DE1793843C2 - Verwendung bestimmter Pyridin-Kohlenwasserstoffe als Geschmacksstoffe oder Geschmacksstoffkomponente - Google Patents

Verwendung bestimmter Pyridin-Kohlenwasserstoffe als Geschmacksstoffe oder Geschmacksstoffkomponente

Info

Publication number
DE1793843C2
DE1793843C2 DE1793843A DE1793843A DE1793843C2 DE 1793843 C2 DE1793843 C2 DE 1793843C2 DE 1793843 A DE1793843 A DE 1793843A DE 1793843 A DE1793843 A DE 1793843A DE 1793843 C2 DE1793843 C2 DE 1793843C2
Authority
DE
Germany
Prior art keywords
pyridine
green
taste
coffee
roasted
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
DE1793843A
Other languages
English (en)
Other versions
DE1793843B1 (de
Inventor
I Flament
F Gautschi
I M Goldman
M Stoll
M Winter
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
Publication of DE1793843B1 publication Critical patent/DE1793843B1/de
Application granted granted Critical
Publication of DE1793843C2 publication Critical patent/DE1793843C2/de
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
    • 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
    • A23L27/2054—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/12—Ketones containing more than one keto group
    • 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
    • C07D213/24—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
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/32—Sulfur atoms
    • 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
    • C07D213/24—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
    • 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
    • C07D213/60—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
    • 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
    • C07D213/60—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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D241/14—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
    • C07D241/18—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D277/24—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/42—Singly bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D307/56—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
    • C07D307/64—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D307/56—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • 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
    • C07D307/80—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • 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
    • C07D333/06—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • 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
    • C07D333/06—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • 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
    • C07D333/28—Halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • 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
    • C07D333/40—Thiophene-2-carboxylic acid

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Seasonings (AREA)
  • Tea And Coffee (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Bakery Products And Manufacturing Methods Therefor (AREA)
  • Non-Alcoholic Beverages (AREA)
  • Pyrrole Compounds (AREA)
  • Furan Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Fats And Perfumes (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)

