JPH0987267A - 3-methyl-5 or 4-decene-4-olide, its production and perfume composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a compound represented by a specific formula, excellent in persistency and diffusing property and exhibiting green, nut-like or milky and extremely strong lactone aroma and useful as a fragrance raw material for foods, etc. SOLUTION: This 3-methyl-5 or 4-decene-4-olide (e.g. a compound of the formula). The compound is obtained by reacting, e.g. 4-hydroxy 2-nonene with orthoacetic acid ester (e.g. ethyl orthoacetate) in the presence of an acid catalyst (e.g. phenol), hydrolyzing the resultant 3-methyl-4-decenoic acid alkyl ester, treating the resultant 3-methyl-4-decenoic acid with an aqueous solution of iodine and potassium iodide and subjecting the resultant product to dehydrohalogenation reaction in the presence of an amine compound [e.g. 1,8- diazabicyclo[5, 4, 0]-7-undecene].

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to 3-methyl-5 or 4-decene-4-olide, a process for producing the same and a fragrance composition. More specifically, the present invention relates to a novel compound, 3-methyl-, which has a very strong lactone scent like green nuts or milk, which is excellent in persistence and diffusivity, and which is useful as a flavoring material for food or cosmetics. 5 or 4-decene-4-
And an odor, a method for producing the compound, and a perfume composition containing the compound.

[0002]

2. Description of the Related Art Conventionally, various lactone compounds have been used as perfume materials for perfume compositions added to foods, cosmetics and the like. Each of these lactone compounds has a characteristic odor characteristic, and is used as a compounding material depending on the purpose. By the way, many aroma components of peach fruits have been investigated and reported (Yamamoto et al., Fragrance, N
o.173, 97 (1992) etc.). As the aroma component, lactones such as γ-octalactone, γ-decalactone, γ-undecalactone, γ-dodecalactone, δ-decalactone, δ-dodecalactone are known.

[0003]

The fragrance composition used in foods, cosmetics and the like diversified in the fragrance industry is required to have a more characteristic, strong, stable, and diffusible or persistent scent. ing. In developing a fragrance composition that satisfies these requirements, the appearance of fragrance materials that exhibit more useful effects is expected.

[0004]

Means for Solving the Problems As a result of searching for aroma components of peach fruits, the present inventors have found the following formula (I), which is an aroma component contained in trace amounts in peach fruits and is not published in the literature.

[0005]

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3-methyl-5-decene-4- represented by
Succeeded in extracting and isolating the oligode, the structure was determined and the present invention was completed. Thus, according to the present invention, there is provided a method for extracting and isolating 3-methyl-5-decene-4-olide which is an aroma component of peach fruit. According to another aspect of the present invention, (A) 4-hydroxy-2-nonene is reacted with orthoacetic acid ester in the presence of an acid catalyst to give 3-methyl-4.
-Decenoic acid alkyl ester is obtained, (B) 3-methyl-
The 4-decenoic acid alkyl ester is hydrolyzed, (C) the obtained 3-methyl-4-decenoic acid is treated with an aqueous solution of iodine and potassium iodide, and (D) the obtained product is
A process for producing 3-methyl-5 or 4-decene-4-olide is provided by performing a dehydrohalogenation reaction in the presence of an amine compound.

Furthermore, according to the invention, 3-methyl-5
Alternatively, 4-decene-4-olide, a fragrance composition containing the compound as an essential component, and 3-methyl-5-iodo-decane-4-olide, which is an intermediate in the synthesis of the compound, are provided.

[0008]

BEST MODE FOR CARRYING OUT THE INVENTION 3-Methyl-5 or 4-of the present invention
Decene-4-olide has asymmetric carbon atoms in the 2- and 3-positions of the γ-lactone ring and includes all stereoisomers and mixtures thereof based on this asymmetric carbon atom. The lactone compounds include not only those extracted from natural products but also those produced synthetically. That is, in the case of a synthetic product, structural isomers in which a double bond located at the 5-position of 3-methyl-5-decene-4-olide is transferred to the 4-position may be mixed, but the present invention is These structural isomers are also included. Also, 3-methyl-5 or 4-decene-4-olide is pure or at least 50%.
It means that it contains a large amount.

