operations and measurements of physical properties, etc. were performed under conditions of room temperature (20 to 25° C.)/relative humidity of 40 to 50% RH, but the conditions are not limited to these.

(Flavoring agent of the present invention)
The flavor imparting agent according to one embodiment of the present invention consists of 10-hydroxy-4,8-dimethyl-4-decenal represented by formula (1). According to the present invention, it is possible to provide an excellent new flavor imparting agent capable of imparting various flavors. Furthermore, the present invention can provide a flavor imparting agent and a fragrance composition that are excellent in natural feel, diffusibility, and residual fragrance. Although the mechanism by which such an effect is obtained is unknown, it is presumed that the E-form has a stronger aroma than the Z-form, and also has higher diffusibility and fragrance retention. However, the above mechanism is a guess and does not limit the scope of the present invention in any way. Another aspect of the present invention provides an application in which 10-hydroxy-4,8-dimethyl-4-decenal represented by formula (1) is used as a flavoring agent.

In addition, in this specification, 10-hydroxy-4,8-dimethyl-4-decenal represented by formula (1) may also be referred to as a compound represented by formula (1) or a compound of formula (1). be.

[In the formula, the wavy line represents a mixture of E-form and Z-form, and represents that the content x of Z-form in the mixture is 0%≦x≦50%. ]
In this specification, 0% content x of Z form in the mixture means that 10-hydroxy-4,8-dimethyl-4-decenal represented by formula (1) is E form (that is, (4E )-10-hydroxy-4,8-dimethyl-4-decenal). In particular, from the viewpoint of having an excellent lily-of-the-valley-like aroma, and excellent natural feeling, diffusibility, and residual fragrance, the content x of the Z-isomer in the compound represented by formula (1) should be 0%≦x≦40%. preferably, 0%≦x≦35%, even more preferably 0%≦x≦25%, even more preferably 0%≦x≦22%, 0%≦x Even more preferably ≦20%, even more preferably 0%≦x≦8%, and particularly preferably 0%≦x≦5%. Moreover, most preferably, the compound represented by formula (1) is substantially only the E form (that is, the content x of the Z form is 0%).

When the Z form is present in the mixture, the range of the content x of the Z form is, for example, the lower limit is 0.01%, 0.1%, 1%, 3%, 5%, 7%, 10%, 15%. %, 20%, 30%, 40%, and the upper limit is 50%, 40%, 35%, 30%, 25%, 22%, 20%, 15%, 8%, 7%, 5%, The range may be set to either 3% or 1%, and any combination of these lower and upper limits may be used. Specifically, 1%≦x≦40%, 3%≦x≦30%, 5%≦x≦25%, 7%≦x≦22%, or 7%≦x≦20%. Not limited to these. When the content x of the Z-form in the mixture is 50% or less, the fragrance diffusivity and fragrance persistence are high, and the lower the content x of the Z-form, the higher the fragrance diffusion and fragrance persistence. . On the other hand, when the content x of the Z-form exceeds 50% (that is, x>50%), the diffusivity and persistence of the fragrance decrease. The upper limit of the Z-isomer content may be determined depending on the desired flavor imparting effect. As described above, the content x of the Z-form in the mixture may be 0% (that is, substantially no Z-form and only the E-form).

Note that the Z-isomer content x can be determined by gas chromatography (GC), and can be measured, for example, using the apparatus and conditions described in Examples.

The present inventors described 10-hydroxy-4,8-dimethyl-4-decenal represented by the formula (1) having a specific isomer ratio as the aroma imparting agent of the present invention in the Examples described below. As shown, we have discovered the surprising usefulness of having a very wide range of flavor improvement effects, leading to the present invention.

The flavor imparting agent of the present invention can be blended into various articles, for example, as a flavoring compound. Articles to which the flavor imparting agent of the present invention can be blended are not particularly limited, but include consumer goods such as cosmetics, food and drinks, and the like. Furthermore, the flavor imparting agent of the present invention can be blended into various flavor compositions to impart aroma to the compositions.

As used herein, flavor refers to one or more types of sensations that can be changed by scent, typically including smell and taste. As used herein, the term "imparting flavor" includes adding or enhancing the flavor, and for example, the flavor may be improved as a result of the addition. Furthermore, as a result of the addition of flavor, sensations other than smell and taste, such as cold sensations, warm sensations, textures (such as down the throat, hardness, viscosity, etc., also referred to as textures), irritating sensations such as carbonic acid and spiciness, etc. It may be something that enhances, suppresses, or improves.

The compounds of formula (1) as flavoring agents of the present invention may be obtained by any method available to those skilled in the art. For example, it can be synthesized by the method described below, but is not limited thereto.

(Production method and synthesis example of compound of formula (1))
As another form of the present invention, the following formula (2):

[In the formula, the wavy line represents a mixture of E-form and Z-form, and represents that the content x' of Z-form in the mixture is 0%≦x'≦55%. ] is prepared, and the compound represented by the above formula (2) is reacted to form the following formula (1):

[In the formula, the wavy line represents a mixture of E-form and Z-form, and represents that the content x of Z-form in the mixture is 0%≦x≦50%. ]
Provided is a method for producing 10-hydroxy-4,8-dimethyl-4-decenal, which comprises obtaining a compound represented by:

In this way, by adjusting the ratio of the E-form and Z-form of the starting material (Z-form content x') to an appropriate range, the final product, the E-form of the compound represented by formula (1), can be obtained. The ratio of Z-form and Z-form (Z-form content x) can be controlled within an appropriate range.

When the content x' of the Z form in the mixture of starting materials is 0%, it means that 2,3-dihydrofarnesol represented by formula (2) is the E form (that is, (6E)-3,7,11- It means that it is a pure substance of trimethyl-6,10-dodecadien-1-ol). From the viewpoint of obtaining a flavor imparting agent that has an excellent lily of the valley aroma, natural aroma, diffusivity, and lingering feeling, the content x' of the Z form of the starting material is set to be 0%≦x'≦45%. Preferably, 0%≦x'≦40%, more preferably 0%≦x'≦30%, even more preferably 0%≦x'≦25%, 0%≦x Even more preferably, '≦22%, even more preferably, 0%≦x'≦8%, and particularly preferably, 0%≦x'≦5%.

