Perfume composition

Abstract

To provide a new aromatic agent and a new perfume composition.SOLUTION: Provided are: an aromatic agent comprising a compound represented by formula (I); and a perfume composition containing the aromatic agent. [In formula (I), R1 is a C1-5 alkyl group and R2 is a hydrogen atom or a C1-4 alkyl group.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a fragrance composition.

Background Art

[0002] α-(2-Alkylcyclohexyloxy)-β-alkanols, especially 1-(2-t-butylcyclohexyloxy)-2-alkanols, are useful fragrance materials having a woody, amber-like aroma, excellent residual fragrance properties, and can be produced at low cost (Patent Document 1).

[0003] For example, 1-(2-t-butylcyclohexyloxy)-2-butanol is a fragrance having a woody-amber-like fragrance note (a refreshing hinoki-like scent) and high residual fragrance properties, and is widely known as Amber Core.

[0004] When producing Amber Core, various by-products are obtained although in trace amounts. Some of such by-products are difficult to remove by purification because their structures are very similar to that of Amber Core. Also, some of such by-products are known to have an adverse effect on the fragrance of Amber Core.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0006] An object of the present invention is to provide a new flavoring agent and a new fragrance composition by studying the conventional Amber Core production technology.

Means for Solving the Problems

[0007] The inventors of the present invention have discovered that ot-butylcyclohexanone, a low-boiling point compound generated during amber core production, is an off-odor component. On the other hand, they have newly discovered that certain ketal compounds possess desirable fruity (apple-like), herbal, and minty aromas on their own. Furthermore, they have found that a composition containing a specific concentration of the aforementioned ketal compound and amber core imparts a honey-like sweetness and increased fragrance volume to the amber core, which is a desirable effect. Based on these findings, the perfumer and fragrance composition of the present invention have been completed.

[0008] [ka]

[0009] The following compounds are known as similar compounds that have a ketal structure. The descriptions of the aromas of these compounds are as follows.

[0010] Japanese Patent Publication No. 56-79686 discloses the following ketal compound. This compound has been reported to have an herbal, fruity, and pungent aroma. However, the herbal, pungent, and chemical-like aroma has the problem of being less versatile when creating blended fragrances.

[0011] [ka]

[0012] Japanese Patent Publication No. 6-305999 discloses the following ketal compounds. These compounds have been reported to have fruity, green, woody, floral, anise-like, aromatic, camphor-like, and tobacco-like aromas. However, the anise-like, camphor-like, and tobacco-like aromas have the problem of being less versatile when creating blended fragrances.

[0013] [ka]

[0014] In other words, the present invention is a fragrance comprising a compound represented by formula (I).

[0015] [ka]

[0016] In the above formula (I), R 1 This is an alkyl group having 1 to 5 carbon atoms. R 2 This is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0017] Furthermore, the present invention relates to a fragrance composition comprising a compound represented by formula (II) and a compound represented by formula (I), The fragrance composition has a mass ratio [compound represented by formula (II):compound represented by formula (I)] of 99.99:0.01 or more and 98:2 or less.

[0018] [ka]

[0019] In equations (I) and (II) above, R 1 and R 3 Each of these is independently an alkyl group having 1 to 5 carbon atoms. R 2 and R 4 Each of these is independently either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. [Effects of the Invention]

[0020] The flavoring agent composed of the compound represented by formula (I) of the present invention and the fragrance composition containing the flavoring agent have a preferable fruity (apple-like), herbal, minty-like scent. Further, the fragrance composition containing the compound represented by formula (II) and the compound represented by formula (I) of the present invention has a preferable effect of imparting honey-like sweetness and scent volume to the amber core.

Mode for Carrying Out the Invention

[0021] As described above, the present invention is a flavoring agent composed of the compound represented by formula (I).

[0022]

Chemical formula

[0023] In the above formula (I), R 1 is an alkyl group having 1 to 5 carbon atoms, R 2 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0024] Preferably, in the above formula (I), R 1 is an alkyl group having 1 to 4 carbon atoms, R 2 is a methyl group or an ethyl group.

[0025] More preferably, in the above formula (I), R 1 is a tert-butyl group, R 2 is an ethyl group.

[0026] [[ID=�5]]The compound represented by the above formula (I) can be produced, for example, by the following method.

[0027]

Chemical formula

[0028] In equations (X), (XI), (XII), and (I) above, R 1 This is an alkyl group having 1 to 5 carbon atoms. R 2 This is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0029] Compound (X) and compound (XI) are heated under basic conditions (e.g., sodium hydroxide) to obtain compound (XII). Compound (XII) is then hydrogenated in the presence of hydrogen using a specific catalyst (e.g., a palladium-containing catalyst) to obtain compound (I). The obtained compound (I) can be separated and purified by distillation or column chromatography.

[0030] Alternatively, the compound represented by formula (I) can be produced using conventionally known methods, for example, under conditions similar to those described in Japanese Patent Application Publication No. 2013-151482.

[0031] Furthermore, the present invention relates to a fragrance composition comprising a compound represented by formula (II) and a compound represented by formula (I), The fragrance composition has a mass ratio [compound represented by formula (II):compound represented by formula (I)] of 99.99:0.01 or more and 98:2 or less. That is, the mass ratio (compound represented by formula (I) / compound represented by formula (II)) is 0.01 / 99.99 or more and 2 / 98 or less.

[0032] [ka]

[0033] In equations (I) and (II) above, R 1 and R 3 Each of these is independently an alkyl group having 1 to 5 carbon atoms. R 2 and R4 Each of these is independently either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0034] In a fragrance composition containing the compound represented by formula (II) and the compound represented by formula (I), the mass ratio of the compound represented by formula (II) to the compound represented by formula (I) [compound represented by formula (II):compound represented by formula (I)] is preferably 99.97:0.03 or higher, more preferably 99.95:0.05 or higher, from the viewpoint of imparting a honey-like sweetness and fragrance volume to the compound represented by formula (II), and preferably 99:1 or lower, more preferably 99.20:0.80 or lower, and even more preferably 99.50:0.50 or lower, from the viewpoint of imparting an amber-like fragrance to the compound represented by formula (II). In a fragrance composition containing the compound represented by formula (II) and the compound represented by formula (I), the mass ratio of the compound represented by formula (II) to the compound represented by formula (I) [compound represented by formula (II):compound represented by formula (I)] is preferably 99.99:0.01 or more and 99:1 or less, more preferably 99.97:0.03 or more and 99.20:0.80 or less, and even more preferably 99.95:0.05 or more and 99.50:0.50 or less, from the viewpoint of imparting honey-like sweetness and fragrance volume to the compound represented by formula (II).

[0035] That is, the mass ratio (compound represented by formula (I) / compound represented by formula (II)) of the compound represented by formula (II) is preferably 0.01 / 99.99 or more and 1 / 99 or less, more preferably 0.03 / 99.97 or more and 0.80 / 99.2 or less, and even more preferably 0.05 / 99.95 or more and 0.50 / 99.50 or less, from the viewpoint of imparting a honey-like sweetness and volume of aroma to the compound represented by formula (II).

[0036] In a fragrance composition comprising the compound represented by formula (II) and the compound represented by formula (I), preferably in formula (I), R 1 This is an alkyl group having 1 to 4 carbon atoms. R2 This is either a methyl group or an ethyl group.