The 3-methyl-5-decene-4-olide of the present invention can be extracted and separated from the peach fruit (Batsch) of the Rosaceae (Prunus) peach subgenus (persica). Examples of the peach fruits include various peach fruits such as white peach, white phoenix, Okubo, Akatsuki, Yamane white peach, Shimizu white peach, Yuzora, Nishiki, can peach, fast gold and early gold.

3-Methyl-5-decene-4-of the present invention
As the method for extracting and isolating the orido, for example, (i) the peach fruit as it is or crushed and immersed in a water-soluble organic solvent, the obtained extract is extracted with a fat-soluble organic solvent, and concentrated under reduced pressure. At least once, it is separated and purified by chromatography, or (ii) seed-free peach fruit is crushed and centrifuged to obtain peach juice, and the peach juice is distilled to obtain the obtained fraction. Examples include a method of extracting and concentrating with an organic solvent, or (iii) separating and concentrating the peach juice by passing it through an adsorption resin.

More specifically, (i) first, peach fruits are used as they are or after being crushed into a water-soluble organic solvent (eg, methanol, ethanol, etc.) or an aqueous solution thereof, usually at room temperature for about 1 to 20 days. Immerse to obtain the extraction solution. After concentrating the obtained extraction solution, this concentrate is further extracted with a fat-soluble organic solvent (for example, n-hexane, diethyl ether, dichloromethane, chloroform, etc.). After concentrating the obtained extract (preferably under reduced pressure), silica gel column chromatography (developing solvent: n-hexane / diethyl ether = 10/0 to 5/5) and high performance liquid chromatography (silica gel 3 μm, 10 × 30
0 mm, mobile phase: n-hexane / ethyl acetate = 95 /
5) to 3-methyl-5-decene-4-
Oride can be extracted and separated.

Also, (ii) peach fruits excluding seeds are crushed to 30
Centrifuge for about 15 to 60 minutes to obtain a peach juice, and distill the peach juice under atmospheric pressure or reduced pressure steam to obtain a fraction. The obtained fraction is an organic solvent (eg, diethyl ether, etc.). ) And concentrated to give 3-methyl-
5-decene-4-olide can be extracted and separated.

Further, (iii) the above peach juice is passed through an adsorption resin (for example, Urbanlite XAD) to adsorb 3-methyl-5-decene-4-olide, and then an organic solvent (for example, diethyl ether). , Ethyl alcohol, etc.) to concentrate the resulting solution to give 3-
Methyl-5-decene-4-olide can be extracted and separated.

The substance thus extracted and isolated from the natural plant has the physical properties shown in FIG. 1 (gas chromatogram), FIG. 2 (mass spectrometry spectrum data) and nuclear magnetic resonance spectrum data (Example 1). Indicates. Therefore, from these data, the extracted isolated material is 3-methyl-5-decene-
It was confirmed to be 4-olid. The 3-methyl-5-decene-4-olide of the formula (I) of the present invention is highly valuable as a raw material for perfume preparation, and therefore, earnest studies have been conducted on a simple and inexpensive method for producing it. as a result,
The reaction pathway shown below, namely (A) 4-hydroxy-
3-Methyl-4-decenoic acid alkyl ester was obtained from 2-nonene, and (B) 3-methyl-4-decenoic acid alkyl ester was hydrolyzed to obtain (C) 3-methyl-4-decane.
Decenoic acid is treated with an aqueous solution of iodine and potassium iodide, and (D) the obtained product is treated in the presence of an amine compound.
By dehydrohalogenation reaction, 3-methyl-
5 or 4-decene-4-olide could be produced in higher yield and economically.

