Fragrance composition

Abstract

The purpose of the present invention is to provide a fragrance composition capable of enhancing citrus-like aroma and fragrance. The present invention relates to a perfume composition containing (5E)-6, 10-dimethyl-11-oxoundec-5, 9-dien-2-yl acetate, and to a method for producing the perfume composition containing (5E)-6, 10-dimethyl-11-oxoundec-5, 9-dien-2-yl acetate.

Description

Technical Field

[0001] This invention relates to compounds and flavor compositions that are useful as raw materials for blending flavorings. Background Technology

[0002] In recent years, due to the diversification of consumer preferences, there has been a strong demand for fruity, natural, and distinctive aromas in flavorings used in food and beverage products. However, traditional combinations of flavoring ingredients sometimes fail to meet these requirements, creating a strong need for new flavoring materials. Summary of the Invention

[0003] The present invention provides a novel aromatic compound useful as a raw material for blending fragrances and the like, and a fragrance composition containing the compound.

[0004] The inventors synthesized various compounds and studied their aromas, and found that compounds with aldehyde and ester structures at the ends have excellent aromas.

[0005] That is, the present invention relates to the following [1] to [6].

[0006] [1] A compound represented by the following formula (1).

[0007]

[0008] (In formula (1), R represents an alkyl group with 1 to 4 carbon atoms, and the wavy line represents cis or trans, or a mixture of cis and trans.)

[0009] [2] According to the compound described in [1] above, wherein R is methyl.

[0010] [3] A fragrance composition comprising the compounds described in [1] or [2] above.

[0011] [4] The spice composition according to [3] above is used in food and beverage products.

[0012] [5] Food and beverage products, oral compositions, tobacco products or consumer products, wherein the product contains the compound described in [1] or [2] above, or the flavoring composition described in [3] or [4].

[0013] [6] A method for manufacturing food and beverage products, oral compositions, tobacco products or consumer products, characterized in that the compound described in [1] or [2] above, or the flavoring composition described in [3] or [4] above, is added.

[0014] According to the present invention, it is possible to provide novel aromatic compounds useful as raw materials for blending fragrances, and fragrance compositions containing such compounds. Detailed Implementation

[0015] The present invention will now be described in detail.

[0016] For the (5E)-6,10-dimethyl-11-oxoundec-5,9-dien-2-ylcarboxylic acid ester (hereinafter also referred to as the compound of the present invention), in the case of an acetate ester, there are two isomers represented by (1a) and (1b) below. Either one can be used alone, or they can be used in the form of a mixture thereof, with compound (1a) being preferred.

[0017]

[0018] In addition, there are two mirror isomers, represented by (1c) and (1d) below. Either one can be used alone, or they can be used in mixtures.

[0019]

[0020] The compounds (1a) and (1b) of the present invention can be prepared by, for example, the following steps.

[0021] NaBH4 was used to act on geranylacetone for ketone reduction, followed by acetylation with acetyl chloride to produce geranylace acetate. Next, allyl chloride was synthesized by chlorination of calcium hypochlorite, followed by the introduction of a hydroxyl group via formate transfer, and then allyl alcohol was synthesized from triethylamine. This was then oxidized with manganese dioxide to obtain a mixture of compounds (1a) and (1b). The above steps are summarized and shown in the following synthetic scheme.

[0022]

[0023] (In the composite scheme, the wavy line represents either a cis or an inverse, or a mixture of both.)

[0024] The compounds (1a) and (1b) of the present invention obtained in this way can be purified by distillation, various chromatographic methods, etc.

[0025] The compounds of this invention have excellent aroma and can be used alone or in combination with other ingredients as flavoring agents in food and beverage products, oral compositions, tobacco products, etc.

