GB1156482A - Pyrrole Flavouring Agents - Google Patents

Pyrrole Flavouring Agents

Info

Publication number
GB1156482A
GB1156482A GB2383/69A GB238369A GB1156482A GB 1156482 A GB1156482 A GB 1156482A GB 2383/69 A GB2383/69 A GB 2383/69A GB 238369 A GB238369 A GB 238369A GB 1156482 A GB1156482 A GB 1156482A
Authority
GB
United Kingdom
Prior art keywords
pyrrole
aldehyde
product
firmenich
furfuryl
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.)
Expired
Application number
GB2383/69A
Inventor
M Winter
F Gautschi
I Flament
M Stoll
I M Goldman
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.)
Firmenich SA
Original Assignee
Firmenich SA
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 Firmenich SA filed Critical Firmenich SA
Priority claimed from GB09260/66A external-priority patent/GB1156472A/en
Publication of GB1156482A publication Critical patent/GB1156482A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/333—Radicals substituted by oxygen or sulfur atoms
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F5/00—Coffee; Coffee substitutes; Preparations thereof
    • A23F5/46—Coffee flavour; Coffee oil; Flavouring of coffee or coffee extract
    • A23F5/465—Flavouring with flavours other than natural coffee flavour or coffee oil
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/56—Flavouring or bittering agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • 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
    • A23L27/204—Aromatic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • 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
    • A23L27/205—Heterocyclic compounds
    • A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • 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
    • A23L27/205—Heterocyclic compounds
    • A23L27/2054—Heterocyclic compounds having nitrogen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • 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
    • A23L27/205—Heterocyclic compounds
    • A23L27/2056—Heterocyclic compounds having at least two different hetero atoms, at least one being a nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
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    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
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    • 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
    • C07D213/24—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 with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals
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    • 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
    • C07D213/60—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 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
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    • 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
    • C07D213/60—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 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
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    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/40—Benzopyrazines
    • C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07—ORGANIC CHEMISTRY
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    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/36—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
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    • C07—ORGANIC CHEMISTRY
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    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07D307/42—Singly bound oxygen atoms
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    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
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    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
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    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
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  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Confectionery (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Tea And Coffee (AREA)
  • Saccharide Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Furan Compounds (AREA)
  • Liquid Crystal Substances (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pyridine Compounds (AREA)

Abstract

1,156,482. Pyrrole derivatives. R. FIRMENICH, G. FIRMENICH, R. E. FIRMENICH, and F. H. FIRMENICH, [trading as FIRMENICH & CIE.]. 2 May, 1966 [30 April, 1965; 18 April, 1966], No. 2383/69. Divided out of 1,156,472. Heading C2C. [Also in Division A2] 1-Ethyl pyrrole-2-aldehyde was prepared from 1-ethyl-pyrrole [obtained by the method described in Helv. 10, 387 (1927)] by introducing a formaldehyde group following the technique described in Org. Synth. 36, 74 (1956). The product boiled at 73-75‹ C./7 mm. Hg. The following were prepared by the same method: 1-Butyl-pyrrole-3-aldehyde, b.p. of 148- 150‹ C./11 mm. Hg. 1-Amyl pyrrole-2-aldehyde, b.p. of 111- 112‹ C./11 mm. Hg. 1-Amyl-pyrrole-3-aldehyde, b.p. of 155- 160‹ C./11 mm. Hg. 1-α-Methylbutyl-pyrrole-2-aldehyde, b.p. of 103-105‹ C./11 mm. Hg. 1-α-Methybutyl-pyrrole-3-aldehyde, b.p. of 150‹ C./11 mm. Hg. 1-Furfuryl-pyrrole-2-aldehyde was prepared starting with 1-furfuryl-pyrrole described by Reichstein in Helv, 15, 1450 (1932) as well as Gianturco et al. in Tetrahedron 20, 1763 (1964). The aldehyde group introduced by the Vilsmeyer reaction (e.g. by the method described in Bull. 1962, 1989). A small amount of the corresponding 3-aldehyde is obtained as a by-product and can be separated by fractional distillation. The 2-aldehyde boils at 139- 140‹ C./12 mm. Hg. and is a viscous colourless oil. The 3-aldehyde has a b.p. of 190‹ C./ 12 mm. Hg. 1-Thienyl-pyrrole-2-aldehyde was prepared by the same method as used for 1-furfuryl-pyrrole- 2-aldehyde. It has a b.p. of 98‹ C./0À005 mm. Hg. 1-Furfuryl-2-acetyl-pyrrole was prepared starting from 1-furfuryl-pyrrole described by Reichstein in Helv, 15, 1450 (1932) as well as Gianturco et al. in Tetrahedron 20, 1763 (1964). Acetylation by reaction of the Grignard intermediate with acetyl chloride [cf. Chem. Ber. 47, 1416 (1914)] led to the desired ketone. (A small amount of the 3-isomer was also obtained, separable by fractional distillation). The product boils at 100-102‹ C./0À03 mm. Hg. and crystallizes on standing. Recrystallization from a mixture of methylene dichloride and petroleum ether gave a white crystalline product with a m.p. of 42-43‹ C. 1,2-Dimethyl-5-acetyl-pyrrole was obtained by acetylating 1,2-dimethylpyrrole according to the method described in Ber. 47, 1416 (1914) [cf. also J.A.C.S. 85, 2859 (1963)]. The product has a b.p. of 102-106‹ C./10 mm. Hg. 1-Methyl-3-acetyl-pyrrole was obtained as a by-product in the synthesis of 1-methyl-2- acetyl-pyrrole according to the method described in Ber 47, 1416 (1914). The product has a b.p. of 130-132‹ C./12 mm. Hg.
GB2383/69A 1965-04-30 1966-05-02 Pyrrole Flavouring Agents Expired GB1156482A (en)