When the Z form is present in the mixture of the starting materials, the range of the content x' of the Z form is, for example, the lower limit is 0.01%, 0.1%, 1%, 3%, 5%, 7%, 10%, 15%, 20%, 30%, 40%, and the upper limit is 55%, 50%, 45%, 40%, 35%, 30%, 27%, 25%, 22%, 20% , 15%, 8%, 7%, 5%, 3%, 1%, and any combination of these lower and upper limits may be used. Specifically, 1%≦x'≦45%, 3%≦x'≦35%, 5%≦x'≦30%, 7%≦x'≦27%, or 7%≦x'≦25% may be used, but is not limited to these. The upper limit of the Z-form content x' of the starting material may be determined depending on the desired flavoring effect. As described above, the Z-form content x' of the starting material may be 0% (that is, substantially no Z-form and only E-form).

The Z-isomer content x' of the starting material can be determined by gas chromatography (GC), for example, using the apparatus and conditions described in Examples.

The Z-isomer content x' of the starting material can be controlled by methods known to those skilled in the art, for example, the method described in JP-A-8-245979 (corresponding to US Pat. No. 5,753,610). A starting material having a desired Z-form content x' can be obtained (prepared) with reference to the following.

The method for producing a flavoring agent according to the present invention may further include the following steps as necessary;
(a) introducing a protecting group that protects the hydroxyl group of the compound represented by the above formula (2);
(b) converting the compound obtained in step (a) above into a halogenhydrin;
(c) epoxidizing the compound obtained in step (b) above;
(d) Optionally, introducing a protecting group to protect the hydroxyl group of the compound obtained in step (c) above, as necessary;
(e) oxidatively cleaving the epoxidized carbon-carbon bond portion of the compound obtained in step (c) or step (d) above;
(f) Removing the protecting group from the compound obtained in step (e) above.

An outline of the above steps is shown below.

[In the above formulas (3), (4), (6) and (7), Pg represents a protecting group, and in the above formula (4), X represents a halogen atom. ]
The protecting group used in the above steps (a) and (d) (i.e., Pg in the above formulas (3), (4), (6) and (7)) is not particularly limited, and for example, an acetyl group. , benzoyl group, pivaloyl group, etc. In step (b) above, it is preferable to carry out bromohydrination using an appropriate reagent. That is, in the above formula (4), X is preferably a bromine atom. Note that the above step (d) is an optional step, and if the epoxidized compound obtained in the step (c) is not deprotected (that is, the compound represented by formula (4) If the compound represented by formula (6) can be obtained directly from the compound), step (d) may be omitted.

In each of the above reactions, those skilled in the art can appropriately select reagents, solvents, and reaction conditions so as to obtain the desired product.

A specific example of the above manufacturing method is as follows. First, the E form or an isomer mixture of E form and Z form of 2,3-dihydrofarnesol is prepared, and the hydroxyl group (also referred to as hydroxyl group, hydroxyl group, or OH group) of the compound is acetylated. After protection, bromohydrin is produced with N-bromosuccinimide (NBS), and then an epoxide is produced by alkali treatment. At this time, it is thought that the acetyl protecting group is removed and becomes a hydroxyl group, so after protecting it again with an acetyl group, the carbon-carbon bond is oxidatively cleaved from the epoxide using an oxidizing agent such as periodic acid to generate an aldehyde. Treatment removes the acetyl group protection and converts it back to a hydroxyl group. Through the above treatment, a compound represented by formula (1) can be obtained. In the compound represented by formula (1), the E of the starting material (2,3-dihydrofarnesol) is adjusted as appropriate so that the content x of the Z form in the mixture of the E form and the Z form falls within a desired numerical range. The ratio of Z-form and Z-form (Z-form content x') can be studied.

(Flavour composition/method for imparting flavor to a perfume composition)
A flavor composition according to yet another embodiment of the present invention includes a flavor imparting agent consisting of a compound represented by formula (1). Furthermore, another aspect of the present invention also provides an application of the compound represented by formula (1) as a fragrance composition. Such fragrance compositions can be blended into various articles for the purpose of imparting flavor. Specific examples include fragrance compositions for cosmetics (also referred to as fragrance compositions) and fragrance compositions for food and drink products (also referred to as flavor compositions). As mentioned above, examples of products to be blended include various consumer goods such as cosmetics, food and beverages, and other miscellaneous goods. The form of the fragrance composition of the present invention is not particularly limited, and examples include water-soluble fragrance compositions, oil-soluble fragrance compositions, emulsified fragrance compositions, and powdered fragrance compositions.

Furthermore, another aspect of the present invention provides a method for imparting flavor to a flavor composition, which includes blending the above-mentioned flavor imparting agent into the flavor composition. The method of blending the flavoring agent is not particularly limited, and may be blended using methods known to those skilled in the art.

The concentration of the flavor imparting agent made of the compound represented by formula (1) in the fragrance composition of the present invention can be arbitrarily determined depending on the target and the purpose of blending the fragrance composition.

For example, in the case of a perfume composition for cosmetics, the concentration is, for example, 0.001% to 50%, preferably 0.01% to 20%, more preferably 0.00% to the total mass of the perfume composition. The range is preferably 1% to 10%, particularly preferably 0.1% to 5%. More specifically, the lower limit value is set to 0.001%, 0.01%, 0.1%, 1%, 5%, 10%, 20%, 30%, or 40%, and the upper limit value is set to 50%. %, 40%, 30%, 20%, 10%, 5%, 1%, 0.1%, 0.01%, within the range of any combination of these lower and upper limits. However, it is not limited to these. Although it depends on the formulation and fragrance tone of the fragrance composition, it is high when the concentration of the flavor imparting agent consisting of the compound represented by formula (1) in the fragrance composition for cosmetics is 0.001% or more. The blending effect can be felt, and if it is 50% or less, the scent derived from the compound represented by formula (1) will not become too strong, causing undesirable changes in the aroma characteristics of the cosmetic fragrance composition to be blended. This can be suppressed. However, depending on the flavor of the perfume composition for cosmetics to be blended, it may be blended at a concentration below the lower limit or above the upper limit.

In the case of a flavor composition for food and drink, the amount may be within the range of, for example, 10 ppb to 10%, preferably 100 ppb to 1%, more preferably 1 ppm to 0.1%, based on the total mass of the flavor composition. More specifically, the lower limit is 10ppb, 100ppb, 1ppm, 10ppm, 100ppm, 0.1%, 1%, and the upper limit is 10%, 1%, 0.1%, 100ppm, 10ppm, 1ppm. , 100 ppb, and any combination of these lower and upper limits, but is not limited thereto. Although it depends on the formulation and flavor tone of the flavoring composition, if the concentration of the flavoring agent made of the compound represented by formula (1) in the flavoring composition for food and drink is 10 ppb or more, a high blending effect can be obtained. If the amount is 10% or less, the aroma derived from the compound represented by formula (1) will not become too strong, and undesirable changes in the flavor characteristics of the flavor composition for food and beverages to be blended will be suppressed. can do. However, depending on the flavor of the food/beverage flavor composition to be blended, it may be blended at a concentration below the lower limit or above the upper limit.