[0037] More preferably, in formula (I), R 1 It is a tert-butyl group, R 2 This is an ethyl group.

[0038] In a fragrance composition comprising the compound represented by formula (II) and the compound represented by formula (I), preferably in formula (II), R 3 This is an alkyl group having 1 to 4 carbon atoms. R 4 This is either a methyl group or an ethyl group.

[0039] More preferably, in formula (II), R 3 It is a tert-butyl group, R 4 This is an ethyl group.

[0040] In a fragrance composition comprising the compound represented by formula (II) and the compound represented by formula (I), preferably in formula (I), R 1 This is an alkyl group having 1 to 4 carbon atoms. R 2 This is a methyl group or an ethyl group, In the above equation (II), R 3 This is an alkyl group having 1 to 4 carbon atoms. R 4 This is either a methyl group or an ethyl group.

[0041] More preferably, in formula (I), R 1 It is a tert-butyl group, R 2 It is an ethyl group, In the above equation (II), R 3 It is a tert-butyl group, R4 This is an ethyl group.

[0042] The compound represented by formula (II) can be produced by conventionally known methods, for example, the method described in Japanese Patent Application Publication No. 4-217937.

[0043] Alternatively, the compound represented by formula (II) can be produced, for example, by the following method.

[0044] [ka]

[0045] In equations (XIII), (XIV), (XV), and (II), R 3 This is an alkyl group having 1 to 5 carbon atoms. R 4 This is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0046] Compound (XV) can be obtained by heating the compound of formula (XIII) and the compound of formula (XIV) in the presence of a base (e.g., sodium hydroxide). Compound (XV) can be hydrogenated in the presence of a catalyst (e.g., a palladium catalyst) and hydrogen to obtain compound (II).

[0047] The fragrance of the present invention, comprising the compound represented by formula (I), has desirable fruity (apple-like), herbal, and minty scents, and therefore exhibits excellent compatibility with various other fragrances, making it possible to create characteristic fragrance effects by blending them. Furthermore, the fragrance of the present invention, comprising the compound represented by formula (I), can be combined with other commonly used fragrance components or blended fragrances of desired composition as fragrances other than the compound represented by formula (I). That is, a fragrance composition containing the fragrance of the present invention comprising the compound represented by formula (I) and fragrances other than the compound represented by formula (I) is preferred, and a fragrance composition containing the fragrance of the present invention comprising the compound represented by formula (I) and fragrances other than the compound represented by formula (II) is also preferred. By combining fragrances other than the compound represented by formula (I), for example, desirable fruity (apple-like), herbal, and minty scents can be imparted to the fragrance composition of the present invention.

[0048] Furthermore, the fragrance composition of the present invention, which contains the compound represented by formula (I) and the compound represented by formula (II), imparts a honey-like sweetness and fragrance volume to the compound represented by formula (II). The fragrance composition of the present invention, which contains the compound represented by formula (I) and the compound represented by formula (II), can be combined with other commonly used fragrance components or blended fragrances of a desired composition as fragrances other than the compounds represented by formula (I) and the compound represented by formula (II). By combining fragrances other than the compounds represented by formula (I) and the compound represented by formula (II), for example, the fragrance and honey-like sweetness and fragrance volume of the compound represented by formula (II) can be imparted to the fragrance composition of the present invention. That is, it is preferable that the fragrance composition of the present invention, which contains the compound represented by formula (I) and the compound represented by formula (II), further contains fragrances other than the compounds represented by formula (I) and the compound represented by formula (II).

[0049] Other fragrances that can be used in combination with the fragrance of the present invention, which consists of the compound represented by formula (I), include fragrance components such as alcohols, hydrocarbons, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, carbones, lactones, nitriles, amines, Schiff bases, natural essential oils and natural extracts (excluding the compound represented by formula (I)). In other words, the present invention is a fragrance composition comprising one or more of the compounds other than those represented by formula (I) and formula (II), namely alcohols, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, nitriles, amines, natural essential oils and natural extracts, and the fragrance of the present invention.

[0050] [ka]

[0051] In equations (I) and (II) above, R 1 and R 3 Each of these is independently an alkyl group having 1 to 5 carbon atoms. R 2 and R 4 Each of these is independently either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0052] The mass ratio (compound represented by formula (I) / other fragrances) of the fragrance agent comprising the compound represented by formula (I) and other fragrances other than the compound represented by formula (I) and the compound represented by formula (II) (hereinafter simply referred to as "other fragrances") is preferably 0.01 / 99.99 or more, more preferably 0.1 / 99.9 or more, and even more preferably 1 / 99 or more, and from the viewpoint of exhibiting the function of a fragrance agent, preferably 1 / 2 or less, more preferably 1 / 3 or less, and even more preferably 1 / 4 or less, preferably 0.01 / 99.99 or more and 1 / 2 or less, more preferably 0.1 / 99.9 or more and 1 / 3 or less, and even more preferably 1 / 99 or more and 1 / 4 or less.

[0053] Furthermore, the content of the fragrance agent consisting of the compound represented by formula (I) in the fragrance composition is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, even more preferably 0.2% by mass or more, preferably 20% by mass or less, more preferably 15% by mass or less, even more preferably 10% by mass or less, preferably 0.01% by mass or more and 20% by mass or less, more preferably 0.1% by mass or more and 15% by mass or less, and even more preferably 0.2% by mass or more and 10% by mass or less.

[0054] In the fragrance composition of the present invention, which comprises a compound represented by formula (I) and a compound represented by formula (II), other fragrances that can be used in combination with the compound represented by formula (I) and the compound represented by formula (II) include fragrance components such as alcohols, hydrocarbons, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, carbones, lactones, nitriles, amines, Schiff bases, natural essential oils and natural extracts (excluding the compound represented by formula (I) and the compound represented by formula (II)).

[0055] In the aforementioned fragrance composition, alcohols, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, nitriles, amines, natural essential oils, and natural extracts are preferred among these.

[0056] Examples of alcohols include aliphatic alcohols, terpene alcohols, aromatic alcohols, and other alcohols. Among these, aliphatic alcohols are preferred.

[0057] Examples of terpene alcohols include linalool, ethyllinalool, citronellol, hydroxycitronellol, geraniol, tetrahydrogeraniol, nerol, terpineol, α-terpineol, dihydromyrcenoyl, farnesol, nerolidol, cedrol, menthol, and borneol.

[0058] Examples of aromatic alcohols include phenylethyl alcohol, benzyl alcohol, dimethylbenzylcarbinol, phenylethyldimethylcarbinol, and phenylhexanol.

[0059] Examples of aliphatic alcohols include cis-3-hexenol, 1-(2,2,6-trimethylcyclohexyl)-3-hexanol, Sandal Mysore Core (Kao Corporation trade name, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol), Amber Core (Kao Corporation trade name, 1-(2-t-butylcyclohexyloxy)-2-butanol), Magnol (Kao Corporation trade name, a mixture mainly composed of ethylnorbonylcyclohexanol), Undecaverthol (Divaudan Corporation trade name, 4-methyl-3-decen-5-ol), isobornylcyclohexanol, Terpirosa (Kao Corporation trade name, 3,6-dimethyl-2-heptanol), etc. However, Amber Core is excluded from "the fragrance composition of the present invention containing the compound represented by formula (I) and the compound represented by formula (II)".