Description

zur Veränderung der Geschmackseigenschaften fester oder flüssiger Nahrungs- und Genußmittel und von Getränken sowie als Geschmacksstoffkomponente in einem geschmacksverändernden Mittel.
2. Verwendung der im Anspruch 1 genannten Verbindungen zur Aromatisierung von löslichen Kaffeeprodukten.
nicht verwendete Rohstoffe erschlossen werden, um der drohenden Verknappung der Nahrungsmittel in gewissen Gebieten des Erdballs entgegezutreten.
Es wurde festgestellt, daß die oben beschriebenen ä Verbindungen entweder einzeln oder in Form zweckentsprechender Mischungen dazu geeignet sind, die Geschmackseigenschaften verschiedenster fester und flüssiger Nahrungs- und Genußmittel oder Getränke im gewünschten Sinne zu verändern. Mittels der vorliegenden Erfindung können beispielsweise Produkte wie Fruchtsäfte, Gemüsesäfte, Milchprodukte, Kaffee-, Tee-, Kakao- und Schokoladeprodukte, Getreideflocken, Mehl, Konfiseriewaren, Fleischprodukte, Backwaren und Speiseeis geschmacklich verändert werden. Die Erfindung eignet sich insbesondere zur Verbesserung oder Verstärkung des Geschmackes von konservierten Lebensmitteln. Ganz besonders eignet 'ich die Erfindung zur Veränderung, Verbesserung oder Verstärkung der Geschmackseigenschaften von sogenannten löslichen Kaffeeprodukten (im englischen Sprachgebrauch als »instant coffee« bezeichnet).
In der folgenden Aufstellung der erfindungsgemäß zu verwendenden Pyridin-Kohlenwasserstoffe ist neben dem chemischen Namen jeder Verbindung ein Literaturhinweis betreffend ein Herstellungsverfahren angegeben. Im Handel erhältliche Produkte sind mit der Abkürzung »i.H.« bezeichnet:
Gegenstand der Erfindung ist die Verwendung der im vorstehenden Anspruch genannten Pyridin-Kohlenwasserstoffe zur Veränderung der Geschmackseigenschaften fester oder flüssiger Nahrungs- und Genußmittel und von Getränken sowie als Geschmacksstoffkomponente in einem geschmacksverändernden Mittel.
Unter »geschmacksverändernd« sind alle Vorgänge oder Behandlungen zu verstehen, durch weiche geschmacksfreien bzw. geschmacksarmen Nahrungsmitteln und Getränken ein bestimmter Geschmack oder ein bestimmtes Aroma verliehen wird, oder durch welche der Geschmack von Nahrungsmitteln und Getränken verstärkt, verbessert, überdeckt, unterdrückt oder sonstwie in einer bestimmten Geschmacksrichtung verändert wird.
Die der vorliegenden Erfindung zugrunde liegende Aufgabe bestand darin, die Auswahl der bisher zur Verfügung stehenden Geschmacksstoffe zu erweitern und dem Lebensmitteltechniker neue und verfeinerte Mittel in die Hand m geben, um die von der Natur erzeugten Aromen auf synthetischem Wege besser nachahmen zu korinen. Die Veränderung öder Verbesserung der geschmacklichen Eigenschaften von Nahrungsmitteln und Getränken durch Verwendung Von künstlichen Aromen mit genau reproduzierbaren Geschmäckseigenschaften und -qualitäten nimmt iri der Lebensmittelindustrie mehr und mehr an Bedeutung zu, seitdem für die Ernährung des Menschen neue, bisher
a. 2-Methyl-pyridin
b. 3-Methyl-pyridin
c. 3-Äthyl-pyridin
d. 2-AlIyl-pyridin
e. 4-Isobutyl-pyridin
f. 2-[Propen-(l)-yl]-pyridin
g. 4-[Propen-(l)-yl]-pyridin
h. 2-Methy!-5-äthyl-pyridin
i. 2,3-Dimethyl-pyridin
j. 2,4-Dimethyl-pyridin
k. 2,5-Dimethyl-pyridin
I. 2,6-Dimethyl-pyridin
m. 3,4-Dimethyl-pyridin
n. 3.5-Dimethyl-pyridin
o. 2-Vinyl-pyridin
p. 4-Methyl-pyridin
q. 2-MethyI-6-vinyl-pyridm
r. 4-Phenyl-pyridin
s. 4-Benzyl-pyridin
t. 2-Benzyl-pyridin
LH.
LH.
LH.
Bull. Soc. chim. France
420 (1955)
Bull, soc chim. France 420(1955)
Liebigs Ann. Chem.
247,1 (1888)
Liebigs Ann. Chem.
247, I (1888)
LH.
LH.
LH.
LH.
i.H.
LH.
LH.
LH.
i.H.
i..-i.
LH.
LH.
LH.
