Perfume composition

Abstract

To provide a perfume composition capable of enhancing citrus-like fragrance and flavor.SOLUTION: A perfume composition contains (5E)-6,10-dimethyl-11-oxoundeca-5,9-diene-2-yl acetate.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to compounds and fragrance compositions that are useful as blended fragrance raw materials and the like. [Background technology]

[0002] In recent years, as consumer preferences have become more diverse, there is a strong demand for flavors that have a strong fruity or natural flavor or a flavor that is differentiated from others, for flavors used in foods, beverages, etc. However, it is sometimes difficult to meet such demands with combinations of conventional flavor raw materials, and there is a strong demand for new flavor materials. Summary of the Invention [Problem to be solved by the invention]

[0003] The present invention provides a novel compound having a fragrant odor useful as a raw material for blended fragrances, etc., and a fragrance composition containing said compound. [Means for solving the problem]

[0004] The present inventors synthesized various compounds and investigated their odors, and found that a compound having an aldehyde group and an ester structure at its terminal has an excellent odor. That is, the present invention relates to the following [1] to [6]. [1] A compound represented by the following formula (1):

[0005] [ka]

[0006] (In formula (1), R represents an alkyl group having 1 to 4 carbon atoms, and the wavy line represents cis or trans, or a mixture of cis and trans.) [2] The compound according to the above [1], wherein R is a methyl group. [3] A fragrance composition containing the compound according to [1] or [2] above. [4] The flavoring composition according to [3] above, which is for use in food or beverages. [5] A food or drink, an oral composition, a tobacco product, or a consumer product, comprising the compound or flavor composition according to any one of [1] to [4] above. [6] A method for producing a food or beverage, an oral composition, a tobacco product, or a consumer product, comprising adding the compound or flavor composition described in [1] to [4] above. Effect of the Invention

[0007] According to the present invention, there can be provided a novel compound having a useful odor as a raw material for blended fragrances, and a fragrance composition containing said compound. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0008] The present invention will be described in detail below. In the present invention, (5E)-6,10-dimethyl-11-oxoundeca-5,9-dien-2-yl carboxylate (hereinafter also referred to as the compound of the present invention) is, for example, an acetate ester, and has two isomers represented by the following (1a) and (1b). Either one may be used alone, or a mixture of these may be used, but compound (1a) is preferred.

[0009] [ka]

[0010] In addition, there are two enantiomers represented by the following (1c) and (1d). Either one may be used alone, or a mixture of these may be used.

[0011] [ka]

[0012] The compounds (1a) and (1b) of the present invention can be prepared, for example, by the following steps. Geranylacetone is treated with NaBH4 to reduce the ketone, and then acetylated with acetyl chloride to give geranyl acetate. Allyl chloride is then synthesized by chlorination with calcium hypochlorite, and allyl alcohol is synthesized with triethylamine after the introduction of a hydroxyl group accompanied by rearrangement with formate. This is then oxidized with manganese dioxide to give a mixture of compounds (1a) and (1b). The above steps are summarized in the following scheme.

[0013] [ka]

[0014] (In the schemes, the wavy lines represent cis or trans, or a mixture of cis and trans.) The thus obtained compound (1a) and compound (1b) of the present invention can be purified by distillation, various types of chromatography, and the like. The compound of the present invention has an excellent aroma and can be used alone or in combination with other components as a flavoring component for foods and beverages, oral compositions, tobacco products, and the like.

[0015] The flavor composition and the compound of the present invention can be added to food and drink in a very small amount as it is to impart or enhance the flavor and aroma, but can also be mixed with other ingredients to impart or enhance the flavor and aroma of food and drink. Examples of other flavor ingredients that can be mixed include various synthetic flavors, natural flavors, natural essential oils, plant extracts, etc., such as the natural essential oils, natural flavors, and synthetic flavors described in "Japan Patent Office Gazette, Collection of Well-Known and Commonly Used Techniques (Flavors), Part II Food Flavors, P88-131, published January 14, 2000." The concentration of the compound of the present invention in the fragrance composition of the present invention varies depending on the other fragrance components to be mixed, and cannot be generalized, but can usually be in the range of 0.00001 to 10,000 ppm, preferably 0.0001 to 1000 ppm, and more preferably 0.001 to 100 ppm based on the weight of the fragrance composition.

