Musk-like composition

Abstract

Provided is a musk-like composition that is excellent in harmony with various other fragrances and that can create a distinctive fragrance effect when blended. The composition includes a compound represented by General Formula (I). The ratio of an E-isomer of the compound represented by General Formula (I) to a Z-isomer of the compound represented by General Formula (I) is E-isomer/Z-isomer=3/7 or more and 7/3 or less. ##STR00001##

Claims

1. A fragrance composition for imparting softness of musk, comprising a compound represented by the formula (I): ##STR00008## wherein a ratio of an E-isomer of the compound represented by the formula (I) to a Z-isomer of the compound represented by the formula (I), E-isomer/Z-isomer, is from 3/7 to 7/3 or less.

2. The composition according to claim 1, wherein the ratio of the E-isomer to the Z-isomer E-isomer/Z-isomer, is from 5/5 to 7/3.

3. The composition according to claim 1, wherein the composition further comprises a fragrance other than the compound represented by the formula (I), and a content of the compound represented by the formula (I) in the composition is from 0.01% by mass to 25% by mass.

4. The composition according to claim 3, wherein the fragrance other than the compound represented by the formula (I) is at least one selected form the group consisting of a hydrocarbon, alcohol, phenol aldehyde, ketone, acetal, ether, ester, carbonate, lactone other than the compound of the formula (I), carboxylic acid, nitrile, Schiff base, natural essential oil, and natural extract.

5. A cleanser, comprising the composition of claim 1.

6. A cosmetic, comprising the composition of claim 1.

7. A fiber treating agent, comprising the composition of claim 1.

8. A method for imparting fragrance, the method comprising adding the composition of claim 1 to a composition, a cleanser, a cosmetic, or a fiber treating agent, thereby imparting fragrance.

9. A method for increasing fragrance intensity, the method comprising adding the composition of claim 1 to a composition, a cleanser, a cosmetic, or a fiber treating agent, thereby increasing fragrance intensity.

10. A method for imparting softness of musk, the method comprising adding the composition of claim 1 to a composition, a cleanser, a cosmetic, or a fiber treating agent, thereby imparting softness of musk.

Description

EXAMPLES

(1) Details of the measurement methods employed in the following examples and comparative examples are described together below.

(2) [Identification of Compound]

(3) Each compound obtained in the following production example was identified by matching data obtained by spectrum analyses using .sup.1H-NMR and a gas chromatograph mass spectrometer (GC-MS) (model: GC-2010, manufactured by Shimadzu Corporation), with compound data disclosed by a known document or the like.

(4) [Odor Evaluation]

(5) Two experts who had an experience of perfume blending and fragrance evaluation determined the fragrance note and the intensity by a smelling strip method. In the evaluation, the tip of a smelling strip (fragrance test paper with a width of 6 mm and a length of 150 mm) was immersed about 5 mm in a sample.

(6) With respect to the odor, fragrances that were sensed secondarily (secondary odors) were noted. In the evaluation of formulated fragrances, a fragrance not containing the composition of the present invention was used as a blank to evaluate the change in the fragrance note from the blank.

(7) The E-isomer and the Z-isomer of the compound (I) used in the examples were produced in accordance with the production examples described below.

(8) Here, the E-isomer of the compound (1) is (E)-oxacycloheptadec-8-en-2-one, and the Z-isomer of the compound (I) is (Z)-oxacycloheptadec-8-en-2-one.

Production Example 1

(9) Synthetic method of a mixture containing oxacycloheptadec-8-en-2-one having an E-isomer/Z-isomer ratio of 91/9

Production Example 1

(10) (a) Production of 9-decenyl-7-octenoate

(11) In a flask, 9-decen-1-ol (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD., 2.2 g, 14.0 mmol) and 7-octenoic acid (manufactured by SIGMA-ALDRICH, 2.0 g, 1.4.0 mmol) were placed and then dissolved in dichloromethane (30 mL). Subsequently, 1-ethyl-3(3-dimethylaminopropyl)carbodiimide hydrochloride (3.2 g, 16.8 mmol) and N,N′-dimethylaminopyridine (171 mg, 1.4 mmol) were added to the flask. This was allowed to react under a nitrogen gas stream at room temperature for three hours. An ammonium chloride aqueous solution was added to the reaction solution obtained after the reaction was completed, which then was stirred. Thereafter, it was subjected to settled separation to extract an aqueous layer, and an oil layer was washed with saturated saline. Then sodium sulfate was added to the oil layer to dehydrate to dryness. After filtration thereof, dichloromethane was evaporated from the oil layer to obtain 9-decenyl-7-octenoate (3.9 g, 14.0 mmol) in a crude yield of 100%.