[0015]

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4-hydroxy-2-nonene as a raw material in the step (A) acts on a known crotonaldehyde, for example, by a Grignard reagent of n-amyl bromide and metallic magnesium in an organic solvent such as tetrahydrofuran or diethyl ether. Can be obtained. In the step (A), examples of the acid catalyst include propionic acid, phenol, ortho-nitrophenol, para-nitrophenol and the like, and examples of the orthoacetic acid ester include methyl orthoacetate, ethyl orthoacetate and the like. When reacting 4-hydroxy-2-nonene with orthoacetic acid ester, stirring is performed for about 1 to 12 hours while heating at about 60 to 150 ° C.
A transfer reaction (sigmatropic transfer) can be progressed, and 3-methyl-4-decenoic acid alkyl ester can be obtained.

In step (B), 3-methyl-4-
Hydrolyze decenoic acid alkyl ester. The hydrolysis at this time can be carried out under either acidic conditions or alkaline conditions. For example, it is carried out by stirring for 30 minutes to 6 hours at a temperature range of 30 to 60 ° C. under alkaline conditions. It is preferable. Examples of the hydrolysis under alkaline conditions include hydrolysis in an aqueous solution containing 5 to 50% potassium hydroxide, sodium hydroxide and the like. By this reaction, 3-methyl-4-decenoic acid can be obtained.

In step (C), the obtained 3-methyl-4-decenoic acid is treated with an aqueous solution of iodine and potassium iodide. At this time, it is preferable that 3-methyl-4-decenoic acid is present in a mixture of an alkaline aqueous solution such as sodium carbonate, potassium carbonate, sodium hydroxide and the like and an organic solvent such as tetrahydrofuran and vigorously stirred at about room temperature. Here, by the iodolactonization reaction, 3-
Methyl-5-iodo-decane-4-olide can be obtained.

In step (D), the obtained 3-methyl-5-iodo-decane-4-olide is subjected to a dehydrohalogenation reaction in the presence of an amine compound. This reaction is preferably carried out in an organic solvent such as toluene or xylene, and examples of the amine compound include 1,8-diazabicyclo [5,4,0] -7-undecene. In addition, the dehydrohalogenation reaction is from 80 to
It is preferably carried out in a temperature range of about 150 ° C.

3-Methyl-5 or 4-decene of the present invention
4-Olide exhibits a green, rather nutty or milky, very strong lactone scent reminiscent of a fresh peach scent, and has a long-lasting and diffusive aroma characteristic not found in previously known compounds. It has an extremely excellent effect as a fragrance / flavor imparting agent or an improving agent. The 3-methyl-5 or 4-decene-4-olide of the present invention is
Used alone or in combination with other perfume ingredients as a perfume composition for the purpose of imparting or improving aroma and flavor in the field of perfumes such as foods and perfumes, shampoos, detergents, indoor air fresheners, bath salts, etc. be able to. The amount of 3-methyl-5 or 4-decene-4-olide used in that case is not particularly limited as long as the effect of imparting aroma / flavor or improving the effect can be sufficiently exerted. Extensive, depending on product form, type, intended use and expected effect profile. For example, in order to impart or improve aroma and flavor, 0.001 to 2 is added to the perfume composition.
It can be contained at about 5% by weight. However, there is no particular problem even if it is used at a concentration other than this concentration.

[0021] Specifically, a fruit-based fragrance used in foods and cosmetics such as peaches and apricots containing benzaldehyde and γ-undecalactone as a main aroma component, 3-methyl-5- or 4-decene is used. -4-Olid to 0.
By adding 001 to 15%, preferably 0.01 to 5.0%, the green or sweet scent of fresh fruits is enhanced and more naturalness can be added.

As a flavoring material for milk-based flavoring compositions such as milk, butter and cheese, 0.01-10% of 3-methyl-5 or 4-decene-4-olide is added to give a natural top. A lasting flavor with notes is obtained. Furthermore, 0.01 to 20.0%, preferably 0.1 to 3.0% is added as a perfume material for a perfume composition used for perfume, such as perfumes, shampoos, detergents, indoor air fresheners and bath salts. As a result, it is possible to impart a characteristic odor characteristic with diffusibility and durability.