[0026] The flavoring compositions and compounds of the present invention can be directly incorporated into food and beverage products in minute quantities to impart or enhance aroma and flavor, or they can be mixed with other ingredients to impart or enhance aroma and flavor. Other flavoring ingredients that can be mixed include various synthetic flavorings, natural flavorings, natural essential oils, plant extracts, etc., for example, as cited in the Patent Office Gazette, publicly known. The natural essential oils, natural flavorings, and synthetic flavorings are recorded in the "Common Techniques (Flavors) Part II Food Flavorings, pp. 88-131, issued on January 14, 2013".

[0027] The compounds of the present invention in the fragrance composition of the present invention vary depending on the other fragrance ingredients mixed in, and cannot be generalized. Generally, based on the weight of the fragrance composition, the concentration range can be 0.00001 to 10000 ppm, preferably 0.0001 to 1000 ppm, and more preferably 0.001 to 100 ppm.

[0028] In addition, when the compounds of the present invention are added to food and beverages to enhance aroma and flavor, the concentration range relative to the weight of the food and beverage can be 0.00001 to 10000 ppb, preferably 0.0001 to 1000 ppb, and more preferably 0.001 to 100 ppb.

[0029] The fragrance compositions of the present invention containing the compounds of the present invention may contain, as needed, commonly used solvents such as water and ethanol; and fixatives such as ethylene glycol, propylene glycol, dipropylene glycol, glycerin, ethylene glycol hexyl ether, benzyl benzoate, triethyl citrate, diethyl phthalate, HERCOLYN, triacetin, medium-chain triglycerides, and medium-chain diglycerides.

[0030] The aroma and flavor of food and beverages can be enhanced by adding flavoring compositions containing compounds of the present invention or by adding the compounds of the present invention themselves.

[0031] Specific examples of food and beverage products whose aroma and flavor can be enhanced by adding the flavoring composition or compound of the present invention include, for example, beverages such as carbonated drinks, refreshing drinks, fruit juice drinks, fruit wines, dairy drinks, lactic acid bacteria drinks, health functional drinks, soy milk, and tea drinks; desserts such as ice cream, popsicles, ice cream, frozen desserts, yogurt, pudding, jelly, and everyday desserts; snacks such as caramel, candy, compressed candy, crispy crackers, biscuits, cookies, pies, chocolate, snacks, chewing gum, steamed buns, and lamb liver soup; soups such as Japanese thick soup, Western thick soup, and Chinese thick soup; breads; jams; flavorings; various instant beverages; and various convenience foods.

[0032] The amount of flavoring composition added to food and beverage varies depending on the type and form of the product. Generally, based on the weight of the food or beverage, the concentration range is 0.1%, preferably 0.001 to 5%.

[0033] Examples of oral compositions that can be imbued with aroma and flavor by the fragrance composition or compound of the present invention include, for example, toothpaste, oral cleansers, mouthwash, lozenges, and chewable gum. The amount of fragrance composition added to the oral composition varies depending on the type and form of the product, and is generally preferably 0.01 to 5% by mass, more preferably 0.1 to 3% by mass, relative to the total mass of the oral composition.

[0034] Examples of tobacco products that can be endowed with aroma and flavor by the flavoring composition or compounds of the present invention include cigarettes and electronic cigarettes. The amount of flavoring composition added to the tobacco product varies depending on the type and form of the product, and for example, it is preferably 0.00001 to 90% by mass, more preferably 0.0001 to 50% by mass, relative to the total mass of the tobacco leaf portion.

[0035] As specific examples of consumer goods, the following can be cited:

[0036] Perfume, eau de parfum, eau de toilette, cologne and other fragrance products;

[0037] Basic cosmetics such as facial cleanser, makeup remover, lotion, toner, and serum;

[0038] Lipstick, lip balm, eyeliner, mascara, eyeshadow, eyebrow powder, eye patches, nail polish, nail polish remover, and other color cosmetics;

[0039] Hair cosmetics such as hair wax, hair oil, styling spray, hair wax sticks, solid hair wax, hair oil, hair conditioner, hair lotion, hair styling liquid, styling spray, hair cream, hair growth agent, and hair dye;

[0040] Sunscreen cosmetics such as tanning products and sun protection products;