The fragrance composition of the present invention contains a flavor imparting agent consisting of a compound represented by formula (1), and "contains" includes an embodiment in which it is contained in an amount capable of producing a desired aroma. Therefore, the fragrance composition of the present invention may contain only the compound represented by formula (1), but may contain other fragrance ingredients and other additives such as solvents as long as the desired fragrance is not impaired. It may also include. Such other fragrance ingredients and other additives are such that the fragrance composition (and the compound represented by formula (1) contained in the composition) is contained in the additive at an appropriate concentration. It can also be added for the purpose of uniform dispersion.

Examples of such compounds or ingredients include various types of flavor compounds or flavor compositions, oil-soluble pigments, vitamins, functional substances, fish and meat extracts, plant extracts, yeast extracts, and animal and plant proteins. Examples include hydrolyzates, animal and plant protein decomposition products, starches, dextrins, sugars, amino acids, nucleic acids, organic acids, and solvents. For example, "Patent Office Bulletin, Collection of Well-Known and Commonly Used Techniques (Fragrances) Part II Food Flavors, Published January 14, 2000," "Survey on the Use of Food Flavor Compounds in Japan" (FY2000 Health Science Research Report, Japan Fragrance Industry Association, published March 2001) and "Synthetic Fragrances Chemistry and Product Knowledge" (published in a new and enlarged edition on December 20, 2016, edited by the Synthetic Fragrances Editorial Committee, published by Kagaku Kogyo Nippo). Examples include natural essential oils, natural fragrances, and synthetic fragrances.

Specific examples of synthetic fragrance compounds include hydrocarbon compounds such as monoterpenes such as α-pinene, β-pinene, γ-terpinene, myrcene, camphene, and limonene; sesquiterpenes such as valencene, cedrene, caryophyllene, and longifolene; Examples include 3,5-undecatriene.

Examples of alcohol compounds include saturated alkanols such as butanol, pentanol, 3-octanol, and hexanol, unsaturated alcohols such as (Z)-3-hexen-1-ol, prenol, and 2,6-nonadienol, linalool, geraniol, and citronellol. , terpene alcohols such as , tetrahydromyrcenol, farnesol, nerolidol, cedrol, α-terpineol, terpinen-4-ol, and borneol, and aromatic alcohols such as benzyl alcohol, phenylethyl alcohol, and cinnamyl alcohol.

Examples of aldehyde compounds include saturated aldehydes such as acetaldehyde, hexanal, octanal, decanal, and hydroxycitronellal, unsaturated aldehydes such as (E)-2-hexenal, 2,4-octadienal, citronellal, citral, myrtenal, and peryl. Examples include terpene aldehydes such as aldehydes, aromatic aldehydes such as benzaldehyde, cinnamyl aldehyde, vanillin, ethyl vanillin, heliotropin, and p-tolyl aldehyde.

Ketone compounds include saturated and unsaturated ketones such as 2-heptanone, 2-undecanone, 1-octen-3-one, acetoin, 6-methyl-5-hepten-2-one (methylheptenone), diacetyl, 2,3 - diketones and hydroxyketones such as pentanedione, maltol, ethyl maltol, cyclotene, 2,5-dimethyl-4-hydroxy-3(2H)-furanone, terpene ketones such as carvone, menthone, nootkatone, α-ionone, β- Examples include ketones derived from terpene decomposition products such as ionone and β-damascenone, and aromatic ketones such as raspberry ketone.

Examples of the furan or ether compound include furfuryl alcohol, furfural, rose oxide, linalool oxide, mentofuran, theaspiran, estragol, eugenol, 1,8-cineol, and the like.

Ester compounds include ethyl acetate, isoamyl acetate, octyl acetate, ethyl butyrate, ethyl isobutyrate, isoamyl butyrate, ethyl 2-methylbutyrate, ethyl isovalerate, 2-methylbutyl isobutyrate, ethyl hexanoate, allyl hexanoate, heptane. Aliphatic esters such as ethyl acid, ethyl caprylate, isoamyl isovalerate, ethyl nonanoate, terpene alcohol esters such as linalyl acetate, geranyl acetate, labandulyl acetate, terpinyl acetate, neryl acetate, benzyl acetate, methyl salicylate, cinnamic acid Examples include aromatic esters such as methyl, cinnamyl propionate, ethyl benzoate, cinnamyl isovalerate, and ethyl 3-methyl-2-phenylglycidate.

Examples of lactone compounds include saturated lactones such as γ-decalactone, γ-dodecalactone, δ-decalactone, and δ-dodecalactone, and unsaturated lactones such as 7-decen-4-olide and 2-decen-5-olide. .

Examples of acid compounds include saturated and unsaturated fatty acids such as acetic acid, butyric acid, isovaleric acid, caproic acid, octanoic acid, stearic acid, oleic acid, linoleic acid, and linolenic acid.

Examples of nitrogen-containing compounds include indole, skatole, pyridine, alkyl-substituted pyrazine, methyl anthranilate, and trimethylpyrazine.

Examples of sulfur-containing compounds include methanethiol, dimethyl sulfide, dimethyl disulfide, allyl isothiocyanate, 3-methyl-2-butene-1-thiol, 3-methyl-2-butanethiol, 3-methyl-1-butanethiol, 2 -Methyl-1-butanethiol, 3-mercaptohexanol, 4-mercapto-4-methyl-2-pentanone, 3-mercaptohexyl acetate, p-mentha-8-thiol-3-one, and furfuryl mercaptan. .

Natural essential oils include sweet orange, bitter orange, petitgrain, lemon, bergamot, mandarin, neroli, peppermint, spearmint, lavender, chamomile, rosemary, eucalyptus, sage, basil, rose, hyacinth, lilac, geranium, jasmine, and ylang-ylang. , anise, clove, ginger, nutmeg, cardamom, cedar, cypress, vetiver, patchouli, and labdanum.

Examples of natural fragrances include jasmine absolute, hyacinth absolute, rose absolute, tuberose absolute, vanilla absolute, and galbanum resinoid.

Examples of various animal and plant extracts include extracts of herbs or spices, extracts of coffee, green tea, black tea, or oolong tea, milk or milk processed products, and various enzymatic decomposition products thereof such as lipase and/or protease.

Furthermore, in addition to the above, other additives described in the (Application Examples) section below can also be used as appropriate. Note that the above-mentioned other fragrance components and other additives may be used alone or in combination of two or more.

