JP2021075467A - γ-METHYL-γ,δ-EPOXY-α,β-UNSATURATED ALDEHYDE COMPOUND AND FLAVOR COMPOSITION CONTAINING THAT COMPOUND - Google Patents

Abstract

To provide a new compound useful as a flavor ingredient or the like, and a flavor composition containing the compound.SOLUTION: The invention provides: a γ-methyl-γ,δ-epoxy-α,β-unsaturated aldehyde compound represented by the general formula (1) in the figure useful as a flavor ingredient and the like; and a flavor composition containing the compound. (In the formula, the solid line, the double line, H, C, O, R1 and R2 are as defined in the specification.)SELECTED DRAWING: None

Description

The present invention relates to a γ-methyl-γ, δ-epoxy-α, β-unsaturated aldehyde compound useful as a fragrance raw material, and a fragrance composition containing the compound.

In recent years, as consumer tastes have diversified, there is a strong demand for fragrances used in foods and drinks, which have excellent natural and fruity sensations and are differentiated from conventional fragrances. On the other hand, since the combination of existing fragrance raw materials cannot meet these demands, research and development of new fragrance raw materials having an unprecedented fragrance tone are still being vigorously carried out.

Against this background, various techniques have been proposed for the purpose of imparting or enhancing a natural feeling. For example, 7,9,11-dodecatorien-4-one and 6,10-undecadien-described in Patent Document 1 have been proposed. 3-On and 6,8-Undecadien-3-one, (2E, 8Z) -Tetradecadienal described in Patent Document 2, γ, δ-epoxy-α, β-unsaturated aldehyde described in Patent Document 3. A method of adding a compound such as (2E) -cis-4,5-epoxydecenal, which is a kind of compound, to a fragrance is disclosed.

JP-A-2010-83913 Japanese Unexamined Patent Publication No. 2016-124833 Japanese Unexamined Patent Publication No. 2005-82771

As mentioned above, although the development of various technologies related to the natural sensation of fragrances is progressing, useful new fragrance raw materials are still awaited from the viewpoint of further enhancing the natural sensation and fruitiness and differentiating from conventional fragrances. It has been. The present invention has been made in view of the current situation surrounding fragrances. That is, an object of the present invention is to provide a novel compound useful as a fragrance raw material and the like, and a fragrance composition containing the compound.

As a result of diligent studies to solve the above problems, the present inventors have succeeded in synthesizing a novel γ-methyl-γ, δ-epoxy-α, β-unsaturated aldehyde compound, and this compound is excellent. It was found to have a strong aroma. The present inventors have completed the present invention by proceeding with further studies based on these basic findings.

That is, the present invention includes the following [1] to [11].
[1] A compound represented by the following general formula (1).

(In the formula, the solid line represents a single bond and the double line represents a double bond. H represents a hydrogen atom, C represents a carbon atom, and O represents an oxygen atom. R ¹ is a hydrogen atom or a direct having 8 to 10 carbon atoms. Represents a chain alkyl group. R ² represents a linear alkyl group having 8 to 10 carbon atoms when R ^{1 is a hydrogen atom, and R 1} represents a linear alkyl group having 8 to 10 carbon atoms. Represents a hydrogen atom.)
[2] The compound according to the above [1], wherein the linear alkyl group has 8 carbon atoms.
[3] The compound according to the above [1] and the above [2], which is an optically active substance.
[4] A fragrance composition containing the compound according to any one of the above [1] to [3].
[5] The fragrance composition according to the above [4], wherein the fragrance composition is a fruit-like fragrance composition.
[6] The perfume composition according to the above [5], wherein the fruit is a citrus fruit.
[7] The flavor composition according to the above [5] and [6], wherein the flavor composition is a food and drink flavor composition.
[8] The flavor composition according to the above [7], wherein the food or drink is a beverage.
[9] The perfume composition according to the above [8], wherein the beverage is a citrus beverage.
[10] Foods and drinks, oral compositions and tobacco products containing the compound according to any one of the above [1] to [3].
[11] Foods and drinks, oral compositions and tobacco products containing the perfume composition according to any one of the above [4] to [9].