[0016] When the compound of the present invention is added to food or drink to enhance its aroma or flavor, the concentration may be in the range of 0.00001 to 10000 ppb, preferably 0.0001 to 1000 ppb, more preferably 0.001 to 100 ppb, based on the weight of the food or drink. The fragrance composition of the present invention containing the compound of the present invention may contain, as necessary, commonly used solvents such as water, ethanol, etc.; and retaining agents such as ethylene glycol, propylene glycol, dipropylene glycol, glycerin, hexyl glycol, benzyl benzoate, triethyl citrate, diethyl phthalate, hercolin, triacetin, medium-chain fatty acid triglycerides, and medium-chain fatty acid diglycerides.

[0017] The flavor and aroma of foods and beverages can be enhanced by adding a flavor composition containing the compound of the present invention or the compound of the present invention itself. Specific examples of foods and beverages whose aroma and flavor can be enhanced by the addition of the flavor composition and compound of the present invention include beverages such as carbonated drinks, soft drinks, fruit juice drinks, fruit liquors, dairy drinks, lactic acid bacteria drinks, energy drinks, soy milk, and tea drinks; desserts such as ice cream, ice milk, lacto ice cream, frozen desserts, yogurt, pudding, jelly, and daily desserts; confectioneries such as caramel, candy, tablet candy, crackers, biscuits, cookies, pies, chocolates, snacks, chewing gum, buns, and yokan; soups such as Japanese soup, Western soup, and Chinese soup; breads; jams; flavor seasonings; various instant drinks; and various instant foods. The amount of the flavor composition added to food or drink varies depending on the type and form of the product, but can usually be 0.1% based on the weight of the food or drink, and preferably the concentration is in the range of 0.001 to 5%.

[0018] Examples of oral compositions that can be scented and flavored with the flavor composition of the present invention and the compound of the present invention include dentifrices, oral cleansers, mouthwashes, lozenges, chewing gums, etc. The amount of the flavor composition added to the oral composition varies depending on the type and form of the product, but can usually be preferably 0.01 to 5% by mass, more preferably 0.1 to 3% by mass, based on the total mass of the oral composition.

[0019] Tobacco products that can be flavored and scented with the flavor composition and the compound of the present invention include cigarettes, electronic cigarettes, etc. The amount of the flavor composition added to a tobacco product varies depending on the type and form of the product, but can be, for example, preferably 0.00001 to 90% by mass, more preferably 0.0001 to 50% by mass, based on the total mass of the tobacco leaf portion.

[0020] Examples of consumer products include fragrance products such as perfume, eau de parfum, eau de toilette, and eau de cologne; Basic cosmetics such as face wash cream, cleansing cream, milky lotion, toner, and serum; Finishing cosmetics such as lipstick, lip balm, eyeliner, mascara, eye shadow, eyebrow pencil, eye mask, nail enamel, enamel remover; Hair cosmetics such as pomades, Brilantin, setting lotions, hair sticks, hair solids, hair oils, hair treatments, hair creams, hair tonics, hair liquids, hair sprays, Bandolin, hair tonics, hair dyes, etc.; Tanning cosmetics such as tanning products and sunscreen products; Medicinal cosmetics such as antiperspirants, aftershave lotions and gels, permanent wave agents, medicinal soaps, medicinal shampoos, medicinal skin cosmetics; Hair care products such as shampoo, rinse, rinse-in shampoo, conditioner, treatment, hair pack, etc. Soaps such as toilet soap, bath soap, perfumed soap, transparent soap, synthetic soap; Personal cleansing products such as body wash, body shampoo, hand soap, and face cream; Bath additives such as bath salts (bath salts, bath tablets, bath liquids, etc.), foam baths (bubble baths, etc.), bath oils (bath perfumes, bath capsules, etc.), milk baths, bath jellies, bath cubes, etc.; Detergents such as heavy duty laundry detergent, light duty laundry detergent, liquid detergent, laundry soap, compact detergent, powdered soap, etc.; Fabric softeners, furniture care products, etc.; Cleaning agents such as cleansers, house cleaners, toilet cleaners, bathroom cleaners, glass cleaners, mould removers, drain cleaners; Kitchen detergents such as kitchen soap, synthetic kitchen soap, and dishwashing detergent; Bleaching agents such as oxidative bleaches (chlorine bleaches, oxygen bleaches, etc.), reductive bleaches (sulfur bleaches, etc.), and optical bleaches; Aerosols such as spray types and powder sprays; Examples include deodorants and air fresheners in solid, gel, and liquid types (water-based and oil-based), daily necessities and miscellaneous items such as tissue paper and toilet paper, non-prescription products such as liquid bath additives, mouthwash, and repellents (mist spray type and water-based liquid type), pharmaceuticals such as medicated cosmetics and medicated lotions, etc.

