JPH1135968A - Perfume having optically active trams-3-isocamphylcyclohexanol as effective component - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a novel perfume having an aroma like that of sandal-wood having an optically active trans-3-isocamphylcyclohexanol as the effective component. SOLUTION: A perfume contains one or more optically active trans-3- isocamphylcyclohexanols selected from (1R,3R,1'S,2'R,4'S,6'S)-3-(5', 5', 6'- trimethylbicyclo[2. 2. 1]hepto-2'-yl) cyclohexan-1-ol, (1S,3S,1'S,2'R,4'S,6' S)-3-(5',5',6'-trimethylbicyclo[2.2.1]hepto-2 '-yl) cyclohexan-1-ol and (1R,3R,1R,2' S,4'R,6'R)-3-(5',5',6'-trimethylbicyclo[2.2.1]hepto-2'-yl) cyclohexan-1-ol.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an optically active trans-3- having sandalwood-like fragrance used for perfuming cosmetics and the like.
The present invention relates to a fragrance composition containing isocampyl cyclohexanol.

[0002]

2. Description of the Related Art 3-Isocamphyl cyclohexanol is the most typical and classical compound which has long been developed as a substitute for Santalols which is an active ingredient of natural sandalwood essential oil which is difficult to synthesize industrially. It is known as a synthetic fragrance (see German Patent No. 834,593 (1952)).

The 3-isocamphyl cyclohexanol is obtained by reacting camphene and guaiacol with boron trifluoride and then hydrogenating it as a mixture of a trans-isomer and a cis-isomer. Santalex T (registered trademark, Takasago International Corporation) Fragrance components marketed under several trade names.

On the other hand, among trans and cis isomers of 3-isocamphylcyclohexanol, only trans-3-isocamphylcyclohexanol having a trans structure has a sandalwood-like aroma, -3-Isocamphlcyclohexanol has two diastereoisomeric stereoisomers, and it is known that both erythro and threo forms have sandalwood odor (E Demole, Helv. Chim. Acta., Vol 4
7, pages 319-338 (1964)).

Since trans-3-isocamphylcyclohexanol has an asymmetric carbon in the molecule, two enantiomers, a (+) form and a (-) form, are used for the erythro form and the threo form, respectively. And there are a total of four optical isomers, but the odor of the optically active isomer of trans-3-isocamphylcyclohexanol has not been reported.
There is no report that an optically active substance was individually synthesized, and of course, no report has been used as a fragrance.

[0006]

With the supply of sandalwood essential oil produced in the eastern part of India being limited, unprecedented demand has risen with the diversification of various cosmetics and health and hygiene materials. There has been a demand for the development of a perfume substance which has good properties, has a fragrance close to that of the essential oil of natural sandalwood, has high palatability, is highly retentive, and has a highly safe sandalwood-like odor. A fragrance having a sandalwood-like fragrance can impart elegance to the product used as a woody note and impart a unique oriental scent. In addition, a product with high added value can be supplied from the excellent residual fragrance. Therefore, an object of the present invention is to provide an optically active substance having a sandalwood-like scent that satisfies the above demand, and a fragrance containing the optically active substance as an active ingredient.

[0007]

The present inventors have made intensive studies to solve these problems, and as a result, the structural formula (1)

[0008]

Embedded image

(1R, 3R, 1'S, 2'R, 4'S, 6'S) -3-
(5 ', 5', 6'-trimethylbicyclo [2.2.1] hept-2'-yl)
Cyclohexane-1-ol, structural formula (2)

[0010]

Embedded image

(1S, 3S, 1'S, 2'R, 4'S, 6'S) -3-
(5 ', 5', 6'-trimethylbicyclo [2.2.1] hept-2'-yl)
Cyclohexane-1-ol and structural formula (3)

[0012]

Embedded image

(1R, 3R, 1'R, 2'S, 4'R, 6'R) -3-
(5 ', 5', 6'-trimethylbicyclo [2.2.1] hept-2'-yl)
One or more optically active trans-3-isocamphyl cyclohexanols selected from cyclohexan-1-ols have a particularly strong odor and a fragrance close to that of natural sandalwood oil, and have a musty odor. It has been found that it can be a useful perfume substance because it is not present.