(12) (b) Production of (E)-oxacycloheptadec-8-en-2-one

(13) In a three-necked flask, 9-decenyl-7-octenoate (3.3 g, 11.8 mmol) obtained in the above process (a), dichloromethane (3 L), and a metathesis catalyst represented by formula below (trade name “Umicore M2” manufactured by Umicore Japan KK, 194 mg, 0.21 mmol) were placed and then heated to reflux (50° C.) under a nitrogen gas stream for 24 hours. Then 130 mg (0.14 mmol) of the metathesis catalyst represented by formula below was further added thereto, and stirring was continued for five hours. The reaction solution obtained after the reaction was completed was subjected to gas chromatography quantitative analysis and found to contain 2.0 g of oxacycloheptadec-8-en-2-one (E/Z=70/30, 7.9 mmol, yield 67%).

(14) ##STR00005##

(15) Dichloromethane was evaporated from the reaction solution and the residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=95:5). Thus, 0.3 g of (E)-oxacycloheptadec-8-en-2-one (E/Z 91/9) was obtained.

Production Example 2

(16) Synthetic Method of a Mixture Containing oxacycloheptadec-8-en-2-one Having an E-isomer/Z-isomer Ratio of 2/98

(17) In a three-necked flask, 9-decenyl-7-octenoate (0.9 g, 3.2 mmol) obtained in Production Example 1 (a), dichloromethane (1.1 L), and a metathesis catalyst represented by formula below (manufactured by SIGMA-ALDRICH, 100 mg, 0.16 mmol) were placed and then heated to reflux (50° C.) under a nitrogen gas stream for 24 hours. Then 100 mg (0.16 mmol) of the metathesis catalyst represented by formula below was further added thereto, and stirring was continued for 24 hours. The reaction solution obtained after the reaction was completed was subjected to gas chromatography quantitative analysis and found to contain 0.4 g of (Z)-oxacycloheptadec-8-en-2-one (E/Z=2/98, 1.6 mmol, yield 49%).

(18) ##STR00006##

(19) Dichloromethane was evaporated from the reaction solution and the residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=99:1). Thus, 0.3 g of (Z)-oxacycloheptadec-8-en-2-one (E/Z=2/98) was obtained.

Examples 1 to 3 and Comparative Examples 1 to 4

(20) Compositions having the constitution indicated in Table 1 were prepared using the mixture containing the compound (I) obtained in Production Example 1 (E-isomer/Z-isomer=91/9) and the mixture containing the compound (I) obtained in Production Example 2 (E-isomer/Z-isomer 2/98) and subjected to odor evaluation. Table 1 also shows the results of the odor evaluation.

(21) ##STR00007##

(22) TABLE-US-00001 TABLE 1 Comp. Comp. Comp. Comp. Fragrance material Ex. 1 Ex. 2 Ex. 1 Ex. 2 Ex. 3 Ex. 3 Ex. 4 Mixture containing 10.0 9.4 7.7 7.3 3.3 1.65 — compound (I) obtained in Production Example 1 (E-isomer/ Z-isomer = 91/9) Mixture containing — 0.7 2.4 2.7 7.0 8.0 10.0 compound (I) obtained in Production Example 2 (E-isomer/ Z-isomer = 2/98) Ratio of 91/9 85/15 70/30 67/33 30/70 17/83 2/98 E-isomer/Z-isomer of compound (I) in composition Result of odor The fragrance The fragrance Musk with a Musk with a Musk with a Musk slightly Musk with a evaluation was stagnant was slightly stronger moist stronger moist stronger moist sweeter than moist scent and and did not stronger than scent as scent as scent as that of Comp. with a clear spread. that of Comp. compared with compared with compared with Ex. 4 profile Ex. 1. those of Comp. those of Comp. those of Comp. Exs. 1 and 4 Exs. 1 and 4 Exs. 1 and 4 and with and with and with aldehyde-like aldehyde-like aldehyde-like sweetness sweetness sweetness *Ex.: Example, Comp. Ex.: Comparative Example

(23) Table 1 above indicates that the compositions of the comparative examples had the odor of slightly sweet musk, or the odor of musk with a moist scent and with a clear profile. Meanwhile, the compositions of the present invention had the odor of musk with a stronger moist scent as compared with those of Comparative Examples 1 and 4 and with aldehyde-like sweetness.

