JP2003096022A - New compound and its usage - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a perfume compound, perfume composition and cosmetics having excellently lasting, luxury jasmine like, and fruity-green type fragrance. SOLUTION: This invention relates to a compound represented by formula (I) [wherein, n is an integer of 0 or 1, R is a (Z)- or (E)-2-pentenyl or 2-pentynyl] and a perfume composition and cosmetics containing the compound.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel compound useful as a fragrance, a fragrance composition containing the compound, and a cosmetic.

[0002]

2. Description of the Related Art Since ancient times, jasmine has been used as a fragrance. Further, in recent years, the aroma of fruity green has been gaining popularity, and a new jasmine-like or fruity green-like aroma raw material is required. The compound according to the present invention is a compound having an excellent jasmine-like odor that expresses a high-class feeling, and also has a fruity green-like odor. However, these compounds are compounds which have not been described in the literature, and their fragrances and uses of fragrances are not known.

[0003]

SUMMARY OF THE INVENTION An object of the present invention is to provide a fragrance composition having an excellent jasmine-like odor that expresses a high-class feeling, and also having a fruity green-like odor, and having an extremely excellent persistence. To provide goods and cosmetics.

[0004]

Under these circumstances, the inventors of the present invention have earnestly studied, and as a result, the specific compound has an excellent jasmine-like aroma, and also has a fruity green-like aroma, and its sustainability is also long. They also found that they are excellent, and completed the present invention.

That is, the present invention has the general formula (I)

[0006]

[Chemical 3]

(Wherein n is 0 or 1, R is a (Z) or (E) -2-pentenyl group, or 2-
A pentynyl group), a fragrance composition and a cosmetic containing the compound.

[0008]

The method for producing the compound according to the present invention is not particularly limited, and the compound may be obtained by any method. A typical manufacturing method will be described below.

[0009]

[Chemical 4]

Production method 1) Compound of the general formula (I) in which n = 0 and R is 2-pentynyl group Commercially available ethyl cyclohexanone-2-carboxylate (1)
And 2-pentynyl chloride (3) are reacted in the presence of an alkali such as potassium carbonate to obtain ethyl 2- (2-pentynyl) cyclohexanone-2-carboxylate (4), which is saponified with an alkali such as sodium hydroxide. After conversion to carboxylic acid, decarboxylation under heating produces the desired 2- (2
-Pentynyl) cyclohexanone (II) can be obtained. The target 2- (2-pentynyl) cyclohexanone (II) can also be obtained by reacting commercially available cyclohexanone (2) with 2-pentynyl chloride (3) in the presence of a strong alkali such as sodium amide or sodium methoxide. You can get it.

[0011]

[Chemical 5]

Production method 2) Compound of the general formula (I) in which n = 0 and R is (Z) -2-pentenyl group. Ethyl 2- (2-pentynyl) cyclohexanone-2-carboxylate (obtained by Production method 1) 4) is reacted with hydrogen in the presence of a Lindlar catalyst, or commercially available ethyl cyclohexanone-2-carboxylate (1) and commercially available (Z)-
(Z) -2-Pentenyl chloride (5) obtained by chlorinating 2-penten-1-ol with phosphorus trichloride or the like is reacted in the presence of an alkali such as potassium carbonate (Z).
Ethyl 2- (2-pentenyl) cyclohexanone-2-carboxylate (6) is obtained, which is saponified with an alkali such as sodium hydroxide to give a carboxylic acid, and then decarboxylated under heating to obtain the desired compound (Z ) -2- (2-Pentenyl) cyclohexanone (III) can be obtained.
In addition, commercially available cyclohexanone (2) was added in the presence of a strong alkali such as sodium amide or sodium methoxide,
It can also be obtained by reacting with (Z) -2-pentenyl chloride (5). Furthermore, the manufacturing method 1
The desired (Z) -2- (2-pentenyl) cyclohexanone (III) can also be obtained by reacting the 2- (2-pentynyl) cyclohexanone (II) obtained in (1) with hydrogen in the presence of a Lindlar catalyst.

