JP2010163491A - Fragrance composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new musk-based fragrance having excellent musky fragrance. <P>SOLUTION: This perfume composition includes 14-n-propyloxycyclotetradecan-2-one as an active ingredient. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to a fragrance composition containing a macrocyclic lactone compound as an active ingredient.

Currently, natural musk fragrances are difficult to obtain from the viewpoint of animal protection, and macrocyclic compounds with many musk fragrances have been researched and reported in order to meet the changing trend of flavor aroma. (For example, Non-Patent Documents 1 and 2). However, since the macrocyclic musk compound is difficult to synthesize and expensive, a nitromusk represented by musk ketone and musk xylol and a polycyclic musk represented by galaxolide (registered trademark) and tonalide (registered trademark) are exclusively musk-based fragrances. As a result, only a few macrocyclic musk compounds were put on the market.
However, due to the recent increase in natural orientation and the emphasis on the environment, macrocyclic musk compounds that have little problem not only in the direct safety of compounds but also in the accumulation and degradability have been attracting attention again. .
As the macrocyclic musk compound, a macrocyclic lactone compound can be mentioned as a representative, but the macrocyclic lactone compounds so far have not been satisfactory in terms of aroma and cost.
Accordingly, there has been a demand for the development of a macrocyclic musk compound that satisfies the effects as a fragrance material during actual preparation and the technical and economic problems associated with synthesis.

  On the other hand, 14-n-propyloxacyclotetradecan-2-one is known as a macrocyclic lactone compound (Non-patent Document 3), but the macrocyclic lactone compound has not been isolated and has any fragrance. It is not known if you have.

I. B. Bersuker et al., New J. et al. Chem. 1991, 15, 307 Shozo Abe, Fragrance, No. 96, September 1970, p. 19 L. Hinkamp et al., Liebigs Ann. Chem. (1992) 559-563

  The present invention relates to providing a fragrance composition having an excellent musk-like fragrance.

  When the present inventors examined the macrocyclic lactone compound, they found that 14-n-propyloxacyclotetradecan-2-one has an excellent musk-like odor and is useful as a fragrance component.

  That is, the present invention relates to a fragrance composition containing 14-n-propyloxacyclotetradecan-2-one as an active ingredient.

  The 14-n-propyloxacyclotetradecan-2-one of the present invention has an excellent musk-like aroma. Therefore, the fragrance composition of the present invention is useful as a fragrance component for cosmetics, health and hygiene materials, miscellaneous goods, foods, quasi drugs, pharmaceuticals and the like.

  14-n-propyloxacyclotetradecan-2-one of the present invention (hereinafter also referred to as the present compound) is represented by the following formula (1).

It is a macrocyclic lactone compound represented by these. Although the compound is known, it has not been isolated so far, and it is not known what fragrance it has.

  The macrocyclic lactone compound represented by the formula (1) has an asymmetric carbon at the ω position of the lactone ring, and there are isomers selected from the S-form and R-form. Any of these may be sufficient and a racemic body may be sufficient.

  This invention compound can be manufactured with a well-known manufacturing method, for example, according to the following process (A) and (B), it can manufacture simply from palmitic acid.

  Step (A) is a reaction for obtaining 13-hydroxypalmitic acid represented by formula (3) by allowing a biocatalyst containing fatty acid hydroxylase to act on palmitic acid represented by formula (2). .

  The fatty acid hydroxylase may be an enzyme that hydroxylates the ω subterminal of fatty acid, and specifically includes CYP102A1 (P450 BM3).

  In the step (A), the biocatalyst can be used in any form as long as it contains the above fatty acid hydroxylase. Examples of biocatalysts containing these enzymes include living cells such as animal cells or plant cells that produce the enzyme of the present invention, or microbial cells (live cells, dead sterilized cells, resting cells, or stationary cells). Examples thereof include cells or cultures thereof.

In the step (A), an enzyme, a coenzyme, or other substances that promote hydroxylation can be used in addition to the above fatty acid hydroxylase as necessary. For example, when NAD (P) H is required, NAD (P) ⁺ , glucose dehydrogenase, glucose and the like can be used as appropriate.