[0023]

EXAMPLES Hereinafter, 3-methyl-5 of the present invention will be described with reference to Examples.
Alternatively, 4-decene-4-olide will be described in more detail. Example 1: Extraction of 3-methyl-5-decene-4-olide About 100 kg of peach fruit was treated with 50% ethyl alcohol aqueous solution 1
The extraction solution obtained by immersing in 00 liters for 7 days was concentrated to 30 liters under reduced pressure and then extracted with 5 liters of diethyl ether. The diethyl ether extraction solution is
The mixture was concentrated under reduced pressure to obtain an aroma component extraction mixture. The extraction mixture was subjected to silica gel column chromatography (developing solvent: n-hexane / diethyl ether = 10/0 to 5 /
5), the obtained fraction was concentrated, separated and purified by high performance liquid chromatography (silica gel 3 μm, 10 × 300 mm, mobile phase: n-hexane / ethyl acetate = 95/5), and colorless. About 1 mg of the desired product which is clear was isolated. The scent had a green, slightly nutty or milky, very strong lactone scent reminiscent of a fresh peach scent. The gas chromatogram and mass spectrum of the obtained product are shown in FIGS. 1 and 2, and the nuclear magnetic resonance spectrum data are shown below. From these data, it was confirmed that the obtained product was 3-methyl-5-decene-4-olide.

MS m / z: 182 (M ⁺ ), 125, 113, 95, 69, 5
7, 55, 41 (100) ¹ H-NMR (500MHz, CDCl _3, δppm): 0.90 (3H, t), 1.12 (3H, d),
1.28-1.45 (4H), 2.05-2.30 (4H), 2.66 (1H, dd), 4.35 (1
H, dd), 5.47 (1H, dd), 5.82 (1H, dt) ¹³ C-NMR (125MHz, CDCl _3, δppm): 13.7, 16.2, 22.0, 30.
8, 31.7, 36.8, 37.0, 87.7, 126.2, 136.7, 176.1

Example 2 1) Preparation of 4-hydroxy-2-nonene A mixture of 49 g (2.0 mol) of metallic magnesium, a small amount of iodine and 500 ml of diethyl ether was kept at room temperature, and 332 g of n-amyl bromide was stirred. 2.
2 mol) and 300 ml of diethyl ether.
The solution was added dropwise at 0 to 30 ° C. over 1 hour and then stirred at the same temperature for 2 hours to prepare a Grignard reagent.

Subsequently, 140 g of crotonaldehyde
A solution of (2.0 mol) and 140 ml of diethyl ether was added dropwise at 20 to 30 ° C over 1.5 hours, and stirred for 3 hours to carry out a Grignard reaction. After the reaction, saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with diethyl ether. The diethyl ether solution was washed with 100 ml of brine three times, dried over anhydrous sodium sulfate, and concentrated to obtain 280 g of a pale yellow oily substance. By distilling this oily substance under reduced pressure, 4-hydroxy-
225 g of 2-nonene as a colorless transparent liquid (yield 79
%) Obtained. The boiling point of this 4-hydroxy-2-nonene was 91 to 93 ° C./12 mmHg.

MS m / z: 142 (M ⁺ ), 127, 99, 86, 71 (10
0), 58, 53, 43 IRν max (cm ^-1 ): 3359, 1672, 1021, 965 ¹ H-NMR (500MHz, CDCl _3, δppm): 0.89 (3H, t), 1.23-1.66 (6
H), 1.69 (3H, d), 2.13 (1H, br), 4.01 (1H, dt), 5.49 (1H,
dd), 5.64 (1H, dq) ¹³ C-NMR (125MHz, CDCl ₃ , δ ppm): 13.9, 17.5, 22.5, 2
5.1, 31.7, 37.2, 73.0, 126.5, 134.4,

