Flavoring composition

Abstract

To provide a new fragrance composition which contains a cis-form of α-(2-alkyl cyclohexyloxy)-β-alkanol at a specific ratio.SOLUTION: A composition contains a cis-form and a trans-form, where the cis-form includes compounds represented by formulas Ia, Ib, IIa and IIb; the trans-form includes compounds represented by formulas IIIa, IIIb, IVa and IVb; and a mass ratio between the cis-form and the trans-form is from 65:35 to 95:5 inclusive.SELECTED DRAWING: None

Description

[Technical Field]

[0001] This invention relates to a fragrance composition. [Background technology]

[0002] α-(2-alkylcyclohexyloxy)-β-alkanols, and in particular 1-(2-t-butylcyclohexyloxy)-2-alkanols, are useful fragrance materials that have woody and amber-like aromas, excellent longevity, and can be manufactured inexpensively (Patent Document 1).

[0003] For example, 1-(2-t-butylcyclohexyloxy)-2-butanol is widely known as Ambercore, a fragrance with a woody-amber scent (a refreshing cypress-like fragrance) and long-lasting fragrance.

[0004] Ambercore is a mixture of the cis and trans isomers of 1-(2-t-butylcyclohexyloxy)-2-butanol (mass ratio of cis:trans isomers:1:0.5~1.0). Of these, the trans isomer has a particularly strong woody-amber fragrance. Note that "cis" and "trans" refer to whether the functional groups bonded to cyclohexane are in the cis or trans configuration. Specifically, the cis and trans isomers of Ambercore have the following stereostructures, respectively.

[0005] [ka] [Prior art documents] [Patent Documents]

[0006] [Patent Document 1] Japanese Patent Publication No. 4-217937 [Overview of the Initiative] [Problems that the invention aims to solve]

[0007] The present invention aims to provide a novel fragrance composition by focusing on the cis isomer of α-(2-alkylcyclohexyloxy)-β-alkanol, which has not been given much attention in conventional amber cores. [Means for solving the problem]

[0008] The inventors have surprisingly discovered that in a fragrance composition containing the trans and cis isomers of α-(2-alkylcyclohexyloxy)-β-alkanol, when the proportion of the cis isomer is dominant, specifically when the mass ratio of the cis isomer to the trans isomer [cis isomer:trans isomer] is between 65:35 and 95:5, a soft, woody, and fresh impression is perceived. This impression is a new one, distinct from amber core. Furthermore, the inventors have found that when this fragrance composition is formulated with other ingredients as a fragrance material, it unexpectedly gives a new impression, such as a sparkling, effervescent top note in a citrus scent, or a natural floral feeling reminiscent of a flower shop, with green and woody nuances added to the floral scent. Based on this finding, the fragrance composition of the present invention was completed.

[0009] In other words, the present invention relates to a fragrance composition comprising a cis isomer and a trans isomer, The cis isomer includes the compound represented by formula (Ia), the compound represented by formula (Ib), the compound represented by formula (IIa), and the compound represented by formula (IIb). The fragrance composition comprises the compound represented by formula (IIIa), the compound represented by formula (IIIb), the compound represented by formula (IVa), and the compound represented by formula (IVb), wherein the mass ratio [cis:trans] of the cis isomer to the trans isomer is 65:35 or more and 95:5 or less. The compound represented by formula (Ia), the compound represented by formula (Ib), the compound represented by formula (IIa), and the compound represented by formula (IIb) are the cis isomers of α-(2-alkylcyclohexyloxy)-β-alkanol, and the compound represented by formula (IIIa), the compound represented by formula (IIIb), the compound represented by formula (IVa), and the compound represented by formula (IVb) are the trans isomers of α-(2-alkylcyclohexyloxy)-β-alkanol.

[0010] [ka]

[0011] In the above formulas (Ia), (Ib), (IIa), (IIb), (IIIa), (IIIb), (IVa), and (IVb), 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. [Effects of the Invention]

[0012] The fragrance composition of the present invention contains a specific ratio of the cis isomer of α-(2-alkylcyclohexyloxy)-β-alkanol, exhibits excellent compatibility with various other fragrances, and can create distinctive fragrance effects when blended. [Modes for carrying out the invention]

[0013] As described above, the present invention relates to a fragrance composition comprising a cis isomer and a trans isomer, The cis isomer includes the compound represented by formula (Ia), the compound represented by formula (Ib), the compound represented by formula (IIa), and the compound represented by formula (IIb). The trans isomer includes a compound represented by formula (IIIa), a compound represented by formula (IIIb), a compound represented by formula (IVa), and a compound represented by formula (IVb). From the viewpoint of the usefulness of the aroma as a perfume material, which has an excellent balance of a woody, soft and fresh impression, a natural-like quality, and residual fragrance, the mass ratio of the cis isomer to the trans isomer [cis isomer: trans isomer] is 65:35 or more and 95:5 or less. From the viewpoint of the usefulness of the aroma as a perfume material, which has an excellent balance of a woody, soft and fresh impression, a natural-like quality, and residual fragrance, the mass ratio of the cis isomer to the trans isomer [cis isomer: trans isomer] is preferably 68:32 or more and 90:10 or less, more preferably 68:32 or more and 85:15 or less, and still more preferably 68:32 or more and 75:25 or less.