[0013]

[Chemical 6]

Production method 3) Compound of the general formula (I) in which n = 0 and R is (E) -2-pentenyl group Commercially available ethyl cyclohexanone-2-carboxylate and commercially available (E) -2-pentene-1 -(E) -2-pentenyl chloride (7) obtained by chlorinating all with phosphorus trichloride or the like is reacted in the presence of an alkali such as potassium carbonate,
(E) -2- (2-Pentenyl) cyclohexanone-2
-Ethyl carboxylate (8) is obtained, which is saponified with an alkali such as sodium hydroxide to give a carboxylic acid, and then decarboxylated under heating to obtain the desired (E) -2- (2-pentenyl) cyclohexanone ( IV) can be obtained. In addition, by reacting commercially available cyclohexanone (2) with (E) -2-pentenyl chloride (7) in the presence of a strong alkali such as sodium amide or sodium methoxide, or by commercially available cyclohexanone (2) and 1-pentene. The desired (E) -2- (2-pentenyl) cyclohexanone (IV) can also be obtained by heating -3-ol (9) in the presence of an acid such as acetone dimethyl acetal and p-toluenesulfonic acid. I can.

[0015]

[Chemical 7]

Production Method 4) 2- (2-pentynyl) cyclohexanone (II) obtained by the Production Method 1 of the compound of the general formula (I) in which n = 1 exists in the presence of 3-chloroperbenzoic acid, magnesium perphthalate and the like. The desired 7- (2-pentynyl) oxep-2-one (VI) can be obtained by conducting a Bayer-Villiger reaction under the conditions below. By the same operation, from (Z) -2- (2-pentenyl) cyclohexanone (III) obtained in Production Method 2 or (E) -2- (2-pentenyl) cyclohexanone (IV) obtained in Production Method 3, (Z) -7- (2-Pentenyl) oxep-2-one (VII) or (E) -7- (2-Pentenyl) oxep-2-one (V) can be obtained. Furthermore, the desired 7- (2-pentynyl) oxep-2-one (VI) is reacted with hydrogen in the presence of a Lindlar catalyst to obtain the desired (Z) -7- (2-pentenyl) oxep-2-. ON (VII) can be obtained.

The compound represented by the general formula (I) has an excellent jasmine-like aroma expressing a high-class feeling, and further has aroma characteristics such as fruity green, and further has an extremely high persistence. And various fragrance compositions,
It can be used by adding it to cosmetics.

The compounds represented by the general formula (I) are (Z) -2- (2-pentenyl) cyclohexanone, (E) -2- (2-pentenyl) cyclohexanone, 2- (2-pentynyl) cyclohexanone, (Z)
-7- (2-Pentenyl) oxep-2-one, (E)
-7- (2-Pentenyl) oxep-2-one, 7-
(2-pentynyl) oxep-2-one. Among these, (E) -2- (2-pentenyl) cyclohexanone and (E) -7- (2-pentenyl) oxep-2-one are compounds not described in the literature and have a green-like lactone odor, but have aroma. Specifically (Z) -2- (2-pentenyl)
Cyclohexanone and (Z) -7- (2-pentenyl) oxep-2-one are more excellent.

The amount of this compound added to the fragrance composition or the cosmetic composition varies depending on the purpose thereof and the type of the fragrance composition or the cosmetic composition.
A range of about 30% by mass can be exemplified. The compound of the present invention can be applied to cosmetics, foods and drinks, insurance, hygiene, pharmaceuticals, tobacco flavor, indoor air fresheners and the like.

[0020]

The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples.