According to the present invention, a γ-methyl-γ, δ-epoxy-α, β-unsaturated aldehyde compound represented by the general formula (1), which is useful as a fragrance raw material (hereinafter, referred to as “the compound (1) of the present invention”). And a fragrance composition containing the compound (hereinafter referred to as "fragrance composition of the present invention") can be provided.

First, the compound (1) of the present invention will be described in detail. In the general formula (1), the solid line represents a single bond and the double line represents a double bond. H represents a hydrogen atom, C represents a carbon atom, and O represents an oxygen atom. R ¹ represents a hydrogen atom or a linear alkyl group. R ^2, when R ¹ is a hydrogen atom represents a linear alkyl group, when R ¹ is a linear alkyl group represents a hydrogen atom. The linear alkyl group in R ¹ and R ² has 8, 9 or 10 carbon atoms, and a particularly preferable carbon number is 8. Since the compound (1) of the present invention has asymmetric carbons at its 4- and 5-positions, it may be an optically active substance. Particularly preferred forms of the compound (1) of the present invention include the following Fig. The compound represented by the planar structural formula (1 ^A ) shown in 1 (hereinafter referred to as “the compound of the present invention (1 ^A )”) and the three-dimensional structural formula ( ^{1 A} ) included in the planar structural formula (1 A). Examples thereof include compounds represented by (4R, 5R) -1 ^A ) to the three-dimensional structural formula ((4S, 5S) -1 ^A). Omitted).

Next, the method for producing the compound (1) of the present invention will be described in detail. The method for producing the compound (1) of the present invention is not particularly limited, but as an example, the following Eq. As shown in 1, the Wittig reaction of pyruvinaldehyde dimethyl acetal and an alkylphosphonium salt (Step 1), the carbonization reaction with a Lewis acid catalyst / ethyl vinyl ether (Step 2), the deprotection-β elimination reaction with an acid catalyst (Step 3), and It can be easily synthesized by an air oxidation reaction (Step 4).

The compound (1) of the present invention thus obtained can be used as a reaction solution or a crude product as it is, but may be post-treated, isolated and purified as necessary. Examples of the post-treatment method include concentration, solvent substitution, washing and extraction, and these post-treatments may be performed alone or in combination. Examples of the purification and isolation methods include decolorization with an adsorbent, distillation, silica gel column chromatography, gas chromatography, high performance liquid chromatography and the like, and these may be performed alone or in combination.

Hereinafter, a method of using the compound (1) of the present invention and a method of using the fragrance composition of the present invention will be described in detail. The compound (1) of the present invention and the perfume composition of the present invention have an excellent aroma, and can be used alone or in combination with other components as a perfume component for foods and drinks, oral compositions, tobacco products, etc. Can be used.

By blending the compound (1) of the present invention or the flavor composition of the present invention into foods and drinks, the aroma and flavor of the foods and drinks themselves can be enhanced, or new flavors and flavors can be imparted to the foods and drinks. Although it is possible, by mixing these with other flavor components and then blending them into the food and drink, it is possible to enhance the aroma and flavor of the food and drink itself, or to add a new aroma and flavor to the food and drink. Is. Examples of other flavor components that can be mixed include various plant extracts, natural essential oils, natural flavors, synthetic flavors, and the like. , P88-131 ”(Patent Office, issued on January 14, 2000), such as natural essential oils, natural fragrances and synthetic fragrances.

The concentration range of the compound (1) of the present invention in the fragrance composition of the present invention varies depending on the other fragrance components to be mixed, but is usually 0.00001 to 10,000 ppm with respect to the weight of the fragrance composition. It is preferably selected from the range of 0.0001 to 1,000 ppm, more preferably 0.001 to 100 ppm.

A solvent and a fixative may be added to the fragrance composition of the present invention, if necessary. Specific examples of the solvent include water and ethanol. Specific examples of the fixative include ethylene glycol, propylene glycol, dipropylene glycol, glycerin, hexyl glycol, benzylbenzoate, triethylcitrate, diethylphthalate, harcholine, medium-chain fatty acid triglyceride, and medium-chain fatty acid diglyceride.