[0014] Also, from the viewpoint of a woody, soft and fresh impression, the mass ratio of the cis isomer to the trans isomer [cis isomer: trans isomer] is 65:35 or more, preferably 68:32 or more, more preferably 82:18 or more, and still more preferably 85:15 or more.

[0015] Also, from the viewpoints of natural-like quality, strength, and residual fragrance, the mass ratio of the cis isomer to the trans isomer [cis isomer: trans isomer] is 95:5 or less, preferably 90:10 or less, more preferably 85:15 or less, still more preferably 78:22 or less, and even more preferably 75:25 or less.

[0016] Therefore, from the viewpoint of a woody, soft and fresh impression, the mass ratio of the cis isomer to the trans isomer [cis isomer: trans isomer] is preferably 82:18 or more and 95:5 or less, more preferably 82:18 or more and 90:10 or less, and still more preferably 85:15 or more and 90:10 or less.

[0017] Also, from the viewpoints of natural-like quality, strength, and residual fragrance, the mass ratio of the cis isomer to the trans isomer [cis isomer: trans isomer] is preferably 65:35 or more and 78:22 or less, more preferably 68:32 or more and 78:22 or less, and still more preferably 68:32 or more and 75:25 or less.

[0018] [ka]

[0019] In the above formulas (Ia), (Ib), (IIa), (IIb), (IIIa), (IIIb), (IVa), and (IVb), 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.

[0020] In the present invention, the cis isomer includes the compound represented by formula (Ia), the compound represented by formula (Ib), the compound represented by formula (IIa), and the compound represented by formula (IIb). In the cis isomer, the mass ratio of the total of the compound represented by formula (Ia) and the compound represented by formula (Ib) to the total of the compound represented by formula (IIa) and the compound represented by formula (IIb) [total of the compound represented by formula (Ia) and the compound represented by formula (Ib): total of the compound represented by formula (IIa) and the compound represented by formula (IIb)] (also called the "cis isomer ratio") is preferably 55:45 to 68:32, more preferably 55.5:44.5 to 66:34, and even more preferably 56:44 to 62:38, from the viewpoint of imparting a sparkling, effervescent impression at the top of the citrus scent, and adding green and woody nuances along with the floral scent to give a natural floral feeling like being in a flower shop.

[0021] Furthermore, in the fragrance composition of the present invention, the mass concentration of the cis isomer is preferably 65% ​​by mass or more, more preferably 66% by mass or more, even more preferably 67% by mass or more, even more preferably 68% by mass or more, and even more preferably 69% by mass or more, from the viewpoint of naturalness, strength and lingering fragrance, for example, preferably 95% by mass or less, more preferably 85% by mass or less, even more preferably 80% by mass or less, and even more preferably 75% by mass or less. Fragrance compositions with such proportions have excellent compatibility with various other fragrances, and it is possible to create characteristic fragrance effects by blending them.

[0022] The compounds represented by formula (Ia), formula (Ib), formula (IIa), formula (IIb), formula (IIIa), formula (IIIb), formula (IVa), and formula (IVb) can be produced by conventionally known methods, for example, the method described in Japanese Patent Application Publication No. 4-217937.

[0023] Alternatively, the compounds represented by formula (Ia), formula (Ib), formula (IIa), formula (IIb), formula (IIIa), formula (IIIb), formula (IVa), and formula (IVb) can be produced, for example, by the following method.

[0024] [ka]

[0025] In equations (X), (XI), (XII), and (XIII) 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.

[0026] Compound (X) and compound (XI) are heated in the presence of a base (e.g., sodium hydroxide) to obtain compound (XII). Compound (XII) is hydrogenated in the presence of a catalyst (e.g., palladium catalyst) and hydrogen to obtain compound (XIII). The obtained compound (XIII) is a mixture of a cis isomer containing the compound represented by formula (Ia), formula (Ib), formula (IIa), and formula (IIb), and a trans isomer containing the compound represented by formula (IIIa), formula (IIIb), formula (IVa), and formula (IVb). The obtained compound (XIII) can be separated by distillation or column chromatography to isolate the cis or trans isomer in high purity. If necessary, a mixture of the compound of formula (XIII) (a mixture of the cis and trans isomers in a specific ratio) and a high-purity cis isomer (including the compound represented by formula (Ia), the compound represented by formula (Ib), the compound represented by formula (IIa), and the compound represented by formula (IIb)) or a high-purity trans isomer (including the compound represented by formula (IIIa), the compound represented by formula (IIIb), the compound represented by formula (IVa), and the compound represented by formula (IVb)) can be mixed to obtain a mixture containing the trans and cis isomers in a desired ratio.