[0060] Other alcohols include glycols such as dipropylene glycol, florosa (Divaudan trade name, chemical name: 4-methyl-2-(2-methylpropyl)tetrahydro-2H-4-pyranol), maltol, and ethylmaltol.

[0061] Examples of hydrocarbons include limonene, α-pinene, β-pinene, terpinene, cedrene, longifolene, and valencene.

[0062] Examples of phenols include guaiacol, eugenol, dihydroeugenol, isoeugenol, thymol, paracresol, vanillin, and ethyl vanillin.

[0063] Examples of esters include aliphatic carboxylic acid esters, aromatic carboxylic acid esters, and other carboxylic acid esters.

[0064] Aliphatic carboxylic acids that form aliphatic carboxylic acid esters include linear and branched carboxylic acids with 1 to 18 carbon atoms, but among them, carboxylic acids with 1 to 6 carbon atoms, such as formic acid, acetic acid, and propionic acid, are particularly important, especially acetic acid. Aromatic carboxylic acids that form aromatic carboxylic acid esters include benzoic acid, anisic acid, phenylacetic acid, cinnamic acid, salicylic acid, and anthranilic acid. Alcohols that form aliphatic and aromatic esters include linear and branched aliphatic alcohols with 1 to 5 carbon atoms and the above-mentioned fragrance component alcohols.

[0065] Examples of formic acid esters include linalyl formate, citronellyl formate, and geranyl formate.

[0066] Examples of acetate esters include ethyl acetate, isoamyl acetate (isopentyl acetate), benzyl acetate, hexyl acetate, phenyl acetate, p-cresyl acetate, cis-3-hexenyl acetate, linalyl acetate, citronellyl acetate, geranyl acetate, neryl acetate, terpinyl acetate, nopyl acetate, bornyl acetate, isobornyl acetate, acetyl eugenol, acetyl isoeugenol, Examples of phenyl acetates include o-tert-butylcyclohexyl acetate, p-tert-butylcyclohexyl acetate, tricyclodecenyl acetate, phenylethyl acetate, styraryl acetate, cinnamyl acetate, dimethylbenzylcarbyl acetate, 3-pentyltetrahydropyran-4-yl acetate, and prenyl acetate; examples of phenyl acetate esters include phenylethylphenyl acetate and p-cresylphenyl acetate.

[0067] Examples of propionic acid esters include ethyl propionate, citronellyl propionate, tricyclodecenyl propionate, benzyl propionate, styraryl propionate, and helvetride (Firmenich trade name, 2-[1-(3,3-dimethylcyclohexyl)ethoxy]-2-methylpropyl)propionate.

[0068] Examples of butyrate esters include citronellyl butyrate, dimethylbenzylcarbin n-butyrate, isoamyl n-butyrate, and n-amyl n-butyrate; examples of isobutyrate esters include tricyclodecenyl isobutyrate and phenoxyethyl isobutyrate.

[0069] Examples of valerate esters include methyl valerate, ethyl valerate, butyl valerate, amyl valerate, benzyl valerate, and phenylethyl valerate; examples of hexanoate esters include methyl hexanoate, ethyl hexanoate, allyl hexanoate, linalyl hexanoate, and citronellyl hexanoate.

[0070] Examples of heptanoic acid esters include methylheptanoate and allylheptanoate.

[0071] Examples of nonenate esters include methyl 2-nonenoate, ethyl 2-nonenoate, and ethyl 3-nonenoate.

[0072] Examples of benzoic acid esters include methyl benzoate, benzyl benzoate, and 3,6-dimethyl benzoate.

[0073] Examples of cinnamic acid esters include methyl cinnamate and benzyl cinnamate.

[0074] Examples of salicylic acid esters include methyl salicylate, n-hexyl salicylate, cis-3-hexenyl salicylate, cyclohexyl salicylate, and benzyl salicylate.

[0075] Furthermore, examples of brassic acid esters include ethylene brassirate.

[0076] Examples of tigrate esters include geranyl tigrate, 1-hexyl tigrate, and cis-3-hexenyl tigrate.

[0077] Examples of jasmonic acid esters include methyl jasmonate, etc.; examples of dihydrojasmonic acid esters include MDJ (a trade name of Kao Corporation, methyl dihydrojasmonate, methyl (2-pentyl-3-oxocyclopentyl) acetate), etc.

[0078] Examples of glycidic acid esters include methyl 2,4-dihydroxy-ethylmethylphenylglycidate and 4-methylphenylethylglycidate.

[0079] Examples of anthranilic acid esters include methyl anthranilate, ethyl anthranilate, and dimethyl anthranilate.

[0080] Examples of glycolic acid esters include allylcyclohexyl glycolate.

[0081] Other esters include ethyl safranate (Divaudan trade name, ethyl dihydrocyclogeraneate), porenate (Kao Corporation trade name, ethyl-2-cyclohexylpropionate), and frutete (Kao Corporation trade name, ethyl tricyclo[5.2.1.0 2.6 Examples include decane-2-carboxylate, ethyl acetoacetate, fructone (IFF trade name, ethyl 2-(2-methyl-1,3-dioxolan-2-yl)acetate), manzanate (Divaudan trade name, ethyl 2-methylpentanoate), ethyl 2-methylbutyrate, and allylcyclohexylpropionate.

[0082] Examples of carbonates include Refalom (IFF product name, cis-3-hexenylmethyl carbonate), JasmaCiclat (Kao Corporation product name, methyl-cyclooctyl carbonate), and Floramat (Kao Corporation product name, ethyl-2-t-butylcyclohexyl carbonate).

[0083] Examples of aldehydes include n-octanal, n-nonanal, n-decanal, n-dodecanal, 2-methylundecanal, 10-undecenal, citronellal, citral, hydroxycitronellal, tripral (IFF brand name, 2,4-dimethyl-3-cyclohexen-1-carboxyaldehyde), cyclobertal (Kao Corporation brand name, dimethyl-3-cyclohexenyl-1-carboxyaldehyde), benzaldehyde, phenylacetaldehyde, phenylpropylaldehyde, cinnamicaldehyde, dimethyltetrahydrobenzaldehyde, burgeonal (Divaudan brand name, 3-(4-tert-butylphenyl)propanal), lyral (IFF brand name, hydroxymylacaldehyde), and polena Examples include aldehyde II (Kao Corporation trade name, 2-cyclohexylpropanal), Lilial (Divaudan Corporation trade name, p-tert-butyl-α-methylhydrocinnamicaldehyde), p-isopropyl-α-methylhydrocinnamicaldehyde, Florarozone (IFF Corporation trade name, 3-(o-(and p-)ethylphenyl)-2,2-dimethylpropionaldehyde), α-amylcinnamicaldehyde, α-hexylcinnamicaldehyde, heliotropin, Helional (IFF Corporation trade name, alpha-methyl-1,3-benzodioxol-5-propanal), Canthoxal (IFF Corporation trade name, 2-methyl-3-(paramethoxyphenyl)propanal), and aldehyde C-6 (Kao Corporation trade name, n-hexanal).