By adding the compound (1) of the present invention and the flavor composition of the present invention, foods and drinks capable of enhancing the aroma / flavor or imparting a new aroma / flavor include, for example, beverages, desserts, and confectionery. , Soups, breads, jams, flavor seasonings, instant beverages, instant foods and the like. Specific examples of the beverages include carbonated beverages, soft drinks, fruit juice beverages, fruit juices, milk beverages, lactic acid bacteria beverages, drinks, soymilk and tea beverages, preferably fruit juice beverages, and particularly preferably citrus fruit juice beverages. Be done. Specific examples of desserts include ice cream, ice milk, lacto ice, frozen desserts, yogurt, pudding, jelly, and daily desserts. Specific examples of confectionery include caramel, candy, tablet confectionery, crackers, biscuits, cookies, pies, chocolate, snacks, chewing gum, buns, and yokan. Specific examples of soups include Japanese-style soups, Western-style soups, and Chinese soups.

The amount of the compound (1) added to the food or drink varies depending on the type and form of the food or drink, but is usually 0.00001 to 10,000 ppb, preferably 0. It is selected from the range of 0001 to 1,000 ppb, more preferably 0.001 to 100 ppb. The amount of the flavor composition added to the food or drink varies depending on the composition of the flavor composition and the type and form of the food and drink, but is usually 0.001 with respect to the total mass of the food and drink. It is selected from the range of 10% by mass, preferably 0.01 to 5% by mass.

Examples of the oral composition capable of imparting aroma and flavor by the compound (1) of the present invention and the fragrance composition of the present invention include dentifrices, mouthwashes, troches and chewing gums. The amount of the perfume composition of the present invention added to the oral composition varies naturally depending on the composition of the perfume composition and the type and form of the oral composition, but is usually based on the total mass of the oral composition. It is selected from the range of 0.01 to 5% by mass, preferably 0.1 to 3% by mass.

Examples of tobacco products that can impart aroma and flavor by the compound (1) of the present invention and the fragrance composition of the present invention include cigarettes and electronic cigarettes. The amount of the fragrance composition of the present invention added to the tobacco product naturally varies depending on the composition of the fragrance composition and the type and form of the tobacco product, but is usually 0.00001 with respect to the mass of the dry leaf component in the tobacco. It is selected from the range of ~ 90% by mass, preferably 0.0001 to 50% by mass.

Hereinafter, the present invention will be specifically described with reference to Examples, but the present invention is not limited thereto. In the examples, the analytical methods and instruments used for measuring the physical properties are as follows.
1) Nuclear Magnetic Resonance Spectroscopy (NMR): AVANCE III500 device (manufactured by Bruker Biospin).
2) Gas chromatography (GC): GC353B type device (manufactured by GL Sciences).
3) Gas chromatograph-precision mass spectrometry (GC-HRMS): TRACE1310 type device (GC; manufactured by Thermo Fisher Scientific), Active GC type device (HRMS; manufactured by Thermo Fisher Scientific).
4) High Performance Liquid Chromatography (HPLC): LC-20A type equipment (pump; manufactured by Shimadzu Corporation), SPD-M20A type equipment (detector; manufactured by GL Sciences), COSMOSIL 5SL-II type equipment (separation column; Nakarai) Made by Tesque).

[Example 1] Production of (2E) -4,5-epoxy-4-methyl-2-trideceneal ( ^1A)

Step 1: 2-Methyl-2-undecenal Synthesis of dimethyl acetal (Int-1 ^A ) (Eq.2)