[0021] The compound of the present invention can be added to a consumer product in a concentration range of 0.00001 to 10000 ppb, preferably 0.0001 to 1000 ppb, more preferably 0.001 to 100 ppb, based on the weight of the consumer product.

[0022] Furthermore, all geometric isomers of the compound of the present invention are useful as fragrance components, and any isomer or mixture of isomers can be used in the fragrance composition of the present invention. EXAMPLES

[0023] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. [Measuring equipment] The analytical instruments used in the examples are as follows:

[0024] NMR measurement device: AVANCEIII 500 (BRUKER BIO SPIN KK: manufactured by Bruker Biospin) Gas chromatograph mass spectrometer: GCMS-QP2010 (Shimadzu Corporation) Gas chromatograph-Orbitrap mass spectrometer: TRACE1310 (GC) + Exactive GC (mass spectrometer) (Thermo Fisher Scientific) High Performance Liquid Chromatograph Pump: LC-20A (Shimadzu Corporation) Detector: SPD-M20A (GL Sciences) Separation column: YMC-Triart C18 ExRS (manufactured by YMC)

[0025] (Example 1) Synthesis of Compound (1a) and Compound (1b) (1) Synthesis of (E)-6,10-dimethylundeca-5,9-dien-2-ol

[0026] [ka]

[0027] A solution of (E)-6,10-dimethylundeca-5,9-dien-2-one (58.30 g, 0.3 mol) in methanol (250 mL) was cooled to 0°C, sodium borohydride (11.35 g, 0.3 mol) was added, and the mixture was reacted for 2 hours. Diethyl ether and water were then added to separate the organic layer. The separated organic layer was purified by distillation to obtain 45.14 g (Yield: 76.6%, GC purity: 92.6%) of (E)-6,10-dimethylundeca-5,9-dien-2-ol.

[0028] (2) Synthesis of (E)-6,10-dimethylundec-5,9-dien-2-yl acetate

[0029] [ka]

[0030] Acetyl chloride (19.85 g, 0.25 mol) and pyridine (22.2 mL, 0.28 mol) were added to a toluene (200 mL) solution of (E)-6,10-dimethylundeca-5,9-dien-2-ol (45.14 g, 0.23 mol) obtained in (1) above, and the mixture was allowed to react at room temperature for 2 hours. Water was added to the reaction solution, and the organic layer was separated. The separated organic layer was purified by distillation to obtain 49.05 g (Yield: 89.5%, GC purity: 93.1%) of (E)-6,10-dimethylundeca-5,9-dien-2-yl acetate.

[0031] (3) Synthesis of (E)-9-chloro-6,10-dimethylundeca-5,10-dien-2-yl acetate

[0032] [ka]

[0033] A solution of calcium hypochlorite (3.57 g, 0.025 mol), tetrabutylammonium bromide (298 mg) and acetic acid (3.30 g, 0.055 mol) in water (15 mL) was added to a solution of (E)-6,10-dimethylundeca-5,9-dien-2-yl acetate (11.92 g, 0.05 mol) obtained in (2) above in ethyl acetate (120 mL), and reacted at 0° C. for 2 hours. Water was added to this reaction solution, and the organic layer was separated. The separated organic layer was concentrated to obtain 15.47 g of crude (E)-9-chloro-6,10-dimethylundeca-5,10-dien-2-yl acetate.

[0034] (4) Synthesis of (5E)-11-formyloxy-6,10-dimethylundec-5,9-dien-2-yl acetate

[0035] [ka]

[0036] Tetrabutylammonium iodide (10.71g, 0.03mol) and potassium formate (12.20g, 0.15mol) were added to a N,N-dimethylformamide (100mL) solution of the mixture (7.91g, 0.03mol) of (E)-9-chloro-6,10-dimethylundec-5,10-dien-2-yl acetate and 5-chloro-10-methyl-6-methyleneundec-9-en-2-yl acetate obtained in (3) above, and the mixture was reacted at 80°C for 2 hours. A 5% aqueous lithium chloride solution (200mL) and hexane were added to the reaction solution, and the organic layer was separated. The separated organic layer was concentrated to obtain crude (5E)-11-formyloxy-6,10-dimethylundec-5,9-dien-2-yl acetate. At this time, (Z)-6-formylmethyl-10-methylundeca-5,9-dien-2-yl acetate was produced as a by-product at a yield of 42%. Purification was performed using silica gel column chromatography (hexane:ethyl acetate=30:1) to obtain 2.93 g of (5E)-11-formyloxy-6,10-dimethylundeca-5,9-dien-2-yl acetate (yield: 39.7%, GC purity: 52.7%).

