GB1156480A - Furan Flavouring Agents - Google Patents

Furan Flavouring Agents

Info

Publication number
GB1156480A
GB1156480A GB2381/69A GB238169A GB1156480A GB 1156480 A GB1156480 A GB 1156480A GB 2381/69 A GB2381/69 A GB 2381/69A GB 238169 A GB238169 A GB 238169A GB 1156480 A GB1156480 A GB 1156480A
Authority
GB
United Kingdom
Prior art keywords
furfuryl
benzofuran
methyl
prepared
product
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
GB2381/69A
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 GB1156480A publication Critical patent/GB1156480A/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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    • 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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    • C07D213/02—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
    • C—CHEMISTRY; METALLURGY
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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
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    • 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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    • 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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    • 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
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    • 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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    • C07D307/46—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
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • 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
    • C—CHEMISTRY; METALLURGY
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    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
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    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
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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

Abstract

1,156,480. Furan 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. 2381/69. Divided out of 1,156,472. Heading C2C. [Also in Division A2] 2-Isopropenyl-benzofuran.-According to the method described in J.A.C.S. 73, 754 (1951), 2-acetyl-benzofuran is reacted with methylmagnesium bromide to form 2-(2-hydroxyisopropyl)-benzofuran which is converted to its acetate. Pyrolysis of the acetate yields 2-isopropenyl-benzofuran of b.p. 81-83‹ C./0À001 mm. Hg. 7-Ethyl-benzofuran is prepared by the method described in J. Chem. Soc. 1920, 1534, but using o-ethylphenol instead of o-cresol. The MS. of the product thus obtained shows the following ion peaks with the relative intensities given within brackets: 131 (100%), 146 (38%) and 77 (10%). 2,7 - Dimethyl - benzofuran.-7 - Methylbenzofuran is subjected to a WILSMEYER reaction to form 7-methyl-benzofuran-2-aldehyde which is converted into 2,7-dimethylbenzofuran by a WOLFF-KISHNER reaction by the method described in Bull. Soc. Chim. France 29, 1875 (1952). The product thus obtained has the following peaks in its MS: 146 (100%), 145 (92%) and 131 (32%). 5 - Methyl - furfuryl furfuryl ether was prepared by the procedure described by J. E. Zanetti in J. Am. Chem. Soc. 49, 1066 (1927) for the difurfuryl ether, starting with 5-methylfurfuryl bromide (Compt. Rend. 222, 1441 (1946)) instead of furfuryl bromide of Zanetti. The product was isolated by ether extraction of the crude mixture after having diluted with water. For purification the ether extract was distilled twice-b.p. 68-70‹ C. at 0À01 mm./Hg vacuum. The product was a viscous colourless liquid, darkening rapidly on contact with air. 7 - Methyl - benzofuran - 2 - aldehyde was prepared by formylating 7-methyl-benzofuran according to the same method as used for the preparation of benzofuran-2-aldehyde. The product thus obtained has the following ion peaks in its mass spectrum: 160 (100%), 159 (62%) and 131 (33%). (5-Methyl-furfuryl) methyl ketone was prepared according to the procedure described by Hass et al. in J. Org. Chem. 15, 8 (1950) by condensing 6-methyl-furfuryl-aldehyde with nitroethane. The product has a b.p. of 75‹ C./ 10 mm. Hg. (5-Methyl-furfuryl) ethyl ketone was prepared by the same method as used for the preceding compound, except that 1-nitropropane was used instead of nitroethane. The product has a b.p. of 97-100‹ C./15 mm. Hg. 1-(5-Methylfuryl)-3-pentanone was prepared by the method described in Ber. 76, 192 (1943). It has a b.p. of 101-102‹ C./11 mm. Hg. The following five compounds can be obtained by reacting the corresponding acid chlorides with furfuryl alcohol, for example by the method described in Houben-Weyl, fourth edition, volume 8, page 543 (1952), and are found to have the following boiling points: Furfuryl isovalerate, b.p. 97-98‹ C./11 mm. Hg. Furfuryl crotonate, b.p. 96-98‹ C./11 mm. Hg. Furfuryl-α-methylbutyrate, b.p. 96‹ C./11 mm. Hg. Furfuryl - #,#<SP>1</SP> - dimethylacrylate, b.p. 113- 115‹ C./11 mm. Hg. Furfuryl valerate, b.p. 100-104‹ C./11 mm. Hg. Furfurylthioacetone was prepared in the same manner as methylthioacetone according to the method described in J.A.C.S. 76, 114 (1954) by condensing 0À122 mole of chloroacetone with 0À11 mole of sodium furfurylmercaptide. After the usual separation and purification of the reaction product there were obtained by distillation 13À9 g. of pure furfurylthioacetone distilling at 115-177‹ C./10 Torr. n D <SP>22À8</SP> = 1À5250; d 4 <SP>23</SP> = 1À150. Difurfurylmercaptal of α-methylbutanal.-This compound was prepared by the same method as furfuryl methyl ether, using 0À11 mole of furfurylmercaptan instead of methanthiol. 6À4g. of difurfurylmercaptal were obtained; b.p. 130‹ C./0À1 Torr; n D <SP>22À8</SP> = 1À5500; d 4 <SP>23</SP> = 1À126.
GB2381/69A 1965-04-30 1966-05-02 Furan Flavouring Agents Expired GB1156480A (en)