Nonyltriphenylphosphonium iodide (2) (91.4 g, 0.177 mol, 1.0 eq), potassium tert-butoxide (purity: 85%, 23.4 g, 0.177 mol, 1.0 eq) under nitrogen atmosphere ) And dehydrated tetrahydrofuran (THF) (500 mL), cooled to −70 ° C. in a dry ice-acetone bath, and then pyruvinaldehyde dimethylacetal (3) (20.9 g, 0) to this solution. A solution of dehydrated THF (30 mL) (.177 mol, 1.0 eq) was added dropwise over 1 hour and stirred at the same temperature for an additional 5 hours. After raising the temperature of the obtained reaction solution to room temperature, water (250 mL) was added, and an extraction operation was performed using an excess amount of n-hexane. The organic layers were collectively concentrated under reduced pressure, and the obtained residue was distilled and purified (boiling point: 68 ° C. to 70 ° C./1 mmHg) to ^{obtain 26.6 g of the desired Int-1 A} as a colorless liquid. .. Purity: 98.6% (GC), E / Z = 43/57, isolation yield: 65.8%.
^{1 1} H NMR (500 MHz, CDCl ₃ ): δ = 5.55 / 5.44 (t, 1H), 4.93 / 4.44 (s, 1H), 3.34 / 3.29 (s, 6H) , 2.27-2.04 (m, 2H), 1.69 / 1.59 (s, 3H), 1.48-1.22 (m, 12H), 0.88 (t, 3H) (However As an E / Z mixture).

Step2: Synthesis of 1,3-dimethoxy-1-ethoxy-4-tridecene (Int-2 ^A ) (Eq.3)

^A solution of Int-1 A (4.57 g, 20.0 mmol, 1.0 eq) in dehydrated THF (40 mL) was cooled in an ice-water bath under a nitrogen atmosphere _{, and then boron trifluoride diethyl ether complex (BF 3-} Et). ₂ O) (200 mg) was added, and a dehydrated THF solution (5 mL) of ethyl vinyl ether (4) (2.16 g, 30.0 mmol, 1.5 equivalents) was added dropwise to this solution over 2 hours. Stirring was carried out for another 2 hours under cooling with an ice water bath. After adding an excess saturated aqueous sodium hydrogen carbonate solution to the obtained reaction solution, extraction was performed using an excess amount of diisopropyl ether, and the organic layers were collectively washed with water. The organic layer was concentrated under reduced pressure, and the obtained residue was distilled and purified (boiling point: 83 ° C. to 87 ° C./1 mmHg) to ^{obtain 4.40 g of the desired Int-2 A} as a colorless liquid. Isolation yield: 73.2%.
^{1 1} H NMR (500 MHz, CDCl ₃ ) δ: 4.55-4.50 (t, 1H), 4.50-4.17 (m, 1H), 3.68-3.42 (m, 3H), 3.31 (s, 3H), 3.25 (s, 3H), 2.05-1.89 (m, 2H), 1.71-1.60 (m, 2H), 1.53 (d, 3H), 1.36-1.19 (15H, m), 0.88 (3H, t) (but as an isomer mixture).

Step3: Synthesis of (2E) -4-methyl-2,4- ^{tridecadienal (Int-3 A} ) (Eq.4)

In a nitrogen atmosphere, of Int-2 ^A (4.20 g, 14.0 mmol, 1.0 eq), sodium acetate (2.87 g, 35.0 mmol, 2.5 eq), acetic acid (30 mL) and water (7 mL). The mixture was stirred for 7 hours while heating in an oil bath at 60 ° C. The obtained reaction solution was cooled to room temperature, an excess amount of diisopropyl ether and a saturated aqueous sodium hydrogen carbonate solution were sequentially added and stirred, and then allowed to stand to separate the aqueous layer. The obtained organic layer was washed with water, concentrated under reduced pressure, and the residue was distilled and purified (boiling point: 85 ° C. to 87 ° C./1 mmHg) to ^{obtain 2.49 g of the target Int-3 A} as a pale yellow liquid. It was. Purity: 97.8% (GC), 4E / 4Z = 45/55, isolation yield: 85.3%. ^A part of Int-3 A was further purified by HPLC (eluent: n-hexane / ethyl acetate = 97/3) to form (2E, 4E) and (2E, 4Z). After the bodies were separated, the structure was determined by performing ^{each 1 H NMR measurement.}

<(2E, 4E) -Int-3 ^A : Physical property data>
^{1 1} H NMR (500 MHz, CDCl ₃ ): δ = 9.56 (d, J = 7.9 Hz, 1H), 7.12 (d, J = 15.6 Hz, 1H), 6.10 (dd, J = 7.9, 15.6Hz, 1H), 6.04 (t, J = 7.7Hz, 1H), 2.24 (q, J = 7.5Hz, 2H), 1.81 (s, 3H), 1.48-1.42 (m, 2H), 1.36-1.21 (m, 10H), 0.89 (t, J = 7.1Hz, 3H).