Applications Claiming Priority (3)

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US45234265A 1965-04-30 1965-04-30
US54306966A 1966-04-18 1966-04-18
GB09260/66A GB1156472A (en) 1965-04-30 1966-05-02 Pyrazine Hydrocarbons

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GB1156482A true GB1156482A (en) 1969-06-25

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GB2380/69A Expired GB1156479A (en) 1965-04-30 1966-05-02 Aromatic Hydrocarbon Flavouring Agents
GB2374/69A Expired GB1156473A (en) 1965-04-30 1966-05-02 Thiazole Alcohols
GB2381/69A Expired GB1156480A (en) 1965-04-30 1966-05-02 Furan Flavouring Agents
GB2379/69A Expired GB1156478A (en) 1965-04-30 1966-05-02 Heterocyclic Carbonyl Compounds
GB2383/69A Expired GB1156482A (en) 1965-04-30 1966-05-02 Pyrrole Flavouring Agents
GB2389/69A Expired GB1156488A (en) 1965-04-30 1966-05-02 Phenolic Flavouring Agents
GB2384/69A Expired GB1156483A (en) 1965-04-30 1966-05-02 Pyridine Flavouring Agents
GB2377/69A Expired GB1156476A (en) 1965-04-30 1966-05-02 Alpha, Beta-Diketones
GB2376/69A Expired GB1156475A (en) 1965-04-30 1966-05-02 Sulphur-Containing Derivatives of 6-Membered Heterocyclic Compounds
GB2390/69A Expired GB1156489A (en) 1965-04-30 1966-05-02 Alcoholic Flavouring Agents
GB2382/69A Expired GB1156481A (en) 1965-04-30 1966-05-02 Thiophene Flavouring Agents
GB2391/69A Expired GB1156490A (en) 1965-04-30 1966-05-02 Pyrone Flavouring Agents
GB2378/69A Expired GB1156477A (en) 1965-04-30 1966-05-02 Pyrrole Aldehydes
GB2386/69A Expired GB1156485A (en) 1965-04-30 1966-05-02 Thiazole Flavouring Agents
GB2387/69A Expired GB1156486A (en) 1965-04-30 1966-05-02 Ketonic Flavouring Agents
GB2385/69A Expired GB1156484A (en) 1965-04-30 1966-05-02 Pyrazine Flavouring Agents
GB2375/69A Expired GB1156474A (en) 1965-04-30 1966-05-02 Sulphur-Containing Derivatives of 5-Membered Heterocyclic, Compounds

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GB2380/69A Expired GB1156479A (en) 1965-04-30 1966-05-02 Aromatic Hydrocarbon Flavouring Agents
GB2374/69A Expired GB1156473A (en) 1965-04-30 1966-05-02 Thiazole Alcohols
GB2381/69A Expired GB1156480A (en) 1965-04-30 1966-05-02 Furan Flavouring Agents
GB2379/69A Expired GB1156478A (en) 1965-04-30 1966-05-02 Heterocyclic Carbonyl Compounds