[0084] Ketones include methylheptenone, dimethyloctenone, 3-octanone, hexylcyclopentanone, dihydrojasmone, beluton (Firmenich trade name, 2,2,5-trimethyl-5-pentylcyclopentanone), nectaril (Divaudan trade name, 2-(2-(4-methyl-3-cyclohexen-1-yl)propyl)cyclopentanone), ionone, β-ionone, methylionone, methylionone-G, γ-methylionone, damascone, α -Damascone, β-Damascone, δ-Damascone, Isodamascone (Symrise brand name, 1-(2,4,4-trimethyl-2-cyclohexyl)-trans-2-butanone), Damascenone, Dynascone (Firmenich brand name, 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one), Ilon, Cashmeran (IFF brand name, 1,2,3,5,6,7-hexahydro-1,1,2,3,3-pentamethyl-4H-inde N-4-one), Iso-E-Super (IFF brand name, 1-(1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-ethane-1-one), Calon (Firmenich brand name, 7-methyl-3,4-dihydro-2H-benzodioxepin-3-one), Carvone, Menthone, Acetylsedrene, Isolongiforanone, Nootkatone, Benzylacetone, Raspberry Ketone, Benzophenone, Tonalid (PF Examples include W Company's product name, 6-acetyl-1,1,2,4,4,7-hexamethyltetrahydronaphthalene, β-methylnaphthylketone, ethyl maltol, camphor, muscone, mucenone (Firmenich product name, 3-methyl-5-cyclopentadecene-1-one), cibetone, globanone (Symrise product name, 8-cyclohexadecenon), methyl nonylketone, cis-jasmone, and paraamylcyclohexanone (4-pentylcyclohexanone). Among these, ionone, damascenone, iso-E-super, or γ-methylionone are preferred from the viewpoint of emphasizing floral sweetness when blended with other fragrances.

[0085] Examples of acetals include acetaldehyde ethylphenylpropyl acetal, citral diethyl acetal, phenylacetaldehyde glyceryl acetal, ethyl acetacetate ethylene glycol acetal, Boazanblenforte (Kao Corporation product name, ethoxymethylcyclododecyl ether), Troenan (Kao Corporation product name, 5-methyl-5-propyl-2-(1-methylbutyl)-1,3-dioxane), Floropal (Symlize product name, 2,4,6-trimethyl-4-phenyl-1,3-dioxane), and Magnolan (Symlize product name, 2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxane).

[0086] Examples of ethers include cedyl methyl ether, estragole, anethole, β-naphthyl methyl ether, β-naphthyl ethyl ether, limonene oxide, rose oxide, nerol oxide, 1,8-cineole, rose furan, ambroxan (Kao Corporation trade name, [3aR-(3aα,5aβ,9aα,9bβ)] dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan), Herbaveil (Kao Corporation trade name, 3,3,5-trimethylcyclohexyl ethyl ether), galaxolide (IFF trade name, hexamethylhexahydrocyclopentabenzopyran), and phenylacetaldehyde dimethyl acetal.

[0087] Examples of carboxylic acids include benzoic acid, phenylacetic acid, cinnamic acid, hydrocinnamic acid, butyric acid, and 2-hexenoic acid.

[0088] Examples of lactones include ambrettelid, γ-decalactone, δ-decalactone, γ-valerolactone, γ-nonalactone, γ-undecalactone, δ-hexalactone, γ-jasmolactone, whiskeylactone, coumarin, cyclopentadecanolide, cyclohexadecanolide, 11-oxahexadecanolide, and butylidenephthalide.

[0089] Examples of nitriles include tridecene-2-nitrile, geranyl nitrile, citronellyl nitrile, and dodecane nitrile.

[0090] Examples of amines include indole, skatole, 6-methylquinoline, 6-isopropylquinoline, and isobutylquinoline.

[0091] Examples of Schiff bases include aurantiol and ligantral.

[0092] Natural essential oils and extracts include those from orange, lemon, lime, bergamot, vanilla, mandarin, peppermint, spearmint, lavender, galbanum, chamomile, rosemary, eucalyptus, sage, basil, rose, rock rose, geranium, jasmine, ylang-ylang, anise, clove, ginger, nutmeg, cardamom, cedar, cypress, vetiver, patchouli, hay, lemongrass, labdanum, grapefruit, elemi oil, and other natural oils, as well as concretes, absolutes, resinoids, oleoresins, tinctures, infusions, and balsams.

[0093] The content of these other fragrances can be appropriately selected depending on the type of blended fragrance, the type of fragrance to be desired, and the strength of the fragrance, but in the composition containing the fragrance composition of the present invention, each is preferably 0.0001% by mass or more, more preferably 0.001% by mass or more, and preferably 99.99% by mass or less, and more preferably 80% by mass or less. Furthermore, the total content of the other fragrances in the composition containing the fragrance composition of the present invention is preferably 5% by mass or more, more preferably 50% by mass or more, and preferably 99.99% by mass or less, and more preferably 99.95% by mass or less.

[0094] The mass ratio (total amount / amount of other fragrances) of the total amount of the compound represented by formula (I) and the compound represented by formula (II) to these other fragrances is preferably 0.01 / 99.99 or more, more preferably 0.1 / 99.9 or more, and even more preferably 1 / 99 or more, and from the viewpoint of exhibiting the function of a fragrance, preferably 1 / 2 or less, more preferably 1 / 3 or less, and even more preferably 1 / 4 or less, preferably 0.01 / 99.99 or more and 1 / 2 or less, more preferably 0.1 / 99.9 or more and 1 / 3 or less, and even more preferably 1 / 99 or more and 1 / 4 or less.

[0095] Furthermore, the content of the compound represented by formula (I) in the fragrance composition is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, even more preferably 0.2% by mass or more, preferably 20% by mass or less, more preferably 15% by mass or less, even more preferably 10% by mass or less, preferably 0.01% by mass or more and 20% by mass or less, more preferably 0.1% by mass or more and 15% by mass or less, and even more preferably 0.2% by mass or more and 10% by mass or less.

[0096] The fragrance composition of the present invention can be combined with an oily agent that itself has no odor as a base. Such an oily agent can uniformly mix the fragrance components, making it easy to incorporate into products and to impart a fragrance of appropriate intensity. Examples of such oily agents include polyhydric alcohols such as ethylene glycol, propylene glycol, butylene glycol, and dipropylene glycol; esters such as isopropyl myristate, dibutyl adipate, and diethyl sebacate; hydrocarbons such as liquid paraffin and squalane; and surfactants such as polyoxyethylene alkyl ethers and sorbitan fatty acid esters.

[0097] Among these, from the viewpoint of the solubility of all fragrance components, polyhydric alcohols and esters are preferred as the oils, and dipropylene glycol and isopropyl myristate are more preferred. The content of such oils in the fragrance composition is preferably 0.01% by mass or more, more preferably 1% by mass or more, even more preferably 5% by mass or more, and preferably 95% by mass or less, more preferably 90% by mass or less, and even more preferably 80% by mass or less.

[0098] The present invention also provides a detergent composition containing the fragrance composition of the present invention, a cosmetic composition containing the fragrance composition of the present invention, and a textile treatment composition containing the fragrance composition of the present invention.

[0099] The detergent compositions of the present invention are preferably body detergent compositions, clothing detergent compositions, and hard surface detergent compositions, more preferably body detergent compositions and clothing detergent compositions, and even more preferably clothing detergent compositions.