<(2E, 4Z) -Int-3 ^A : Physical property data>
^{1 1} H NMR (500 MHz, CDCl ₃ ): δ = 9.64 (d, J = 7.9 Hz, 1H), 7.57 (d, J = 15.5 Hz, 1H), 6.17 (dd, J = 7.8, 15.5Hz, 1H), 5.88 (t, J = 7.8Hz, 1H), 2.30 (q, J = 7.8Hz, 2H), 1.89 (d, J = 1) .2Hz, 3H), 1.47-1.40 (m, 2H), 1.35-1.20 (m, 10H), 0.88 (t, J = 7.1Hz, 3H).

Step4: (2E) -4,5- Synthesis of epoxy-4-methyl-2- Toridesenaru ^{(1 A)} (Eq.5)

When Int-3 ^A (1.0 g) was weighed in a 10 mL glass sample tube, closed with a cotton plug, and allowed to stand in the air at room temperature for 1 month, the compound of the present invention was accompanied by the by-product of nonanal (5). (1 ^A ) was generated. By purifying this crude product by silica gel column chromatography (eluent: n-hexane / ethyl acetate), the compound (1 ^A ) of the present invention was obtained as a mixture of four types of diastereomers. This compound has a characteristic and preferable aroma such as oily, metallic and uri-like aldehyde odor, which is different from γ, δ-epoxy-α and β-unsaturated aldehyde compounds having no methyl group at the γ position. Was there. In addition, a part of this compound is further purified by HPLC (eluent: n-hexane / ethyl acetate = 97/3) to form (4R, 5S) / (4S, 5R) (that is, trans). After separating the body) and the (4R, 5R) / (4S, 5S) body (that is, the cis body), the structure was determined by performing NMR measurement and GC-HRMS measurement of each.

<Trans-1 ^A : Physical property data>
^{1 1} H NMR (500 MHz, (Deuterated-d ₆ ): δ = 9.56 (d, J = 7.70 Hz, 1H), 6.57 (d, J = 15.82 Hz, 1H), 6.29 ( dd, J = 7.70, 15.82Hz, 1H), 2.91 (t, J = 6.12Hz, 1H), 1.47 (s, 3H), 1.80-1.18 (m, 14H), 0.88 (t, J = 7.01Hz, 3H).
¹³ C NMR (125 MHz, Acetone-d ₆ ): δ = 192.97, 158.81, 131.96, 66.09, 58.47, 31.81,29.44, 29.39, 29.16, 28.53, 26.31, 22.63, 14.95, 14.07.
GC-HRMS (CI +): calcd, C14H25O2 ([M + H] +) 225.1849; found, 225.1849.

<Cis-1 ^A : Physical property data>
¹ H NMR (500 MHz, Deuterated-d ₆ ): δ = 9.58 (d, J = 7.70 Hz, 1H), 6.72 (d, J = 15.85 Hz, 1H), 6.30 (dd, dd, J = 7.70, 15.85Hz, 1H), 3.06 (t, J = 6.05Hz, 1H), 1.52 (s, 3H), 1.74-1.16 (m, 14H), 0.88 (t, J = 6.88Hz, 3H).
¹³ C NMR (125 MHz, Deuterated-d6): δ = 192.72, 154.53, 133.99, 67.19, 59.48, 31.80, 29.42, 29.28, 29.14, 28 .30, 26.29, 22.63, 20.96, 14.07.
GC-HRMS (CI +): calcd, C14H25O2 ([M + H] +) 225.1849; found, 225.1849.

[Example 2] Production and sensory test of a food-grade grapefruit flavor composition derived from a natural essential oil containing ^{the compound (1 A) of the present invention.}

^A food-grade grapefruit flavor composition (A) was prepared using the natural essential oil, the solvent and the compound (1 A) of the present invention prepared in Example 1 according to the formulation shown in Table 1 below.