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

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GB2374/69A Expired GB1156473A (en) 1965-04-30 1966-05-02 Thiazole Alcohols
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

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GB2390/69A Expired GB1156489A (en) 1965-04-30 1966-05-02 Alcoholic Flavouring Agents
GB2378/69A Expired GB1156477A (en) 1965-04-30 1966-05-02 Pyrrole Aldehydes
GB2387/69A Expired GB1156486A (en) 1965-04-30 1966-05-02 Ketonic Flavouring Agents
GB2389/69A Expired GB1156488A (en) 1965-04-30 1966-05-02 Phenolic Flavouring Agents
GB2376/69A Expired GB1156475A (en) 1965-04-30 1966-05-02 Sulphur-Containing Derivatives of 6-Membered Heterocyclic Compounds
GB2386/69A Expired GB1156485A (en) 1965-04-30 1966-05-02 Thiazole Flavouring Agents
GB2383/69A Expired GB1156482A (en) 1965-04-30 1966-05-02 Pyrrole Flavouring Agents
GB2380/69A Expired GB1156479A (en) 1965-04-30 1966-05-02 Aromatic Hydrocarbon Flavouring Agents
GB2375/69A Expired GB1156474A (en) 1965-04-30 1966-05-02 Sulphur-Containing Derivatives of 5-Membered Heterocyclic, Compounds
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
GB2385/69A Expired GB1156484A (en) 1965-04-30 1966-05-02 Pyrazine Flavouring Agents
GB2379/69A Expired GB1156478A (en) 1965-04-30 1966-05-02 Heterocyclic Carbonyl Compounds

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Cited By (2)

* 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
EP2128227A1 (en) * 2008-05-19 2009-12-02 Furanix Technologies B.V Monosubstituted furan derivatives via decarboxylation and use thereof as (aviation) fuel

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* 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
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
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.
DE3915450A1 (en) * 1989-05-11 1990-11-15 Gerd Prof Dr Dannhardt SUBSTITUTED PYRROL COMPOUNDS AND THEIR USE IN PHARMACY
US5260451A (en) * 1989-05-11 1993-11-09 Merckle Gmbh Substituted pyrrole compounds and use thereof in pharmaceutical compositions
DE69112316T2 (en) * 1990-08-10 1996-03-14 Firmenich & Cie 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

Cited By (2)

* 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
EP2128227A1 (en) * 2008-05-19 2009-12-02 Furanix Technologies B.V Monosubstituted furan derivatives via decarboxylation and use thereof as (aviation) fuel

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GB1156476A (en) 1969-06-25
GB1156473A (en) 1969-06-25
GB1156486A (en) 1969-06-25
GB1156490A (en) 1969-06-25
GB1156485A (en) 1969-06-25
GB1156482A (en) 1969-06-25
GB1156479A (en) 1969-06-25
GB1156474A (en) 1969-06-25
GB1156483A (en) 1969-06-25
GB1156488A (en) 1969-06-25
GB1156478A (en) 1969-06-25
GB1156484A (en) 1969-06-25
GB1156481A (en) 1969-06-25
GB1156475A (en) 1969-06-25
GB1156489A (en) 1969-06-25

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