The fragrance composition of the present invention can be prepared by blending the compound represented by formula (1) with an appropriate solvent or dispersion medium by a known method.

The fragrance composition of the present invention may be in the form of a solution, emulsion, powder, or other solid preparation (solid fat, etc.) in which the compound represented by formula (1) and other components are dissolved in a water-soluble or oil-soluble solvent. etc. are preferable.

Examples of water-soluble solvents include ethanol, methanol, acetone, tetrahydrofuran, acetonitrile, 2-propanol, methyl ethyl ketone, glycerin, propylene glycol, and dipropylene glycol. Among these, ethanol or glycerin is particularly preferred from the viewpoint of use in foods and drinks. Oil-soluble solvents include vegetable oils, animal oils, refined oils and fats (for example, processed oils and fats such as medium-chain fatty acid triglycerides, and short-chain fatty acid triglycerides such as triacetin and tripropionine), various essential oils, and triethyl citrate. For example,

Further, in order to obtain an emulsified preparation, the compound represented by formula (1) can be obtained by emulsifying it with a water-soluble solvent and an emulsifier. The method of emulsifying the compound represented by formula (1) is not particularly limited, and various types of emulsifiers conventionally used in foods and drinks, such as fatty acid monoglyceride, fatty acid diglyceride, fatty acid triglyceride, propylene glycol. Fatty acid ester, sucrose fatty acid ester, polyglycerin fatty acid ester, lecithin, modified starch, sorbitan fatty acid ester, Quillaya extract, gum arabic, gum tragacanth, guar gum, gum Karaya, xanthan gum, pectin, alginic acid and its salts, carrageenan, gelatin, casein Quillaya An emulsion with excellent stability can be obtained by emulsification treatment using an emulsifier such as saponin or sodium caseinate using a homomixer, colloid mill, rotating disk homogenizer, high-pressure homogenizer, or the like. The amount of these emulsifiers to be used is not strictly limited and can be varied over a wide range depending on the type of emulsifier used, but usually, for 1 part by mass of the compound represented by formula (1), A range of from about 0.01 to about 100 parts by weight, preferably from about 0.1 to about 50 parts by weight, is suitable. In order to stabilize the emulsification, the aqueous solvent solution may contain, in addition to water, polyhydric alcohols such as glycerin, propylene glycol, sorbitol, maltitol, sucrose, glucose, trehalose, sugar solution, and reduced starch syrup. One type or a mixture of two or more types can be blended.

Moreover, the emulsion thus obtained can be made into a powder formulation by drying, if desired. When powdering, saccharides such as gum arabic, trehalose, dextrin, sugar, lactose, glucose, starch syrup, reduced starch syrup, etc. can be added as necessary. The amounts used can be appropriately selected depending on the desired properties of the powder formulation.

The perfume composition of the present invention may further contain components commonly used in perfume compositions, if necessary. For example, retaining solvents such as water and ethanol, and fragrances such as ethylene glycol, propylene glycol, dipropylene glycol, glycerin, hexyl glycol, benzyl benzoate, triethyl citrate, diethyl phthalate, Herkolin, medium chain fatty acid triglyceride, and medium chain fatty acid diglyceride. can contain agents.

(Application example)
The flavor imparting agent made of the compound represented by formula (1) or the flavor composition containing the same may be blended into arbitrary articles such as various consumer goods. That is, still another embodiment of the present invention provides a consumer product containing the flavor imparting agent or the flavor composition. The above-mentioned flavor imparting agent and the above-mentioned fragrance composition are preferably used in consumer goods such as cosmetics, foods and drinks, and particularly preferably used in cosmetics.

Still another aspect of the present invention provides a method for imparting flavor to consumer goods, which includes blending the above flavor imparting agent or the above flavor composition into consumer goods. The method of blending the flavor imparting agent and/or the flavor composition is not particularly limited, and may be blended using methods known to those skilled in the art.

Examples of cosmetics as consumer goods include, but are not limited to, perfumes such as eau de cologne, eau de toilette, eau de parfum, and parfum; hair care products such as shampoos, conditioners, and hair conditioners (hair creams, pomades, etc.); Cosmetics such as foundation, lipstick, lip balm, lip gloss, lotion, cosmetic emulsion, cosmetic cream, cosmetic gel, serum, pack agent; Deodorant such as antiperspirant spray, deodorant sheet, deodorant cream, deodorant stick, etc. Products; Inorganic salt-based, cooling-based, carbon dioxide-based, skin care-based, enzyme-based, herbal medicine-based bath additives; Suntan cosmetics such as suntan products and sunscreen products; Facial cleansers such as face soaps and face creams, and body products Cleaning agents such as soap, body soap, laundry soap, laundry detergent, disinfectant detergent, deodorant detergent, fabric softener, kitchen detergent, cleaning detergent, disinfectant, bleach, toothpaste, mouthwash; dry or wet Examples include health and hygiene products or quasi-drugs such as tissue paper, toilet paper, masks, bandages, bandages, and compresses; aromatic deodorizers for rooms and cars; etc.

Further, the form (dosage form) of the cosmetic product is not particularly limited. For example, it is applicable to various forms such as liquid, emulsion, cream, paste, solid, and multilayer. In addition to these, it can also be applied as a sheet agent, spray agent, or mousse agent.

Such cosmetics containing a flavoring agent made of the compound represented by formula (1) or a fragrance composition containing the same can be produced using methods known to those skilled in the art.

The cosmetic product according to one embodiment of the present invention contains the flavoring agent consisting of the compound represented by formula (1) or the flavoring composition of the present invention containing the same at an appropriate concentration as long as the desired aroma is not impaired. , and may contain other additives so as to be uniformly dispersed.