[0037] (5) Synthesis of (5E)-11-hydroxy-6,10-dimethylundec-5,9-dien-2-yl acetate

[0038] [ka]

[0039] Triethylamine (1.44 mL, 0.01 mol) was added to a methanol (50 mL) solution of (5E)-11-formyloxy-6,10-dimethylundeca-5,9-dien-2-yl acetate (2.93 g, 0.01 mol) obtained in (4), and the mixture was heated under reflux for 2 hours to obtain 1.56 g (5E)-11-hydroxy-6,10-dimethylundeca-5,9-dien-2-yl acetate (yield: 59.1%, GC purity: 90.1%).

[0040] (6) Synthesis of (5E,9E)-6,10-dimethyl-11-oxoundeca-5,9-dien-2-yl acetate and (5E,9Z)-6,10-dimethyl-11-oxoundeca-5,9-dien-2-yl acetate

[0041] [ka]

[0042] Manganese dioxide (5.33 g, 0.06 mol) was added to a hexane (50 mL) solution of (5E)-11-hydroxy-6,10-dimethylundec-5,9-dien-2-yl acetate (1.56 g, 0.006 mol) obtained in (5), and the reaction solution obtained by reacting for 8 hours at room temperature was purified using silica gel column chromatography (hexane:ethyl acetate=30:1) to obtain 0.6 g of a mixture of (5E,9E)-6,10-dimethyl-11-oxoundeca-5,9-dien-2-yl acetate (1a) and (5E,9Z)-6,10-dimethyl-11-oxoundeca-5,9-dien-2-yl acetate (1b) (yield 38.7%, GC purity 90.4%, 9Z / 9E=68 / 32). The synthesized mixture was purified by HPLC (eluent: water:acetonitrile = 36:64 (volume ratio)) to obtain (5E,9E)-6,10-dimethyl-11-oxoundeca-5,9-dien-2-yl acetate (1a) (purity 100%) and (5E,9Z)-6,10-dimethyl-11-oxoundeca-5,9-dien-2-yl acetate (1b) (purity 100%).

[0043] <Physical data for (5E,9E)-6,10-dimethyl-11-oxoundeca-5,9-dien-2-yl acetate> 1H NMR (500MHz, CDCl3) δ: 9.39(s,1H),6.46(t,J=7.33Hz,1H),5.15(t,J=7.16Hz,1H),4.88(m,1H),2.46(q,J=7.33Hz,2H),2.17(t,J =7.33Hz,2H),2.03(s,3H),2.03(m,2H),1.48-1.68(m,2H),1.75(s,3H),1.62(s,3H),1.21(d,J=6.25Hz,3H) 13C NMR(125MHz,CDCl3) δ: 195.31, 170.72, 154.26, 139.42, 134.20, 124.71, 70.46, 37.96, 35.80, 27.32, 23.88, 21.36, 19.97, 15.80, 9.21 HRMS(CI+):calcd C15H25O3([M+H]+)253.1798;found,253.1799

[0044] <Physical data of (5E,9Z)-6,10-dimethyl-11-oxoundeca-5,9-dien-2-yl acetate> 1H NMR (500MHz, CDCl3) δ: 10.12(s,1H),6.48(t,J=7.51Hz,1H),5.13(t,J=7.15Hz,1H),4.88(m,1H),2.66(q,J=7.51Hz,2H),2.15(t,J =7.51Hz,2H),2.03(s,3H),2.03(m,2H),1.48-1.68(m,2H),1.77(s,3H),1.60(s,3H),1.21(d,J=6.25Hz,3H) 13C NMR(125MHz,CDCl3) δ: 191.13,170.72,149.00,136.16,133.90,125.07,70.47,39.32,35.77,25.08,23.87,21.35,19.96,15.85,9.20 HRMS(CI+):calcd C15H25O3([M+H]+)253.1798;found,253.1797