That is, the present invention provides a compound represented by the structural formula (1)

[0015]

Embedded image

(1R, 3R, 1'S, 2'R, 4'S, 6'S) -3-
(5 ', 5', 6'-trimethylbicyclo [2.2.1] hept-2'-yl)
Cyclohexan-1-ol, i.e., d-(+)-threo-
Trans-3-Isocamphylcyclohexanol, structural formula (2)

[0017]

Embedded image

(1S, 3S, 1'S, 2'R, 4'S, 6'S) -3-
(5 ', 5', 6'-trimethylbicyclo [2.2.1] hept-2'-yl)
Cyclohexan-1-ol, i.e., d-(+)-erythro-trans-3-isocamphylcyclohexanol,
And structural formula (3)

[0019]

Embedded image

(1R, 3R, 1'R, 2'S, 4'R, 6'R) -3-
(5 ', 5', 6'-trimethylbicyclo [2.2.1] hept-2'-yl)
Cyclohexan-1-ol, i.e., l-(-)-erythro-trans-3-isocamphylcyclohexanol,
A fragrance composition containing one or more of optically active trans-3-isocamphylcyclohexanol represented by the formula: A fragrance composition containing 3-isocamphylcyclohexanol, and 3-isocamphylcyclohexanol in which optically active trans-3-isocamphylcyclohexanol is at least 5% by weight. It is a fragrance composition characterized by the above-mentioned.

Hereinafter, the present invention will be described in more detail.
The optically active trans-3-isocamphylcyclohexanol of the present invention can be obtained, for example, by the following method.

That is, it can be obtained by separating racemic trans-3-isocamphylcyclohexanol by liquid chromatography or the like having an optically active holding layer. Liquid chromatography columns with optically active retention layers have CHIRALCEL OD-H or OJ (Daicel Chemical Industries, Ltd.) or CHIRALPAK AD (Daicel Chemical Industries, Ltd.), or other optically active retention layers It is possible by using a liquid chromatography column or the like, but it is not limited to these.

The racemic trans-3-isocamphylcyclohexanol can be synthesized, for example, using the known methods of camphene and guaiacol as raw materials.
Isocamphlveratrol is synthesized using camphene and veratrol (catechol dimethyl ether), and is hydrolyzed followed by hydrogenation to synthesize isocampylcyclohexanol (see JP-A-54-148753). And hydrogenation after synthesizing isocamphyl catechol using catechol and catechol (see JP-A-57-118507), and the like, but are not limited thereto.

The obtained racemic trans-3-isocamphylcyclohexanol was subjected to liquid chromatography using a CHIRALCEL OD and a differential refractometer as a detector, and hexane / isopropyl alcohol =
Separation is carried out at 100/1, and four kinds of optically active substances are respectively collected. The eluate used can be separated by a combination of a hydrocarbon solvent and a polar solvent such as hexane / ethanol = 300/1.
It is not limited to these.

The optically active transformer thus obtained
-3- Fragrance evaluation of isocampyl cyclohexanol was performed by a specialized panelist. As a result, among the threo bodies having this trans structure, the optically active form d-
(+)-threo-trans-3-isocamphylcyclohexanol (i.e., (1R, 3R, 1'S, 2'R, 4'S, 6'S) -3- (5 ', 5', 6'-trimethylb
While icyclo [2.2.1] hept-2'-yl) cyclohexan-1-ol has a very strong sharp, especially diffusible and almost sandalwood-like aroma similar to natural sandalwood oil, Enantiomer l-
(-)-threo-trans-3-isocamphylcyclohexanol (i.e., (1S, 3S, 1'R, 2'S, 4'R, 6'R) -3- (5 ', 5', 6'-trimethylb
The odor of icyclo [2.2.1] hept-2'-yl) cyclohexan-1-ol) is weak, musty and poor in odor value. It is clear that the presence of this compound greatly affects the odor and increases the threshold value. It became.

Also, in particular, d-(+)-threo-trans-3-isocam
phylcyclohexanol (that is, (1R, 3R, 1'S, 2'R, 4'S, 6 '
S) -3- (5 ', 5', 6'-trimethylbicyclo [2.2.1] hept-2'-yl) c
yclohexan-1-ol) is excellent, and the threshold value alone is 0.
2 ppb, which proved to be very preferable.