On the other hand, according to the formulation shown in Table 2 below, a food-grade grapefruit flavor composition (B) to which ^{the compound (1 A) of the present invention was not added was produced.}

Next, two types of evaluation samples were prepared by adding 0.1% of each of the fragrance composition (A) and the fragrance composition (B) to water, and a sensory test was conducted by six specialized panelists. As a result, ^{the perfume composition (A) containing the compound (1 A} ) of the present invention is imparted with a citrus-like juicy voluminous feeling and a sand-like crushing feeling, and thus is different from the perfume composition (B). All the panelists agreed that they were far superior in comparison.

[Example 3] Effect of addition of the compound (1 ^A ) of the present invention to a commercially available grapefruit juice beverage An evaluation sample is prepared by adding 0.1 ppb ^{of the compound (1 A) of the present invention to a commercially available grapefruit juice beverage.} Then, a sensory test was conducted by 6 specialized panelists. As a result, a voluminous fruit juice feeling and a natural fruit feeling were given, and it was said that it was significantly superior to that before the addition, and the evaluations of all the panelists agreed.

[Example 4] Production and sensory test of a food-grade grapefruit flavor composition derived from a single flavor containing ^{the compound (1 A) of the present invention.}

^A food-grade grapefruit flavor composition (C) was produced using various single flavors, solvents and the compound (1 A) of the present invention according to the formulations shown in Table 3 below.

On the other hand, a food-grade grapefruit flavor composition (D) containing no ^{compound (1 A} ) of the present invention was produced according to the formulation shown in Table 4 below.

Next, two types of evaluation samples were prepared by adding 0.1% of each of the fragrance composition (C) and the fragrance composition (D) to water, and a sensory test was conducted by six specialized panelists. As a result, ^{the perfume composition (C) containing the compound (1 A} ) of the present invention is imparted with a citrus-like juicy voluminous feeling and a sand-like crushing feeling, and thus is different from the perfume composition (D). All the panelists agreed that they were far superior in comparison.

[Example 5] Production and sensory test of a food-grade orange flavor composition derived from a natural essential oil containing ^{the compound (1 A) of the present invention.}

^A food-grade orange flavor composition (E) was prepared using a natural essential oil, a solvent and the compound (1 A) of the present invention according to the formulation shown in Table 5 below.

On the other hand, according to the formulation shown in Table 6 below, a food-grade orange flavor composition (F) to which ^{the compound (1 A) of the present invention was not added was produced.}

Next, two types of evaluation samples were prepared by adding 0.1% of each of the fragrance composition (E) and the fragrance composition (F) to water, and a sensory test was conducted by six specialized panelists. As a result, ^{the fragrance composition (E) containing the compound (1 A} ) of the present invention has a enhanced natural peeling sensation and a citrus-like voluminous sensation, and thus is significantly more than the fragrance composition (F). All the panelists agreed that it was excellent.

[Example 6] Effect of addition of the compound (1 ^A ) of the present invention to a commercially available orange juice beverage An evaluation sample was prepared by adding 0.1 ppb ^{of the compound (1 A) of the present invention to a commercially available orange juice beverage.} Then, a sensory test was conducted by 6 specialized panelists. As a result, the natural peeling feeling and fruitiness were enhanced, and it was said that it was significantly superior to that before the addition, and the evaluations of all the panelists agreed.

[Example 7] Production and sensory test of a food-grade orange flavor composition derived from a single flavor containing ^{the compound (1 A) of the present invention.}

According to the formulation shown in Table 7 below, a food-grade orange flavor composition (G) was produced using various single flavors, solvents and the compound (1 ^{A) of the present invention.}

On the other hand, a food-grade orange flavor composition (H) containing no ^{compound (1 A} ) of the present invention was produced according to the formulation shown in Table 8 below.

