WO2024252982A1 - Composition de parfum - Google Patents

Composition de parfum Download PDF

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Publication number
WO2024252982A1
WO2024252982A1 PCT/JP2024/019524 JP2024019524W WO2024252982A1 WO 2024252982 A1 WO2024252982 A1 WO 2024252982A1 JP 2024019524 W JP2024019524 W JP 2024019524W WO 2024252982 A1 WO2024252982 A1 WO 2024252982A1
Authority
WO
WIPO (PCT)
Prior art keywords
pentylpyridine
ethyl
compound
fragrance
flavor
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/JP2024/019524
Other languages
English (en)
Japanese (ja)
Inventor
明宏 瓦谷
太久 山田
高 相田
恭子 木嶋
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Takasago International Corp
Original Assignee
Takasago International Corp
Takasago Perfumery Industry Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Takasago International Corp, Takasago Perfumery Industry Co filed Critical Takasago International Corp
Publication of WO2024252982A1 publication Critical patent/WO2024252982A1/fr
Anticipated expiration legal-status Critical
Pending legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • A23L2/52—Adding ingredients
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
    • A24B15/36—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes

Definitions

  • the present invention relates to compounds and fragrance compositions that are useful as ingredients for blended fragrances.
  • Patent Document 1 describes that confectionery such as chewing gum in which the high-sensitivity sweetener aspartame is combined with a certain type of fruit flavoring or the like has a problem of developing a grassy odor, i.e., a dusty odor, over time, which becomes dusty, earthy, powdery, medicinal, or moldy.
  • a grassy odor i.e., a dusty odor
  • the present invention provides novel compounds with odors that are useful as blended fragrance ingredients and samples for fragrance development and research, fragrance compositions containing said compounds, and consumer products containing them.
  • the present inventors synthesized various compounds and investigated their odors, and found that alkyl-substituted pyridine compounds have an excellent and characteristic odor. That is, the present invention relates to the following [1] to [6].
  • R 1 to R 5 each represent the following (a) or (b): (a) R1 is a pentyl group, R2 is an ethyl group, and R3 to R5 are hydrogen atoms; (b) R1 is an ethyl group, any one of R2 to R5 is a pentyl group, and the remaining groups are hydrogen atoms.
  • a fragrance composition comprising the compound according to [1] above.
  • [4] A food or drink, an oral composition, a tobacco product, or a consumer product containing the compound according to [1] above or the flavor composition according to [2] or [3] above.
  • [5] A method for producing a food or beverage, an oral composition, a tobacco product, or a consumer product, comprising adding the compound according to [1] above or the flavor composition according to [2] or [3] above.
  • the present invention provides novel compounds with odors that are useful as ingredients for blended fragrances, fragrance compositions containing said compounds, and consumer products containing them.
  • R 1 to R 5 represent the following (a) or (b).
  • R 1 is a pentyl group
  • R 2 is an ethyl group
  • R 3 to R 5 are hydrogen atoms
  • R 1 is an ethyl group
  • any one of R 2 to R 5 is a pentyl group
  • the remaining groups are hydrogen atoms
  • R 1 to R 5 are (b)
  • the compound is 2-ethyl-3-pentylpyridine, 2-ethyl-4-pentylpyridine, 2-ethyl-5-pentylpyridine, or 2-ethyl-6-pentylpyridine.
  • the compounds of the present invention can be obtained by reacting an alkyllithium with a pyridine to alkylate the carbon atom (position 2) adjacent to the nitrogen atom of the pyridine ring.
  • a pyridine for example, 3-ethyl-2-pentylpyridine, described in the examples, can be obtained by the following method.
  • the compounds of the present invention each have a characteristic odor, they can be suitably used as blended fragrance materials.
  • the compounds of the present invention are also useful as samples for the development and examination of fragrances, such as indicators for determining off-odors.
  • fragrances such as indicators for determining off-odors.
  • 3-ethyl-2-pentylpyridine has an odor tone that corresponds to the dusty odor or earthy odor in foods and beverages, and can therefore be used as an indicator for determining off-odors.
  • the compounds of the present invention can be used as indicators for determining off-odors in the development of fragrances for effectively masking off-odors in foods and beverages.
  • the compound of the present invention When the compound of the present invention is used as a sample for developing and examining a fragrance, such as a blended fragrance raw material or an indicator for determining off-flavors, the compound of the present invention may be used alone or in combination of two or more kinds. Furthermore, the compound of the present invention may be used in combination with other fragrance ingredients as long as the characteristic odor of the compound of the present invention is not significantly impaired.