Further, these d-(+)-threo-trans-3-is
ocamphylcyclohexanol (ie, (1R, 3R, 1'S, 2'R, 4 '
S, 6'S) -3- (5 ', 5', 6'-trimethylbicyclo [2.2.1] hept-2'-
yl) cyclohexan-1-ol), d-(+)-erythro-trans-3-isoca
mphylcyclohexanol (that is, (1S, 3S, 1'S, 2'R, 4'S, 6 '
S) -3- (5 ', 5', 6'-trimethylbicyclo [2.2.1] hept-2'-yl) c
yclohexan-1-ol), and l-(-)-erythro-trans-3-isoca
mphylcyclohexanol (that is, (1R, 3R, 1'R, 2'S, 4'R, 6 '
R) -3- (5 ', 5', 6'-trimethylbicyclo [2.2.1] hept-2'-yl) c
It has been revealed that yclohexan-1-ol) can be a useful fragrance substance since it has no odor particularly accompanied by musty odor (see Tables 1, 2 and 3).

These compounds are superior in the aroma intensity to conventionally known racemic trans-3-isocamphylcyclohexanol and exhibit the same effect with a small amount of use, so that the amount of use can be reduced. It is also excellent in terms of environmental issues and safety.

The compound of the present invention, d-(+)-threo-trans-3-is
ocamphylcyclohexanol, d-(+)-erythro-trans-3-isocam
phylcyclohexanol and l-(-)-erythro-trans-3-isocamph
Each of ylcyclohexanol is contained in the perfume as a single item.
When used at a concentration of 0001% by weight or more, the fragrance can impart a sandalwood-like fragrance close to natural sandalwood oil. These three optically active substances may be mixed and used at a concentration of 0.0001% or more. . 50% by weight of a conventionally used racemic trans-3-isocamphylcyclohexanol is used.
Even when used in a mixture at the above concentration, a sandalwood-like fragrance without moldy odor can be imparted to the fragrance.

These optically active trans-3-isocamphylcyclohexanols, when added to perfume preparations,
Diffusivity, increase the retention, and close to natural sandalwood oil, impart a sandalwood-like fragrance, and further provide a fresh, highly fragrant fragrance imparting no odor with moldy odor, or a fragrance improving reinforcing agent, Further, as a fragrance component, it can be suitably used for cosmetics, health and hygiene materials, pharmaceuticals and the like. That is, shampoos, rinses, perfumes, colons, hair tonics, hair creams, and other cosmetic base materials and cosmetic detergents, soaps, detergents, indoor fragrances, disinfectants, and other health and hygiene detergents , Etc. to enhance their commercial value.

[0031]

EXAMPLES The present invention will be described in more detail with reference to the following Examples, which should not be construed as limiting the present invention.

In the present embodiment, the following analyzer was used. The determination of each absolute structure was determined by the method reported by Kusumi et al. (Kusumi et al., Tetrahedron Lett., 32, 2
923 (1991)).

High performance liquid chromatography Pump: LC-6A (manufactured by Shimadzu Corporation) Column: CHIRALCEL OD (manufactured by Daicel Chemical Industries, Ltd.) Detector: YRD-880 type differential refraction detector (manufactured by Shimamura Corporation) Gas Chromatography mass spectrometer Equipment: HP-5890 Series II (manufactured by Hewlett-Packard) and M-2000A (manufactured by Hitachi, Ltd.) Column: BC-WAX (0.25 mm x 50 m, 0.15 μm) Measurement temperature: 70-220 ° C (The temperature is raised at 4 ° C / min.) Injection temperature: 250 ° C Proton nuclear magnetic resonance spectrum ( ¹ H NMR) Equipment: AMX-400 (400 MHz) FT-NMR spectrometer (manufactured by Bruker) Internal standard: tetramethylsilane ¹³ C Nuclear magnetic resonance spectrum ( ¹³ C NMR) Instrument: AMX-400 (100 MHz) FT-NMR spectrometer (manufactured by Bruker) Internal standard: Tetramethylsilane Infrared absorption spectrum (IR) Instrument: FT-IR-8200PC ( (Made by Shimadzu Corporation) Measuring method: Phil Optical rotation device: DIP-360 type optical rotation meter (manufactured by JASCO Corporation)

[0034]