Other additives are not particularly limited and known ones can be used, including hydrocarbons such as squalane, petrolatum, and microcrystalline wax; jojoba oil, carnauba wax, octyldodecyl oleate, and phenylethyl acetate. , phenylethyl butyrate, phenylethyl formate, phenylethyl phenylacetate, phenylethyl isobutyrate, benzyl benzoate, phenylethyl propionate, phenylpropyl acetate, and other esters; phenylacetaldehyde, benzaldehyde, cinnamic aldehyde, hexylcinnamic aldehyde, etc. aldehydes; triglycerides such as olive oil, beef tallow, and coconut oil; fatty acids such as stearic acid, oleic acid, and ritinoleic acid; linalool, citronellol, bakudanol, dihydromircenol, dihydrolinalool, geraniol, nerol, sandalol, Alcohols such as Santarex, terpineol, tetrahydrolinalool, benzyl alcohol, phenylethyl alcohol, phenylethyldimethylcarbinol, hydroxycitronellal; Higher alcohols such as oleyl alcohol, stearyl alcohol, octyldodecanol; ethylene glycol, propylene glycol , glycerin, polyhydric alcohols such as 1,3-butanediol; indole, 5-methyl-3-heptanone oxime, limonenethiol, 1-p-menthene-8-thiol, butyl anthranilate, cis-3 anthranilate -Nitrogen-containing and/or sulfur-containing compounds such as hexenyl, phenylethyl anthranilate, cinnamyl anthranilate, dimethyl sulfide, and 8-mercaptomenthone; anionic surfactants such as sulfosuccinate and sodium polyoxyethylene alkyl sulfate; alkyl Amphoteric surfactants such as betaine salts; cationic surfactants such as dialkyl ammonium salts; Examples include ionic surfactants; thickening/gelling agents; antioxidants; ultraviolet absorbers; coloring agents; preservatives; powders and the like.

In addition to these, other fragrance ingredients listed in the above section (Flavor composition and method for imparting flavor to fragrance composition) can also be used as other additives in cosmetics. Note that the other additives mentioned above may be used alone or in combination of two or more.

The fragrance tone of the cosmetics is not particularly limited, and may be any fragrance tone that can be imparted with a flavor imparting agent made of the compound represented by formula (1) or a fragrance composition containing the same, but for example, Suitable for , citrus tone, floral tone, fougere tone, fruity tone, green tone, woody tone, moss tone, tropical flower tone, lily of the valley (also called lily of the valley) tone, oriental tone, chypre tone, etc. It can be used for. More specific examples include, but are not limited to, lemon, orange, grapefruit, lime, yuzu, kabosu, rose, geranium, jasmine, lily of the valley, hyacinth, lilac, plumeria, pineapple, mango, and peach. For example, it can be preferably used in cosmetics that have a floral, lily of the valley, citrus, fougere, or woody scent, and is more preferably used in cosmetics that have a floral, lily of the valley, or citrus scent. It can be particularly preferably used in cosmetics having a lily of the valley or citrus scent.

In the present invention, the concentration of the flavor imparting agent made of the compound represented by formula (1) in the cosmetic product can be arbitrarily determined depending on the aroma of the product and the desired degree of effect.

For example, the concentration of the flavoring agent made of the compound represented by formula (1) is, for example, 10 ppb to 10%, preferably 100 ppb (0.1 ppm) to 5%, more preferably 3 ppm, based on the total mass of the cosmetic product. 5%, particularly preferably 50 ppm to 0.5%. More specifically, the lower limit is 10ppb, 100ppb, 1ppm, 3ppm, 5ppm, 10ppm, 50ppm, 100ppm, 0.1%, 1%, 5%, and the upper limit is 10%, 5%, 4%. , 2%, 1%, 0.5%, 0.1%, 100ppm, 10ppm, 5ppm, 1ppm, and any combination of these lower and upper limits may be mentioned, but is limited to these. Not done. Examples of preferred concentrations include, for example, 5 ppm to 4%, or 5 ppm to 2% as the concentration of the flavor imparting agent made of the compound represented by formula (1) based on the total mass of the cosmetic. It can be selected depending on the aroma characteristics of, but is not limited to. Although it depends on the type and fragrance of the cosmetic product, if the concentration of the flavor imparting agent made of the compound represented by formula (1) in the cosmetic product is 10 ppb or more, and even 0.1 ppm or more, the concentration is high. The effect can be felt, and when the amount is 10% or less, and even 5% or less, it is possible to suppress excessive imparting of the aroma derived from the flavoring agent to the cosmetics to be blended. However, depending on the fragrance of the cosmetic product, it may be blended at a concentration below the lower limit or above the upper limit.

By blending a flavor imparting agent made of the compound represented by formula (1) or a fragrance composition containing the same into cosmetics as described above, it is possible to improve, for example, the persistence and persistence of the fragrance of cosmetics. Improving diffusivity, imparting lily of the valley and/or floral tone, imparting lily of the valley and/or citrus tone, imparting freshness, imparting transparency, imparting volume, masking off-odor of cosmetic materials themselves. Perfuming effects including at least one of the following effects can be obtained.

Examples of food and drink products as consumer goods include, but are not limited to, various citrus flavors such as lemon, orange, grapefruit, lime, mandarin, mandarin orange, kabosu, sudachi, hassaku, iyokan, yuzu, shikwasa, and kumquat. ; Various fruit flavors such as strawberry, blueberry, raspberry, apple, cherry, plum, apricot, peach, pineapple, banana, melon, mango, papaya, kiwi, pear, grape, Muscat, Kyoho; Milk, yogurt, butter, etc. Flavor: Vanilla flavor; various tea flavors such as green tea, black tea, oolong tea, herbal tea; coffee flavor; cola flavor; cacao flavor; cocoa flavor; various mint flavors such as spearmint and peppermint; cinnamon, chamomile, cardamom, caraway, cumin various spices or herbal flavors such as , cloves, pepper, coriander, sansho, perilla, ginger, star anise, thyme, capsicum, nutmeg, basil, marjoram, rosemary, laurel, garlic, wasabi; almonds, cashews, walnuts, etc. Various nut flavors; Various alcohol flavors such as wine, brandy, whisky, rum, gin, liqueur, sake, shochu, beer; Vegetable flavors such as onion, celery, carrot, tomato, cucumber; Chicken, duck, pork, beef, Various meat flavors such as mutton and horsemeat; red fish such as tuna, white fish such as mackerel, sea bream, salmon and horse mackerel, freshwater fish such as sweetfish, trout and carp, shellfish such as turban shell, clam, clam and freshwater clam, shrimp and crab. Various seafood and seaweed flavors such as various crustaceans such as various seaweeds such as wakame and kelp; Various grain flavors such as wheat such as rice, barley, wheat, and malt; Livestock flavors such as beef tallow, chicken oil, and lard. Examples include foods and drinks having one or more flavors of various oils and fats such as fats and oils and various fish oils. In particular, it can be suitably used for foods and drinks with citrus flavor, black tea, and muscat flavor. In addition, the flavor of the food/beverage product may be a food/drink that makes you feel only one type of flavor mentioned above, or a food/drink that makes you feel two or more types of flavor, and even if the multiple types of flavors are similar, they may be different. For example, examples of the former include fruit flavors with multiple fruit flavors such as banana, peach, and apple flavors (so-called mixed fruit flavors), and examples of the latter include citrus flavors such as lemon and milk flavors. (such as a citrus-flavored lactic acid bacteria drink), and those that give a feeling of mint, citrus, or cola flavor (such as a mint- or lemon-flavored cola drink).