Example 1 Synthesis of 2- (2-pentynyl) cyclohexanone [Compound of the general formula (I) in which n = 0 and R is 2-pentynyl group] (1-a) 2- (2-pentynyl) Cyclohexanone-
Synthesis of ethyl 2-carboxylate 17.02 g (100 mmol) of ethyl cyclohexanone-2-carboxylate in a flask replaced with argon, 2
-Pentynyl chloride 12.82 g (125 mmo
1), potassium carbonate (41.5 g, 300 mmol) and dehydrated acetone (85 mL) were charged, and the mixture was heated under reflux for 30 hours. After the reaction was completed, the solid content was filtered off, and the filtrate was evaporated under reduced pressure. This residue was distilled under reduced pressure using a Vigreux tube (boiling point 9
4-105 ° C / 0.05 mmHg), and colorless oily 2-
18.28 g (yield 94.6%) of ethyl (2-pentynyl) cyclohexanone-2-carboxylate was obtained. The purity of the obtained compound was 9 by gas chromatography.
It was 4.6%.

(1-b) Synthesis of 2- (2-pentynyl) cyclohexanone 11.82 g (50 mmol) of ethyl 2- (2-pentynyl) cyclohexanone-2-carboxylate, 18 m of water
L and 16 mL of methanol were charged and heated to reflux. Pre-adjusted potassium hydroxide 8.97g (137mm
A mixed solution of 9 mL of water and 16 mL of methanol was added dropwise over 2 hours, and the mixture was heated under reflux for 3 hours. After completion of the reaction, extraction with ether was performed, and the obtained organic layer was 1 mol / L.
The solution was washed with an aqueous solution of sulfuric acid and then with saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was distilled under reduced pressure (boiling point 92-107 ° C / 9 mmHg) to give 2- (2-pentynyl) cyclohexanone as a pale yellow oil.
8.10 g (yield 74.0%) was obtained. The purity of the obtained compound was 98.7% by gas chromatography.

From the results of infrared absorption spectrum measurement, the fact that a molecular ion peak was observed at 164 by mass spectrometry, the data of the nuclear magnetic resonance spectrum shown below, and the relationship of the raw materials used, 2 It was confirmed to be-(2-pentynyl) cyclohexanone.

¹ H-NMR (CDCl ₃ ) δ1.11 (t, J = 7.6Hz, 3H), 1.34
-1.44 (m, 1H), 1.60-1.75 (m, 2H), 1.90-1.95 (m, 1H), 2.06-
2.18 (m, 4H), 2.26-2.48 (m, 4H), 2.55-2.62 (m, 1H)

Example 2 Synthesis of 2- (2-pentynyl) cyclohexanone [Compound of the general formula (I) where n = 0 and R is 2-pentynyl group] sodium amide 1.9 in a flask replaced with argon.
7 g (50.5 mmol) and 20 mL of dehydrated ether were charged, and 5.40 g (5
A 10 mL solution of dehydrated ether (5 mmol) was added dropwise, and the mixture was reacted for 3 hours with heating under reflux. The reaction solution was ice-cooled again, a solution of 5.13 g (50 mmol) of 2-pentynyl chloride in 20 mL of dehydrated ether was added dropwise, and the mixture was further reacted with heating under reflux for 3 hours. After completion of the reaction, the reaction solution was washed with water and the aqueous layer was washed with water.
Extract three times with tell and combine with the previous organic layer. The obtained organic layer was washed with a small amount of saturated saline and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. 8.78 g of the obtained residue
Vacuum distillation using a 3 cm long Vigreux tube (boiling point 13
9 to 142 ° C./24 mmHg) and pale yellow oily 2- (2
-Pentynyl) cyclohexanone 4.90 g (yield
60.0%) was obtained. The purity of the obtained compound was 95.1% by gas chromatography.

From the results of the infrared absorption spectrum measurement, the fact that a molecular ion peak was observed at 164 by mass spectrometry, the data of the nuclear magnetic resonance spectrum shown below, and the relationship of the raw materials used, 2 -It was confirmed to be pentynylcyclohexanone.