The production of 13-hydroxypalmitic acid using the biocatalyst can be performed under milder conditions than chemical methods. For example, the pH is usually adjusted using a buffer solution around the optimum pH of the enzyme (pH 5-9, preferably pH 7-8). The reaction temperature is 20-60 ° C, preferably 25-30 ° C. The reaction time is 1 minute to 48 hours, preferably 1 to 12 hours.
In order to improve the solubility of palmitic acid, a surfactant or an organic solvent may be added to the reaction system. The organic solvent may be any solvent that does not inhibit enzyme activity and dissolves palmitic acid, but is preferably acetone.

  When using a living cell culture as a biocatalyst, for example, palmitic acid can be added to the culture. As the coenzyme and the like necessary for the hydroxylation reaction, intracellular ones may be used, but they may be added to the culture as necessary. By holding the culture to which the raw materials and appropriate substances have been added for a certain period of time under appropriate culture conditions, the enzyme of the present invention in the culture and palmitic acid react to produce 13-hydroxypalmitic acid. . The appropriate culture conditions and time vary depending on the type of cells used, but may be set as appropriate according to ordinary knowledge of those skilled in the art.

  The concentration of the substrate is not particularly limited, but is preferably 0.001 to 20%, more preferably 0.05 to 1%. The fatty acid can be added to the reaction system all at once or continuously.

  The 13-hydroxypalmitic acid obtained by the step (A) may be used in the step (B) with or without isolation by a known method, but is preferably used after being isolated.

  Step (B) is a reaction for obtaining the compound of the present invention by cyclization of 13-hydroxypalmitic acid.

  Step (B) can be carried out in the presence or absence of a cyclization catalyst under the usual conditions used for the cyclization reaction. For example, dicyclohexylcarbodiimide (hereinafter also referred to as DCC) is used. Mixture (hereinafter also referred to as DCC / DMAP) with 4-dimethylaminopyridine (hereinafter also referred to as DMAP), magnesium compound such as magnesium oxide and magnesium chloride, benzenesulfonic acid, p-toluenesulfonic acid, carboxylic acid activation reagent (For example, trifluoroacetic anhydride, N, N′-carbonylimidazole, a mixture of di (2-pyridyl) disulfide and triphenylphosphine), a mixture of triphenylphosphine and diethylazocarboxylate, sodium t-amyl alkoxide, etc. It is preferable to carry out in the presence of a cyclization catalyst. When DCC / DMAP is used as the cyclization catalyst, 4-dimethylaminopyridine hydrochloride (hereinafter also referred to as DMAP · HCl) is preferably used in addition to DCC / DMAP.

  In the step (B), when DCC / DMAP is used, it is preferably performed in the presence of a solvent. Although it does not specifically limit as the said solvent, For example, chloroform and a dichloromethane are mentioned, Chloroform is preferable.

  That is, as a specific example of a suitable cyclization reaction, there is a method (KecK macrolactonization method) in which a fatty acid hydroxide is dissolved in a chloroform solution of DCC, DMAP, and DMAP · HCl and heated to reflux.

  In the step (B), when DCC / DMAP is used, the amount of DCC, DMAP, and DMAP · HCl may be appropriately selected so that the reaction time is not delayed and the reaction rate is not lowered. Are preferably used in an amount of 1.5 to 10 equivalents, 1.5 to 10 equivalents, and 1.5 to 10 equivalents, respectively.

  In the step (B), when DCC / DMAP is used, it is usually 30 to 100 ° C., preferably 50 to 70 ° C., usually about 10 to 24 hours, preferably about 15 to 20 hours, with shaking and stirring. It can be carried out.

  The target compound can be separated from the reaction system by isolation and purification by appropriately combining ordinary means such as filtration, washing, drying, recrystallization, centrifugation, extraction with various solvents, chromatography and the like.

  The compound of the present invention has an excellent musk-like fragrance, as shown in Examples below. Therefore, this invention compound can be used as an active ingredient of a fragrance | flavor composition, and can be used in order to manufacture a fragrance | flavor composition.

  The compounding quantity of this invention compound to a fragrance | flavor composition is 0.01-50 mass% in the point of fragrance, and 0.1-20 mass% is more preferable.