  • a fragrance such as a blended fragrance raw material or an indicator for determining off-flavors
  • the compound of the present invention may be used alone or in combination of two or more kinds. Furthermore, the compound of the present invention may be used in combination with other fragrance ingredients as long as the characteristic odor of the compound of the present invention is not significantly impaired.
  • the content of the compound of the present invention in the fragrance composition of the present invention is preferably 0.0001 to 100,000 ppm, more preferably 0.001 to 10,000 ppm, and even more preferably 0.01 to 1,000 ppm, based on the mass of the fragrance composition.
  • the compound of the present invention and the flavor composition of the present invention can be added in extremely small amounts as is to foods and beverages, oral compositions, tobacco products, consumer products, etc., to impart or enhance aroma and flavor to the products.
  • the content of the compound of the present invention in each product is not particularly limited as long as it is an effective amount, but is preferably 10 ppt to 100 ppm, more preferably 100 ppt to 10 ppm, and even more preferably 1 ppb to 1 ppm, based on the weight of each product.
  • Each product can be obtained by adding the compound of the present invention to a predetermined content.
  • food and beverages include beverages such as carbonated drinks, soft drinks, fruit juice drinks, dairy drinks, lactic acid bacteria drinks, energy drinks, soy milk, and tea drinks; alcoholic beverages such as chuhai, cocktail drinks, sparkling wine, fruit wine, and condiment wine; desserts such as ice cream, ice milk, lacto ice cream, frozen desserts, yogurt, pudding, jelly, and daily desserts; sweets such as caramel, candy, candy tablets, crackers, biscuits, cookies, pies, chocolate, snacks, and chewing gum; soups such as Japanese-style soup and Western-style soup; jams; flavor seasonings; various instant drinks; and various instant foods.
  • beverages such as carbonated drinks, soft drinks, fruit juice drinks, dairy drinks, lactic acid bacteria drinks, energy drinks, soy milk, and tea drinks
  • alcoholic beverages such as chuhai, cocktail drinks, sparkling wine, fruit wine, and condiment wine
  • desserts such as ice cream, ice milk, lacto ice cream, frozen desserts, yogurt, pudding, jelly, and daily desserts
  • sweets such
  • oral compositions examples include toothpaste, mouthwash, mouthwash, lozenges, chewing gums, etc.
  • Tobacco products include cigarettes and e-cigarettes.
  • consumer products include fragrance products such as perfume, eau de perfume, 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, etc.; 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.; Suntanning cosmetics such as tanning products and sunscreen products; Medicinal cosmetics such as antiperspirants, aftershave lotions and gels, permanent wave agents, medicinal soaps, medicinal shampoos, and medicinal skin cosmetics; Hair care products such as shampoo, rinse, rinse-in shampoo, conditioner, treatment, hair pack, etc.
  • Basic cosmetics such as face wash cream, cleansing cream, milky lotion, toner, and serum
  • Finishing cosmetics such
  • Soaps such as toilet soap, bath soap, perfumed soap, transparent soap, synthetic soap, etc.
  • Personal cleansing products such as body soap, 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.
  • Cleaning agents such as cleansers, house cleaners, toilet cleaners, bathroom cleaners, glass cleaners, mould removers, drain cleaners, etc.
  • Kitchen detergents such as kitchen soap, synthetic kitchen soap, and dishwashing detergent
  • Bleaching agents such as oxidative bleaching agents (chlorine bleaching agents, oxygen bleaching agents, etc.), reductive bleaching agents (sul
  • the compound or flavor composition of the present invention can also be mixed with other flavor ingredients and added to each of the above-mentioned products and compositions to impart or enhance the desired aroma or flavor, for example, a citrus-like aroma or flavor.
  • other flavor ingredients 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 the Japan Patent Office Gazette, Well-Known and Commonly Used Technology Collection (Fragrances), Part II Food Flavors, p. 88-131, published January 14, 2000.
  • the aromas and flavors that are imparted or enhanced in the present invention include, but are not limited to, galbanum-like, green, floral, spicy, chemical, earthy, dusty, citrus-like, tropical fruit-like, sweet, powdery, clay-like, and rubber-like.