More specific food and drink examples include rice crackers, arare, okoshi, rice cakes, steamed buns, sweet bean paste, yokan, water yolk, nishikidama, jelly, castella, hard candy, biscuits, crackers, potato chips, cookies, Confectionery such as pies, puddings, butter cream, custard cream, cream puffs, waffles, sponge cakes, donuts, chocolate, chewing gum, caramels, candies, pastes such as peanut paste; bread, udon, ramen, Chinese noodles, sushi, Gomokumeshi, fried rice, pilaf, gyoza skin, shumai skin, okonomiyaki, takoyaki, and other breads, noodles, and rice; rice bran pickles, pickled plums, fukujinzuke, bettarazuke, senmaizuke, rakkyo, miso pickles, takuan pickles, and, Pickles such as mackerel, sardines, saury, salmon, tuna, bonito, whale, flounder, sand eel, sweetfish, squid such as common squid, spear squid, crested squid, firefly squid, octopus, Seafood such as octopuses such as octopus, shrimp such as kuruma prawn, botan prawn, spiny lobster, and black tiger; crabs such as red king crab, snow crab, blue crab, and king crab; shellfish such as clams, clams, scallops, oysters, and mussels; Canned fish, boiled fish, tsukudani, surimi, fish paste products (chikuwa, kamaboko, fried kamaboko, crab leg kamaboko, etc.), fried foods, tempura, and other processed seafood foods; chicken, pork, beef, mutton, horse meat, etc. Meat products: curry, stew, beef stew, hayashi rice sauce, meat sauce, mapo tofu, hamburgers, gyoza, kamameshi base, soups (corn soup, tomato soup, consommé soup, etc.), meat balls, braised braised meat, canned meat, etc. Processed foods and drinks using livestock meat; table salt, seasoned salt, soy sauce, powdered soy sauce, miso, powdered miso, moromi, hishio, furikake, ochazuke base, margarine, mayonnaise, dressing, vinegar, sambai vinegar, powdered sushi vinegar, Chinese food Soy sauce, tempura soup, mentsuyu (kelp stock or bonito stock, etc.), sauce (chuno sauce, tomato sauce, etc.), ketchup, yakiniku sauce, curry roux, stew stock, soup stock, dashi stock (konbu stock or bonito stock) seasonings such as dashi (soup stock, etc.), compound seasonings, hon mirin, new mirin (simmered mirin), mixed powders such as fried chicken powder and takoyaki powder, and animal or vegetable products to which these seasonings have been added. Dashi-flavored foods and drinks; Dairy products such as cheese, yogurt, and butter; Various yeasts such as brewer's yeast and baker's yeast, and various microbial fermented products such as lactic acid bacteria; Boiled dishes such as simmered vegetables, Chikuzen-ni, oden, and hot pot; Take-out lunch boxes Ingredients and side dishes: Fruit juice drinks and fruit juice-containing soft drinks made from fruits such as apples, grapes, and citrus fruits (grapefruit, oranges, lemons, etc.); Fruit pulp drinks and fruit drinks containing fruit granules; Tomatoes, green peppers, celery, gourds, bitter gourds , vegetables such as carrots, potatoes, asparagus, bracken, and Japanese sagebrush, vegetable drinks containing these vegetables, and vegetable-containing foods and drinks such as vegetable soup; coffee, cocoa, green tea, black tea, oolong tea, soft drinks, cola drinks, Favorite drinks such as carbonated drinks (ciders with various flavors such as citrus flavors), lactic acid bacteria drinks; drinks containing crude drugs and herbs; cola drinks, fruit juice drinks, milk drinks, non-alcoholic beer and so-called "third beer", etc. Functional drinks such as beer-taste drinks, sports drinks, honey drinks, vitamin supplement drinks, mineral supplement drinks, nutritional drinks, nourishing drinks, lactic acid bacteria drinks; Alcohol-flavored alcoholic beverages (beer flavor, plum wine flavor, chuhai flavor, etc.) Non-alcoholic beverages such as wine, shochu, awamori, sake, beer, chuhai, cocktail drinks, low-malt beer, fruit liquor, condiments, and other brewed liquors (sparkling) such as so-called "third beer"; Examples include liqueurs (foaming) and alcoholic beverages containing these.

In the present invention, the concentration of the flavor imparting agent made of the compound represented by formula (1) in the food or drink can be arbitrarily determined depending on the flavor of the food or drink, the desired degree of effect, and the like.

As an example of the concentration, the concentration of the flavoring agent made of the compound represented by formula (1) with respect to the total mass of the food or drink may be in the range of 10 ppt to 10 ppm, more preferably 100 ppt to 10 ppm. More specifically, the lower limit value is set to 10 ppt, 100 ppt, 1 ppb, 10 ppb, 100 ppb, or 1 ppm, and the upper limit value is set to 10 ppm, 1 ppm, 100 ppb, 10 ppb, 1 ppb, or 100 ppt, and these lower limit values and upper limit values are Examples include, but are not limited to, any combination. Examples of preferable concentrations include 100 ppt to 1 ppm or 1 ppb to 100 ppb as the concentration of the flavor imparting agent made of the compound represented by formula (1) relative to the total mass of the food and drink, which improves the flavor characteristics of the food and drink. It can be selected accordingly, but is not limited to these. Although it depends on the type and flavor of the food and drink, if the concentration of the flavoring agent made of the compound represented by formula (1) in the food and drink is 10 ppt or more, and even 100 ppt or more, a high combination effect can be obtained. If the amount is 10 ppm or less, the aroma of the flavor imparting agent itself consisting of the compound represented by formula (1) can be prevented from being prominent and imparting undesirable alteration to the flavor of the food or drink to be blended. However, depending on the flavor of the food or drink, it may be blended at a concentration below the lower limit or above the upper limit.

By blending a flavor imparting agent made of the compound represented by formula (1) or a flavor composition containing the same into foods and drinks as described above, for example, flavor enhancement, imparting bitterness such as the feel of fruit skin, or reducing the appearance of fruit wax It is possible to obtain a flavoring effect including at least one of imparting a feeling of oil and fat, imparting a feeling of volume, imparting a citrus feeling, etc.

Hereinafter, the present invention will be explained in more detail with reference to Examples. Note that the present invention is not limited to these.

[Example 1] Production of a flavor imparting agent of the present invention A flavor imparting agent of the present invention was obtained according to the method described below.

Hereinafter, details of the synthesis method will be described with reference to the above reaction formula.