  In addition, although the compound of the present invention may be incorporated alone in the fragrance composition of the present invention, a surfactant such as polyoxyethylene lauryl sulfate ether; dipropylene glycol as long as the fragrance of the compound of the present invention is not inhibited Solvents such as diethyl phthalate, ethylene glycol, propylene glycol, methyl myristate, triethyl citrate; hydrocarbons such as limonene, α-pinene, β-pinene, terpinene, cedrene, longifolene, valencene; linalool, citronellol, geraniol, Nerol, terpineol, dihydromyrsenol, ethyl linalool, farnesol, nerolidol, cis-3-hexenol, cedrol, menthol, borneol, β-phenylethyl alcohol, benzyl alcohol, phenylhexanol, 2, 2,6-trimethylcyclohexyl-3-hexanol, 1- (2-t-butylcyclohexyloxy) -2-butanol, 4-isopropylcyclohexanemethanol, 4-methyl-2- (2-methylpropyl) tetrahydro-2H-pyran -4-ol, 2-methyl-4- (2,2,3-trimethyl-3-cyclopenten-1-yl) -2-buten-1-ol, 2-ethyl-4- (2,2,3- Alcohols such as trimethyl-3-cyclopenten-1-yl) -2-buten-1-ol, isocamphylcyclohexanol, 3,7-dimethyl-7-methoxyoctane-2-ol;

Phenols such as eugenol, thymol, vanillin; linalyl formate, citronellyl formate, geranyl formate, n-hexyl acetate, cis-3-hexenyl acetate, linalyl acetate, citronellyl acetate, geranyl acetate, neryl acetate, terpi Nyl acetate, nopylacetate, bornyl acetate, isobornyl acetate, ot-butylcyclohexyl acetate, pt-butylcyclohexyl acetate, tricyclodecenyl acetate, benzyl acetate, styrylyl acetate, cinnamyl acetate, Dimethylbenzylcarbinyl acetate, 3-pentyltetrahydropyran-4-yl acetate, citronellyl propionate, tricyclodecenyl propionate, ant Cyclohexylpropionate, ethyl 2-cyclohexylpropionate, benzylpropionate, citronellyl butyrate, dimethylbenzylcarbinyl n-butyrate, tricyclodecenyl isobutyrate, methyl 2-nonenoate, methyl benzoate, benzyl benzoate , Methyl cinnamate, methyl salicylate, n-hexyl salicylate, cis-3-hexenyl salicylate, geranyl tiglate, cis-3-hexenyl tiglate, methyl jasmonate, methyl dihydrojasmonate, methyl 2,4-dihydroxy- Esters such as 3,6-dimethylbenzoate, ethyl methylphenyl glycidate, methyl anthranilate, flutate;

n-octanal, n-decanal, n-dodecanal, 2-methylundecanal, 10-undecenal, citronellal, citral, hydroxycitronellal, dimethyltetrahydrobenzaldehyde, 4 (3)-(4-hydroxy-4-methylpentyl) -3-cyclohexene-1-carbaldehyde, 2-cyclohexylpropanal, pt-butyl-α-methylhydrocinnamic aldehyde, p-isopropyl-α-methylhydrocinnamic aldehyde, p-ethyl-α, α- Aldehydes such as dimethylhydrocinnamic aldehyde, α-amylcinnamic aldehyde, α-hexylcinnamic aldehyde, piperonal, α-methyl-3,4-methylenedioxyhydrocinnamic aldehyde; methylheptenone, 4-methyl Tylene-3,5,6,6-tetramethyl-2-heptanone, amylcyclopentanone, 3-methyl-2- (cis-2-penten-1-yl) -2-cyclopenten-1-one, methylcyclo Pentenolone, rose ketone, γ-methyl ionone, α-ionone, carvone, menthone, show brain, nootkatone, benzylacetone, anisylacetone, methyl β-naphthylketone, 2,5-dimethyl-4-hydroxy-3 (2H) -Furanone, maltol, 7-acetyl-1,2,3,4,5,6,7,8-octahydro-1,1,6,7-tetramethylnaphthalene, muscone, cybetone, cyclopentadecanone, cyclohexade Ketones such as senone;

Acetaldehyde and ketals such as acetaldehyde ethylphenylpropyl acetal, citral diethyl acetal, phenylacetaldehyde glycerin acetal, ethyl acetoacetate ethylene glycol ketal; anethole, β-naphthylmethyl ether, β-naphthylethyl ether, limonene oxide, rose oxide, 1 , 8-cineole, racemic or optically active dodecahydro-3a, 6,6,9a-ethers such as tetramethylnaphtho [2,1-b] furan; nitriles such as citronellyl nitrile;