2) Preparation of 3-methyl-4-decenoic acid ethyl ester 100 g of 4-hydroxy-2-nonene obtained in 1)
(0.7 mol), triethyl orthoacetate 341 g
80 parts of a mixture of (2.1 mol) and 10 g of phenol.
It heated at -120 degreeC and stirred for 4 hours, distilling off the produced methanol. After the reaction, the mixture was cooled and concentrated under reduced pressure to obtain 148 g of a pale yellow oily mixture containing 88% of 3-methyl-4-decenoic acid ethyl ester. MS m / z: 212 (M ⁺ ), 116, 124, 95, 81, 69, 55 (100),
41 IR ν max (cm ^-1 ): 1738, 1458, 1241, 967 ¹ H-NMR (500MHz, CDCl _3, δppm): 1.02 (3H, t), 1.25 (3H,
t), 1.1-2.7 (10H), 4.12 (2H, q), 5.31 (1H, dd), 5.42 (1
H, dt)

3) Production of 3-methyl-4-decenoic acid Next, the ethyl ester of 3-methyl-4-decenoic acid obtained above was added to a mixed solution of 200 g of 20% sodium hydroxide and 10 ml of methanol, Hydrolysis was performed by stirring at 50 ° C. for 2 hours. After the reaction, 200 ml of saline was added, and the mixture was extracted with 200 ml of diethyl ether.
It was washed 3 times with 00 ml, concentrated and vacuum-distilled to obtain 110 g (yield 85%) of 3-methyl-4-decenoic acid as a viscous colorless liquid. This 3-methyl-
The boiling point of 4-decenoic acid is 108 to 109 ° C./0.6 mm
Hg. MS m / z: 184 (M ⁺ ), 166, 124, 95, 81, 68, 55, 41 (1
00) IR ν max (cm ^-1 ): 1710, 1294, 969 ¹ H-NMR (500MHz, CDCl _3, δppm): 0.88 (3H, t), 1.03 (3H,
d), 1.22-1.38 (8H), 1.96 (2H, q), 2.23-2.40 (2H), 2.55
-2.68 (1H), 5.33 (1H, dd), 5.46 (1H, dt) ¹³ C-NMR (125MHz, CDCl ₃ , δ ppm): 14.0, 20.4, 22.5, 2
9.1, 31.3, 32.4, 33.4, 41.8, 129.9, 133.6, 179.2

4) 3-Methyl-5-iodo-decane-4
-Preparation of Olide 92 g of 3-methyl-4-decenoic acid obtained in 3) (0.
5 mol), 0.5 N sodium carbonate aqueous solution 3 liters and tetrahydrofuran 300 ml while stirring vigorously at room temperature, iodine 254 g (1.0 mol),
493 g (3.0 mol) of potassium iodide, 1750 of water
The solution of g was added dropwise over 4 hours. After completion of dropping, the mixture was stirred at the same temperature for 4 hours to carry out an iodolactonization reaction. After the reaction, the mixture was extracted with 500 ml of diethyl ether. The diethyl ether solution was washed with 500 ml of a 3% aqueous sodium hydrogen sulfite solution and then with 300 ml of water three times, dried over anhydrous sodium sulfate, and then concentrated to give 3-
150 g of methyl-5-iodo-decane-4-olide were obtained as a yellow oil. This 3-methyl-5
As shown in the gas chromatogram of FIG. 3 (performed under the same conditions as in Example 1), iodo-decane-4-olide was converted into 3
It is believed that the isomers of the species (Ai, Bi, Ci) are included. Mass spectrum data of these substances are shown in FIGS. 4 to 6, and other physical properties are shown below.

Product Bi MS m / z: 239 (M ⁺ ), 211, 183, 168, 123, 99, 83, 7
1, 69, 55 (100), 41 IRν max (cm ^-1 ): 1784, 1458, 1210, 1165, 967, 931,
606 ¹ H-NMR (500MHz, CDCl _3, δppm): 0.91 (3H, t), 1.04 (3H,
d), 1.18-2.91 (11H), 3.71-4.01 (1H), 4.15-4.56 (1H) -Product Ai MS m / z: 183 (M ⁺ ), 165, 147, 123, 99, 81, 71, 69,
55, 41 (100) ・ Product Ci MS m / z: 183 (M ⁺ ), 165, 147, 123, 99, 81, 71, 69,
55, 43, 41 (100)