Examples 4 to 6 and Comparative Examples 5 to 9

(24) Perfumes having the constitution indicated in Table 2 were prepared using the mixture containing the compound (I) obtained in Production Example 1 (E-isomer/Z-isomer=91/9) and the mixture containing the compound (I) obtained in Production Example 2 (E-isomer/Z-isomer=2/98). The obtained perfumes were subjected to odor evaluation. Table 8 shows the results of the odor evaluation.

(25) TABLE-US-00002 TABLE 2 Comp. Comp. Comp. Ex. Ex. Ex. Comp. Comp. Ex. 5 Ex. 6 Ex. 7 4 5 6 Ex. 8 Ex. 9 Allyl heptanoate 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 AMBROXAN .sup.1) 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 Coumarin 3.0 3.0 3.0 3.0 3.6 3.0 3.0 3.6 D.P.G .sup.2) 180.6 180.6 180.6 180.6 180.6 1806 180.6 180.6 α-Damascone 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 γ-Decalactone 1.5 1.5 1.5 1.5 1.5 1.5 1.5 1.5 Ethyl linalool 30.0 30.0 30.0 30.0 30.0 30.0 30.0 30.0 Ethyl maltol 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 Ethylene brassylate 60.0 60.0 60.0 60.0 60.0 60.0 60.0 60.0 MDJ .sup.3) 270.0 270.0 270.0 270.0 270.0 270.0 270.0 270.0 cis-3-Hexenol 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 cis-3-Hexenyl salicylate 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 Hexyl acetate 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 Hydroxycitronellal 15.0 15.0 15.0 15.0 15.0 15.0 15.0 15.0 β-Ionone 25.0 25.0 25.0 25.0 25.0 25.0 25.0 25.0 Iso E Super .sup.4) 120.0 120.0 120.0 120.0 120.0 120.0 120.0 120.0 LIFFAROME .sup.5) 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 LILIAL .sup.6) 45.0 45.0 45.0 45.0 45.0 45.0 45.0 45.0 Methylionone-G 45.0 45.0 45.0 45.0 45.0 45.0 45.0 45.0 o-tert-Butylcyclohexyl 4.0 4.0 4.0 4.0 4.0 4.0 4.0 4.0 acetate Raspberry ketone 6.0 6.0 6.0 6.0 6.0 6.0 6.0 6.0 Styralyl acetate 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 VELOUTONE .sup.7) 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 Damascenone 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 AMBER CORE .sup.8) 10.0 10.0 10.0 10.0 10.0 10.0 10.0 10.0 Lemon oil 40.0 40.0 40.0 40.0 40.0 40.0 40.0 40.0 FLOROSA .sup.9) 40.0 40.0 40.0 40.0 40.0 40.0 40.0 40.0 Mixture containing — — 0.7 2.4 2.7 7.0 8.0 10.0 compound (I) obtained in Production Example 2 (E-isomer/Z-isomer = 2/98) Mixture containing — 10.0 9.4 7.7 7.3 3.3 1.65 — compound (I) obtained in Production Example 1 (E-isomer/Z-isomer = 91/9) Total amount 910.0 920.0 920.0 920.0 920.0 920.0 920.0 920.0 Ratio of E-isomer/Z-isomer None 91/9 85/15 70/30 67/33 30/70 17/83 2/98 of compound (I) in composition * Numbers in Table indicate weight ratios. .sup.1) AMBROXAN (trade name of Kao Corporation, [3aR-(3aα,5aβ,9aα,9bβ)]-dodecahydro-3a,6,6,9a-tetramethyl naphto[2,1-b]furan) .sup.2) D.P.G: Dipropylene glycol .sup.3) MDJ (trade name of Kao Corporation, methyl dihydrojasmonate, methyl (2-pentyl-3-oxocyclopentyl)acetate) .sup.4) Iso E Super (trade name of IFF, 1-(1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-napthalenyl)-ethan-1-one) .sup.5) LIFFAROME (trade name of IFF, cis-3-hexenyl methyl carbonate) .sup.6) LILIAL (trade name of Givaudan, p-tert-butyl-α-methyl hydrocinnamaldehyde) .sup.7) VELOUTONE (trade name of Firmenich, 2,2,5-trimethyl-5-pentylcyclopentanone) .sup.8) AMBER CORE (trade name of Kao Corporation, 1-(2-tert-butyl cyclohexyloxy)-2-butanol), SANDALMYSORE CORE (trade name of Kao Corporation) .sup.9) FLOROSA (trade name of Givaudan, chemical name: 4-methyl-2-(2-methylpropyl)tetrahydro-2H-4-pyranol)