γ-nonalactone, γ-undecalactone, δ-decalactone, γ-jasmolactone, coumarin, cyclopentadecanolide, cyclohexadecanolide, ambridolide, ethylene brushate, 11-oxahexadecanolide, etc. Lactones other than the compounds of the present invention: orange, lemon, bergamot, mandarin, peppermint, spearmint, lavender, camomil, rosemary, eucalyptus, sage, basil, rose, geranium, jasmine, ylang ylang, anise, clove, ginger, nutmeg Natural essential oils such as cardamom, cedar, cypress, vetiver, patchouli, labdanum, and other perfume substances such as natural extracts can be blended. These other components may be used alone or in combination.

The macrocyclic lactone compound represented by the formula (1) is used for cosmetics, hygiene materials, miscellaneous goods, foods, pharmaceuticals in order to improve the aroma of the blended object in order to impart an excellent aroma with high palatability. It can be used as an aroma component in various products such as quasi-drugs and pharmaceuticals.
For example, fragrance products such as perfumes and colons; shampoos, rinses, hair arts, hair creams, mousses, gels, pomades, sprays and other cosmetics for hair; skin lotions, cosmetic liquids, creams, milky lotions, packs, foundations, Cosmetics for skin such as funny, lipstick, various make-ups; soap, dishwashing detergent, laundry detergent, softeners, disinfecting detergent, deodorant detergent, indoor air freshener, furniture care, glass cleaner, furniture cleaner , Floor cleaners, disinfectants, insecticides, bleaches, and other various hygiene detergents; toothpastes; mouthwashes, bath preparations, antiperspirants, perfumes and other quasi-drugs; toilet paper, tissue paper, etc. Miscellaneous goods; pharmaceuticals, etc .; can be used as aroma components for foods and the like.

  Moreover, 0.001-50 mass% is preferable as a macrocyclic lactone compound represented by Formula (1), and, as for the compounding quantity to the product of the fragrance composition of this invention, 0.01-20 mass% is more preferable. .