Die organoleptische Bewertung der obenzitierten Verbindungen wurde mittels der Prüfmethoden A, B und C durchgeführt. Die Methode A diente dazu, den Eigengeschmack der einzelnen Substanzen zu ermitteln. Die geschmacksverändernden Eigenschaften der Substanzen wurden mittels der Methoden B und C ermittelt. Es wurde insbesondere die geschmacksverändernde Wirkung der Pfiifsubstanzen (im folgenden »Geschmäcksstöffe« genannt) auf Kaffeeprodukle Und speziell auf sprühgetrocknete lösliche Kaffeepulver geprüft.
Methode A
Die Geschmacksstoffe wurden in eifief 65%igen Zuckersirup-Lösung, bestehend aus Rohrzucker in
Leitungswasser, gekostet. Die zu prüfenden Ge- Tabelle
schmacksstoffe wurden dem Sirup in Form von
Lösungen von 1 Gew.-% oder 1 Gew.-%o in 96%igem Ver- VerAlkohol zugegeben. Die Konzentration der Ge- bindung such
schmacksstoffe im Zuckersirup schwankte entspre- s
chend der Geschmacksintensität zwischen 0,005 und 5 g pro 100 Liter Sirup. Proben des aromatisierten Sirups wurden einer Gruppe von Geschmacksprüfern vorgelegt Nach dem Kosten der Proben mußte jeder Prüfer b B eine Beschreibung des Geschmacks der einzelnen ι ο Geschmacksstoffe abgeben. c A
Menge Organoleptische Bewertung
Methode B
Als Substrat für die Prüfung wurde ein Kaffeegetränk verwendet, das durch Auslösen eines im Handel erhältlichen, sprühgetrockneten Kaffeepulvers in siedendem Was-ei im Verhältnis von 1 g Pulver auf 80 ml Wasser hergestellt wurde. Für jeden zu prüfenden Geschmacksstoff wurde ein Gefäß mit Kaffeegetränk bereitgestellt Die Geschmacksstoffe wurden dem Kaffeegetränk in Form von Lösungen von 1 Gew.-°/o oder 1 Gew.-%o in 96%igem Alkohol in Konzentrationen von 0,005 bis 5 g auf 100 Lite- Getränk zugegeben. Nach Zugabe der abgemessenen Menge der Geschmacksstofflösung wurde das Kaffeegetränk gut gerührt und sofort in eine Reihe von Tassen für die organoleptische Prüfung gegossen. Das Kosten des Getränkes wuule so rasch als möglich, auf jeden Fall nicht später als 15 Minuten r°ch der Zubereitung vorgenommen.
Die nur mit einer Kennzahl '-Tsehenen gefüllten Tassen wurden in einer Reihe aufgestellt, wobei die erste Tasse eine nicht aromatisierte Vergleichsprobe des Kaffeegetränkes enthielt. Die Geschmacksprüfer mußten feststellen, ob zwischen der Vergleichsprobe und den anderen Proben geschmacklich ein Unterschied bestand oder nicht. Die Prüfer mußten ferner die Geschmacksunterschiede beschreiben und charakterisieren.
Methode C
Als Substrat für die Geschmacksprüfung wurde eine l,35%ige Lösung eines im Handel erhältlichen, sprühgetrockneten Kaffeepulvers mit verhältnismäßig »flachem« Geschmack und Aroma in Quellwasser verwendet. Die einzelnen Geschmacksstoffe wurden je einer Portion des Kaffeegetränkes mittel einer Mikrospritze in Mengen von 2 bis 150 Mikroliter zugegeben. Alle für die Zubereitung des Kaffeegetränkes, sowie für die Aromatisierung, verwendeten Gefäße und sonstigen Geräte wurden peinlichst gesäubert. Für die Geschmacksprüfung wurden insgesamt mindestens 5 erfahrene Geschmacksprüfer eingesetzt. Im übrigen wurde gleich wie bei Methode B gearbeitet.
Die Resultate der organoleptischen Prüfungen sind in der nachfolgenden Tabelle, 1 zusammengefaßt In der ersten Kolonne der Tabelle sind die Buchstaben der einzelnen Verbindungen Innerhalb der genannten Stoffklasse. Die zweite Kölörtne Verweist auf die angewendete Prüfmethode/ In der dritten Kolonne sind die verwendeten Mengen der Prüfsubstanzen in g pro 100 Liter Öetfänk (Zuckefsifup öder Käffeegetfänk) angegeben-
15
20
25 h
30 . J J j
35 ^
B 0,6 astringierend;
haselnußartig; basisch B 0,25 grün; erdig;
haselnußartig
c A 0,25 karamellenartig;
geröstete Haselnüsse
c C 0,095 butterig; grün;
kornähnlich;
karamellenartig
d A 0,5 grün; melonenartig
e A 0,5-1,0 fettiger Geschmack
f A 0,25 grün; verbrannt;
kaffeeartig
A 0,25 grün, fruchtartig,