¹ H-NMR (CDCl ₃ ) δ1.11 (t, J = 7.6Hz, 3H), 1.34
-1.44 (m, 1H), 1.60-1.75 (m, 2H), 1.90-1.95 (m, 1H), 2.06-
2.18 (m, 4H), 2.26-2.48 (m, 4H), 2.55-2.62 (m, 1H)

Example 3 Synthesis of (Z) -2- (2-pentenyl) cyclohexanone [Compound of the general formula (I) where n = 0 and R is (Z) -2-pentenyl group] Hydrogenation under normal pressure 2- (2-Pentynyl) cyclohexanone 12.32 g (75 mmol) and Lindlar catalyst (N. Chem. Cat Lot.No.287-90130)
0.62 g, 0.62 mL of quinoline and 25 mL of cyclohexane were charged, and hydrogenation was carried out under normal pressure until the theoretical amount of hydrogen was absorbed. The reaction solution was filtered through high flow, and hexane was added to the filtrate to make the total volume 200 mL. This one
It was washed with 40 mL of a mol / L sulfuric acid aqueous solution and then with saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was distilled under reduced pressure using a Vigreux tube (boiling point 120-122 ° C./17 mmHg) to obtain colorless oily (Z) -2- (2-pentenyl) cyclohexanone 1.
0.76 g (yield 86.3%) was obtained. The purity of the obtained compound is 95.9% by gas chromatography.
It was (E-form mixed with 3.0%).

From the results of infrared absorption spectrum measurement, the fact that a molecular ion peak was observed at 166 by mass spectrometry, the data of the nuclear magnetic resonance spectrum shown below, and the relationship of the raw materials used, the obtained substance was ( Z) -2- (2-
It was confirmed to be pentenyl) cyclohexanone.

¹ H-NMR (CDCl ₃ ) δ 0.95 (t, J = 7.6 Hz, 3 H), 1.31
-1.41 (m, 1H), 1.59-1.73 (m, 2H), 1.83-1.88 (m, 1H), 2.00-
2.18 (m, 5H), 2.26-2.49 (m, 4H), 5.25-5.31 (m, 1H), 5.40-5.
48 (m, 1H) (Proton decoupling was further measured, and it was confirmed that this configuration was the Z configuration because the hydrogen coupling constant of the double bond was 11.3 Hz.)

Example 4 Synthesis of (Z) -2- (2-pentenyl) cyclohexanone [compound of general formula (I) in which n = 0 and R is (Z) -2-pentenyl group] (4-a ) Synthesis of ethyl (Z) -2- (2-pentenyl) cyclohexanone-2-carboxylate In a flask equipped with a stirring motor, cyclohexanone-2-
65.19 g (383 mmol) of ethyl carboxylate,
(Z) -2-Pentenyl chloride 47.48 g (4
54 mol), potassium carbonate 105.9 g (766 m)
mol), potassium iodide 1.3 g (7.7 mmo)
1) and 325 mL of acetone were charged, and the mixture was heated under reflux for 20 hours. After the reaction was completed, the solid content was filtered off, and the filtrate was evaporated under reduced pressure. After dissolving 98 g of this residue in 300 mL of toluene,
It was washed twice with 100 mL of water, the organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was distilled under reduced pressure (boiling point 91 to 99 ° C./0.2 mmHg) to obtain 87.01 g of ethyl (Z) -2- (2-pentenyl) cyclohexanone-2-carboxylate as a pale yellow oil (yield 9
5.3%) was obtained. The purity of the obtained compound was 98.2% by gas chromatography.

(4-b) Synthesis of (Z) -2- (2-pentenyl) cyclohexanone Ethyl (Z) -2- (2-pentenyl) cyclohexanone-2-carboxylate was added to a flask equipped with a stirring motor.
2.90 g (180 mmol), 49.6 ml of water and 42.9 mL of methanol were charged and the mixture was heated under reflux. 24.22 g (3
69 mmol: calculated as a purity of 85.5%) 24.2
A mixed solution of mL and methanol 42.9 mL was added dropwise over 2 hours, and the mixture was heated under reflux for 5 hours. After completion of the reaction, extracted three times with isopropyl ether (200 mL, 100 m
L, 100 mL), 600 mL of the obtained organic layer is 1 m
ol / L sulfuric acid aqueous solution 50 mL, then saturated saline solution 50 m
The extract was washed twice with L, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. 28.9 g of the obtained yellow oily substance was distilled under reduced pressure (boiling point 50 to 51 ° C./0.3 mmHg) to obtain 24.13 g (yield 80.6%) of colorless oily (Z) -2- (2-pentenyl) cyclohexanone. Got The purity of the obtained compound was 99.
It was 0% (containing 1.0% of E form).