[0027] [ka]

[0028] In the above formulas (Ia), (Ib), (IIa), (IIb), (IIIa), (IIIb), (IVa), and (IVb), 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] In the above formulas (Ia), (Ib), (IIa), (IIb), (IIIa), (IIIb), (IVa), and (IVb), R1 is preferably an alkyl group having 1 to 4 carbon atoms, more preferably an alkyl group having 3 to 4 carbon atoms, and still more preferably a t-butyl group. Also, R 2 is preferably a methyl group or an ethyl group.

[0030] Since the composition of the present invention contains the cis form and the trans form in a specific ratio, it has excellent compatibility with various other fragrances, and it is possible to create a characteristic fragrance effect by blending. Further, the fragrance composition of the present invention can combine other commonly used fragrance components or compounded fragrances of a desired composition as fragrances other than the cis form and the trans form. By combining fragrances other than the cis form and the trans form, for example, an impression such as a sparkling and bouncing top note, and nuances such as green and woody along with a floral fragrance can be added to give the fragrance composition of the present invention a natural floral feeling as if in a flower shop. That is, the fragrance composition of the present invention preferably is a composition further containing a fragrance other than the group consisting of the cis form and the trans form.

[0031] In the composition of the present invention, other fragrances that can be used in combination with the cis form and the trans form include alcohols, hydrocarbons, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, carboxylic acids, lactones, nitriles, Schiff bases, natural essential oils, natural extracts, etc. (excluding the cis form and the trans form) of fragrance components.

[0032] Among these, alcohols, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, nitriles, natural essential oils, and natural extracts are preferred.

[0033] In this specification, the "class" of each fragrance means a single compound or a mixture of two or more compounds.

[0034] Examples of alcohols include aliphatic alcohols, terpene alcohols, aromatic alcohols, and other alcohols. Among these, aliphatic alcohols are preferred.

[0035] Examples of terpene alcohols include limonene, linalool, citronellol, geraniol, nerol, terpineol, α-terpineol, dihydromyrcenoyl, farnesol, nerolidol, cedrol, menthol, borneol, and phlorol (florosa).

[0036] Examples of aromatic alcohols include phenylethyl alcohol, benzyl alcohol, dimethylbenzylcarbinol, phenylethyldimethylcarbinol, and phenylhexanol.

[0037] Examples of aliphatic alcohols include cis-3-hexenol, 1-(2,2,6-trimethylcyclohexyl)-3-hexanol, Sandal Mysore Core (Kao Corporation product name, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol), Magnol (Kao Corporation product name, a mixture mainly composed of ethylnorbonylcyclohexanol), Undecaverthol (Givaudan Co., Ltd. product name, 4-methyl-3-decen-5-ol), and isobornylcyclohexanol.

[0038] Other alcohols include glycols such as dipropylene glycol, and Florosa (Divaudan trade name, chemical name: 4-methyl-2-(2-methylpropyl)tetrahydro-2H-4-pyranol).

[0039] Examples of hydrocarbons include limonene, α-pinene, β-pinene, terpinene, cedrene, longifolene, and valencene.

[0040] Examples of phenols include guaiacol, eugenol, dihydroeugenol, isoeugenol, thymol, paracresol, vanillin, and ethyl vanillin.

[0041] Examples of esters include aliphatic carboxylic acid esters, aromatic carboxylic acid esters, and other carboxylic acid esters.

[0042] 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.

[0043] Examples of formic acid esters include linalyl formate, citronellyl formate, and geranyl formate.

[0044] Examples of acetate esters include ethyl acetate, isoamyl acetate (isopentyl acetate), benzyl acetate, hexyl 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, o-tert-butylcyclohexyl acetate, p-tert-butylcyclohexyl acetate, tricyclodecenyl acetate, benzyl acetate, phenylethyl acetate, styraryl acetate, cinnamyl acetate, dimethylbenzylcarbinyl acetate, phenylethylphenyl acetate, 3-pentyltetrahydropyran-4-yl acetate, and paracresylphenyl acetate.

[0045] Examples of propionic acid esters include citronellyl propionate, tricyclodecenyl propionate, allylcyclohexyl propionate, ethyl 2-cyclohexyl propionate, benzyl propionate, and styraryl propionate.

[0046] Examples of butyrate esters include citronellyl butyrate, dimethylbenzylcarbinyl n-butyrate, and tricyclodecenyl isobutyrate.

[0047] 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.

[0048] Examples of heptanoic acid esters include methylheptanoate and allylheptanoate.

[0049] Examples of nonenate esters include methyl 2-nonenoate, ethyl 2-nonenoate, and ethyl 3-nonenoate.

[0050] Examples of benzoic acid esters include methyl benzoate, benzyl benzoate, and 3,6-dimethyl benzoate.

[0051] Examples of cinnamic acid esters include methyl cinnamate and benzyl cinnamate.

[0052] Examples of salicylic acid esters include methyl salicylate, n-hexyl salicylate, cis-3-hexenyl salicylate, cyclohexyl salicylate, and benzyl salicylate.

[0053] Furthermore, examples of brassic acid esters include ethylene brassirate.

[0054] Examples of tigrate esters include geranyl tigrate, 1-hexyl tigrate, and cis-3-hexenyl tigrate.