5) Preparation of 3-methyl-5-decene-4-olide and 3-methyl-4-decene-4-olide Subsequently, 3-methyl-5-iodo-decane-4 obtained in 4) was obtained. -Oride 150 g, toluene 500 ml and 1.8-diazabicyclo [5,4,0] -7-undecene 100 g (0.66 mol) were stirred at 100 to 110 ° C for 1.5 hours to carry out the dehydroiodination reaction. . After the reaction, the reaction mixture was mixed with 5% aqueous hydrochloric acid solution (500 ml) and water (500 ml).
ml, 5% aqueous sodium carbonate solution and water 500 ml (3
The reaction oil obtained by concentration and subsequent washing was vacuum distilled to obtain 75 g (yield: 82%) of a colorless transparent final product. The boiling point of this product is 109-114 ° C / 1.5 mm
Hg.

A gas chromatogram of this product is shown in FIG. From this chromatogram, it is considered that the product contains 7 isomers (Af to Gf).
Mass spectrum data of these seven isomers are shown in FIGS. 8 to 14, and other physical properties are shown below. The product Af was isolated by fractional vacuum deposition and high performance liquid chromatography, and its mass spectrum and nuclear magnetic resonance spectrum were measured.
Since it was completely in agreement with the spectrum of methyl-5-decene-4-olide, Af was extracted and isolated from 3-methyl-5.
-It was confirmed that it had the same structure as decene-4-olide. The product Ff was isolated by fractional vacuum deposition and high performance liquid chromatography, and the mass spectrum and the nuclear magnetic resonance spectrum were measured to confirm that it was 3-methyl-4-decene-4-olide.

Product Af MS m / z: 182 (M ⁺ ), 125, 113, 95, 69, 57, 55, 41 (1
00) IR ν max (cm ^-1 ): 1782, 1672, 1458, 1212, 1167, 99
0, 970, 939 ¹ H-NMR (500MHz, CDCl _3, δppm): 0.90 (3H, t), 1.12 (3H,
d), 1.28-1.45 (4H), 2.05-2.30 (4H), 2.66 (1H, dd), 4.3
5 (1H, dd), 5.47 (1H, dd), 5.82 (1H, dt) ¹³ C-NMR (125MHz, CDCl ₃ , δ ppm): 13.7, 16.2, 22.0, 3
0.8, 31.7, 36.8, 37.0, 87.7, 126.2, 136.7, 176.1

Product Bf MS m / z: 182 (M ⁺ ), 125, 113, 95, 69, 57, 55, 41 (1
00) ¹ H-NMR (500MHz, CDCl _3, δppm): 0.90 (3H, t), 1.02 (3H,
d), 1.23-1.45 (4H), 2.03-2.30 (4H), 2.66 (1H, dd), 4.9
0 (1H, dd), 5.45 (1H, dd), 5.80 (1H, dt) ¹³ C-NMR (125MHz, CDCl ₃ , δ ppm): 13.9, 14.8, 22.1, 3
1.0, 32.0, 34.2, 36.6, 84.1, 123.7, 136.5, 176.8

Product Cf MS m / z: 125, 113, 95, 81, 69, 57, 55, 41 (100)

Product Df MS m / z: 125, 113, 95, 81, 69, 57, 55, 41 (100)

Product Ef MS m / z: 167, 126, 111 (100), 99, 83, 67, 55, 43,
41, 39 ¹ H-NMR (500MHz, CDCl _3, δppm): 0.90 (3H, t, -CH ₃ ), 1.16
(3H, d, -CH-CH ₃ ), 1.2-1.7 (6H), 1.80 (1H, d), 4.32 (1H) ¹³ C-NMR (125MHz, CDCl ₃ , δ ppm): 14.0, 20.6, 22.5, 2
5.5, 29.7, 30.2, 31.4, 36.7, 105.0 (= CH-), 153.9 (-O-
C =), 174.5 (-C = O)