(26) TABLE-US-00003 TABLE 3 Ratio of E-isomer/Z-isomer Evaluation results Comp. None Reference (formulated fragrances: sweet, fruity Ex. 5 gourmand-like fragrance) Comp. 91/9  Sweetness of musk was imparted to the blank (Comp. Ex 5). Ex. 6 Comp. 85/15 Sweetness of musk was imparted to the blank (Comp. Ex. 5), Ex. 7 and the fragrance as a whole was harmonized. Ex. 4 70/30 Sweetness of musk was imparted to the blank (Comp. Ex. 5), and the fragrance as a whole was harmonized. Fragrance intensity as a whole was increased by aldehyde-like sweetness. Ex. 5 67/33 Sweetness of musk was imparted to the blank (Comp. Ex. 5), and the fragrance as a whole was harmonized. Fragrance intensity as a whole was increased by aldehyde-like sweetness. Ex. 6 30/70 Sweetness of musk was imparted to the blank (Comp. Ex. 5), and the fragrance as a whole was harmonized. Fragrance intensity as a whole was increased by aldehyde-like sweetness. Comp. 17/83 Sweetness of musk was imparted to the blank (Comp. Ex. 5), Ex. 8 and the fragrance as a whole was harmonized. Comp.  2/98 Sweetness of musk was imparted to the blank (Comp. Ex. 5), Ex. 9 and the fragrance as a whole was harmonized.

(27) Table 3 indicates that, as to the perfumes of the comparative examples, the sweetness of musk was imparted to the blank not containing the compound (I) (Comparative Example 5), and the fragrance as a whole was harmonized. Meanwhile, as to the perfumes of the present invention, the sweetness of musk was imparted to the blank not containing the compound (I) (Comparative Example 5), the fragrance as a whole was harmonized, and the fragrance intensity as a whole was increased by aldehyde-like sweetness.

Examples 7 to 9 and Comparative Examples 10 to 14

(28) Perfumes having the constitution indicated in Table 4 were prepared using the mixture containing the compound (I) obtained in Production Example 1 (E-isomer/Z-isomer 91/9) and the mixture containing the compound (I) obtained in Production Example 2 (E-isomer/Z-isomer=2/98). The obtained perfumes were subjected to odor evaluation. Table 5 shows the results of the odor evaluation.