[0055] Examples of jasmonic acid esters include methyl jasmonate and methyl dihydrojasmonate.

[0056] Examples of glycidic acid esters include methyl 2,4-dihydroxy-ethylmethylphenylglycidate and 4-methylphenylethylglycidate.

[0057] Examples of anthranilic acid esters include methyl anthranilate, ethyl anthranilate, and dimethyl anthranilate.

[0058] Examples of glycolic acid esters include allylcyclohexyl glycolate.

[0059] Other esters include ethyl safranate (Divaudan trade name, ethyl dihydrocyclogeraneate), poirenate (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, methyl jasmonate, MDJ (Kao Corporation product name, methyl dihydrojasmonate, methyl (2-pentyl-3-oxocyclopentyl) acetate), and cyclohexyl salicylate (Kao Corporation product name).

[0060] Examples of carbonates include Rifalom (IFF trade name, cis-3-hexenylmethyl carbonate), Jasma Cyclat (Kao Corporation trade name, methyl-cyclooctyl carbonate), and Floramat (Kao Corporation trade name, ethyl-2-t-butylcyclohexyl carbonate).

[0061] Aldehydes include n-octanal, n-nonanal, n-decanal, n-dodecanal, 2-methylundecanal, 10-undecenal, citronellal, citral, hydroxycitronellal, tripral (IFF trade name, 2,4-dimethyl-3-cyclohexenyl-1-carboxyaldehyde), cyclobertal (Kao Corporation trade name, dimethyl-3-cyclohexenyl-1-carboxyaldehyde), benzaldehyde, phenylacetaldehyde, phenylpropylaldehyde, cinnamicaldehyde, dimethyltetrahydrobenzaldehyde, burgeonal (Givaudan trade name, 3-(4-tert-butylphenyl)propanal), lyral (IFF trade name, hydroxy Examples include Mylac aldehyde, Polenal II (Kao Corporation trade name, 2-cyclohexylpropional), Lilial (Givaudan trade name, p-tert-butyl-α-methylhydrocinnamicaldehyde), p-isopropyl-α-methylhydrocinnamicaldehyde, Flora Rozone (IFF trade name, 3-(o-(and p-)ethylphenyl)-2,2-dimethylpropionaldehyde), α-amyl cinnamicaldehyde, α-hexyl cinnamicaldehyde, heliotropin, Helional (IFF trade name, alpha-methyl-1,3-benzodioxol-5-propional), and Canthoxal (IFF trade name, 2-methyl-3-(paramethoxyphenyl)propional).

[0062] 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 trade name, 1-(2,4,4-trimethyl-2-cyclohexyl)-trans-2-butanone), Damascenone, Dynascone (Firmenich trade name, 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one), Ilon, Cashmeran (IFF trade 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.

[0063] Examples of acetals include acetaldehyde ethylphenylpropyl acetal, citral diethyl acetal, phenylacetaldehyde glyceryl acetal, ethyl acetacetate ethylene glycol acetal, Boazan Blenforte (Kao Corporation product name), and Troenan (Kao Corporation product name).

[0064] Examples of ethers include ethyl linalool, cedyl methyl ether, estragol, 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.

[0065] Examples of carboxylic acids include benzoic acid, phenylacetic acid, cinnamic acid, hydrocinnamic acid, butyric acid, and 2-hexenoic acid.

[0066] 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.

[0067] Examples of nitriles include tridecene-2-nitrile, geranyl nitrile, citronellyl nitrile, and dodecane nitrile.

[0068] Examples of Schiff bases include aurantiol and ligantral.

[0069] Examples of natural essential oils and extracts include orange, lemon, lime, bergamot, vanilla, mandarin, peppermint, spearmint, lavender, chamomile, rosemary, eucalyptus, sage, basil, rose, rock rose, geranium, jasmine, ylang-ylang, anise, clove, ginger, nutmeg, cardamom, cedar, cypress, vetiver, patchouli, lemongrass, labdanum, grapefruit, and elemi oil.

[0070] Among these, from the viewpoint of providing a sparkling, effervescent impression as the top note of the citrus scent, the fragrance composition of the present invention preferably further contains one or more selected from lime essential oil, limonene, and menthol.

[0071] Furthermore, among these, it is preferable that the fragrance composition of the present invention further contains one or more selected from phlorol, hexyl acetate, and methyl dihydrojasmonate, in order to impart a natural floral feeling reminiscent of being in a flower shop, by adding green and woody nuances along with the floral scent.

[0072] 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.

[0073] 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.

[0074] 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.

[0075] 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.

[0076] 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.

[0077] Examples of body cleansing compositions include skin cleansing compositions, hair cleansing compositions, and soap compositions, with skin cleansing compositions being preferred.

[0078] Examples of cleaning agent compositions for hard surfaces include all-purpose cleaners and dishwashing detergent compositions.

[0079] A softening agent composition is preferred as the fiber treatment composition of the present invention.

[0080] The cosmetic composition of the present invention is preferably perfume, lotion, toner, or sunscreen, with perfume being more preferred.

[0081] 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.

[0082] 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.