Example 1 Synthesis of optically active trans-3-isocamphylcyclohexanol 4 g of camphene, 20 g of guaiacol and 45 ml of toluene were placed in a reaction flask, and 10 g of acid clay and 1 g of sulfuric acid were added.
Stirred at -70 ° C for 4 hours. Then, the mixture was stirred at 120 ° C. for 1.5 hours. After the reaction, the acid clay is filtered, and the reaction solution is neutralized.
Toluene and unreacted guaiacol were distilled off to obtain 7 g of isocampyl guaiacol. 10 g of n-butanol and 100 mg of potassium hydroxide were added to 7 g of the obtained isocampyl guaiacol, and using a Raney Nickel catalyst 500 mg in an autoclave, hydrogen pressure 90-100 kg / cm ² , temperature 180-
Hydrogenation was performed at 200 ° C. After the reaction, the solvent was distilled off to obtain 6.5 g of a mixture of isocamphyl cyclohexanol isomers. Further purification was carried out by distillation to obtain 480 mg of trans-3-isocamphylcyclohexanol. This trans-3-isocamphyl cyclohexanol is used in CHIRALCEL
Using an OD, a liquid chromatograph with a differential refractometer as a detector was used to perform optical resolution at a flow rate of 10 ml / min with hexane / isopropyl alcohol = 100/1 as an eluent, separated, and separated at a retention time of 39.5 minutes. d-(+)-erythro-tran
s-3-isocamphylcyclohexanol, 110mg and retention time 47.0
L-(-)-erythro-trans-3-isocamphylcyclohexanol in minutes,
120 mg and d-(+)-threo-trans- with a retention time of 44.0 minutes
3-isocamphylcyclohexanol, 105mg and l-(-)-threo-trans-3-isocamphylcyclohexanol, 115m with a retention time of 52.0 minutes
g were separated and obtained as optically active substances. The physical properties of the obtained optically active trans-3-isocamphylcyclohexanol were as follows.

(+)-Erythro-trans-3-isocamphylcyclohexanol [α] _D ²⁵ +28.1 (c, 1.2 CHCl ₃ ) MS (EI) (m / z) 95 (100), 81 (52), 135 (43 ), 110 (33),
236 (4) IR 3420, 2900, 1450, 1385, 1140, 1030 ¹ H NMRδ 1.06 (1H, brs), 1.87-0.65 (18H, m), 0.90
(3H, s), 0.84 (3H, s), 0.82 (3H, d, J = 7.4) ¹³ C NMR δ 66.8, 49.4, 48.9, 48.0, 47.9, 40.4, 38.
8, 36.3, 33.4, 33.4, 31.1, 29.4, 27.4, 24.8, 20.0, 1
6.2

(-)-Erythro-trans-3-isocamphylcyclohexanol [α] _D ²⁵ -26.5 (c, 1.1 CHCl ₃ ) MS (EI) (m / z) 95 (100), 81 (52), 135 (43 ), 110 (33),
236 (4) IR 3420, 2900, 1450, 1385, 1140, 1030 ¹ H NMRδ 4.06 (1H, brs), 1.87-0.65 (18H, m), 0.90
(3H, s), 0.84 (3H, s), 0.82 (3H, d, J = 7.4) ¹³ C NMR δ 66.8, 49.4, 48.9, 48.0, 47.940.4, 38.
8, 36.3, 33.4, 33.4, 31.1, 29.4, 27.4, 24.8, 20.0,
16.2

(+)-Threo-trans-3-isocamphylcyclohexanol [α] _D ²⁵ +29.6 (c, 1.3 CHCl ₃ ) MS (EI) (m / z) 97 (100), 135 (94), 81 (72 ), 123 (42),
236 (4) IR 3400, 2900 , 2450, 1385, 1140, 1030, 1020 1 H NMRδ 4.06 (1H, brs) 1.82-0.65 (18H, m) 0.91 (3
(H, s) 0.84 (3H, s) 0.83 (3H, d, J = 7.5) ¹³ C NMR δ 66.8, 49.5, 49.0, 48.0, 48.0, 39.2, 37.
0, 36.4, 33.3, 33.0, 31.4, 31.1, 27.4, 24.8, 20.0, 1
6.2

(-)-Threo-trans-3-isocamphylcyclohexanol [α] _D ²⁵ -32.1 (c, 1.5 CHCl ₃ ) MS (EI) (m / z) 97 (100), 135 (94), 81 (72 ), 123 (42),
236 (4) IR 3400, 2900 , 2450, 1385, 1140, 1030, 1020 1 H NMRδ 4.06 (1H, brs) 1.82-0.65 (18H, m) 0.91 (3
(H, s) 0.84 (3H, s) 0.83 (3H, d, J = 7.5) ¹³ C NMR δ 66.8, 49.5, 49.0, 48.0, 48.0, 39.2, 37.
0, 36.4, 33.3, 33.0, 31.4, 31.1, 27.4, 24.8, 20.0, 1
6.2

Evaluation of perfume A mixture of 50% by weight of the optically active substance of the present invention and 50% by weight of a conventionally known racemic trans-3-isocamphylcyclohexanol was evaluated by five expert panelists. As a result, as shown in Table 1, a sufficiently remarkable difference was recognized as compared with 100% by weight of racemic trans-3-isocamphylcyclohexanol.