[0100] Examples of body cleansing compositions include skin cleansing compositions, hair cleansing compositions, and soap compositions, with skin cleansing compositions being preferred.

[0101] Examples of cleaning agent compositions for hard surfaces include all-purpose cleaners and dishwashing detergent compositions.

[0102] A softening agent composition is preferred as the fiber treatment composition of the present invention.

[0103] The cosmetic composition of the present invention is preferably perfume, lotion, toner, or sunscreen, with perfume being more preferred.

[0104] The detergent composition of the present invention preferably contains an anionic surfactant in addition to the fragrance composition of the present invention, and may further contain nonionic surfactants, pH adjusters, viscosity adjusters, solvents, oils, preservatives, water, etc.

[0105] The fiber treatment composition of the present invention preferably contains a cationic surfactant in addition to the fragrance composition of the present invention, and may further contain pH adjusters, solvents, oils, preservatives, water, etc.

[0106] In addition to the fragrance composition of the present invention, the perfume of the present invention may contain solvents, water, and the like.

[0107] The fragrance formulation comprising the compound represented by formula (I) and the fragrance composition of the present invention containing said fragrance formulation have desirable fruity (apple-like), herbal, and minty-like scents. Furthermore, the fragrance composition of the present invention containing the compound represented by formula (I) and the compound represented by formula (II) can give a new impression to amber core by imparting a honey-like sweetness and fragrance volume.

[0108] Accordingly, the present invention relates to a method of using the fragrance agent or fragrance composition of the present invention ("a fragrance composition of the present invention comprising a fragrance agent comprising a compound represented by formula (I)" and "a fragrance composition of the present invention comprising a compound represented by formula (I) and a compound represented by formula (II)") as a fragrance component, specifically, a method of using it as a fragrance component in a fragrance composition, a detergent composition, a cosmetic, or a textile treatment composition. The detergent composition is preferably a body detergent composition, a laundry detergent composition, or a hard surface detergent composition, more preferably a body detergent composition or a laundry detergent composition, and even more preferably a laundry detergent composition. Examples of the body detergent composition include a skin detergent composition, a hair detergent composition, and a soap composition, with the skin detergent composition being preferred. Examples of the hard surface detergent composition include an all-purpose cleaner and a dishwashing detergent composition. The cosmetic is preferably a perfume. The textile treatment composition is preferably a fabric softener composition.

[0109] In the method of use described above, the fragrance composition of the present invention is used in an amount of preferably 0.0001% by mass or more, more preferably 0.001% by mass or more, preferably 30% by mass or less, more preferably 20% by mass or less, even more preferably 10% by mass or less, 1% by mass or less, and more preferably 0.1% by mass or less, relative to the detergent composition, cosmetic composition, or softener composition. By using this amount, when this fragrance composition is formulated with other components as a fragrance material, it is possible to give a new impression, such as a sparkling, effervescent impression at the top of a citrus scent, or a natural floral feeling like being in a flower shop, with green and woody nuances added along with the floral scent.

[0110] In the method of use described above, the fragrance composition of the present invention may be combined with an oil that itself has no odor. The oil is the same as that described in the fragrance composition. In addition, in the method of use described above, the fragrance composition of the present invention may also contain other fragrances, such as other commonly used fragrance components or blended fragrances of a desired composition. Such other fragrances are the same as those described in the fragrance composition.

[0111] The present invention includes the following embodiments. <1> A fragrance consisting of the compound represented by formula (I).

[0112] [ka]

[0113] In the above formula (I), R 1 This is an alkyl group having 1 to 5 carbon atoms. R 2 This is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0114] <2> R 1 However, it is a tert-butyl group, R 2 However, it is an ethyl group. <1> The fragrances listed.

[0115] <3> Compounds other than those represented by formula (I) and formula (II), comprising one or more of the following: alcohols, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, nitriles, amines, natural essential oils, and natural extracts. <1> or <2> A fragrance composition comprising the fragrance agent described in [reference].

[0116] [ka]

[0117] In equations (I) and (II) above, R 1 and R 3 Each of these is independently an alkyl group having 1 to 5 carbon atoms. R 2 and R 4 Each of these is independently either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0118] <4> A fragrance comprising a compound represented by formula (I) and one or more other fragrances (hereinafter simply referred to as "other fragrances") other than the compounds represented by formula (I) and formula (II), wherein the mass ratio (amount of compound represented by formula (I) / total amount of other fragrances) is 0.01 / 99.99 or more and 1 / 2 or less. <3> The fragrance composition described above.

[0119] <5> A fragrance comprising a compound represented by formula (I) and one or more other fragrances (hereinafter simply referred to as "other fragrances") other than the compounds represented by formula (I) and formula (II), wherein the mass ratio (amount of compound represented by formula (I) / total amount of other fragrances) is 0.1 / 99.9 or more and 1 / 3 or less. <3> or <4> The fragrance composition described above.

[0120] <6> A fragrance comprising a compound represented by formula (I) and one or more other fragrances (hereinafter simply referred to as "other fragrances") other than the compounds represented by formula (I) and formula (II), wherein the mass ratio (amount of compound represented by formula (I) / total amount of other fragrances) is 1 / 99 or more and 1 / 4 or less. <3> ~ <5> A fragrance composition as described in any of the following.

[0121] <7> The content of the fragrance agent comprising the compound represented by formula (I) in the fragrance composition is 0.01% by mass or more and 20% by mass or less. <3> ~ <6> A fragrance composition as described in any of the following.

[0122] <8> In the fragrance composition, the content of the fragrance agent consisting of the compound represented by formula (I) is 0.1% by mass or more and 15% by mass or less. <3> ~ <7> A fragrance composition as described in any of the following.

[0123] <9> In the fragrance composition, the content of the fragrance agent consisting of the compound represented by formula (I) is 0.2% by mass or more and 10% by mass or less. <3> ~ <8> A fragrance composition as described in any of the following.

[0124] <10> <3> ~ <9> A cosmetic containing the fragrance composition described in any of the following.

[0125] <11> <3> ~ <9> A detergent composition comprising the fragrance composition described in any of the above.

[0126] <12> <3> ~ <9> A fiber treatment agent composition comprising the fragrance composition described in any of the above.

[0127] <13> <1> or <2> A method of using the fragrances described above as fragrance components.

[0128] <14> A fragrance composition comprising a compound represented by formula (II) and a compound represented by formula (I), wherein the mass ratio of the compound represented by formula (II) to the compound represented by formula (I) [compound represented by formula (II):compound represented by formula (I)] is 99.99:0.01 or more and 98:2 or less.

[0129] [ka]

[0130] In equations (I) and (II) above, R 1 and R 3 Each of these is independently an alkyl group having 1 to 5 carbon atoms. R 2 and R 4 Each of these is independently either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0131] <15> The mass ratio of the compound represented by formula (II) to the compound represented by formula (I) [compound represented by formula (II):compound represented by formula (I)] is between 99.99:0.01 and 99:1. <14> The fragrance composition described above.

[0132] <16> The mass ratio of the compound represented by formula (II) to the compound represented by formula (I) [compound represented by formula (II):compound represented by formula (I)] is between 99.97:0.03 and 99.20:0.80. <14> or <15> The fragrance composition described above.