[0045] Example 2 Grapefruit Food Flavor Composition Grapefruit food flavor composition (A) was prepared according to the following recipe using the compound of the present invention produced by the method described in Example 1. The mixture in Example 1 refers to a mixture of (5E,9E)-6,10-dimethyl-11-oxoundeca-5,9-dien-2-yl acetate and (5E,9Z)-6,10-dimethyl-11-oxoundeca-5,9-dien-2-yl acetate (the same applies to the following Examples). <Fragrance composition (A) formulation> (Ingredients) (Parts by weight) Mixture of Example 1 0.0001 Grapefruit oil (cold pressed) 50.0 Ethanol Residual Total 1000.0

[0046] Comparative Example 1 As Comparative Example 1, a grapefruit food flavor composition (B) was prepared according to the following recipe. <Fragrance composition (B) formulation> Grapefruit oil (cold pressed) 50.0 Ethanol Residual Total 1000.0 (Comparative Experimental Example 1) The grapefruit food flavor compositions (A) and (B) obtained in Example 2 and Comparative Example 1 were each added to water at 0.1% and subjected to a sensory test by six expert panelists. All panelists pointed out that the flavor composition (A) of Example 2 was far superior to the flavor composition (B) of Comparative Example 1, imparting a juicy citrus-like volume and a sandbag-like granular texture. The same was true when the 5E,9E isomer and the 5E,9Z isomer were used.

[0047] (Example 3) Addition to a commercially available grapefruit juice drink The 5E,9E and 5E,9Z isomers obtained in Example 1, or a mixture thereof, were added at 0.1 ppb to a commercially available grapefruit juice beverage, and a sensory test was conducted by six expert panelists. All panelists pointed out that the addition of the 5E,9E and 5E,9Z isomers, or a mixture thereof, gave the beverage a rich, juicy, and natural fruity feel, making it far superior.

[0048] Example 4 Grapefruit Food Flavor Composition According to the following formulation, a grapefruit food flavor composition (C) was prepared. <Fragrance composition (C) formulation> (Ingredients) (Parts by weight) Mixture of Example 1 0.0001 Nootkaton 2.0 Octanal 0.3 Decal 0.2 Dodecanal 0.1 Linalool 0.8 cis-3-hexenol 0.5 Ethanol Residual Total 1000.0

[0049] Comparative Example 2 As Comparative Example 2, a grapefruit food flavor composition (D) was prepared according to the following recipe. <Fragrance composition (D) formulation> (Ingredients) (Parts by weight) Nootkaton 2.0 Octanal 0.3 Decal 0.2 Dodecanal 0.1 Linalool 0.8 cis-3-hexenol 0.5 Ethanol Residual Total 1000.0 (Comparative Experimental Example 2) The grapefruit food flavor compositions (C) and (D) obtained in Example 4 and Comparative Example 2 were each added to water at 0.1% and subjected to a sensory test by six expert panelists, who all pointed out that the flavor composition (C) of Example 4 was far superior to the flavor composition (D) of Comparative Example 2, imparting a juicy citrus-like volume and a sandbag-like granular texture. The same was true when the 5E,9E isomer and the 5E,9Z isomer were used.

[0050] Example 5: Orange food flavor composition According to the following recipe, an orange food flavor composition (E) was prepared. <Fragrance composition (E) formulation> (Ingredients) (Parts by weight) Mixture of Example 1 0.0001 Orange oil (cold pressed) 50.0 Ethanol Residual Total 1000.0

[0051] Comparative Example 3 As Comparative Example 3, an orange food flavor composition (F) was prepared according to the following recipe. <Fragrance composition (F) formulation> Orange oil (cold pressed) 50.0 Ethanol Residual Total 1000.0 (Comparative Experimental Example 3) The orange food flavor compositions (E) and (F) obtained in Example 5 and Comparative Example 3 were each added to water at 0.1% and subjected to a sensory test by six expert panelists, who all pointed out that the flavor composition (E) of Example 5 had a more natural peel feeling and a more citrus-like volume feeling, and was far superior to the flavor composition (F) of Comparative Example 3. The same was true when the 5E,9E isomer and the 5E,9Z isomer were used.

[0052] (Example 6) Addition to a commercially available orange juice drink The 5E,9E and 5E,9Z isomers obtained in Example 1, or a mixture thereof, were added at 0.1 ppb to a commercially available orange juice beverage, and a sensory test was conducted by six expert panelists. All panelists pointed out that the addition of the 5E,9E and 5E,9Z isomers, or a mixture thereof, enhanced the natural peel and fruity feel, making the beverage far superior.