(29) TABLE-US-00004 TABLE 4 Comp. Comp. Comp. Ex. Ex. Ex. Comp. Comp. Ex. 10 Ex. 11 Ex. 12 7 8 9 Ex. 13 Ex. 14 AMBER CORE .sup.1) 1.42 1.42 1.42 1.42 1.42 1.42 1.42 1.42 AMBRINOL .sup.2) 0.60 0.60 0.60 0.60 0.60 0.60 0.60 0.60 AMBRINOL 20T .sup.3) 0.12 0.12 0.12 0.12 0.12 0.12 0.12 0.12 AMBROTECH .sup.4) 0.36 0.36 0.36 0.36 0.36 0.30 0.36 0.36 AMBROXAN .sup.5) 1.50 1.50 1.50 1.50 1.50 1.50 1.50 1.50 BOISAMBRENE FORTE .sup.6) 0.08 0.08 0.08 0.08 0.08 0.08 0.08 0.08 Cyclohexyl salicylate 0.36 0.36 0.36 0.36 0.36 0.36 0.36 0.36 D.P.G .sup.7) 428.87 428.87 428.87 428.87 428.87 428.87 428.87 428.87 FLORANTONE T .sup.8) 0.04 0.04 0.04 0.04 0.04 0.04 0.04 0.04 FLOREX .sup.9) 0.60 0.60 0.60 0.60 0.60 0.60 0.60 0.60 GALAXOLIDE .sup.10) 520.00 520.00 520.00 520.00 520.00 520.00 520.00 520.00 GLOBANONE .sup.11) 6.00 6.00 6.00 6.00 6.00 6.00 6.00 6.00 HABANOLIDE .sup.12) 30.00 30.00 30.00 30.00 30.00 30.00 30.00 30.00 INDOLENE 50BB .sup.13) 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 1-Muscone .sup.14) 0.04 0.04 0.04 0.04 0.04 0.04 0.04 0.04 Muscone .sup.15) 0.60 0.60 0.60 0.60 0.60 0.60 0.60 0.60 MUSK TM-II .sup.16) 1.20 1.20 1.20 1.20 1.20 1.20 1.20 1.20 MUSK Z-4 .sup.17) 1.80 1.80 1.80 1.80 1.80 1.80 1.80 1.80 POLYMEFLOR .sup.18) 0.11 0.11 0.11 0.11 0.11 0.11 0.11 0.11 Mixture containing compound (I) — — 0.7 2.4 2.7 7.0 8.0 10.0 obtained in Production Example 2 (E-isomer-Z-isomer = 2/98) Mixture containing compound (I) — 10.0 9.4 7.7 7.3 3.3 1.65 — obtained in Production Example 1 (E-isomer/Z-isomer = 91/9) Total 910.0 920.0 920.0 920.0 920.0 920.0 920.0 920.0 Ration of E-isomer/isomer of None 91/9 85/15 70/30 67/33 30/70 17/83 2/98 compound (I) in composition * Numbers in Table indicate weight ratios. .sup.1) AMBER CORE (trade name of Kao Corporation, 1-(2-tert-butyl cyclohexyloxy)-2-butanol) .sup.2) AMBRINOL (trade name, 1,2,3,4,4a,5,6,7-octahydro-2,5,5-trimethyl-naphthalene-2-ol) .sup.3) AMBRINOL 20T (trade name of Takasago International Corporation, 1,2,3,4,4a,5,6,7-octahydro-2,5,5-trimethyl-naphthalene-2-ol) .sup.4) AMBROTECH (trade name of Kao Corporation, dodecahydro-3a,6,6,9a-tetramethylnaphto[2,1-b]furan) .sup.5) AMBROXAN (trade name of Kao Corporation, [3aR-(3aα,5aβ,9aα,9bβ)]-dodecahydro-3a,6,6,9a-tetramethyl naphto[2,1-b]furan) .sup.6) BOISAMBRENE FORTE (trade name of Kao Corporation, ethoxymethyl-cyclododecyl ether) .sup.7) D.P.G: Dipropylene gylcol .sup.8) FLORANTONE T (trade name of Takasago International Corporation, 1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethanone) .sup.9) FLOREX (trade name of Firmenich, 6-ethylideneoctahydro-5,8-methano-2H-1-benzopyran) .sup.10) GALAXOLIDE (trade name of IFF, hexamethylhexahydrocyclopentabenzopyran) .sup.11) GLOBANONE (trade name of Symrise, 8-cyclohexadecenone) .sup.12) HABANOLIDE (trade name Firmenich, cyclopentadecenolide) .sup.13) INDOLENE 50BB (trade name of IFF, 7,7-bis(1H-indol-3-yl)-1,1,5-trimethyl-1-heptanol) .sup.14) 1-Muscone ((R)-3-methyl cyclopentadecanone) .sup.15) Muscone (3-methyl cyclopentadecanone) .sup.16) MUSK TM-II (trade name of SODA AROMATIC CO., LTD., 5-cyclohexadecen-1-one) .sup.17) MUSK Z-4 (trade name of IFF, (Z)-4-cyclopentadecen-1-one) .sup.18) POLYMEFLOR (trade name of Takasago International Corporation, 1-(2-methyl-2-propenyloxy)-2,2,4-trimethylpentan-3-ol)