[0040]

[Table 1]

Further, 1 to 5% by weight of the optically active product of the present invention.
And racemic 3-isocamphylcyclohexanol 9
When a mixture consisting of 9 to 95% by weight was evaluated by five expert panelists, as shown in Table 2, racemic 3-isocamphylcyclohexanol 100 was obtained.
A sufficiently remarkable difference was recognized as compared with the weight%.

[0042]

[Table 2]

Measurement of Threshold and Flavor Various optically active trans-3s obtained by the above method
-The respective threshold values were determined for isocampyl cyclohexanol. Ethanol solutions of various concentrations of optically active trans-3-isocamphylcyclohexanol were prepared, and 10 microliters of the solution was infused with 20 milliliters of distilled water as a sample for threshold measurement. The control was carried out using a three-point method in which a substance having an aroma was selected from those two points and one point of the sample as a control.
The evaluation was performed by 10 expert panelists, and the lowest concentration that could be correctly answered by 7 out of 10 panelists was set as the threshold.

As a result, as shown in Table 3, d-(+)-th
reo-trans-3-isocamphylcyclohexanol had a concentration threshold of 0.2 ppb, and its odor was similar to that of natural sandalwood oil. L-(-)-threo-trans-3-iso
Camphylcyclohexanol has a musty odor at 0.2 ppm, and it develops aroma only in a 1000-fold concentrated solution compared to d-(+)-threo-trans-3-isocamphylcyclohexanol, and a remarkable threshold value between enantiomers Had a difference of Furthermore, d-(+)-
erythro-trans-3-isocamphylcyclohexanol is 7 ppb and l-(-)-erythro-trans-3-isocamphylcyclohexanol is
It had a warm sandalwood-like odor at 3 ppb. Compared to the conventionally known racemic trans-3-isocamphylcyclohexanol, d-(+)-erythro-trans-
3-isocamphylcyclohexanol, l-(-)-erythro-trans-3-is
ocamphylcyclohexanol and d-(+)-threo-trans-3-isocam
It was revealed that each of the phylcyclohexanols had a high aroma intensity. Among them, d-(+)-threo-trans-3-
Isocamphylcyclohexanol was found to have an especially strong sharp, highly diffusive, and sandalwood-like odor close to natural sandalwood oil.

[0045]

[Table 3]

[0046]

Example 2 Sandalwood Fragrance Base Various optically active trans-3-isocamphylcyclohexanols obtained in the present invention or various optically active trans-3-isocamphylcyclohexanols were mixed at a fixed ratio. Using an optically active trans-3-isocamphylcyclohexanol, a sandalwood fragrance base was prepared according to the following formulation, and the effects were compared and examined by five specialized panelists. As a result, by adding the optically active trans-3-isocamphylcyclohexanol, a sandalwood scent close to natural sandalwood scent can be imparted. The one used was overwhelmingly excellent in strength, and showed no moldy odor and excellent in aroma.

Sandalwood fragrance base Ingredients parts by weight 4-phenylpropylpyridine 28 4-methyl-5-thiazolylethanol 14 amyris oil 42 benzylbenzoate 478 galaxolide (trade name, manufactured by International Flavors and Fragrances) 30 gamma-undeca Lactone 3 Methyl dihydroabietic acid 320 Acetylsedren 50 Trans-3-isocamphyl cyclohexanol 35 Total 1000

[0048]

Example 3 Sandalwood fragrance base Various optically active trans-3-isocamphyl cyclohexanols or various optically active trans-3-isocamphyl cyclohexanols obtained in the present invention according to the formulation of Example 2 Was prepared by using an optically active trans-3-isocamphylcyclohexanol mixed at a ratio of 0.0001% by weight with sandalwood fragrance base, and the effect was compared and examined by five specialized panelists. On the other hand, a comparison was made with a conventionally known formulation prepared using 0.0005% by weight of racemic trans-3-isocamphylcyclohexanol. As a result, as shown in Table 4, it was shown that the effect was obtained by adding 0.0001% by weight of optically active trans-3-isocamphylcyclohexanol.