[0041] Antiperspirants, aftershave lotions and shaving gels, hair perming agents, medicated soaps, medicated shampoos, medicated skin cosmetics, and other medicated cosmetics;

[0042] Shampoo, conditioner, 2-in-1 shampoo, hair conditioner, repair cream, hair mask and other hair care products;

[0043] Soaps including cosmetic soaps, bath soaps, perfumed soaps, transparent soaps, and synthetic soaps;

[0044] Body washes, shower gels, shampoos, hand soaps, face creams, and other body cleansing agents;

[0045] Bath products (bath salts, bath sheets, shower gel, etc.), foam baths (bubble baths, etc.), bath oils (bath perfumes, bath capsules, etc.), milk baths, bath gels, bath fragrance blocks, and other bath products;

[0046] Heavy-duty laundry detergent, light-duty laundry detergent, liquid laundry detergent, laundry soap, concentrated laundry detergent, powdered soap, and other laundry detergents;

[0047] Fabric softener, furniture conditioner, and other fabric softening and conditioning products;

[0048] Cleaning agents such as scouring powder, household cleaners, toilet cleaners, bathroom cleaners, glass cleaners, mold removers, and drain cleaners;

[0049] Kitchen detergents, including kitchen soaps, synthetic kitchen soaps, and dishwashing liquids;

[0050] Oxidizing bleaching agents (chlorine-based bleaching agents, oxygen-based bleaching agents, etc.), reducing bleaching agents (sulfur-based bleaching agents, etc.), optical bleaching agents, and other bleaching agents;

[0051] aerosols such as spray type and powder spray;

[0052] Deodorizers include solid, gel, and liquid (water-based and oil-based) types. daily necessities such as air fresheners, tissues, and toilet paper Groceries, liquid bath products, mouthwash, repellents (water spray type, water-based liquid type) and other quasi-drugs, pharmaceutical cosmetics, pharmaceutical lotions and other pharmaceutical products, etc.

[0053] The amount of the compound of the present invention added to a consumer product relative to the weight of the consumer product can be in the concentration range of 0.00001 to 10000 ppb, preferably 0.0001 to 1000 ppb, and more preferably 0.001 to 100 ppb.

[0054] In addition, the geometric isomers of the compounds of the present invention are useful as aroma components, and any isomers and mixtures of isomers can be used in the fragrance compositions of the present invention.

[0055] Example

[0056] The present invention will now be described in more detail with reference to embodiments, but the present invention is not limited to these embodiments.

[0057] [Measuring Instruments]

[0058] The analytical instruments used in the examples are shown below.

[0059] NMR measuring apparatus: AVANCEIII 500 (BRUKER BIO SPIN KK: Bruker BioSpin)

[0060] Gas Chromatograph-Mass Spectrometer: GCMS-QP2010 (Shimadzu Corporation)

[0061] Gas Chromatography-Orbitrap Mass Spectrometer: TRACE1310 (GC) + Exactive GC (Mass Spectrometer) (Thermo Fisher Scientific)

[0062] High Performance Liquid Chromatography

[0063] Pump: LC-20A (manufactured by Shimadzu Corporation)

[0064] Detector: SPD-M20A (manufactured by GL Sciences)

[0065] Separation column: YMC-Triart C18 ExRS (manufactured by YMC)

[0066] (Example 1) Synthesis of compounds (1a) and (1b)

[0067] (1) Synthesis of (E)-6,10-dimethylundec-5,9-dien-2-ol

[0068]

[0069] A methanol (250 mL) solution of (E)-6,10-dimethylundec-5,9-dien-2-one (58.30 g, 0.3 mol) was cooled to 0 °C, and sodium borohydride (11.35 g, 0.3 mol) was added. After reacting for 2 hours, diethyl ether and water were added, and the organic layer was separated. The separated organic layer was purified by distillation to obtain 45.14 g of (E)-6,10-dimethylundec-5,9-dien-2-ol (yield: 76.6%, GC purity: 92.6%).