The present invention will be described in detail below based on examples.
Reference Example 1 Expression of P450 BM3 (i) Construction of E. coli co-expressing P450 BM3 and GDH Escherichia coli BL21Star (DE3) (manufactured by Invitrogen) was used as a protein production host. PET21a (manufactured by Novagene) was used as a plasmid for high expression vectors. E. coli as a host for E. coli used for gene subcloning. E. coli HB101 strain (Takara Bio Inc.) was used.
As a gene source of P450 BM3 (SEQ ID NO: 1), Bacillus megaterium ATCC 14581 strain was used. As a gene source of glucose dehydrogenase (GDH) (SEQ ID NO: 2), Bacillus subtilis 168 strain (ATCC 23857) was used.
PETBM3-gdh, a vector that highly expresses P450 BM3 and GDH, is a plasmid in which the BM3 gene is inserted into the multicloning site of pET21a and then the GDH gene is inserted downstream of the BM3 gene. Amplification of BM3 gene B. The megaterium ATCC 14581 strain genome as a template, was performed using the BM3 / BamHI FW, BM3 / EcoRI RV as a primer. (SEQ ID NO: 3, 4). Pyrobest DNA polymerase (manufactured by Takara Bio Inc.) was used for PCR. The PCR composition and reaction conditions followed the attached protocol.
The amplified DNA fragment of about 3.2 kbp Bam HI, treated with Eco RI, and inserted into Bam HI, Eco RI sites of pET21a, was constructed PETBM3. Amplification of GDH gene B. The subtilis 168 strain genome was used as a template and BSgdh / EcoRI f1 and BSgdh / XhoI r1 (SEQ ID NOs: 5 and 6) were used as primers. The amplified DNA fragment of about 0.8 kbp Eco RI, treated with Xho I, to construct the inserted pETBM3-gdh into Eco RI, Xho I sites PETBM3.
For confirmation of the gene sequence, ABI PRISM ^™ 3100 Genetic Analyzer (Applied Biosystems) was used as a DNA base sequence analyzer, and Big Dye ^™ Terminator Ready Bio (available from Cycle Sequencing Ready Reagent, Inc.) according to the attached protocol. A sample was prepared using a plasmid as a template.
The constructed expression vector was introduced into Escherichia coli by the competent cell method. E. thawed on ice. E. coli HB101 competent cell 40 μL or E. An appropriate amount of plasmid DNA was added to 40 μL of E. coli BL21 Star (DE3) competent cell and allowed to stand on ice for 30 minutes. A heat shock was applied at 42 ° C. for 45 seconds and immediately left on ice for 2 minutes. 360 μL of SOC medium (manufactured by Takara Bio Inc.) that had been incubated at 37 ° C. in advance was added, followed by shaking at 37 ° C. and 150 rpm for 60 minutes. The shaken solution was applied on an LB agar medium containing 100 ppm of ampicillin sodium salt, and cultured at 37 ° C. for 16 hours, and the grown bacteria were isolated as transformants.
The isolated transformant was streaked on LB agar medium and then cultured at 30 ° C. for 16 hours. The grown bacteria were suspended in 0.5 mL of sterilized 20% glycerol, and then frozen and stored at -80 ° C., and used as cryopreserved cells.
(Ii) Induced expression of target protein using E. coli as host and preparation of enzyme solution Culture of E. coli and induced expression of protein were carried out as follows. Inoculate 1% (v / v) of the seed culture solution, which was shake-cultured at 37 ° C and 300 rpm for 8 hours in a large test tube (prepared with 4 mL of LB medium) into a φ24 mm x 200 mm LB medium in a 500 mL Sakaguchi flask (containing 100 mL of LB medium). Then, shaking culture was performed at 37 ° C. and 120 rpm until OD600 = about 0.4 (about 2.5 hours). Next, as final concentrations, IPTG was added to 0.5 mM, 5-aminolevulinic acid to 1 mM, and FeCl ₃ .6H ₂ O to 0.001%, and the mixture was shaken at 25 ° C. and 120 rpm for 16 hours. All reagents were filtered and used. The culture broth was collected by centrifugation at 8000 rpm for 10 minutes, and washed once with 50 mM Tris-HCl buffer (pH 8.0).
The cells recovered from 100 mL of the culture solution were suspended in 2 mL of 50 mM Tris-HCl (pH 8.0) in which 1 tablet / 50 mL of complete EDTA-free (Roche) was dissolved. The bacterial suspension was subjected to FastPrep (manufactured by Q-Bio gene), Lysing Matrix B (manufactured by Q-Bio gene) was used as the crushing beads, and the bacterial cells were disrupted according to the attached protocol. When the culture solution exceeds 1 L, a cell suspension is prepared at the same ratio as described above and passed once using FRENCH PRESS (manufactured by Thermo Spectronic) at 15000 psi to 100 drops / min. A cell disruption solution was obtained. The crushed liquid was centrifuged at 15000 rpm for 10 minutes to obtain a supernatant. An equal amount of glycerol was added to the supernatant and stored at −30 ° C. This stock solution was used as a bacterial cell extract.

Example 1 Fatty Acid Hydroxylation Reaction Using an enzyme solution prepared as described in Reference Example 1, palmitic acid (SIGMA, purity 99%) was hydroxylated. The enzyme reaction was performed as follows.

Thirty 200 mL reaction solutions were prepared in a 500 mL Sakaguchi flask so that the final concentration was 100 mM potassium phosphate buffer (pH 8.0), 0.5 g / L palmitic acid, 5 mM glucose, and bacterial cell extract 50 mL / L. And incubated at 25 ° C. for 2 minutes. NADP ⁺ was added to the incubated solution to a final concentration of 0.05 mM and incubated at 25 ° C. and 120 rpm for 14 hours. Concentrated hydrochloric acid was added to the reaction solution at 2% (v / v), followed by extraction with hexane 50% (v / v). After extraction, it was dried under reduced pressure to obtain 1.70 g of hexane extract. The amount of hydroxide contained in the hexane extract was analyzed by GC-MS after methyl esterification and trimethylsilylation.
The apparatus is HP 6890/5973 GC-MS (manufactured by Agilent), the column is DB-1 MS 30 m × 200 μm × 0.25 μm (manufactured by J & W scientific), high purity helium is used for the mobile phase, and the flow rate is 1 mL / min. The temperature program was performed at 100 ° C. (1 minute), 20 ° C./minute, and 300 ° C. (5 minutes). 16-Hydroxypalmitic acid was used as a control for hydroxylated fatty acids.