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GB2389/69A Expired GB1156488A (en) 1965-04-30 1966-05-02 Phenolic Flavouring Agents
GB2384/69A Expired GB1156483A (en) 1965-04-30 1966-05-02 Pyridine Flavouring Agents
GB2377/69A Expired GB1156476A (en) 1965-04-30 1966-05-02 Alpha, Beta-Diketones
GB2376/69A Expired GB1156475A (en) 1965-04-30 1966-05-02 Sulphur-Containing Derivatives of 6-Membered Heterocyclic Compounds
GB2390/69A Expired GB1156489A (en) 1965-04-30 1966-05-02 Alcoholic Flavouring Agents
GB2382/69A Expired GB1156481A (en) 1965-04-30 1966-05-02 Thiophene Flavouring Agents
GB2391/69A Expired GB1156490A (en) 1965-04-30 1966-05-02 Pyrone Flavouring Agents
GB2378/69A Expired GB1156477A (en) 1965-04-30 1966-05-02 Pyrrole Aldehydes
GB2386/69A Expired GB1156485A (en) 1965-04-30 1966-05-02 Thiazole Flavouring Agents
GB2387/69A Expired GB1156486A (en) 1965-04-30 1966-05-02 Ketonic Flavouring Agents
GB2385/69A Expired GB1156484A (en) 1965-04-30 1966-05-02 Pyrazine Flavouring Agents
GB2375/69A Expired GB1156474A (en) 1965-04-30 1966-05-02 Sulphur-Containing Derivatives of 5-Membered Heterocyclic, Compounds

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5554588A (en) * 1991-11-08 1996-09-10 Lever Brothers Company, Division Of Conopco, Inc. Perfume compositions

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE755421A (en) * 1969-08-29 1971-03-01 Gen Foods Corp ENHANCEMENT OF THE TASTE OF FOOD
US3767428A (en) * 1970-08-03 1973-10-23 Int Flavors & Fragrances Inc Process of flavoring of foodstufs with 2-acetyl-3-ethylpyrazine
BE786192A (en) * 1971-07-12 1973-01-12 Int Flavors & Fragrances Inc SEASONING COMPOSITIONS CONTAINING ALPHA-KETOTHIOLS AND THEIR METHOD OF USE
FR2345090A1 (en) * 1976-03-26 1977-10-21 Gen Foods Corp Reducing stimulating activity of methyl-xanthines in food - by adding pyridine antagonists pref. nicotinic acid
CH643733A5 (en) * 1980-02-06 1984-06-29 Firmenich & Cie NITROGENATED HETEROCYCLIC COMPOUNDS AS PERFUMING INGREDIENTS.
DE3025305A1 (en) * 1980-07-04 1982-01-28 Haarmann & Reimer Gmbh, 3450 Holzminden Flavorings for animal feed
NL8502530A (en) * 1985-09-16 1987-04-16 Naarden International Nv FLAVOR AND PERFUME COMPOSITIONS, FLAVORED EDIBLE PREPARATIONS, RESP. PERFUMED PRODUCTS CONTAINING ONE OR MORE SUBSTITUTED THIOPHENES AS RAW MATERIAL AND SUBSTITUTED THIOPHENES.
US5368876A (en) * 1985-09-16 1994-11-29 Naarden-International N.V. Flavoring and perfume compositions and flavored and perfumed products which contain one or more substituted thiophenes
US5260451A (en) * 1989-05-11 1993-11-09 Merckle Gmbh Substituted pyrrole compounds and use thereof in pharmaceutical compositions
DE3915450A1 (en) * 1989-05-11 1990-11-15 Gerd Prof Dr Dannhardt SUBSTITUTED PYRROL COMPOUNDS AND THEIR USE IN PHARMACY
EP0470391B1 (en) * 1990-08-10 1995-08-23 Firmenich Sa Use of pyridines as perfume or aroma ingredients
FR2687672B1 (en) * 1992-02-20 1995-05-12 Atochem Elf Sa NOVEL SULFUR ACRYLIC DERIVATIVES AND THEIR PREPARATION PROCESS.
DE69507382T2 (en) * 1994-06-21 2009-09-17 Firmenich S.A. Use of an alkyl-substituted pyridine as a fragrance
WO2009017412A1 (en) * 2007-08-01 2009-02-05 Koninklijke Coöperatie Cosun U.A. Sugar proces-derived aroma composition and its preparation and use
EP2128227A1 (en) * 2008-05-19 2009-12-02 Furanix Technologies B.V Monosubstituted furan derivatives via decarboxylation and use thereof as (aviation) fuel

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5554588A (en) * 1991-11-08 1996-09-10 Lever Brothers Company, Division Of Conopco, Inc. Perfume compositions

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GB1156476A (en) 1969-06-25
GB1156488A (en) 1969-06-25
GB1156481A (en) 1969-06-25
GB1156480A (en) 1969-06-25
GB1156473A (en) 1969-06-25
GB1156477A (en) 1969-06-25
GB1156489A (en) 1969-06-25
GB1156479A (en) 1969-06-25
GB1156486A (en) 1969-06-25
GB1156475A (en) 1969-06-25
GB1156485A (en) 1969-06-25
GB1156484A (en) 1969-06-25
GB1156474A (en) 1969-06-25
GB1156478A (en) 1969-06-25
GB1156483A (en) 1969-06-25
GB1156490A (en) 1969-06-25

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