Sandalwood fragrance base Ingredients by weight 4-Phenylpropylpyridine 28 4-Methyl-5-thiazolylethanol 14 Amiris oil 42 Benzylbenzoate 512.9 Galaxolide (trade name, manufactured by International Flavors and Fragrances) 30 Gamma-Undeca Lactone 3 Methyl dihydroabietic acid 320 Acetylsedren 50 Trans-3-isocamphyl cyclohexanol 0.1 Total 1000

[0050]

[Table 4]

[0051]

Example 4 Perfume composition for soap Optically active trans-3-isocamphylcyclohexanol or racemic trans-3-isocamphylcyclohexanol was added at the ratio shown in the following table. A prescription soap fragrance composition was prepared, and its effects were compared and examined by five specialized panelists. As a result, it was shown that the one using optically active trans-3-isocamphylcyclohexanol had a coherent scent, had a residual scent, and was excellent.

Perfume composition for soap Ingredients parts by weight Dodecanal 6.5 Coumarin 60.0 Ethyl vanillin 1.0 Geranium oil 6.0 Covanol (trade name, manufactured by Takasago International Corporation) 20.0 l-citronellol 100.0 l-citronellyl acetate 50.0 Liliar (manufactured by Givaudan) 80.0 Tetrahydrolinalool 100.0 Linalyl acetate 50.0 Methyl dihydroabietic acid 70.0 Limonene 10.0 Berbetone (trade name, manufactured by Takasago International Corporation) 120.0 Patchouli oil 13.0 Phenylethyl alcohol 116.0 Raspberry ketone 2.0 Styralyl acetate 8.0 Tonalide (PFW) 50.0 Towanal (manufactured by Takasago International Corporation) 11.0 trans-3-isocamphyl cyclohexanol 12.0 benzyl benzoate 114.5 Total 1000

[0053]

Example 5 Women's mug-like perfume composition Using optically active trans-3-isocamphylcyclohexanol or racemic trans-3-isocamphylcyclohexanol, added in the ratio shown in the following table, Prepare a mug-like perfume composition for women of the following formula,
The effects were compared by five expert panelists. As a result, it was shown that those using optically active trans-3-isocamphylcyclohexanol have a good balance as a mug-like perfume for women, and have excellent residual fragrance and are excellent.

Women's mug-like perfume composition Ingredients: parts by weight Laurinal (trade name, manufactured by Takasago International Corporation) 50 Covanol (trade name, manufactured by Takasago International Corporation) 300 Lilyal (trade name, manufactured by Givaudan) 100 Phenyl Ethyl alcohol 150 Hexylcinnamic aldehyde 185 Citronellol 70 Geraniol 30 Benzyl acetate 20 Indole 3 Citral 1 Linalool 50 Terpineol 30 Phenylacetaldehyde dimethyl acetal 5 Citronellal 1 Benzyl benzoate 4.5 Trans-3-Isocampyl cyclohexanol 0.5 Total 1000

[0055]

The present invention provides a novel fragrance containing optically active trans-3-isocamphylcyclohexanol as an active ingredient. Optically active trans-3-isocamphylcyclohexanol has excellent properties as a fragrance, and as a result, fragrances containing optically active trans-3-isocamphylcyclohexanol as an active ingredient can be used in various cosmetics, health and hygiene materials, etc. Used for a wide range.

Claims (4)

[Claims] (1) (1R, 3R, 1'S, 2'R, 4'S, 6'S) -3- (5 ', 5', 6'-
Trimethylbicyclo [2.2.1] hept-2'-yl) cyclohexan-1-ol, (1S, 3S, 1'S, 2'R, 4'S, 6'S) -3- (5 ',
5 ', 6'-trimethylbicyclo [2.2.1] hept-2'-yl) cyclohexan-1-ol, and (1R, 3R, 1'R, 2'S, 4'R, 6'
R) -3- (5 ', 5', 6'-trimethylbicyclo [2.2.1] hept-2 '
-Ill) A fragrance composition containing one or more optically active trans-3-isocamphylcyclohexanols selected from cyclohexane-1-ol. 2. The optically active trans-3 according to claim 1.
-A fragrance composition comprising trans-3-isocamphylcyclohexanol in which isocampylcyclohexanol is 50% by weight or more. 3. The optically active trans-3 according to claim 1.
-A fragrance composition comprising 3-isocamphylcyclohexanol in which isocampylcyclohexanol is 5% by weight or more. 4. The optically active trans-3- according to claim 1.
A fragrance composition containing 0.0001% by weight or more of isocampyl cyclohexanol.