Next, two types of evaluation samples were prepared by adding 0.1% of each of the fragrance composition (G) and the fragrance composition (H) to water, and a sensory test was conducted by six specialized panelists. As a result, ^{the perfume composition (G) containing the compound (1 A} ) of the present invention is significantly superior to the perfume composition (H) because it imparts a natural peeling feeling and a fruity feeling. The evaluations of all the panelists agreed.

[Example 8] Production and sensory test of a food-grade lemon flavor composition derived from a natural essential oil containing ^{the compound (1 A) of the present invention.}

^A food-grade lemon flavor composition (I) was prepared using a natural essential oil, a solvent and the compound (1 A) of the present invention according to the formulation shown in Table 9 below.

On the other hand, according to the formulation shown in Table 10 below, a food-grade lemon flavor composition (J) to which ^{the compound (1 A) of the present invention was not added was produced.}

Next, two types of evaluation samples were prepared by adding 0.1% of each of the fragrance composition (I) and the fragrance composition (J) to water, and a sensory test was conducted by six specialized panelists. As a result, ^{the fragrance composition (I) containing the compound (1 A} ) of the present invention has a enhanced natural peeling sensation and a citrus-like voluminous sensation, and thus is significantly more than the fragrance composition (J). All the panelists agreed that it was excellent.

[Example 9] ^{Effect of addition of compound (1 A} ) of the present invention to a commercially available lemon juice beverage An evaluation sample is prepared by adding 0.1 ppb ^{of the compound (1 A) of the present invention to a commercially available lemon juice beverage.} Then, a sensory test was conducted by 6 specialized panelists. As a result, the natural peeling feeling and fruitiness were enhanced, and it was said that it was significantly superior to that before the addition, and the evaluations of all the panelists agreed.

[Example 7] Production and sensory test of a food-grade lemon flavor composition derived from a single flavor containing ^{the compound (1 A) of the present invention.}

^A food-grade lemon flavor composition (K) was produced using various single flavors, solvents and the compound (1 A) of the present invention according to the formulations shown in Table 11 below.

On the other hand, according to the formulation shown in Table 12 below, a food-grade lemon flavor composition (L) containing no ^{compound (1 A) of the present invention was produced.}

Next, two types of evaluation samples were prepared by adding 0.1% of each of the fragrance composition (K) and the fragrance composition (L) to water, and a sensory test was conducted by six specialized panelists. As a result, ^{the perfume composition (K) containing the compound (1 A} ) of the present invention is significantly superior to the perfume composition (L) because it imparts a natural peeling feeling and a fruity feeling. The evaluations of all the panelists agreed.

INDUSTRIAL APPLICABILITY According to the present invention, a γ-methyl-γ, δ-epoxy-α, β-unsaturated aldehyde compound useful as a raw material for blended flavors and a flavor composition containing the compound are provided, and a composition for foods and drinks and oral use It can be expected to be widely used in the fields of tobacco products and the like.

Claims (11)

A compound represented by the following general formula (1).

(In the formula, the solid line represents a single bond and the double line represents a double bond. H represents a hydrogen atom, C represents a carbon atom, and O represents an oxygen atom. R ¹ is a hydrogen atom or a direct having 8 to 10 carbon atoms. represents an alkyl group .R ^2, if R ¹ is a hydrogen atom represents the number 8-10 straight chain alkyl group having a carbon if R ¹ is a number 8-10 straight chain alkyl group having a carbon hydrogen Represents an atom.) The compound according to claim 1, wherein the linear alkyl group has 8 carbon atoms. The compound according to claim 1 or 2, which is an optically active substance. A fragrance composition containing the compound according to any one of claims 1 to 3. The perfume composition according to claim 4, wherein the perfume composition is a fruit-like perfume composition. The perfume composition according to claim 5, wherein the fruit is a citrus fruit. The flavor composition according to claim 5 or 6, wherein the flavor composition is a food and drink flavor composition. The flavor composition according to claim 7, wherein the food or drink is a beverage. The perfume composition according to claim 8, wherein the beverage is a citrus beverage. Foods and drinks, oral compositions and tobacco products containing the compound according to any one of claims 1 to 3. Foods and drinks, oral compositions and tobacco products containing the perfume composition according to any one of claims 4 to 9.