[0133] <17> The mass ratio of the compound represented by formula (II) to the compound represented by formula (I) [compound represented by formula (II):compound represented by formula (I)] is 99.95:0.05 or more and 99.50:0.50 or less. <14> ~ <16> A fragrance composition as described in any of the following.

[0134] <18> In the above equation (II), R 3 However, it is a tert-butyl group, R 4However, it is an ethyl group. <14> ~ <17> A fragrance composition as described in any of the following.

[0135] <19> In equations (I) and (II) above, R 1 and R 3 However, it is a tert-butyl group, R 2 and R 4 However, it is an ethyl group. <14> ~ <18> A fragrance composition as described in any of the following.

[0136] <20> A compound other than the compound represented by formula (I) and the compound represented by formula (II), further comprising one or more of the following: alcohol, phenol, ester, carbonate, aldehyde, ketone, acetal, ether, lactone, nitrile, amine, natural essential oil, and natural extract. <14> ~ <19> A fragrance composition as described in any of the following.

[0137] <21> The total amount of the compound represented by formula (I) and the compound represented by formula (II) and the mass ratio of one or more substances other than the compounds represented by formula (I) and formula (II), which are alcohols, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, nitriles, amines, natural essential oils, and natural extracts (hereinafter simply referred to as "other fragrances"), is 0.01 / 99.99 or more and 1 / 2 or less. <14> ~ <20> A fragrance composition as described in any of the following.

[0138] <22> The total amount of the compound represented by formula (I) and the compound represented by formula (II) and the mass ratio of one or more substances other than the compounds represented by formula (I) and formula (II), which are alcohols, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, nitriles, amines, natural essential oils, and natural extracts (hereinafter simply referred to as "other fragrances"), is 0.1 / 99.9 or more and 1 / 3 or less. <14> ~ <21> A fragrance composition as described in any of the following.

[0139] <23> The total amount of the compound represented by formula (I) and the compound represented by formula (II) and the mass ratio of one or more substances other than the compounds represented by formula (I) and formula (II), which are alcohols, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, nitriles, amines, natural essential oils, and natural extracts (hereinafter simply referred to as "other fragrances"), is 1 / 99 or more and 1 / 4 or less. <14> ~ <22> A fragrance composition as described in any of the following.

[0140] <24> The content of the compound represented by formula (I) in the fragrance composition is 0.01% by mass or more and 20% by mass or less. <14> ~ <23> A fragrance composition as described in any of the following.

[0141] <25> The content of the compound represented by formula (I) in the fragrance composition is 0.1% by mass or more and 15% by mass or less. <14> ~ <24> A fragrance composition as described in any of the following.

[0142] <26> The content of the compound represented by formula (I) in the fragrance composition is 0.2% by mass or more and 10% by mass or less. <14> ~ <25> A fragrance composition as described in any of the following.

[0143] <27> <14> ~ <26> A cosmetic containing the fragrance composition described in any of the following.

[0144] <28> <14> ~ <26> A detergent composition comprising the fragrance composition described in any of the above.

[0145] <29> <14> ~ <26> A fiber treatment agent composition comprising the fragrance composition described in any of the above.

[0146] <30> <14> ~ <26> A method of using any of the fragrance compositions described above as a fragrance component.

[0147] In the following reference examples, examples, and comparative examples, "%" refers to "mass%" unless otherwise specified. Furthermore, the mass of the catalyst is the mass in a dry state.

[0148] <Gas chromatography equipment and analytical conditions> GC system: Agilent Technologies, Inc. 7890B, flame ionization detector; Column: For yield analysis, DB-1 (capillary column, 100% dimethylpolysiloxane, inner diameter 0.25 mm, length 30 m, film thickness 0.25 μm, manufactured by Agilent Technologies, Inc.) was used.

[0149] For the analysis of cis and trans isomers, DB-WAX (capillary column, polyethylene glycol, inner diameter 0.25 mm, length 30 m, film thickness 0.25 μm, manufactured by Agilent Technologies, Inc.) was used.

[0150] Carrier gas: He, 1.5 mL / min Injection conditions: 300°C, split ratio 100 / 1 Injection volume: 1 μL Detection conditions: FID method, 300°C Column temperature conditions: Starting at 80°C, the temperature was increased to 300°C at a rate of 10°C / min. The temperature was then maintained at 300°C for 10 minutes.

[0151] [Reference example 1] Preparation of 1-(2-t-butylphenyloxy)-2-butanol (3)

[0152] [ka]

[0153] In a 1-liter round-bottom flask fitted with a Liebig lid and a dropping funnel, 350 g of 2-t-butylphenol (1) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) and 35 g of 48% sodium hydroxide aqueous solution (manufactured by Kanto Chemical Co., Ltd.) were added under a nitrogen stream and heated to 80°C. 1,2-butylene oxide (2) (manufactured by Tokyo Chemical Industries, Ltd., 176 g) was added dropwise over approximately 2 hours, and the mixture was then stirred at 80°C for 5 hours. After the reaction mixture cooled, the lower layer of sodium hydroxide aqueous solution was separated from the organic layer, and the organic layer was distilled to obtain 1-(2-t-butylphenoxy)-2-butanol (3) in 96% yield.

[0154] [Reference example 2] Preparation of 1-(2-t-butylcyclohexyloxy)-2-butanol (4)

[0155] [ka]

[0156] 1-(2-t-butylphenyloxy)-2-butanol(3) (250g) obtained in Reference Example 1, activated carbon-supported palladium catalyst (manufactured by N.E. Chemcat Co., Ltd., product name: S type, 50% hydrated, palladium load 2%, 4.75g), and activated carbon-supported ruthenium catalyst (manufactured by N.E. Chemcat Co., Ltd., 50% hydrated, ruthenium load 5%, 0.25g) were added to a 500ml autoclave, and the reaction was carried out at a hydrogen pressure of 2.0 MPa and 190°C for 6 hours.

[0157] After the reaction was complete, the catalyst was filtered and the filtrate was distilled to obtain 1-(2-t-butylcyclohexyloxy)-2-butanol (4) in a yield of 70%.

[0158] [Reference example 3] Preparation of 6-t-butyl-2-ethyl-1,4-dioxaspiro[4,5]decane(5)

[0159] [ka]

[0160] 1-(2-t-butylphenyloxy)-2-butanol(3) (250g) obtained in Reference Example 1, activated carbon-supported palladium catalyst (manufactured by N.E. Chemcat Co., Ltd., product name: S type, 50% hydrated, 2% palladium load, 4.75g), and activated carbon-supported ruthenium catalyst (manufactured by N.E. Chemcat Co., Ltd., 50% hydrated, 5% ruthenium load, 0.25g) were added to a 500ml autoclave, and the reaction was carried out at a hydrogen pressure of 2.0 MPa and 190°C for 2 hours.

[0161] After the reaction was complete, the catalyst was filtered and the filtrate was distilled to obtain 6-t-butyl-2-ethyl-1,4-dioxaspiro[4,5]decane(5) as a mixture of four diastereomers in a yield of 18% and purity of 99.6%.