[0083] In addition to the fragrance composition of the present invention, the perfume of the present invention may contain solvents, water, and the like.

[0084] The fragrance composition of the present invention, comprising the cis and trans isomers in a specific ratio, gives a soft, woody, and refreshing impression. Furthermore, as described above, when this fragrance composition is formulated with other components as a fragrance material, it can create new impressions, such as a sparkling, effervescent top note in the citrus scent, or a natural floral feel reminiscent of a flower shop, with green and woody nuances added to the floral scent.

[0085] Accordingly, the present invention relates to a method of using a fragrance composition of the present invention, which contains the cis and trans isomers in a specific ratio, as a fragrance component, specifically, as a fragrance component of a fragrance composition, a detergent composition, a cosmetic, or a textile treatment composition. The detergent composition is preferably a body detergent composition, a clothing detergent composition, or a hard surface detergent composition, more preferably a body detergent composition or a clothing detergent composition, and even more preferably a clothing 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.

[0086] In the method of use described above, the fragrance composition of the present invention is used in an amount of preferably 0.00001% by mass or more, more preferably 0.0001% by mass or more, and preferably 0.01% by mass or less, and more preferably 0.001% 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.

[0087] 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.

[0088] The present invention includes the following embodiments. <1> A fragrance composition containing a cis isomer and a trans isomer, The cis isomer includes the compound represented by formula (Ia), the compound represented by formula (Ib), the compound represented by formula (IIa), and the compound represented by formula (IIb). The trans compound comprises a compound represented by formula (IIIa), a compound represented by formula (IIIb), a compound represented by formula (IVa), and a compound represented by formula (IVb). A fragrance composition in which the mass ratio [cis:trans] of the cis isomer to the trans isomer is 65:35 or more and 95:5 or less.

[0089] [ka]

[0090] [In formulas (Ia), (Ib), (IIa), (IIb), (IIIa), (IIIb), (IVa), and (IVb), 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.

[0091] <2> The mass ratio [cis:trans] of the cis isomer to the trans isomer is between 68:32 and 90:10. <1> The fragrance composition described above.

[0092] <3> The mass ratio [cis:trans] of the cis isomer to the trans isomer is 68:32 or greater and 85:15 or less. <1> or <2> The fragrance composition described above.

[0093] <4> The mass ratio [cis:trans] of the cis isomer to the trans isomer is 68:32 or greater and 75:25 or less. <1> ~ <3> A fragrance composition as described in any of the above.

[0094] <5> The mass concentration of the cis isomer is 65% by mass or more and 95% by mass or less. <1> ~ <4> A fragrance composition as described in any of the above.

[0095] <6> The mass concentration of the cis isomer is 66% by mass or more and 85% by mass or less. <1> ~ <5> A fragrance composition as described in any of the above.

[0096] <7> The mass concentration of the cis isomer is 67% by mass or more and 80% by mass or less. <1> ~ <6> A fragrance composition as described in any of the above.

[0097] <8> The mass concentration of the cis isomer is 68% by mass or more and 75% by mass or less. <1> ~ <7> A fragrance composition as described in any of the above.

[0098] <9> The mass ratio of the total of the compound represented by formula (Ia) and the compound represented by formula (Ib) to the total of the compound represented by formula (IIa) and the compound represented by formula (IIb) [total of the compound represented by formula (Ia) and the compound represented by formula (Ib):total of the compound represented by formula (IIa) and the compound represented by formula (IIb)] is 55:45 or more and 68:32 or less. <1> ~ <8> A fragrance composition as described in any of the above.

[0099] <10> The mass ratio of the total of the compound represented by formula (Ia) and the compound represented by formula (Ib) to the total of the compound represented by formula (IIa) and the compound represented by formula (IIb) is 55.5:44.5 or more and 66:34 or less. <1> ~ <9> A fragrance composition as described in any of the above.

[0100] <11> The mass ratio of the total of the compounds represented by formula (Ia) and formula (Ib) to the total of the compounds represented by formula (IIa) and formula (IIb) is 56:44 or more and 62:38 or less. <1> ~ <10> A fragrance composition as described in any of the above.

[0101] <12> The mass ratio [cis:trans] of the cis isomer to the trans isomer is 65:35 or greater and 78:22 or less. <1> ~ <11> A fragrance composition as described in any of the above.

[0102] <13> The mass ratio [cis:trans] of the cis isomer to the trans isomer is 68:32 or greater and 78:22 or less. <1> ~ <12> A fragrance composition as described in any of the above.

[0103] <14> The mass ratio [cis:trans] of the cis isomer to the trans isomer is 68:32 or greater and 75:25 or less. <1> ~ <13> A fragrance composition as described in any of the above.

[0104] <15> The mass ratio [cis:trans] of the cis isomer to the trans isomer is 82:18 or greater and 95:5 or less. <1> ~ <14> A fragrance composition as described in any of the above.

[0105] <16> The mass ratio [cis:trans] of the cis isomer to the trans isomer is between 82:18 and 90:10. <1> ~ <15> A fragrance composition as described in any of the above.