Product Ff MS m / z: 182 (M ⁺ ), 139, 125, 112, 97, 79, 69, 55 (1
00), 41 IR ν max (cm ^-1 ): 1802, 1698, 1288, 1170, 1138, 111
8, 1111, 935 ¹ H-NMR (500MHz, CDCl _3, δppm): 0.90 (3H, t, -CH ₃ ), 1.22
(3H, d, -CH-CH ₃ ), 1.2-1.47 (6H, m), 2.00 (2H, dt, = CH-C
H ₂ -CH _2- ), 2.27 (1H, dd), 2.87 (1H, dd, -CO-CH-), 3.22 (1
H, m, -CO-CH-), 5.14 (1H, t, = CH-CH ₂ ) ¹³ C-NMR (125MHz, CDCl ₃ , δ ppm): 14.0, 20.6, 22.5, 2
5.5, 29.7, 30.2, 31.4, 36.7, 105.0 (= CH-), 153.9 (-O-
C =), 174.5 (-C = O)

Product Gf MS m / z: 182 (M ⁺ ), 139, 125, 112, 97, 79, 69, 55 (1
00), 41

[0041] As shown in the above formulation example, by adding 4% of the product obtained in Example 2, a peach flavor having a natural green note, enhanced diffusibility and expressing a ripe peach-like flavor was obtained. It was

[0042] By adding 6% of the product obtained in Example 2 as shown in the above-mentioned formulation example, a butter-based flavorer with enhanced buttery flavor and excellent in diffusivity and sustainability was obtained. Was obtained.

[0043] As shown in the above formulation example, by adding 1.5% of the product obtained in Example 2, width and depth are added to the body,
A base flavor with a diffuse, fresh strawberry-like aroma was obtained.

[0044] As shown in the above formulation example, by adding 2% of the product obtained in Example 2, a jasmine-based fragrance having enhanced dazzling top notes, enhanced diffusivity and durability was obtained.

[0045] As shown in the above formulation example, by adding 6.2% of the product obtained in Example 2, a bouquet type fragrance having a more natural floral scent and excellent sustainability was obtained.

[Brief description of drawings]

FIG. 1 is a chromatogram of 3-methyl-5-decene-4-olide, which is an extract of the present invention.

FIG. 2 is mass spectrum data of 3-methyl-5-decene-4-olide, which is an extract and isolate of the present invention.

FIG. 3 is a gas chromatogram of the intermediate obtained by the synthesis method of the present invention.

FIG. 4 is a mass spectrum of the product Ai in the chromatogram of FIG.

5 is a mass spectrum of the product Bi in the chromatogram of FIG.

6 is a mass spectrum of the product Ci in the chromatogram of FIG.

FIG. 7 is a gas chromatogram of the final product obtained by the synthesis method of the present invention.

8 is a mass spectrum of the product Af in the chromatogram of FIG.

9 is a mass spectrum of the product Bf in the chromatogram of FIG. 7.

FIG. 10 is a mass spectrum of the product Cf in the chromatogram of FIG.

FIG. 11 is a mass spectrum of the product Df in the chromatogram of FIG. 7.

FIG. 12 is a mass spectrum of the product Ef in the chromatogram of FIG.

FIG. 13 is a mass spectrum of the product Ff in the chromatogram of FIG. 7.

FIG. 14 is a mass spectrum of the product Gf in the chromatogram of FIG.

Claims (4)

[Claims] 1. 3-Methyl-5 or 4-decene-4-olide. 2. (A) 4-hydroxy-2-nonene,
By reacting orthoacetic acid ester in the presence of an acid catalyst,
Methyl-4-decenoic acid alkyl ester is obtained, (B) 3
-Methyl-4-decenoic acid alkyl ester is hydrolyzed and (C) the obtained 3-methyl-4-decenoic acid is treated with an aqueous solution of iodine and potassium iodide to give (D) the obtained product. , A dehydrohalogenation reaction in the presence of an amine compound to obtain 3-methyl-5 or 4-decene-4-olide. 3. A perfume composition comprising 3-methyl-5 or 4-decene-4-olide as an active ingredient. 4. 3-Methyl-5-iodo-decane-4-
Orido.