erdbeerähnlich, melonenartig
A 0,3 fettig; grün
C 0,054 weinartit, butterähnlich,
sauer kornähnlich, schwefelig
A 0,6 kaffeeähnlich
B 0,5 geröstet, gummiartig
A 1,0 grün
B 1,0 basisch; bitter;
astringierend
A 0,3 rum-ähnlich
k B 0,15 geröstet; grün; erdig
I A 1,0 grün
1 B 0,2 grün; astringierend;
erdip,
m A 2,0 grün
Die nachfolgenden Tabellen 2 bis 8 zeigen die Aromatisierung von verschiedenen weiteren Getränken und Speisen sowie eines Karamelgeschmacksstoffes mit den erfindungsgemäß zu verwendenden Pyridin-Koh-Ienwasserstoffen:
50
55
6Q
65
Tabelle 2 Menge verdünntem Zuckersirup')
(ppm2) Organoleptische Bewertung
Aromatisierung von 2,5
Ver karamellenartig;
bindung 5,0 geröstete Haselnüsse
C 5-10 grün; melonenartig
2,5 fettiger Geschmack
d 2,5 grün; verbrannt; käffeeartig
e grün, fluchtartig,
f 3,0 erdbeerähnlich, melonenartig
tra: 6,0 fettig; grün
kaffeeähnlich
h
i
10
gfun
Fortsetzung 1 7 no
i / 3J 		5 (parts per million). (parts per million). Kaffeegetränk abgegeben. 5 843 6 Tabelle 5
I wurden von einer Prüfungskommis- Aromatisierung von Salzwasser1)
I Ver- Menge sion von Geschmacksexperten nach Vergleich mit einem
I bindung (ppm2) Organoleptischß Bewertung löslichem Kaffee1) nichl-aromalisierlen Milch Ver- Menge Organoleptische Bewertung
Organoleptische Bewertung3) Organoleptische Bewertung') in bindung (ppm)
j k 3,0
I 10		 Tabelle 4 tu
m 20 τι im π hnl ir* H astringierend; haselnußartig; Aromatisierung von karamellenartig; c 0,5 geröstet; verbrannt
η 8,0 I Ulff f+lllUK-ll
grün		 basisch Ver- Menge
bindung (ppm)		 geröstete Haselnüsse e 0,5 wie heißes tierisches Fett
'i ο 2,0 grün priin prdii** hnsplniiR^rtip fettig; grün; melonenartig m 1,0 grün; verbrannt; würzig;
H grün; Fettig; geröstet 11,1 Uli, \*l UJK1 llUowlll UUtIl LJK
butterig; grün;		 c 0,5 r 15 safranartig
i grün kornähnlich, karamellenartig lettig; gerostet η 1,0 fettig; grün;
I ') 10% Zucker in Wasser (vergl. Methode A). weinartig, butterähnlich,
sauer, kornähnlich		 d 0,5-1,0 grün, kaffeeartig geräuchertes Fleisch
y
I		 2) 1 g/100 1 = 10 ppm geröstet; gummiartig grün; fruchtartig; 20 q 1,0 grün; erdig; leicht schimmelig
basisch; bitter; astringierend e υ, j erdbeerähnlich; melonenartig
E Tabelle 3 geröstet; grün; erdig f 0,5 fruchtig ') 0,5% Lösung von NaCI in Wasser.
5 Aromatisierung von grün; astringierend; erdig g 0,5 geröstet; rumähnlich Tabelle 6
Ver- Menge ι τη grüiij haseliiußartig 25 Aromatisierung von Rinderbraiensauc')
bindung (ppm7) ') 2,50 g eines handelsüblichen löslichen Kaffees in 200 ml ι 2,0 grüri; würzig Ver- Menge Organoleptische Bewertung2)
a 6,0 heißem Wasser (vergl. Methode B). k 1,0-2,0 grün; würzig bindung (ppm)
2) 1 g/100 I = 10 ppm I 2,0-3,0 grün; erdig 30
b 2,5 3) Diese Bewertungen m 2,0 ') Diese Bewertungen wurden von einer Prüfungskommis e 1,0-2,0 verstärktes Gesamtaroma;
c 0,96 ο 1,0 sion von Geschmacks« (iirten nach Vergleich mit nichu gebratenes Fleisch
el 1,0-2,0 aromatisierlef Milch abgegeben. m 2,0 würzig, safranartig
h 0,54 35 ο 1,0 grün, würzig, senfartig
i 5,0 ') Hergestellt aus 45 g eines handelsüblichen Bratensaucen
j 10 pulvers und 300 ml Wasser.
k 1,5 2) Diese Bewertungen wurden von einer Prüfungskommis
I 2,0 sion von Geschmacksexperten nach Vergleich mit nicht-
40 aromaüsiertem Material abgegeben.
Tabelle 7
Aromatisierung von handelsüblichem Apfelmus
45 Ver- Menge Organoleplische Bewertung1)
bindung (ppm)
50 d 0,5-1,0 grün, melonenartig
g 0,5-1,0 verstärkt fruchtartig,
grün, erdbeerartig
i 1,0-2,0 grün, fruchlartig,
ungekochte Äpfel
') Diese Bewertungen wuTdcn von einer Prüfungskommis
55 sion von Geschmacksexperten nach Vergleich mit einem
nicht-aromatisierlen Apfelmus abgegeben.
Tabelle 8
60 Verwendung von 3-Älhyl-pyridin (Verbindung c) als
aromatisierender Zusatz zu einem Karamelgeschmacks-