[0106] <17> The mass ratio [cis:trans] of the cis isomer to the trans isomer is 85:15 or greater and 90:10 or less. <1> ~ <16> A fragrance composition as described in any of the above.

[0107] <18> R 1 This is an alkyl group having 1 to 4 carbon atoms. <1> ~ <17> A fragrance composition as described in any of the above.

[0108] <19> R 1 This is an alkyl group having 3 or more carbon atoms and 4 or fewer carbon atoms. <1> ~ <18> A fragrance composition as described in any of the above.

[0109] <20> R 1 This is a t-butyl group, <1> ~ <19> A fragrance composition as described in any of the above.

[0110] <21> R 2 is a methyl group or an ethyl group. <1> ~ <20> A fragrance composition as described in any of the above.

[0111] <22> A compound other than the compound represented by formula (Ia), the compound represented by formula (Ib), the compound represented by formula (IIa), the compound represented by formula (IIb), the compound represented by formula (IIIa), the compound represented by formula (IIIb), the compound represented by formula (IVa), and the compound represented by formula (IVb), further comprising one or more of the following: alcohols, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, nitriles, natural essential oils, and natural extracts. <1> ~ <21> A fragrance composition as described in any of the above.

[0112] <23> Furthermore, it contains one or more selected from lime essential oil, limonene, and menthol. <1> ~ <22> A fragrance composition as described in any of the above.

[0113] <24> Furthermore, it includes one or more selected from phlorol, hexyl acetate, and methyl dihydrojasmonate. <1> ~ <23> A fragrance composition as described in any of the above.

[0114] <25> <1> ~ <24> A fragrance composition having a citrus or floral scent, comprising the fragrance composition described in any of the above.

[0115] <26> <1> ~ <25> A cosmetic containing the fragrance composition described in any of the above.

[0116] <27> <1> ~ <25> A detergent composition comprising the fragrance composition described in any of the above.

[0117] <28> <1> ~ <25> A method of using any of the fragrance compositions described in the above as a fragrance component.

[0118] 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. <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. 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. 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.

[0119] [Reference example 1] Preparation of 1-(2-t-butylphenyloxy)-2-butanol (3)

[0120] [ka]

[0121] 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 Industry Co., 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-butylphenyloxy)-2-butanol (3) in 96% yield.

[0122] [Reference example 2] Preparation of 1-(2-t-butylcyclohexyloxy)-2-butanol (4)

[0123] [ka]

[0124] 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.

[0125] 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%. Analysis of the product by gas chromatography revealed that the mass ratio of the cis isomer to the trans isomer was cis:trans = 57:43. The cis isomer includes the compound represented by formula (Ia-1), the compound represented by formula (Ib-1), the compound represented by formula (IIa-1), and the compound represented by formula (IIb-1), and the trans isomer includes the compound represented by formula (IIIa-1), the compound represented by formula (IIIb-1), the compound represented by formula (IVa-1), and the compound represented by formula (IVb-1). Furthermore, the isomer ratio of the cis isomer [total of the compound represented by formula (Ia-1) and the compound represented by formula (Ib-1):total of the compound represented by formula (IIa-1) and the compound represented by formula (IIb-1) (mass ratio)] was 48:52.

[0126] [ka]

[0127] [Reference example 3] Preparation of 1-(cis-2-t-butylcyclohexyloxy)-2-butanol (100% cis isomer) Furthermore, 1-(cis-2-t-butylcyclohexyloxy)-2-butanol (100% cis isomer) is a mixture of the compound represented by formula (Ia-1), the compound represented by formula (Ib-1), the compound represented by formula (IIa-1), and the compound represented by formula (IIb-1).

[0128] [ka]

[0129] 137 g of a mixture of the cis and trans isomers of 1-(2-t-butylcyclohexyloxy)-2-butanol obtained in Reference Example 2 was rectified using a 20-stage rectification column at a reflux ratio of 40 to obtain 8 g of 1-(cis-2-t-butylcyclohexyloxy)-2-butanol (purity 98%, 100% cis isomer). Analysis of the product by gas chromatography revealed that the isomer ratio of the above 1-(cis-2-t-butylcyclohexyloxy)-2-butanol (purity 98%, 100% cis isomer) [total of the compound represented by formula (Ia-1) and the compound represented by formula (Ib-1): total of the compound represented by formula (IIa-1) and the compound represented by formula (IIb-1) (mass ratio)] was 70:30.

[0130] [Example 1] To 1 g of 1-(cis-2-t-butylcyclohexyloxy)-2-butanol (100% cis) obtained in Reference Example 3, 2.8 g of 1-(2-t-butylcyclohexyloxy)-2-butanol (cis:trans (mass ratio) = 57:43) obtained in Reference Example 2 was added and mixed to obtain a fragrance composition. The mass ratio of cis:trans in the obtained fragrance composition and the isomer ratio of the cis isomer are as follows. <Sys: Transformer mass ratio> cis:trans (mass ratio) = 68:32 <Isomer ratio of the cis isomer> The total mass ratio of the compound represented by formula (Ia-1) and the compound represented by formula (Ib-1) is 56.5:43.5.