  • Example 1 Synthesis of 3-ethyl-2-pentylpyridine 5.0 g of pentyl chloride was reacted with 0.65 g of metallic lithium in tetrahydrofuran (THF) at -20 to -10°C to prepare pentyllithium, and then 5.0 g of 3-ethylpyridine was added while cooling with dry ice, and the mixture was stirred and then allowed to warm to room temperature. Water was added, the solvent was distilled off, and the mixture was extracted with toluene, washed with water, and separated by silica gel column chromatography to obtain 296 mg of the target 3-ethyl-2-pentylpyridine as a deep yellow oil.
  • THF tetrahydrofuran
  • Example 2 Synthesis of 3-pentylpyridine 39.6 mL of toluene was added to 39.6 mL of 1.2 M sec-butyllithium hexane solution, and 5.0 g of 3-bromopyridine was added while cooling with dry ice to react, and then 4.54 g of pentyl bromide in THF solution was added and stirred, and the temperature was raised to room temperature. Water was added, the solvent was distilled off, and the product was extracted with toluene, washed with water, and separated by silica gel column chromatography to obtain 829 mg of the target 3-pentylpyridine as a deep yellow oil.
  • Example 3 Synthesis of 2-ethyl-3-pentylpyridine and 2-ethyl-5-pentylpyridine A THF solution of 810 mg of 3-pentylpyridine was cooled with dry ice, and 23.9 mL of a benzene solution of 0.5 M ethyllithium was added to react, and the temperature was then raised to room temperature. Water was added, the solvent was distilled off, and the mixture was extracted with toluene, washed with water, and separated by silica gel column chromatography to obtain 121 mg and 100 mg of the desired 2-ethyl-3-pentylpyridine and 2-ethyl-5-pentylpyridine as reddish brown oils, respectively.
  • Example 4 Synthesis of 2-ethyl-4-pentylpyridine A THF solution of 1.0 g of 4-pentylpyridine was cooled with dry ice, and 14.7 mL of a 0.5 M ethyllithium benzene solution was added and stirred, and then the mixture was allowed to warm to room temperature. Water was added, the solvent was distilled off, and the mixture was extracted with toluene, washed with water, and separated by silica gel column chromatography to obtain 694 mg of the target 2-ethyl-4-pentylpyridine as a deep yellow oil.
  • Example 5 Synthesis of 2-ethyl-6-pentylpyridine A THF solution of 2.5 g of pentyl chloride was reacted with 0.33 g of metallic lithium at -20 to -10°C to prepare pentyllithium, and then 2.0 g of 2-ethylpyridine was added while cooling with dry ice, and the mixture was stirred and then allowed to warm to room temperature. Water was added, the solvent was distilled off, and the mixture was extracted with toluene, washed with water, and separated by silica gel column chromatography to obtain 209 mg of the target 2-ethyl-6-pentylpyridine as a deep yellow oil.
  • Example 6 Aroma evaluation of synthesized 3-ethyl-2-pentylpyridine, 2-ethyl-3-pentylpyridine, 2-ethyl-4-pentylpyridine, 2-ethyl-5-pentylpyridine, and 2-ethyl-6-pentylpyridine An aroma evaluation was carried out on the alkyl-substituted pyridines obtained in Examples 1, 3, 4, 5, and 6. Representative comments from expert panelists are shown in Table 1 below.
  • Example 7 Fragrance composition with floral, green and powdery notes containing 3-ethyl-2-pentylpyridine Fragrance compositions having floral, green and powdery notes were prepared using the 3-ethyl-2-pentylpyridine obtained in Example 1, and the odor was evaluated.
  • the formulation containing 3-ethyl-2-pentylpyridine (fragrance composition 1) and the formulation not containing 3-ethyl-2-pentylpyridine (fragrance composition 2) are listed in Table 2 below. The amount of each component is expressed in parts by mass.
  • fragrance composition 1 which contains 3-ethyl-2-pentylpyridine, imparts a natural galbanum-like green, earthy note.
  • Example 8 Fragrance composition with citrus, fruity and grapefruit notes containing 3-ethyl-2-pentylpyridine Fragrance compositions with citrus, fruity and grapefruit notes were prepared using the 3-ethyl-2-pentylpyridine obtained in Example 1, and the odor was evaluated.
  • the formulation containing 3-ethyl-2-pentylpyridine (fragrance composition 3) and the formulation not containing 3-ethyl-2-pentylpyridine (fragrance composition 4) are listed in Table 3 below. The amount of each component is expressed in parts by mass.
  • fragrance composition 3 which contains 3-ethyl-2-pentylpyridine, imparts a fresh, green note reminiscent of citrus peel.
  • Apple fragrance composition containing 3-ethyl-2-pentylpyridine Using the 3-ethyl-2-pentylpyridine obtained in Example 1, apple fragrance composition 5 was prepared according to the recipe in Table 4.
  • apple fragrance composition 6 was prepared according to the recipe in Table 4. The amount of each component is expressed in parts by mass.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nutrition Science (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Toxicology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Pyridine Compounds (AREA)