[0070] (2) Synthesis of (E)-6,10-dimethylundec-5,9-diene-2-yl acetate

[0071]

[0072] 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-dimethylundec-5,9-dien-2-ol (45.14 g, 0.23 mol) obtained in (1) above, and the mixture was reacted at room temperature for 2 hours. Water was added to the reaction mixture, and the organic layer was separated. The separated organic layer was purified by distillation to obtain 49.05 g of (E)-6,10-dimethylundec-5,9-dien-2-yl acetate (yield: 89.5%, GC purity: 93.1%).

[0073] (3) Synthesis of (E)-9-chloro-6,10-dimethylundec-5,10-diene-2-yl acetate

[0074]

[0075] To a solution of (E)-6,10-dimethylundec-5,9-dien-2-yl acetate (11.92 g, 0.05 mol) in ethyl acetate (120 mL) obtained in (2) above, 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) were added, and the mixture was reacted at 0 °C for 2 hours. Water was added to the 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-dimethylundec-5,10-dien-2-yl acetate.

[0076] (4) Synthesis of (5E)-11-formyloxy-6,10-dimethylundec-5,9-diene-2-yl acetate

[0077]

[0078] In a solution of N,N-dimethylformamide (100 mL), a mixture (7.91 g, 0.03 mol) 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 was added, tetrabutylammonium iodide (10.71 g, 0.03 mol) and potassium formate (12.20 g, 0.15 mol) were added, and the mixture was reacted at 80 °C for 2 hours. A 5% lithium chloride aqueous solution (200 mL) 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.

[0079] At this point, as a byproduct, 42% of (Z)-6-formylmethyl-10-methylundec-5,9-diene-2-yl acetate was generated.

[0080] Purification was performed using silica gel column chromatography (hexane:ethyl acetate = 30:1) to obtain 2.93 g of (5E)-11-formyloxy-6,10-dimethylundec-5,9-diene-2-yl acetate (yield: 39.7%, GC purity: 52.7%).

[0081] (5) Synthesis of (5E)-11-hydroxy-6,10-dimethylundec-5,9-diene-2-yl acetate

[0082]

[0083] Triethylamine (1.44 mL, 0.01 mol) was added to a methanol (50 mL) solution of (5E)-11-formyloxy-6,10-dimethylundec-5,9-dien-2-yl acetate (2.93 g, 0.01 mol), and the mixture was heated under reflux for 2 hours. 1.56 g of (5E)-11-hydroxy-6,10-dimethylundec-5,9-dien-2-yl acetate was obtained (yield: 59.1%, GC purity: 90.1%).

[0084] (6) Synthesis of (5E,9E)-6,10-dimethyl-11-oxoundec-5,9-dien-2-yl acetate and (5E,9Z)-6,10-dimethyl-11-oxoundec-5,9-dien-2-yl acetate

[0085]

[0086] In a hexane (50 mL) solution of (5E)-11-hydroxy-6,10-dimethylundecane-5,9-diene-2-yl acetate (1.56 g, 0.006 mol), manganese dioxide (5.33 g, 0.06 mol) was added and reacted at room temperature for 8 hours. The resulting reaction solution was purified by silica gel column chromatography (hexane: ethyl acetate = 30:1) to obtain a mixture of 0.6 g of (5E,9E)-6,10-dimethyl-11-oxoundecane-5,9-diene-2-yl acetate (1a) and (5E,9Z)-6,10-dimethyl-11-oxoundecane-5,9-diene-2-yl acetate (1b) (yield 38.7%, GC purity 90.4%, 9Z / 9E = 68 / 32).

[0087] The synthesized mixture was purified by HPLC (elution buffer; water: acetonitrile = 36:64 (volume ratio)) to obtain (5E,9E)-6,10-dimethyl-11-oxoundec-5,9-dien-2-yl acetate (1a) (purity 100%) and (5E,9Z)-6,10-dimethyl-11-oxoundec-5,9-dien-2-yl acetate (1b) (purity 100%).