[0131] [Example 2] Following the same procedure as in Example 1, 1.3 g of 1-(2-t-butylcyclohexyloxy)-2-butanol (cis:trans (mass ratio) = 57:43) obtained in Reference Example 2 was added to 1 g of 1-(cis-2-t-butylcyclohexyloxy)-2-butanol (cis 100%) obtained in Reference Example 3 and mixed to obtain a fragrance composition. The mass ratio of cis to trans and the isomer ratio of the cis isomer of the obtained fragrance composition are as follows. <Sys: Transformer mass ratio> cis:trans (mass ratio) = 75:25 <Isomer ratio of the cis isomer> The total mass ratio of the compound represented by formula (Ia-1) and the compound represented by formula (Ib-1) is 60.6:39.4.

[0132] [Example 3] Similar to Examples 1 and 2, 0.8 g of 1-(2-t-butylcyclohexyloxy)-2-butanol (cis:trans (mass ratio) = 57:43) obtained in Reference Example 2 was added to 1 g of 1-(cis-2-t-butylcyclohexyloxy)-2-butanol (cis 100%) obtained in Reference Example 3 and mixed to obtain a fragrance composition. The mass ratio of cis to trans and the isomer ratio of the cis isomer of the obtained fragrance composition are as follows. <Sys: Transformer mass ratio> cis:trans (mass ratio) = 80:20 <Isomer ratio of the cis isomer> The total mass ratio of the compound represented by formula (Ia-1) and the compound represented by formula (Ib-1) is 63.1:36.9.

[0133] [Example 4] Similar to Examples 1-3, 1 g of 1-(cis-2-t-butylcyclohexyloxy)-2-butanol (100% cis) obtained in Reference Example 3 was mixed with 0.5 g of 1-(2-t-butylcyclohexyloxy)-2-butanol (cis:trans mass ratio = 57:43) obtained in Reference Example 2 to obtain a fragrance composition. The cis:trans mass ratio of the obtained fragrance composition and the isomer ratio of the cis isomer are as follows. <Sys: Transformer mass ratio> cis:trans mass ratio = 85:15 <Isomer ratio of the cis isomer> The total mass ratio of the compound represented by formula (Ia-1) and the compound represented by formula (Ib-1) is 65.1:34.9.

[0134] [Example 5] Similar to Examples 1-4, 0.3 g of 1-(2-t-butylcyclohexyloxy)-2-butanol (cis:trans mass ratio = 57:43) obtained in Reference Example 2 was added to 1 g of 1-(cis-2-t-butylcyclohexyloxy)-2-butanol (cis 100%) obtained in Reference Example 3 and mixed to obtain a fragrance composition. The cis:trans mass ratio of the obtained fragrance composition and the isomer ratio of the cis isomer are as follows. <Sys: Transformer mass ratio> cis:trans (mass ratio) = 90:10 <Isomer ratio of the cis isomer> The total mass ratio of the compound represented by formula (Ia-1) and the compound represented by formula (Ib-1) is 66.8:33.2.

[0135] [Comparative Example 1] The 1-(2-t-butylcyclohexyloxy)-2-butanol (cis:trans (mass ratio) = 57:43, the isomer ratio of the cis isomer is the total ratio (mass ratio) of the compound represented by formula (Ia-1) and the compound represented by formula (Ib-1) to the total ratio (mass ratio) of the compound represented by formula (IIa-1) and the compound represented by formula (IIb-1) = 48.0:52.0) obtained in Reference Example 2 was used as the fragrance composition for sensory evaluation in Comparative Example 1.

[0136] [Comparative Example 2] Similar to Examples 1-5, 1 g of 1-(cis-2-t-butylcyclohexyloxy)-2-butanol (100% cis) obtained in Reference Example 3 was mixed with 6.0 g of 1-(2-t-butylcyclohexyloxy)-2-butanol (cis:trans (mass ratio) = 57:43) obtained in Reference Example 2 to obtain a fragrance composition. The mass ratio of cis:trans and the isomer ratio of the cis isomer of the obtained fragrance composition are as follows. <Sys: Transformer mass ratio> cis:trans mass ratio = 63:37 <Isomer ratio of the cis isomer> The ratio (by mass) of the total of the compound represented by formula (Ia-1) and the compound represented by formula (Ib-1) to the total of the compound represented by formula (IIa-1) and the compound represented by formula (IIb-1) is 53.0:47.0.

[0137] [Comparative Example 3] The 1-(cis-2-t-butylcyclohexyloxy)-2-butanol (100% cis, ratio (mass ratio) of the total of the compound represented by formula (Ia-1) and the compound represented by formula (Ib-1) to the total of the compound represented by formula (IIa-1) and the compound represented by formula (IIb-1) = 70:30) obtained in Reference Example 3 was used as the fragrance composition for sensory evaluation in Comparative Example 3.

[0138] [Sensory evaluation] The fragrances of the fragrance compositions obtained in Examples 1-5 and Comparative Examples 1-3 were evaluated by three expert panelists. The evaluation was performed using odor test paper (Daimonji Western Paper Co., Ltd., 150mm x 7mm). Examples 1-5 and Comparative Examples 1-3, 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 conducted 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.