From the results of infrared absorption spectrum measurement, the fact that a molecular ion peak was observed at 166 by mass spectrometry, the following nuclear magnetic resonance spectrum data, and the relationship of the raw materials used, the obtained substance was ( Z) -2- (2-
It was confirmed to be pentenyl) cyclohexanone.

¹ H-NMR (CDCl ₃ ) δ 0.95 (t, J = 7.6 Hz, 3 H), 1.31
-1.41 (m, 1H), 1.59-1.73 (m, 2H), 1.83-1.88 (m, 1H), 2.00-
2.18 (m, 5H), 2.26-2.49 (m, 4H), 5.25-5.31 (m, 1H), 5.40-5.
48 (m, 1H) (Proton decoupling was further measured, and it was confirmed that this configuration was the Z configuration because the hydrogen coupling constant of the double bond was 11.3 Hz.)

Example 5 Cyclohexanone 70 in a synthetic flask of (E) -2- (2-pentenyl) cyclohexanone [compound of general formula (I) with n = 0 and R being (E) -2-pentynyl group] 70 0.7 g (0.72 m
ol), 1-penten-3-ol 86.1 g (0.
01 mol), acetone dimethyl acetal 85.0 g
(0.82 mol), p-toluenesulfonic acid monohydrate (0.05 g) and xylene (100 mL) were charged and reacted under heating under reflux for 3 hours, and methanol and acetone flowing out during this period were distilled off. Then, the pressure in the flask was reduced by an aspirator to distill off unreacted 1-penten-3-ol and xylene. After the reaction solution was cooled to room temperature, a 0.5 mL aqueous solution of 1.0 g of calcium carbonate was added, and the mixture was stirred and dried over anhydrous magnesium sulfate. The crude product obtained was distilled under reduced pressure using a 3 cm long Vigreux tube (boiling point 78-
82 ° C./1.5 mmHg), and a colorless oily (E) -2-
77.7 g (yield 65.0%) of (2-pentenyl) cyclohexanone was obtained. The purity of the obtained compound was 99.1% by gas chromatography.

From the results of infrared absorption spectrum measurement, the fact that a molecular ion peak was observed at 166 by mass spectrometry, the data of the nuclear magnetic resonance spectrum shown below, and the relationship of the raw materials used, the obtained substance was ( E) -2- (2-
It was confirmed to be pentenyl) cyclohexanone.

¹ H-NMR (CDCl ₃ ) δ 0.95 (td, J = 1.7 Hz, 3 H), 1.
29-1.40 (m, 1H), 1.58-1.73 (m, 2H), 1.82-2.13 (m, 6H), 2.27
-2.49 (m, 4H), 5.31-5.38 (m, 1H), 5.43-5.50 (m, 1H) (In addition, proton decoupling measurement was performed, and the hydrogen coupling constant of the double bond part was 15.3Hz. Therefore, it was confirmed that this configuration is the E form.)

Example 6 7- (2-Pentynyl) oxep-2-one [Compound of the general formula (I) where n = 1 and R is 2-pentynyl group] was placed in a 2- (2-pentynyl) flask. ) Cyclohexanone
10.68 g (65 mmol), methanol 260 m
L and 260 mL of water were charged, and 10.92 g (130 mmol) of sodium hydrogen carbonate and then 64.30 g of magnesium monoperoxyphthalate hexahydrate.
(130 mmol) was added, and the reaction was performed at room temperature for 24 hours. Add 300 mL of water to the reaction mixture, and add ethyl acetate 5
It was extracted twice with 00 mL and then 250 mL, and the organic phases were combined. This was twice with 5% -hydrochloric acid aqueous solution 300 mL, saturated sodium hydrogen carbonate aqueous solution 300 mL, 10% sodium sulfite aqueous solution 150 mL, and then saturated saline.
The extract was washed with 100 mL, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. 10.05 g of the obtained residue was subjected to column chromatography (500 g of Kieselgel 60 manufactured by Merck & Co., Ltd., and methylene chloride was used as a developing solvent).
To obtain 6.95 g of crude product, and then to distill under reduced pressure using a Vigreux tube (boiling point 115 to 118 ° C./0.1 mmH
g) and colorless oily 7- (2-pentynyl) oxepa-2
5.72 g (yield 48.8%) of -one was obtained. The purity of the obtained compound was 9 by gas chromatography.
It was 9.8%.