[0088] <Physical data of (5E,9E)-6,10-dimethyl-11-oxoundec-5,9-diene-2-yl acetate>

[0089] 1H NMR (500MHz, CDCl3) δ:

[0090] 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)

[0091] 13C NMR (125MHz, CDCl3) δ:

[0092] 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

[0093] HRMS (CI+): calcd C15H25O3 ([M+H]+) 253.1798; found, 253.1799

[0094] <Physical data of (5E,9Z)-6,10-dimethyl-11-oxoundec-5,9-diene-2-yl acetate>

[0095] 1H NMR (500MHz, CDCl3) δ:

[0096] 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)

[0097] 13C NMR (125MHz, CDCl3) δ:

[0098] 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

[0099] HRMS (CI+): calcd C15H25O3 ([M+H]+) 253.1798; found, 253.1797

[0100] (Example 2) Grapefruit food flavoring composition

[0101] Grapefruit food flavoring composition (A) was prepared according to the following formulation using the compound of the present invention manufactured by the method described in Example 1. It should be noted that the mixture in Example 1 refers to a mixture of (5E,9E)-6,10-dimethyl-11-oxoundec-5,9-dien-2-yl acetate and (5E,9Z)-6,10-dimethyl-11-oxoundec-5,9-dien-2-yl acetate (the same applies to the following examples).

[0102]

[0103] (Comparative Example 1)

[0104] As a comparative example 1, a grapefruit food flavoring composition (B) was prepared according to the following formulation.

[0105]

[0106] (Comparative Experiment Example 1)

[0107] Grapefruit flavoring compositions (A) and (B) obtained in Example 2 and Comparative Example 1 were added to water at 0.1% each. Sensory tests were conducted by six evaluators. The results showed that flavoring composition (A) of Example 2 imparted a superior citrus-like juiciness and a more grainy texture compared to flavoring composition (B) of Comparative Example 1. The same result was observed when using either the 5E,9E or 5E,9Z formulation alone.

[0108] (Example 3) Added to commercially available grapefruit juice beverages

[0109] In a commercially available grapefruit juice beverage, 0.1 ppb of the 5E,9E, 5E,9Z, or a mixture thereof obtained in Example 1 was added. A sensory test was conducted by six evaluators. The results showed that all evaluators noted that the addition of the 5E,9E, 5E,9Z, or a mixture thereof imparted a full-bodied, natural fruity flavor, which was exceptionally good.

[0110] (Example 4) Grapefruit food flavoring composition

[0111] Prepare a grapefruit flavoring composition (C) according to the following formula.

[0112]

[0113] (Comparative Example 2)

[0114] As a comparative example 2, a grapefruit food flavoring composition (D) was prepared according to the following formulation.

[0115]

[0116] (Comparative Experiment Example 2)

[0117] Grapefruit flavoring compositions (C) and (D) obtained in Example 4 and Comparative Example 2 were added to water at 0.1% each. Sensory tests were conducted by six evaluators. The results showed that flavoring composition (C) of Example 4 imparted a more citrusy, juicy, and full-bodied feel, as well as a more grainy, granular texture, compared to flavoring composition (D) of Comparative Example 2. The same result was observed when using either the 5E,9E or 5E,9Z formulation alone.

[0118] (Example 5) Orange food flavoring composition

[0119] Prepare an orange flavoring composition (E) according to the following formula.

[0120]

[0121] (Comparative Example 3)

[0122] As a comparative example 3, an orange food flavoring composition (F) was prepared according to the following formulation.

[0123]

[0124] (Comparative Experiment Example 3)

[0125] The orange flavoring compositions (E) and (F) obtained in Example 5 and Comparative Example 3, respectively, were added to water at 0.1% and subjected to sensory testing by six evaluators. The results showed that all evaluators indicated that flavoring composition (E) of Example 5, compared to flavoring composition (F) of Comparative Example 3, exhibited a significantly enhanced natural peel texture and a full, citrus-like quality, demonstrating superior performance. The same effect was observed when using either 5E,9E or 5E,9Z formulations alone.