(30) TABLE-US-00005 TABLE 5 Ratio of E-isomer/Z-isomer Evaluation results Comp. None Reference (formulated fragrance: musk-like fragrance) Ex. 10 Comp. 91/9  A musk scent was imparted to the blank (Comp. Ex. 10), but Ex. 11 the fragrance was not harmonized and the intensity was weakened. Comp. 85/15 A feeling of clearness of musk was imparted to the blank Ex. 12 (Comp. Ex. 10), but fragrance intensity was slightly weakened. Ex. 7 70/30 Softness of musk was imparted to the blank (Comp. Ex. 10), and the fragrance as a whole was harmonized. Depth and a feeling of cleanliness were imparted to the fragrance. Ex. 8 67/33 Softness of musk was imparted to the blank (Comp. Ex. 10), and the fragrance as a whole was harmonized. Depth, voluminousness and a feeling of cleanliness were imparted to the fragrance. Ex. 9 30/70 Sweetness of musk was imparted to the blank (Comp. Ex. 10), and the fragrance as a whole was harmonized. Whiteness of moist musk was felt. Comp. 17/83 Sweetness of musk was imparted to the blank (Comp. Ex. Ex. 13 10). The fragrance was gentler than that of Comp. Ex. A8 but stiff and slightly animalic, and did not harmonized. Comp.  2/98 An animalic scent of musk was imparted to the blank Ex. 14 (Comp. Ex. 10), but the fragrance was slightly oily and stiff.

(31) Table 5 indicates that, as to the perfumes of the comparative examples, the sweetness of musk was imparted to the blank not, containing the compound (I) (Comparative Example 10). Meanwhile, as to the perfumes of the present invention, the sweetness of musk was imparted to the blank not containing the compound (I) (Comparative Example 10), the fragrance as a whole was harmonized, and the depth, and a feeling of cleanliness were imparted to the fragrance.

Examples 10 to 12 and Comparative Examples 15 and 19

(32) Perfumes having the constitution indicated in Table 6 were prepared using the mixture containing the compound (I) obtained in Production Example 1 (E-isomer/Z-isomer=91/9) and the mixture containing the compound (I) obtained in Production Example 2 (E-isomer/Z-isomer=2/98). The obtained perfumes were subjected to odor evaluation. Table 7 shows the results of the odor evaluation.