From the results of infrared absorption spectrum measurement, the fact that a molecular ion peak was observed at 180 in mass spectrometry, the data of the nuclear magnetic resonance spectrum shown below, and the relationship of the raw materials used, 7 substances were obtained. It was confirmed to be-(2-pentynyl) oxep-2-one.

¹ H-NMR (CDCl ₃ ) δ1.12 (t, J = 7.6Hz, 3H), 1.56
-1.62 (m, 3H), 1.94-2.04 (m, 2H), 2.16 (qt, J = 7.6Hz, 2.3H
z, 2H), 2.21-2.25 (m, 1H), 2.44 (tdd, J = 2.3Hz, 8.5Hz, 16.
7Hz, 1H), 2.57-2.63 (m, 2H), 2.66-2.71 (m, 1H), 4.32 (td, J
= 8.5Hz, 5.1Hz, 1H)

Example 7 Synthesis of (Z) -7- (2-pentenyl) oxep-2-one [where n = 1 in the general formula (I) and R is a (Z) -2-pentenyl group] 7- (2-Pentynyl) oxepa-2 with atmospheric pressure hydrogenator
-ON 5.41 g (30 mmol), Lindlar catalyst (Lochem No.287-90130 manufactured by NE Chemcat)
0.27 g, quinoline 0.27 mL and cyclohexane 11 mL were charged, and hydrogenation was carried out under atmospheric pressure until the theoretical amount of hydrogen was absorbed. The reaction solution was filtered through high flow, and ethyl acetate was added to the filtrate to make the total volume about 100 mL. This was washed with 20 mL of 1 mol / L sulfuric acid aqueous solution and then with saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. 5.51 g of the obtained residue was distilled under reduced pressure using a Vigreux tube (boiling point 106-111 ° C./0.05 mmH
g) to give 4.93 g (yield 90.2%) of colorless oily (Z) -7- (2-pentenyl) oxep-2-one. The purity of the obtained compound was 100.0% by gas chromatography.

From the results of the infrared absorption spectrum measurement, the fact that a molecular ion peak was observed at 182 by mass spectrometry, the data of the nuclear magnetic resonance spectrum shown below, and the relationship of the raw materials used, the obtained substance was ( Z) -7- (2-
It was confirmed to be pentenyl) oxep-2-one.

¹ H-NMR (CDCl ₃ ) δ 0.98 (td, J = 7.6 Hz, 0.7 Hz,
3H), 1.53-1.55 (m, 3H), 1.82-1.96 (m, 3H), 2.02-2.10 (m, 2
H), 2.32-2.48 (m, 2H), 2.57-2.70 (m, 2H), 4.22-4.27 (m, 1
H), 5.33-5.39 (m, 1H), 5.50-5.56 (m, 1H) (Proton decoupling was measured, and the hydrogen coupling constant of the double bond was 11.4 Hz. It was confirmed that the arrangement was Z-shaped.)

[Example 8] Single floral (jasmine) type compounded fragrance composition component parts by mass benzyl acetate 460 α-hexyl cinnamic aldehyde 180 indole 20 linalyl acetate 25 maltol 1% 20 cis-3-hexenol 10% 10 Cis-3-hexenyl acetate 10% 5 Eugenol 10 Benzylbenzoate 270 Total 1000 In 100 g of the above mixture, (Z) -2- (2-pentenyl).
5 g of cyclohexanone was added. The new formulation composition with the addition of (Z) -2- (2-pentenyl) cyclohexanone emphasizes jasmine and fruity floral notes compared to the one without it. It had a complex and natural voluminous feel, and was far superior in terms of sustainability.
Similarly, the one to which (E) -2- (2-pentenyl) cyclohexanone was added exhibited a similar effect although it was slightly weak.