[0126] (Example 6) Added to commercially available orange juice beverages

[0127] In a commercially available orange juice beverage, 0.1 ppb of the 5E,9E, 5E,9Z, or a mixture thereof obtained in Example 1 was added. A sensory test was conducted by six evaluators. The results showed that the addition of the 5E,9E, 5E,9Z, or a mixture thereof enhanced the natural peel and fruit texture, resulting in exceptionally good sensory evaluation.

[0128] (Example 7) Orange food flavoring composition

[0129] Prepare an orange flavoring composition (G) according to the following formula.

[0130]

[0131] (Comparative Example 4)

[0132] As a comparative example 4, an orange food flavoring composition (H) was prepared according to the following formulation.

[0133]

[0134] (Comparative Experiment Example 4)

[0135] The orange flavoring compositions (G) and (H) obtained in Example 7 and Comparative Example 4, respectively, were added to water at 0.1%. Sensory tests were conducted by six evaluators. The results showed that flavoring composition (G) of Example 7 imparted a more natural peel and fruit flavor compared to flavoring composition (H) of Comparative Example 4, and was therefore superior. The same result was observed when using either the 5E,9E or 5E,9Z formulation alone.

[0136] (Example 8) Lemon food flavoring composition

[0137] Prepare a lemon food flavoring composition (I) according to the following formula.

[0138]

[0139] (Comparative Example 5)

[0140] As a comparative example 5, a lemon food flavoring composition (J) was prepared according to the following formulation.

[0141]

[0142] (Comparative Experiment Example 5)

[0143] The lemon flavoring compositions (I) and (J) obtained in Example 8 and Comparative Example 5, respectively, were added to water at 0.1% and subjected to sensory testing by six evaluators. The results showed that, compared to the flavoring composition (J) of Comparative Example 5, the flavoring composition (I) of Example 8 exhibited a significantly enhanced natural peel-like texture and a full, citrus-like quality, demonstrating exceptional superiority. The same effect was observed when using either the 5E,9E or 5E,9Z formulation alone.

[0144] (Example 9) Added to commercially available lemon juice beverages

[0145] In a commercially available lemon juice beverage, 0.1 ppb of the 5E,9E, 5E,9Z, or a mixture thereof obtained in Example 1 was added. A sensory test was conducted by six evaluators. The results showed that the addition of the 5E,9E, 5E,9Z, or a mixture thereof enhanced the natural peel and fruit texture, resulting in exceptionally good sensory evaluation.

[0146] (Example 10) Lemon food flavoring composition

[0147] Prepare a lemon food flavoring composition (K) according to the following formula.

[0148]

[0149] (Comparative Example 6)

[0150] As a comparative example 6, a lemon food flavoring composition (L) was prepared according to the following formulation.

[0151]

[0152] (Comparative Experiment Example 6)

[0153] The lemon flavoring compositions (K) and (L) obtained in Example 10 and Comparative Example 6 were added to water at 0.1% each. Sensory tests were conducted by six evaluators. The results showed that flavoring composition (K) of Example 10 imparted a more natural peel and fruity texture compared to flavoring composition (L) of Comparative Example 6, and was therefore superior. The same result was observed when using either the 5E,9E or 5E,9Z formulation alone.

Claims

1. A compound represented by the following formula (1), In formula (1), R represents an alkyl group with 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 claim 1, wherein, R stands for methyl.

3. A fragrance composition comprising the compound of any one of claims 1 or 2.

4. The flavoring composition according to claim 3, for use in food and beverage products.

5. Food and beverage products, oral care compositions, tobacco products, or consumer products, wherein, A flavoring composition containing any one of the compounds of claim 1 or 2, or any one of the flavorings of claim 3 or 4.

6. A method for manufacturing food and beverage products, oral compositions, tobacco products, or consumer products, characterized in that, Add the compound of any one of claims 1 or 2, or the flavoring composition of any one of claims 3 or 4.

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