stolT
a) Karamelgrundstoff
65
Zutaten Gew.-Teile
1
Melhyl-cycloperttenolön 50
-3
:ϊ
Ei 		AcetyNmelhyNcarbinol 30
S1
ΐ- 		Diacetyl 5
Fortsetzung
(2) Auswertung in Milch
Zutaten
Öew.'Teile
Dipropionyl
Furfurylalkohol
Furfurylaldehyd
Glycerintriacelat
Cäesaml
35
25
850,
JOOO
b) KaramelgeschmacksstorfzUsarnrnenselzung
Zulaten
Gew.-teile Io
15
Ver Dosis Bemerkungen*)
bindung ppm
Pyridin 2,0 kein Effekt
8,0 typisch" Pyridin, abstoßend
C 1,0 grün, geröstet^ an geröstete
Haselnüsse erinnernd
e 2,0 retlig, fleischig
k 2,0 grün, geröstet,
leicht fruchtig und blumig
I 3,0 grün, nuüartig, an frische
Haselnüsse erinnernd
KnramelgnindstnfT
Äthylalkohol
3-Älhyl-pyridin; l%ig*)
Gesamt
*) Lösung in Äthylalkohol.
100 100
890 900
10 -
*) Durch ein Aromaexpertengremium nach Vergleich mit Unafomatisieftef Milch.
20
1000
(3) Auswertung in löslichem Kaffee*)
25 Verbindung
Dosis ppm
Bemerkungen*·)
30
Die obengenannten Geschmacksstoffzusammensetzungen (A und B) wurden für die Aromatisierung von Milch in einer Menge von 200 g Geschmacksstoff pro 1001 Milch verwendet und das aromatisierte Milchgetränk sodann einer Geschmacksbewertung durch Geschmacksexperten unterworfen, welche zu folgendem Resultat kamen:
Milch aromatisiert mit A:
zeigt guten karamellenartigen und butterartigen Geschmack;
Milch aromatisiert mit B:
Gesamtgeschmack wie mit A; intensiverer Geschmack nach gebranntem Zucker. Pyridin
35
2,5 kein niTekt
10,0 grüne Note, unausgeglichenes
Kaffeearoma, typisch Pyridin
1,0 verbesserte giüne Note,
karamellartig
2,5 fettige Note
5,0 verbesserte grüne Note,
nußartig
Die folgenden Verbindungen wurden mit Pyridin (vgl. US-PS 16 96419) bezüglich ihrer Geschmackseigenschaften verglichen:
*) Hergestellt aus 2,5 g handelsüblichem löslichem Kaffee
und 200 ecm Wasser.
**) Durch ein Aromaexpertengremium nach Vergleich mit unaromatisiertem Kaffeegetränl;.
(4) Auswertung in handelsüblichem Apfelpüree
Verbindung
Dosis ppm
Bemerkungen*)
Verbindung c 3-Äthylpyridin
Verbindung e 4-Isobutylpyridin
Verbindung k 2,5-Dimethylpyridin
verbindung I 2,6-Dimethylpyndin
(1) Auswertung in Mineralwasser (Typ EVIAN)
Ver- Dosis Bemerkungen
bindung ppm*)
Pyridin 2,0 praktisch geschmacklos
5,0 typisch Pyridin, abstoßend
c 1,0 grün, geröstet
e 2,0 fettig, leicht fleischig
k 2,0 grün, leicht verbrannt.
fruchtig, mangoartig
1 2.0 grün, geröstet, leicht Fettig,
fleischig und nußartig
Pyridin 2,0 kein Effekt
8,0 typisch Pyridin, abstoßend
2,0 verbesserte grüne und
fruchtige Note, leicht blumig
3,0 verbesserte grüne Note,
nußartig
55
*) Durch ein Aromaexpertengremium nach Vergleich mit unaromatisiertem Apfelpüree.
(5) Auswertung in handelsüblicher Fleischbrühe*)
\fer- Dosis
bindung ppm
Bemerkungen**)
65 Pyridin 2,0 8,0
*) Teile pro Mill.
kein Effekt
leicht grün, typisch Pyridin,
unausgeglichenes Aroma
Fortsetzung
Vferbindung
Dosis ppm
Bemerkungen**}
c 2,0 verbesserte geröstete Note,
leicht grün e 2,0 fettig, verbesserter
fleischaftigef Geschmack I 4,0 fettig, leicht grür
♦) Hergestellt aus 20 g Handelsüblicher Riridfleischbrühe Und 1 1 Wasser.
*·) Durch ein Aromaexpertengremiiim nach Vergleich mit tinaromalisierter Brühe.
Allgemeine Bemerkungen
Bei Verwendung in denselben Verhältnissen wie die erfirtdungsgemäßen Alkylpyridine war Pyridin praktisch geschmacklos. Zur Erzielung eines bestimmten Geschmackseffektes müssen (4^ bis 5mal) höhere Verhall· nisse verwendet werden.- Dabei wird jedoch keine positive Wirkung festgestellt, man merkt jedoch immer die für Pyridin abstoßende, grün-metallische Arornanote. In den meisten Fällen wurde der erzielte Effekt als »unausgeglichenes Aroma« qualifiziert.
Die Verwertung der Erfindung kann durch gesetzliche Bestimmungen, insbesondere durch das Lebensmittejgesetz, beschränkt sein.