By the reaction, 13-hydroxypalmitic acid was obtained with a yield of 0.8%.
The total amount of 13-hydroxypalmitic acid, 14-hydroxypalmitic acid and 15-hydroxypalmitic acid was 120 mg, and the hydroxylation ratio was ω-1 position: 32.9%, ω-2 position: 47.1%. , Ω-3 position: 20.0%.

Example 2 Intramolecular Cyclization of Hydroxylated Fatty Acid Dicyclohexylcarbodiimide (2.72 g), 4-dimethylaminopyridine (2.42 g), 4-dimethylaminopyridine hydrochloride (2.09 g) in chloroform (294.92 g) 1.70 g of the product obtained in Example 1 in 39.6 mL of THF was added dropwise over 16 hours using a syringe pump. After completion of the dropping, the mixture was stirred for 30 minutes under reflux with heating, and then cooled to room temperature. After evaporating the solvent under reduced pressure, the residue was diluted with diethyl ether and the insoluble material was filtered off.
The solvent of the obtained filtrate was distilled off under reduced pressure to obtain 2.77 g of a crude product. The resulting crude product was purified by column chromatography (silica gel; 1.6% -THF-hexane) to obtain 0.98 g of a lactonate (total isomer purity: 4.8%).

Example 3 Structure confirmation and sensory evaluation of macrocyclic lactone compound Since the obtained product contains impurities such as dicyclohexylcarbodiimide, the macrocyclic lactone compound was separated by preparative gas chromatography.
First, 0.1 g of the product obtained in Example 2 was prepared with ethanol to a concentration of 10%, and 5 μL was injected by splitless measurement to obtain a chromatogram. After the injection, it was introduced into a cooling concentration apparatus (Preparative Fraction Collector made by Gerstel) for the retention time of the main product, and this operation was repeated 80 times to obtain a concentrate of the main component. This was poured out with 0.5 ml of ethanol, and the three components of 7.3%, 53.9%, and 38.8% were isolated from normal gas chromatography in the order of short retention time. From the mass fragment, the above three components were identified as 14-n-propyloxacyclotetradecan-2-one, 15-ethyloxacyclopentadecan-2-one and 16-methyloxacyclohexadecan-2-one. . From the sensory evaluation, it was confirmed that the mixture of the three components had a gorgeous and beautiful musk fragrance reminiscent of muskinki. Compared with commercially available cyclohexadecanolide having the same molecular weight, the product of the present invention has a strong sweetness, and therefore, the branched alkyl group is considered to bring a more natural odor like muscone.
Moreover, it confirmed that 14-n-propyl oxacyclotetradecan-2-one had musk fragrance | flavor by smell smell gas chromatography (GC-Olfatomometry).

16-methyloxacyclohexadecan-2-one MS; 254 (4, M ⁺ ), 237 (10, M ⁺ -CH ₃ ), 236 (51, M ⁺ -H ₂ O), 210 (27, M ⁺ - HCOCH ₃ ), 98 (48), 97 (61), 96 (44), 84 (41), 83 (59), 69 (64), 55 (100), 41 (66)

15 ethyl oxacyclopenta decan-2-one ^{MS; 254 (4, M +} ), 236 (47, M + - H 2 O), 225 (41, M + - C 2 H 5), 196 (29, M ⁺ −HCOC ₂ H ₅ ), 98 (48), 97 (66), 96 (41), 95 (42), 83 (60), 69 (68), 55 (100), 41 (69)

14-n-propyl-oxa cyclotetradecane-2-one ^{MS; 254 (3, M +} ), 236 (41, M + - H 2 O), 211 (55, M + - C 3 H 7), 182 (46 , M ⁺ -HCOC ₃ H ₇ ), 111 (41), 98 (63), 97 (53), 83 (57), 69 (52), 55 (100), 43 (46), 41 (72)

Example 4 Fragrance composition for detergents for clothes By adding 15 parts by mass of the lactonized product obtained in Example 2 to 85 parts by mass of the fragrance composition having the composition shown in Table 1, there is a flowery and clean feeling. Thus, a fragrance composition for detergents for clothing characterized by a soft musk fragrance could be obtained.

Claims (2)

  A fragrance composition containing 14-n-propyloxacyclotetradecan-2-one as an active ingredient.   The fragrance composition according to claim 1, wherein the content of 14-n-propyloxacyclotetradecan-2-one is 0.01 to 50 mass% with respect to the entire composition.