[0139] [Table 1]

[0140] As shown in Table 1, the fragrance composition of the present invention exhibited the effect of enhancing the soft, fresh, woody impression while maintaining residual fragrance.

[0141] [Example of compounding 1] Sensory evaluations were conducted on compositions prepared by adding 100 parts by mass each of the fragrance compositions obtained in Examples 1-5 and Comparative Examples 1-3 to 900 parts by mass of a citrus fragrance (lime sparkling) blend with the composition described below. The results are shown in Table 3. The evaluation results were assessed on a 5-point scale, with higher values ​​indicating a more favorable result.

[0142] [Table 2]

[0143] [Table 3]

[0144] As shown in Table 3, sensory evaluation by three expert panelists revealed that using the fragrance composition of the present invention newly imparts a bright, sparkling, and effervescent impression, and also improves the fragrance's release.

[0145] [Example of compounding 2] Similar to Formulation Example 1, sensory evaluations were conducted on compositions prepared by adding 100 parts by mass each of the fragrance compositions obtained in Examples 1-5 and Comparative Examples 1-3 to 900 parts by mass of a floral fragrance formulation (floral bouquet, white floral) with the following composition. The results are shown in Table 5. For the evaluation results, the degree of effect was evaluated on a 5-point scale, with higher values ​​indicating a preference.

[0146] [Table 4]

[0147] 1) Calon: Firmenich trade name, 7-methyl-3,4-dihydro-2H-benzodioxepin-3-one 2) Canthoxal: IFF brand name, 2-methyl-3-(paramethoxyphenyl)propanal 3) Tripral: IFF trade name, 2,4-dimethyl-3-cyclohexene-1-carboxyaldehyde

[0148] [Table 5]

[0149] A sensory evaluation by three expert panelists revealed that the floral notes were enhanced, a new sense of quality and luxury was added, and the fragrance's development was improved.

[0150] According to the present invention, it is possible to provide a fragrance composition that gives a soft and fresh impression reminiscent of wood. Furthermore, when this fragrance composition is formulated with other ingredients as a fragrance material, it can unexpectedly create a new impression, such as a sparkling, effervescent top note, or a floral scent with added green and woody nuances, giving a natural floral feel like being in a flower shop.

Claims

1. A fragrance composition containing a cis isomer and a trans isomer, The cis isomer includes the compound represented by formula (Ia), the compound represented by formula (Ib), the compound represented by formula (IIa), and the compound represented by formula (IIb), The trans isomer includes a compound represented by formula (IIIa), a compound represented by formula (IIIb), a compound represented by formula (IVa), and a compound represented by formula (IVb), The mass ratio of the cis isomer to the trans isomer [cis isomer:trans isomer] is 65:35 or more and 95:5 or less. A fragrance composition in which the total mass ratio of the compound represented by formula (Ia) and the compound represented by formula (Ib) to the total mass of the compound represented by formula (IIa) and the compound represented by formula (IIb) is 55:45 or more and 68:32 or less. 【Chemistry 11】 [In formulas (Ia), (Ib), (IIa), (IIb), (IIIa), (IIIb), (IVa), and (IVb), 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.

2. The fragrance composition according to claim 1, wherein the mass concentration of the cis isomer is 65% by mass or more and 95% by mass or less.

3. The fragrance composition according to claim 1 or 2, wherein the mass ratio [cis:trans] of the cis isomer to the trans isomer is 65:35 or more and 78:22 or less.

4. The fragrance composition according to claim 1 or 2, wherein the mass ratio [cis:trans] of the cis isomer to the trans isomer is 82:18 or more and 95:5 or less.

5. R 1 The fragrance composition according to any one of claims 1 to 4, wherein is a t-butyl group.

6. R 2 The fragrance composition according to any one of claims 1 to 5, wherein is a methyl group or an ethyl group.

7. A fragrance composition according to any one of claims 1 to 6, which further comprises one or more alcohols, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, nitriles, natural essential oils, and natural extracts, other than the compound represented by formula (Ia), the compound represented by formula (Ib), the compound represented by formula (IIa), the compound represented by formula (IIb), the compound represented by formula (IIIa), the compound represented by formula (IIIb), the compound represented by formula (IVa), and the compound represented by formula (IVb).

8. Furthermore, the fragrance composition according to any one of claims 1 to 7 further comprises one or more selected from lime essential oil, limonene, and menthol.

9. Furthermore, the fragrance composition according to any one of claims 1 to 7 further comprises one or more selected from phlorol, hexyl acetate, and methyl dihydrojasmonate.

10. A fragrance composition having a citrus or floral scent, comprising the fragrance composition according to any one of claims 1 to 9.

11. A cosmetic composition comprising the fragrance composition according to any one of claims 1 to 10.

12. A detergent composition comprising the fragrance composition according to any one of claims 1 to 10.

13. A method for using the fragrance composition described in any one of Claims 1 to 10 as a fragrance component.

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