(1) Synthesis of Compound 3 10.00 g of a commercially available compound 2 (E:Z≒6:1, Z-form content x' = about 14%) as a starting material was added to 16.00 g (202.3 mmol) of pyridine. After melting, 7.37 g (72.2 mmol) of acetic anhydride was added under ice-cooling, and the mixture was stirred at 0°C for 1 hour and then at room temperature (approximately 25°C) for 92 hours. After the reaction was completed, the reaction solution was poured into ice water and extracted with ether. The extracted organic layer was washed in the order of 1 mol/L hydrochloric acid aqueous solution, saturated sodium bicarbonate aqueous solution, and saturated saline, dried over anhydrous magnesium sulfate, and the solvent was distilled off using an evaporator to obtain 13.27 g of a colorless oily substance. Ta. This was purified using a silica gel column (48 mm i.d. Obtained.

The content ratio (content x') of the E-form and Z-form of Compound 2 was determined in the same manner as the gas chromatography (GC) analysis described below.

(2) Synthesis of Compound 4 Take 5.00 g (18.8 mmol) of Compound 3 obtained in (1), suspend in a mixed solvent of 1,2-dimethoxyethane (40 mL) and water (25 mL), and cool on ice. Below, a solution of 3.57 g (20.1 mmol) of N-bromosuccinimide dissolved in 1,2-dimethoxyethane (60 mL) was added dropwise over 25 minutes (at the end of the dropwise addition, it became a transparent homogeneous solution). , and stirred at 0°C for 4 hours. After the reaction was completed, saturated brine (150 mL) was added to the reaction solution and extracted with ether. The organic layer obtained by ether extraction was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off using an evaporator to obtain 7.15 g of a colorless oily substance as Compound 4. This oil was used in the next reaction without further purification.

(3) Synthesis of Compound 5 Take 7.15 g of Compound 4 obtained in (2), dissolve it in methanol (100 mL), add 8.30 g (60.1 mmol) of potassium carbonate, and let it cool at room temperature (about 25°C). Stirred overnight. The next day, celite filtration was performed to remove solid matter, and the filtrate was concentrated to about one-half volume using an evaporator. After adding saturated brine (120 mL), ether extraction was performed. The organic layer obtained by ether extraction was washed twice with saturated brine (80 mL), dried over potassium carbonate, and the solvent was distilled off using an evaporator to obtain 4.72 g of a colorless oily substance as Compound 5. This oil was used in the next reaction without further purification.

(4) Synthesis of Compound 6 4.72 g (19.6 mmol) of Compound 5 obtained in (3) was dissolved in 5.97 g (75.5 mmol) of pyridine, and 3.83 g (37 mmol) of acetic anhydride was dissolved under ice-cooling. .5 mmol) was added dropwise, and the mixture was stirred for 17.5 hours while raising the temperature to room temperature (about 25°C). After the reaction was completed, the reaction solution was poured into ice water and extracted with ether. The organic layer obtained by ether extraction was washed three times with a saturated aqueous copper sulfate solution, once with a saturated aqueous sodium bicarbonate solution, and once with a saturated saline solution, dried over anhydrous magnesium sulfate, and the solvent was distilled off using an evaporator. , 5.15 g of colorless oil was obtained. This was purified using a silica gel column (46 mm i.d. x 19 cm L, n-hexane: ethyl acetate = 15:1), and Compound 3 (0.48 g, 1.8 mmol), which was a colorless oil, was recovered. Then, Compound 6 (3.01 g, 10.7 mmol), a colorless oil, was eluted.

(5) Synthesis of Compound 7 Take 2.92 g (10.3 mmol) of Compound 6 obtained in (4), dissolve it in ether (50 mL), and add periodic acid dihydrate (HIO _4.2H ) under ice cooling. A solution of 2.64 g (11.6 mmol) of ₂ O) in tetrahydrofuran (24 mL) was added dropwise over 25 minutes (a colorless precipitate was formed during the dropwise addition), and the mixture was stirred at 0° C. for 1 hour. After the reaction was completed, water (50 mL) was added to the reaction solution, the organic layer was separated, and the aqueous layer was extracted with ether. The separated organic layer and the organic layer extracted from the aqueous layer were combined, washed sequentially with water, saturated aqueous sodium bicarbonate solution, and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off using an evaporator to obtain an off-white color. 2.72 g of oily substance was obtained. This was purified using a silica gel column (33 mm i.d. x 21 cm L, n-hexane:ethyl acetate = 15:1) to obtain 2.05 g (8.53 mmol) of a colorless oily substance as Compound 7.

(6) Synthesis of compound of formula (1) 2.02 g (8.40 mmol) of compound 7 obtained in (5) was dissolved in methanol (50 mL), 3.48 g (25.2 mmol) of potassium carbonate was added, and the mixture was heated at room temperature. The mixture was stirred at (approximately 25°C) for 1 hour. After the reaction was completed, the colorless solid was filtered off and washed well with ether. The ether layer was collected, washed successively with saturated ammonium chloride aqueous solution and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off using an evaporator to obtain 1.73 g of a slightly yellow oily substance. This was purified using a silica gel column (33 mm i.d. .99 g (5.0 mmol) was obtained.

The compound of formula (1) obtained by the above reaction was a mixture of E form and Z form, and the content x of Z form in the mixture was about 10%. The isomer ratio was calculated by separation by gas chromatography (GC). The GC conditions are described below;
GC device: GC-2025 (manufactured by Shimadzu Corporation)
Column: TC-1, 0.53mm I. D. ×30m L, df 1.50μm (manufactured by GL Sciences Inc.)
Detector: Flame ionization detector (FID)
Injection temperature: 300℃
Detector temperature: 300℃
Temperature increase conditions: 100℃ → 300℃ (temperature increase by 20℃ per minute)
Linear speed: 60.0cm/S
The GC retention time was measured, and the ratio of the respective peak areas was determined, which was defined as the isomer ratio.

The obtained compound of formula (1), namely 10-hydroxy-4,8-dimethyl-4-decenal (mixture of E-form and Z-form, Z-form content x is about 10%, flavor imparting agent of the present invention) 1) had a lily of the valley, green, ozone, and woody scent. In addition, when the E and Z isomers were separated using GC (using InertCap (registered trademark) WAX), the scent of each isomer was confirmed, and the E isomers were lily of the valley, green, floral, ozone, woody, metallic, The Z-type has a weaker aroma than the E-type, and like the E-type it has a lily of the valley scent, but it also has a citrus-like, rose-like, and amber-like aroma. Met.