[0162] 1 H-NMR (400MHz, CDCl3): δ(ppm)0.8-1.1(m,12H),1.1-2.0(m,11H),3.3-3.7(m,1H),3.9-4.2(m,2H) IR(neat):ν(cm -1 )511,530,592,678,750,792,808,856,866,904,930,954,975,995,1044,1083,1113,1151,1195,1214,1245,1257,1281,1305,1335,1366,1394,1445,1461,1477,2865,2934.

[0163] [Example 1] 6-t-butyl-2-ethyl-1,4-dioxaspiro[4,5]decane (5) obtained in Reference Example 3 was used as the fragrance composition of Example 1 for sensory evaluation (mass ratio of compound (4) to compound (5) = 0 / 100).

[0164] [Example 2] To 50 g of 1-(2-t-butylcyclohexyloxy)-2-butanol (4) obtained in Reference Example 2, 5 mg of 6-t-butyl-2-ethyl-1,4-dioxaspiro[4,5]decane (5) obtained in Reference Example 3 was added and mixed to obtain a fragrance composition (mass ratio of compound (4) to compound (5) in the mixture = 99.99 / 0.01).

[0165] [Example 3] To 10 g of 1-(2-t-butylcyclohexyloxy)-2-butanol (4) obtained in Reference Example 2, 5 mg of 6-t-butyl-2-ethyl-1,4-dioxaspiro[4,5]decane (5) obtained in Reference Example 3 was added and mixed to obtain a fragrance composition (mass ratio of compound (4) to compound (5) in the mixture = 99.95 / 0.05).

[0166] [Example 4] To 5 g of 1-(2-t-butylcyclohexyloxy)-2-butanol (4) obtained in Reference Example 2, 5 mg of 6-t-butyl-2-ethyl-1,4-dioxaspiro[4,5]decane (5) obtained in Reference Example 3 was added and mixed to obtain a fragrance composition (mass ratio of compound (4) to compound (5) in the mixture = 99.90 / 0.10).

[0167] [Example 5] To 1 g of 1-(2-t-butylcyclohexyloxy)-2-butanol (4) obtained in Reference Example 2, 5 mg of 6-t-butyl-2-ethyl-1,4-dioxaspiro[4,5]decane (5) obtained in Reference Example 3 was added and mixed to obtain a fragrance composition (mass ratio of compound (4) to compound (5) in the mixture = 99.50 / 0.50).

[0168] [Example 6] To 1 g of 1-(2-t-butylcyclohexyloxy)-2-butanol (4) obtained in Reference Example 2, 7.5 mg of 6-t-butyl-2-ethyl-1,4-dioxaspiro[4,5]decane (5) obtained in Reference Example 3 was added and mixed to obtain a fragrance composition (mass ratio of compound (4) to compound (5) in the mixture = 99.26 / 0.74).

[0169] [Example 7] To 1 g of 1-(2-t-butylcyclohexyloxy)-2-butanol (4) obtained in Reference Example 2, 10 mg of 6-t-butyl-2-ethyl-1,4-dioxaspiro[4,5]decane (5) obtained in Reference Example 3 was added and mixed to obtain a fragrance composition (mass ratio of compound (4) to compound (5) in the mixture = 99.01 / 0.99).

[0170] [Comparative Example 1] 1-(2-t-butylcyclohexyloxy)-2-butanol (4), obtained in Reference Example 2, was used as the fragrance composition for Comparative Example 1 in the sensory evaluation. (Mass ratio of compound (4) to compound (5) = 100 / 0)

[0171] [Example 8] To 1 g of 1-(2-t-butylcyclohexyloxy)-2-butanol (4) obtained in Reference Example 2, 30 mg of 6-t-butyl-2-ethyl-1,4-dioxaspiro[4,5]decane (5) obtained in Reference Example 3 was added and mixed to obtain a fragrance composition (mass ratio of compound (4) to compound (5) in the mixture = 97.09 / 2.91).

[0172] [Example 9] To 1 g of 1-(2-t-butylcyclohexyloxy)-2-butanol (4) obtained in Reference Example 2, 50 mg of 6-t-butyl-2-ethyl-1,4-dioxaspiro[4,5]decane (5) obtained in Reference Example 3 was added and mixed to obtain a fragrance composition (mass ratio of compound (4) to compound (5) in the mixture = 95.24 / 4.76).

[0173] [Sensory evaluation] The fragrances of the fragrance compositions obtained in Examples 2-9 and Comparative Example 1 were evaluated by three expert panelists. The evaluation was performed using odor test paper (Daimonji Western Paper Co., Ltd., 150mm x 7mm). Examples 1-9 and Comparative Example 1, each with different isomer ratios, were applied to the tip of the odor test paper, and the evaluation was performed indoors after one hour. Sensory evaluation was performed from the perspective of odor characteristics and intensity. Odor characteristics and intensity were evaluated on a 5-point relative scale, with higher values ​​indicating a more desirable scent. For residual fragrance, the duration of the fragrance was confirmed and the number of days it lasted was indicated. In addition, the overall quality and characteristics of the fragrance as perceived by the three expert panelists in the sensory evaluation were also described. The results are shown in Table 1.

[0174] [Evaluation of Example 1] The fragrance composition obtained in Example 1 (a composition of 6-t-butyl-2-ethyl-1,4-dioxaspiro[4,5]decane alone) was evaluated, and a desirable fragrance was confirmed, with fruity, apple-like, and honey-like sweetness, and slight herbal, minty, and woody aspects. No chemical irritation, tobacco-like, or leathery aromas were detected, confirming its high versatility when used in blended fragrances.

[0175] [Table 1]

[0176] In Table 1, "volume" refers to the strength, depth, and richness of the fragrance, and having volume is desirable for a fragrance. As shown in Table 1, the fragrance composition of the present invention exhibited the effect of adding honey-like sweetness and fragrance volume while maintaining a strong amber-like, woody, and slightly camphor-like fragrance.

[0177] [Example 10: Formulation Example 1] A sensory evaluation was conducted on a composition in which 900 parts by mass of a jasmine-scented fragrance blend with the composition described below was added to 6-t-butyl-2-ethyl-1,4-dioxaspiro[4,5]decane (5) obtained in Reference Example 3. The sensory evaluation was performed using the same method as that used to evaluate Examples 1-9 and Comparative Example 1. The results are shown in Table 4. For the evaluation results, the degree of effect was relatively evaluated on a 5-point scale, with higher values ​​being preferable.

[0178] [Table 2]

[0179] [Table 3]

[0180] [Table 4]

[0181] As shown in Table 4, the sensory evaluation by three expert panelists revealed that when the fragrance composition of the present invention is used, a honey-like sweetness is added to the jasmine-like fragrance blend, enhancing its naturalness and overall fragrance volume.

[0182] [Example 11: Formulation Example 2] A sensory evaluation was conducted on a composition in which 925 parts by mass of a pear-scented fragrance blend with the composition described below was added to 6-t-butyl-2-ethyl-1,4-dioxaspiro[4,5]decane (5) obtained in Reference Example 3. The sensory evaluation was performed using the same method as that used to evaluate Examples 1-10 and Comparative Examples 1-2. The results are shown in Table 7. The degree of effect was evaluated on a 5-point scale, with higher values ​​indicating a preference.

[0183] [Table 5]

[0184] [Table 6]

[0185] [Table 7]

[0186] As shown in Table 7, sensory evaluation by three expert panelists revealed that using the fragrance composition of the present invention enhances the naturalness and overall volume of the pear-like fragrance blend.