Abstract

La présente invention concerne : un composé capable d'améliorer un arôme caractéristique ; et une composition de parfum. La présente invention concerne : un composé représenté par la formule générale (1) ; et une composition de parfum contenant le composé. (Dans la formule (1), R1 à R5 sont tels que définis dans la description.)
PCT/JP2024/019524 2023-06-07 2024-05-28 Composition de parfum Pending WO2024252982A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2023-093963 2023-06-07
JP2023093963 2023-06-07

Publications (1)

Publication Number Publication Date
WO2024252982A1 true WO2024252982A1 (fr) 2024-12-12

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04255796A (ja) * 1991-02-07 1992-09-10 Kao Corp 香料組成物
JPH04312573A (ja) * 1991-04-11 1992-11-04 Shiono Koryo Kk ピリジン誘導体及び該誘導体を含有する香料組成物
JPH0517445A (ja) * 1991-07-12 1993-01-26 Shiono Koryo Kk ピリジン誘導体及び該誘導体を含有する香料組成物
WO2011121469A1 (fr) * 2010-03-29 2011-10-06 Firmenich Sa Pyridines 2,4-disubstituées comme ingrédients parfumants
WO2017046060A1 (fr) * 2015-09-17 2017-03-23 Henkel Ag & Co. Kgaa Composition de parfum contenant des composés modulateurs de fragrance pour augmenter l'intensité de parfum

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04255796A (ja) * 1991-02-07 1992-09-10 Kao Corp 香料組成物
JPH04312573A (ja) * 1991-04-11 1992-11-04 Shiono Koryo Kk ピリジン誘導体及び該誘導体を含有する香料組成物
JPH0517445A (ja) * 1991-07-12 1993-01-26 Shiono Koryo Kk ピリジン誘導体及び該誘導体を含有する香料組成物
WO2011121469A1 (fr) * 2010-03-29 2011-10-06 Firmenich Sa Pyridines 2,4-disubstituées comme ingrédients parfumants
WO2017046060A1 (fr) * 2015-09-17 2017-03-23 Henkel Ag & Co. Kgaa Composition de parfum contenant des composés modulateurs de fragrance pour augmenter l'intensité de parfum

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
WU CHONGYANG, YING TAO, FAN HANGQIAN, HU CHENHUI, SU WEIKE, YU JINGBO: "C-4 Regioselective Alkylation of Pyridines Driven by Mechanochemically Activated Magnesium Metal", ORGANIC LETTERS, vol. 25, no. 14, 14 April 2023 (2023-04-14), US , pages 2531 - 2536, XP093246148, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.3c00684 *

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