A compound of formula (1) was synthesized using the same reaction route as described above except that the isomer ratio of compound 2 (starting material) was changed. Specifically, with reference to the method described in JP-A-8-245979, compounds 2 with an isomer ratio of Z-isomer content x' of 0%, 5%, 20%, and 40% were prepared. Then, the above reactions (1) to (6) were performed using the compound 2. As a result, compounds of formula (1) with Z-form contents x of 0%, about 3%, about 18%, and about 37% were obtained (flavor imparting agents 2 to 5 of the present invention). . When the scent of each flavor imparting agent 2 to 5 was confirmed, all of them had lily of the valley, green, ozone, and woody scents.

[Example 2] Example of blending into a fragrance composition As shown in Table 1 below, a lily of the valley-like basic blended fragrance composition was prepared.

Flavoring agents 1 to 5 of the present invention obtained in Example 1 were each added to the above-mentioned lily of the valley-like basic blended flavor composition as shown in Table 2 below to prepare a flavor composition of the present invention. Next, a sensory evaluation of the scent of each fragrance composition was performed. In the sensory evaluation, scent paper was impregnated with the fragrance composition of the present invention, and 15 well-trained perfumers with over 10 years of experience evaluated the scent. Participants were asked to give scores based on the following evaluation criteria and to comment on the quality of the aroma. Table 2 shows the average scores and representative comments of the 15 perfumers.

(Evaluation criteria for lily of the valley feeling)
4 points: The refreshing scent of fresh lily of the valley flowers was greatly enhanced;
3 points: The refreshing scent of lily of the valley flowers was enhanced;
2 points: The refreshing scent of fresh lily of the valley flowers was slightly enhanced;
1 point: The lily of the valley scent was slightly enhanced;
0 points: It has a scent different from lily of the valley.

As described above, it was confirmed that all of the flavoring agents 1 to 5 of the present invention can impart a distinctive green and refreshing aroma with an excellent lily of the valley aroma, and can create a high-quality aroma reminiscent of fresh flowers. It was also confirmed that the flavor improving agent with a higher proportion of E-isomer has a higher flavor imparting effect even at a low concentration.

[Example 3] Example 1 of formulation in cosmetics
Flavoring agents 2 and 5 of the present invention obtained in Example 1 were blended into a commercially available hand soap with a lily of the valley fragrance at a concentration of 50 ppb, 1 ppm, 100 ppm, and 1% (based on the total amount of hand soap), respectively. A hand soap of the present invention was prepared and packed into commercially available empty hand soap bottles. Six well-trained perfumers with over 10 years of experience were asked to wash their hands in lukewarm water (approximately 35 degrees Celsius) using one pump (approximately 1 mL) of a hand soap bottle in a closed laboratory. Participants were asked to perform a sensory evaluation of the scent in the laboratory and the scent of their hands after washing. In the sensory evaluation, the natural feel of the lily of the valley scent, the diffusion of the scent into the space, and the lingering scent on the skin compared to the commercially available hand soaps were evaluated as follows: Very improved = 4 points, Increased = 3 points. , slightly increased = 2 points, no change = 1 point, and deteriorated = 0 points. Note that the natural feeling of the lily of the valley fragrance means that a fresh scent with a slight green tinge reminiscent of fresh lily of the valley flowers can be felt. Table 3 shows the average scores of the six perfumers.

As described above, it was confirmed that the flavor imparting agent of the present invention improves not only the fragrance itself but also the diffusivity and residual fragrance by adding it to existing consumer goods exhibiting a lily of the valley-like fragrance. It was also confirmed that the more the E-isomer was present, the more natural the fragrance, the diffusivity, and the persistence of the fragrance.

[Example 4] Example 2 of formulation in cosmetics
Flavoring agents 1 to 5 of the present invention obtained in Example 1 were added to commercially available lemon-like perfumes, mango-like perfumes, and ozone-based men's perfumes at a concentration of 300 ppm based on the total amount of perfume. The cosmetics of the present invention were obtained by blending. The cosmetics of the present invention were then subjected to sensory evaluation by eight well-trained perfumers with over 10 years of experience. In the sensory evaluation, each commercially available perfume was used as a control product, and participants were asked to comment on changes in aroma caused by blending the flavor imparting agent of the present invention. Typical comments obtained are shown in Table 4 below.

As described above, it was confirmed that all of the flavor imparting agents of the present invention can enhance various aromas, impart new aroma characteristics, impart lingering aroma, aroma diffusivity, and the like.

[Example 5] Example of blending into food and drink Flavoring agents 1 to 5 of the present invention obtained in Example 1 were blended into commercially available lemonade containing 50% fruit juice to a concentration of 10 ppt, 1 ppb, and 10 ppm. Thus, a beverage of the present invention was prepared. Seven panelists with 10 years or more of experience were asked to comment on the flavor of the beverage of the present invention compared to the commercially available lemonade to which the flavor imparting agent of the present invention was not added. Typical comments are shown in Table 5 below.

As described above, it was confirmed that all of the flavor imparting agents 1 to 5 of the present invention can impart a characteristic citrus flavor to foods and drinks, and are also useful as flavoring compounds for foods and drinks.

As described above, the compound represented by formula (1) of the present invention exhibits an excellent flavor imparting effect on a wide range of flavors including lily of the valley aroma.

This application is based on Japanese Patent Application No. 2020-028028 filed on February 21, 2020, the disclosure content of which is incorporated by reference in its entirety.

Claims (7)

A flavoring agent consisting of 10-hydroxy-4,8-dimethyl-4-decenal represented by the following formula (1).

[In the formula, the wavy line represents a mixture of E-form and Z-form, and represents that the content x of Z-form in the mixture is 0.01% ≦x≦50%. ] The flavor imparting agent according to claim 1, wherein the flavor is a lily of the valley or a citrus flavor. A flavor imparting agent consisting of 10-hydroxy-4,8-dimethyl-4-decenal represented by the following formula (1),
A flavoring agent, wherein the flavor is a lily of the valley or a citrus flavor.

[In the formula, the wavy line represents a mixture of E-form and Z-form, and represents that the content x of Z-form in the mixture is 0%≦x≦50%. ] A fragrance composition containing the flavor imparting agent according to any one of claims 1 to 3 . A consumer product containing the flavor imparting agent according to any one of claims 1 to 3 or the flavor composition according to claim 4 . A method for imparting flavor to a flavor composition, comprising blending the flavor imparting agent according to any one of claims 1 to 3 into a flavor composition. A method for imparting flavor to consumer goods, which comprises incorporating the flavor imparting agent according to any one of claims 1 to 3 or the flavor composition according to claim 4 into consumer goods.