[0187] [Example 12: Formulation Example 3] A sensory evaluation was conducted on a composition in which 970 parts by mass of a lime-scented fragrance blend with the composition described below was added to 6-t-butyl-2-ethyl-1,4-dioxaspiro[4,5]decane (5) obtained in Reference Example 3. The sensory evaluation was performed using the same method as that used to evaluate Examples 1 to 11 and Comparative Examples 1 to 3. The results are shown in Table 10. The degree of effect was evaluated on a 5-point scale, with higher values ​​indicating a preference.

[0188] [Table 8]

[0189] [Table 9]

[0190] [Table 10]

[0191] As shown in Table 10, the results of sensory evaluation by three expert panelists revealed that when the fragrance composition of the present invention is used, it enhances the lime-like green scent in a lime-like fragrance blend, harmonizes the overall fragrance, and imparts a natural feel.

[0192] [Example 13: Formulation Example 4] A sensory evaluation was conducted on a composition in which 950 parts by mass of a rose-scented fragrance blend with the composition described below was added to 6-t-butyl-2-ethyl-1,4-dioxaspiro[4,5]decane (5) obtained in Reference Example 3. The sensory evaluation was performed using the same method as that used to evaluate Examples 1 to 12 and Comparative Examples 1 to 4. The results are shown in Table 13. The degree of effect was evaluated on a 5-point scale, with higher values ​​indicating a preference.

[0193] [Table 11]

[0194] [Table 12]

[0195] [Table 13]

[0196] As shown in Table 13, sensory evaluation by three expert panelists revealed that using the fragrance composition of the present invention imparts sweetness to rose-like fragrances, enhancing their naturalness and overall fragrance volume.

[0197] [Example 14: Formulation Example 5] A sensory evaluation was conducted on a composition in which 900 parts by mass of a lychee-scented fragrance blend with the composition described below was added to 6-t-butyl-2-ethyl-1,4-dioxaspiro[4,5]decane (5) obtained in Reference Example 3. The sensory evaluation was performed using the same method as that used to evaluate Examples 1 to 13 and Comparative Examples 1 to 5. The results are shown in Table 16. For the evaluation results, the degree of effect was relatively evaluated on a 5-point scale, with higher values ​​being preferable.

[0198] [Table 14]

[0199]

Table 15

[0200]

Table 16

[0201] As shown in Table 16, as a result of sensory evaluation by three professional panelists, when the fragrance composition of the present invention was used, it was found that the fragrance was emphasized and sweetness and fragrance volume were imparted to the lychee-like compounded fragrance.

[0202] [Example 15: Formulation Example 6] Sensory evaluation was carried out on a composition obtained by adding 6-t-butyl-2-ethyl-1,4-dioxaspiro[4,5]decane (5) obtained in Reference Example 3 to 900 parts by mass of a compounded fragrance having a fusel fragrance of the following composition. The sensory evaluation was carried out in the same manner as in Examples 1 to 14 and Comparative Examples 1 to 6. The results obtained are shown in Table 19. Regarding the evaluation results, the degree of effect was relatively evaluated in five grades, and a larger numerical value is preferable.

[0203]

Table 17

[0204]

Table 18

[0205]

Table 19

[0206] As shown in Table 19, as a result of sensory evaluation by three professional panelists, when the fragrance composition of the present invention was used, it was found that for the compounded fragrance having a fusel-like fragrance, the gloss and powdery impression were emphasized and the fragrance volume was imparted.

[0207] [Example 16: Formulation Example 7] A sensory evaluation was conducted on a composition in which 730 parts by mass of a green apple fragrance blend with the following composition was added to 1-(2-t-butylcyclohexyloxy)-2-butanol (4) obtained in Reference Example 2 and 6-t-butyl-2-ethyl-1,4-dioxaspiro[4,5]decane (5) obtained in Reference Example 3. The sensory evaluation was performed using the same method as that used to evaluate Examples 1-15 and Comparative Examples 1-7. The results are shown in Table 22. The degree of effect was evaluated on a 5-point scale, with higher values ​​being preferable.

[0208] [Table 20]

[0209] [Table 21]

[0210] [Table 22]

[0211] As shown in Table 22, the results of sensory evaluation by three expert panelists revealed that when the fragrance composition of the present invention is used, a freshness and fruity sweetness are newly imparted to fruity fragrance blends, and volume is also added.

[0212] The fragrance agent comprising the compound of formula (I) of the present invention and the fragrance composition containing the fragrance agent can provide fragrance compositions with desirable fruity (apple-like), herbal, and minty scents. Furthermore, the fragrance composition containing the compound of formula (I) and the compound of formula (II) imparts a honey-like sweetness and fragrance volume to the amber core.

Claims

1. A fragrance comprising a compound represented by formula (I): 【Chemistry 17】 [In the formula (I), R 1 is an alkyl group having 1 to 5 carbon atoms, R 2 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

2. R 1 is a tert-butyl group, R 2 2. The fragrance according to claim 1, wherein is an ethyl group.

3. one or more of alcohols, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, nitriles, amines, natural essential oils, and natural extracts other than the compounds represented by formula (I) and formula (II); A fragrance composition comprising the fragrance according to claim 1 or 2. 【Chemistry 18】 [In the formula (I) and formula (II), R 1 and R 3 each independently represents an alkyl group having 1 to 5 carbon atoms, R 2 and R 4 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

4. A cosmetic comprising the fragrance composition according to claim 3.

5. A cleaning composition comprising the fragrance composition according to claim 3.

6. A fabric treatment composition comprising the fragrance composition according to claim 3.

7. 3. A method for using the fragrance according to claim 1 or 2 as a fragrance ingredient.

8. A fragrance composition comprising a compound represented by formula (II) and a compound represented by formula (I), wherein the mass ratio of the compound represented by formula (II) to the compound represented by formula (I) [compound represented by formula (II) : compound represented by formula (I)] is 99.99:0.01 or more and 98:2 or less. 【Chemistry 19】 [In the formula (I) and formula (II), R 1 and R 3 each independently represents an alkyl group having 1 to 5 carbon atoms, R 2 and R 4 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

9. The fragrance composition according to claim 8, wherein a mass ratio of the compound represented by formula (II) to the compound represented by formula (I) [compound represented by formula (II):compound represented by formula (I)] is 99.97:0.03 or more and 99.20:0.80 or less.

10. In the formula (II), R 3 is a tert-butyl group, R 4 The fragrance composition according to claim 8, wherein is an ethyl group.

11. In the above formula (I) and formula (II), R 1 and R 3 is a tert-butyl group, R 2 and R 4 The fragrance composition according to claim 8, wherein is an ethyl group.

12. The fragrance composition according to claim 8, further comprising at least one of alcohols, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, nitriles, amines, natural essential oils and natural extracts, other than the compounds represented by formula (I) and formula (II).

13. A cosmetic comprising the fragrance composition according to any one of claims 8 to 12.

14. A cleaning composition comprising the fragrance composition according to any one of claims 8 to 12.

15. A fabric treatment composition comprising the fragrance composition according to any one of claims 8 to 12.

16. A method for using the fragrance composition according to any one of claims 8 to 11 as a fragrance ingredient.

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