(33) TABLE-US-00006 TABLE 6 Comp. Comp. Comp. Ex. Ex. Ex. Comp. Comp. Ex. 15 Ex. 16 Ex. 17 10 11 12 Ex. 18 Ex. 19 α-Pinene 30.00 30.00 30.00 30.00 30.00 30.00 30.00 30.00 α-Terpineol .sup.1) 10.00 10.00 10.00 10.00 10.00 10.00 10.00 10.00 β-Pinene 6.50 6.50 6.50 6.50 6.50 6.50 6.50 6.50 Citronellol 110.00 110.00 110.00 110.00 110.00 110.00 110.00 110.00 Citronellyl acetate 4.00 4.00 4.00 4.00 4.00 4.00 4.00 4.00 Desenol 1.50 1.50 1.50 1.50 1.50 1.50 1.50 1.50 Eucalyptus oil 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 Eugenol 4.00 4.00 4.00 4.00 4.00 4.00 4.00 4.00 Geraniol 50.00 50.00 50.00 50.00 50.00 50.00 50.00 50.00 Geranyl acetate 13.00 13.00 13.00 13.00 13.00 13.00 13.00 13.00 Guaiacwood oil 85.00 85.00 85.00 85.00 85.00 85.00 85.00 85.00 I.P.M .sup.2) 41.80 41.80 41.80 41.80 41.80 41.80 41.80 41.80 Limonene 1.50 1.50 1.50 1.50 1.50 1.50 1.50 1.50 Linalool 40.00 40.00 40.00 40.00 40.00 40.00 40.00 40.00 Linalyl acetate 55.00 55.00 55.00 55.00 55.00 55.00 55.00 55.00 1-Menthone 1.20 1.20 1.20 1.20 1.20 1.20 1.20 1.20 MDJ .sup.3) 120.00 120.00 120.00 120.00 120.00 120.00 120.00 120.00 Nerol 13.00 13.00 13.00 13.00 13.00 13.00 13.00 13.00 Neryl acetate 4.00 4.00 4.00 4.00 4.00 4.00 4.00 4.00 Ocimane 2.00 2.00 2.00 2.00 2.00 2.00 2.00 2.00 Phenylethyl alcohol 325.00 325.00 325.00 325.00 325.00 325.00 325.00 325.00 Phenylethyl cinnamate 5.00 5.00 5.00 5.00 5.00 5.00 5.00 5.00 Rose oxid 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 TRIPLAL .sup.4) 10.00 10.00 10.00 10.00 10.00 10.00 10.00 10.00 VELOUTONE .sup.5) 15.50 15.50 15.50 15.50 15.50 15.50 15.50 15.50 Mixture containing — — 0.7 2.4 2.7 7.0 8.0 10.0 compound (I) obtained in Production Example 2 (E-isomer/Z-isomer = 2/98) Mixture containing — 10.0 9.4 7.7 7.3 3.3 1.65 — compound (I) obtained in Production Example 1 (E-isomer/Z-isomer = 91/9 Total amount 910.0 920.0 920.0 920.0 920.0 920.0 920.0 920.0 Ratio of E-isomer/Z-isomer None 91/9 85/15 70/30 67/33 30/70 17/83 2/98 of compund (I) in composition * Numbers in Table indicate weight ratios. .sup.1) α-Terpineol (2-(4-methylcyclohex-3-enyl)propan-2-ol) .sup.2) I.P.M (isopropyl myristate) .sup.3) MDJ (trade name of Kao Corporation, methyl dihydrojasmonate, methyl (2-pentyl-3-oxocyclopentyl)acetate) .sup.4) TRIPLAL (trade name of IFF, 2,4-dimethyl-3-cyclohexene-1-carboxaldehyde) .sup.5) VELOUTONE (trade name of Firmenich, 2,5,5-trimethyl-2-pentylcyclopentanone)

(34) TABLE-US-00007 TABLE 7 Ratio of E-isomer/Z-isomer Evaluation results Comp. None Reference (formulated fragrance: rose woody fragrance) Ex. 15 Comp. 91/9  A feeling of clearness of musk was imparted to the blank Ex. 16 (Comp. Ex. 15), but the voluminousness was insufficient. Comp. 85/15 A feeling of clearness and softness of musk were imparted to Ex. 17 the blank (Comp. Ex. 15), but the voluminousness was slightly less than that of Ex. B1. Ex. 10 70/30 Sweetness and softness of musk were imparted to the blank (Comp. Ex. 15), and the fragrance as a whole was harmonized. A rose scent spread softly, and the voluminousness of the fragrance as a whole increased. Ex. 11 67/33 Sweetness and softness of musk were imparted to the blank (Comp. Ex. 15), and the fragrance as a whole was harmonized. A rose scent spread softly, and the voluminousness of the fragrance as a whole increased. Ex. 12 30/70 Sweetness of musk was imparted to the blank (Comp. Ex. 15), and the fragrance as a whole was harmonized. The profile of the whole fragrance became clearer, and the fresh green aide of rose became clearer. Comp. 17/83 Sweetness and an animalic scent of musk were imparted to Ex. 18 fee blank (Comp. Ex. 15). The profile of the whole fragrance was more emphasized, but the fragrance was slightly stiff and not harmonized as a whole. Comp.  2/98 An animalic scent of musk was imparted to the blank Ex. 19 (Comp. Ex. 15), but the fragrance as a whole was not harmonized.

(35) Table 7 indicates that, as to the perfumes of the comparative examples, the sweetness of musk was imparted to the blank not containing the compound (I) (Comparative Example 15). Meanwhile, as to the perfumes of the present invention, the sweetness of musk was imparted to the blank not containing the compound (I) (Comparative Example 15), a rose scent spread softly, and the voluminousness of the fragrance as a whole increased.

INDUSTRIAL APPLICABILITY

(36) Since the composition of the present invention has a musk-tone odor useful as a fragrance, it can be used as a fragrance material. Moreover, since the composition of the present invention is excellent in harmony with various other fragrances and can create a distinctive fragrance effect when blended, it can be used as a fragrance-imparting component.