[0053] Example 7: Orange food flavor composition According to the following recipe, an orange food flavor composition (G) was prepared. <Fragrance composition (G) formulation> (Ingredients) (Parts by weight) Mixture of Example 1 0.0001 Ethyl butyrate 0.5 Octanal 1.0 Nonanal 0.1 Decal 0.5 Linalool 2.0 Ethanol Residual Total 1000.0

[0054] Comparative Example 4 As Comparative Example 4, an orange food flavor composition (H) was prepared according to the following recipe. <Fragrance composition (H) formulation> (Ingredients) (Parts by weight) Ethyl butyrate 0.5 Octanal 1.0 Nonanal 0.1 Decal 0.5 Linalool 2.0 Ethanol Residual Total 1000.0 (Comparative Experimental Example 4) The orange food flavor compositions (G) and (H) obtained in Example 7 and Comparative Example 4 were each added to water at 0.1% and subjected to a sensory test by six expert panelists. All panelists pointed out that the flavor composition (G) of Example 7 was far superior to the flavor composition (H) of Comparative Example 4 in that it imparted a more natural peel feeling and fruit feeling. The same was true when the 5E,9E isomer and the 5E,9Z isomer were used.

[0055] Example 8: Lemon food flavor composition According to the following recipe, a lemon food flavor composition (I) was prepared. <Fragrance composition (I) formulation> (Ingredients) (Parts by weight) Mixture of Example 1 0.0001 Lemon Oil (Cold Press) 50.0 Ethanol Residual Total 1000.0

[0056] Comparative Example 5 As Comparative Example 5, a lemon food flavor composition (J) was prepared according to the following recipe. <Fragrance composition (J) formulation> Lemon Oil (Cold Press) 50.0 Ethanol Residual Total 1000.0 (Comparative Experimental Example 5) The lemon food flavor compositions (I) and (J) obtained in Example 8 and Comparative Example 5 were each added to water at 0.1% and subjected to a sensory test by six expert panelists. All panelists pointed out that flavor composition (I) of Example 8 had a stronger natural peel feeling and citrus-like volume feeling and was far superior to flavor composition (J) of Comparative Example 5. The same was true when the 5E,9E isomer and the 5E,9Z isomer were used.

[0057] (Example 9) Addition to a commercially available lemon juice drink A commercially available lemon juice beverage was added with 0.1 ppb of the 5E,9E and 5E,9Z isomers obtained in Example 1, or a mixture thereof, and a sensory test was conducted by six expert panelists. All panelists pointed out that the addition of the 5E,9E and 5E,9Z isomers, or a mixture thereof, enhanced the natural peel and fruity feel, making the beverage far superior.

[0058] (Example 10) Lemon food flavor composition A lemon food flavor composition (K) was prepared according to the following recipe. <Fragrance composition (K) formulation> (Ingredients) (Parts by weight) Mixture of Example 1 0.0001 Citral 3.0 α-Terpineol 1.0 Geraniol 0.5 Geranyl acetate 0.5 Neryl acetate 0.5 Ethanol Residual Total 1000.0

[0059] Comparative Example 6 As Comparative Example 6, a lemon food flavor composition (L) was prepared according to the following recipe. <Fragrance composition (L) formulation> (Ingredients) (Parts by weight) Citral 3.0 α-Terpineol 1.0 Geraniol 0.5 Geranyl acetate 0.5 Neryl acetate 0.5 Ethanol Residual Total 1000.0 (Comparative Experimental Example 6) The lemon food flavor compositions (K) and (L) obtained in Example 10 and Comparative Example 6 were each added to water at 0.1% and subjected to a sensory test by six expert panelists. All panelists pointed out that the flavor composition (K) of Example 10 imparted a more natural peel feeling and fruit feeling than the flavor composition (L) of Comparative Example 6 and was far superior. The same was true when the 5E,9E and 5E,9Z forms were used.

Claims

1. A compound represented by the following formula (1): 【Chemistry 1】 (In formula (1), R represents an alkyl group having 1 to 4 carbon atoms, and the wavy line represents cis or trans, or a mixture of cis and trans.)

2. 2. The compound according to claim 1, wherein R is a methyl group.

3. A fragrance composition comprising the compound according to claim 1 or 2.

4. The flavor composition according to claim 3, which is for use in food or beverage.

5. A food or drink, an oral composition, a tobacco product, or a consumer product comprising the compound or flavor composition according to any one of claims 1 to 4.

6. A method for producing a food or drink, an oral composition, a tobacco product, or a consumer product, comprising adding a compound or a flavor composition according to any one of claims 1 to 4.

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