[Example 9] Peachfruit-type compounded fragrance composition component parts by mass cis-3-hexenol 5 cis-3-hexenyl acetate 2 ethyl acetate 45 isoamyl butyrate 30 linalool 10 linalyl acetate 10 orange oil 5 benzyl alcohol 35 γ-undecalactone 20 vanillin 10 ethylvanillin 5 propylene glycol 823 1000 (Z) -7- (2-pentenyl) in 100 g of the above mixture.
The newly formulated fragrance composition containing 10 g of oxepa-2-one has a complex natural peach characteristic with emphasized jasmine and fruity aroma, and has a voluminous feeling, and is also durable in comparison with the composition without addition. It was much better. Similarly, (E) -7- (2-pentenyl) oxepa-
The addition of 2-one produced a similar effect, albeit slightly weaker.

[Example 10] Ingredients for floral bouquet type fragrance composition Ingredients by mass Ambroxan 10 Bergamot oil 130 Lemon oil 100 Dihydromyrcenol 50 Lilal 50 Methyl dehydrojasmonate 450 Linalyl acetate 100 Timberol 10 Methyl anthrani Rate 10% 10 Damascon β 10% 50 Vanillin 10% 40 1000 A new formulation composition in which 10 g of 7- (2-pentynyl) oxep-2-one was added to 100 g of the above mixture was jasmine, The floral scent emphasized the fruity fragrance, and it was voluminous and outstandingly durable. The same was true for the case where 2- (2-pentynyl) cyclohexanone was added instead of 7- (2-pentynyl) oxepa-2-one.

[Example 11] Ingredient for perfume composition of floral type Aldehyde C-11 Undecylen 10% 10 Bergamot oil 50 Styralyl acetate 10 Eugenol 30 Ylang ylang 40 Terpineol 10 γ-methylionone 100 Vetiver acetate 50 Cyclopentadeca Nolide 150 Benzyl salicylate 550 1000 (Z) -2- (2-pentenyl) was added to 100 g of the above mixture.
The new formulation composition containing 10 g of cyclohexanone had a floral scent in which jasmine and fruity aroma were emphasized, and had a voluminous feeling and was far superior in sustainability, as compared with the composition without addition. Similarly, the one to which (E) -2- (2-pentenyl) cyclohexanone was added exhibited a similar effect although it was slightly weak.

[0048]

INDUSTRIAL APPLICABILITY According to the present invention, a new type of unique fragrance material having an excellent jasmine-like fragrance that expresses a high-class feeling and also a fruity green-like fragrance and having excellent sustainability as a fragrance It is possible to obtain a useful perfume composition containing the compound represented by the above general formula (I). This fragrance composition is preferably used for cosmetics, foods and drinks, insurance, hygiene, pharmaceuticals, tobacco flavor, indoor air fresheners, and the like.

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁷ Identification code FI theme code (reference) C11B 9/00 C11B 9/00 X (72) Inventor Junichi Sakamoto 1-7-1 Inari, Soka-shi, Saitama Kanto Chemical Co., Ltd. Central Research Laboratory F-term (reference) 4C062 JJ03 4H006 AA01 AA03 AB12 AB14 4H059 BA23 BA36 BB15 BB45 BB46 DA09

Claims (3)

[Claims] 1. A compound represented by the general formula (I): (In the formula, n is 0 or 1, and R is a (Z) or (E) -2-pentenyl group, or a 2-pentynyl group) (provided that 2- (2-pentynyl) cyclohexanone is present. except for). 2. A compound represented by the general formula (I): (In the formula, n is 0 or 1, and R is a (Z) or (E) -2-pentenyl group, or a 2-pentynyl group). . 3. A cosmetic comprising the compound according to claim 2.