Claims (1)

Patentansprüche; !.Verwendung von a. 2-Methyl-pyridin b. 3-Methyl-pyridin c. 3-Äthyl-pyridin d. 2-AIIyI-pyridin e. 4-Isobutyl-pyridin f. 2-[Propen-(l)-yl]-pyridin g. 4-[Propen-(l)-yl]-pyridin h. 2-MethyI-5-äthyi-pyridin i. 2r3-DimethyI-pyridia j. 2,4-Dimethyl-pyridin k. 24-Dimethyl-pyridin
1. 2,6-Dimethyl-pyridin
m. 3,4-Dimethyl-pyridin
n. 3,5-DimethyI-pyridin
o. 2-VinyI-pyridin
p. 4-Methyl-pyridir.
q. 2-Methyl-6-vinyI-pyridin
r. 4-Phenyl-pyridin
s. 4-Benzyl-pyridin
L 2-Benzyl-pyridin
DE1793843A 1965-04-30 1966-04-29 Verwendung bestimmter Pyridin-Kohlenwasserstoffe als Geschmacksstoffe oder Geschmacksstoffkomponente Expired DE1793843C2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US45234265A 1965-04-30 1965-04-30
US54306966A 1966-04-18 1966-04-18

Publications (2)

Publication Number Publication Date
DE1793843B1 DE1793843B1 (de) 1980-04-30
DE1793843C2 true DE1793843C2 (de) 1981-01-15

Family

ID=27036753

Family Applications (12)

Application Number Title Priority Date Filing Date
DE1793844A Expired DE1793844C2 (de) 1965-04-30 1966-04-29 Verwendung von Pyrazin-Verbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten
DE1793843A Expired DE1793843C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Pyridin-Kohlenwasserstoffe als Geschmacksstoffe oder Geschmacksstoffkomponente
DE1793852A Expired DE1793852C2 (de) 1965-04-30 1966-04-29 4-Methyl-2-propionyl-und-butyrylthiazol und Verwendung von Thiazolcarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten
DE1793846A Expired DE1793846C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Pyrazincarbonylverbindungen als Geschmacksstoffe und Geschmacksstoffkomponente
DE1793851A Expired DE1793851C2 (de) 1965-04-30 1966-04-29 Verwendung von schwefelhaltigen Furanverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten und solche Verbindungen
DE1793850A Expired DE1793850C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Thiophan-Verbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente
DE1793848A Expired DE1793848C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter aromatischer Thiole, Sulfide und Disulfide als Geschmacksstoffe oder Geschmacksstoff komponente
DE1793845A Expired DE1793845C2 (de) 1965-04-30 1966-04-29 Verwendung von Chinoxalin-Kohlenwasserstoffen als Geschmacksstoffe oder Geschmacksstoffkomponenten
DE1695505A Expired DE1695505C3 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Alkylnaphthaline als Geschmacksstoffe oder Geschmacksstoffkomponenten
DE1793842A Expired DE1793842C3 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Benzofuranverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente
DE1793847A Expired DE1793847C3 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Pyridincarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente
DE1793849A Expired DE1793849C2 (de) 1965-04-30 1966-04-29 Verwendung von schwefelhaltigen Ketonen als Geschmacksstoffe oder Geschmacksstoffkomponenten und Furfurylthioaceton

Family Applications Before (1)

Application Number Title Priority Date Filing Date
DE1793844A Expired DE1793844C2 (de) 1965-04-30 1966-04-29 Verwendung von Pyrazin-Verbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten

Family Applications After (10)

Application Number Title Priority Date Filing Date
DE1793852A Expired DE1793852C2 (de) 1965-04-30 1966-04-29 4-Methyl-2-propionyl-und-butyrylthiazol und Verwendung von Thiazolcarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten
DE1793846A Expired DE1793846C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Pyrazincarbonylverbindungen als Geschmacksstoffe und Geschmacksstoffkomponente
DE1793851A Expired DE1793851C2 (de) 1965-04-30 1966-04-29 Verwendung von schwefelhaltigen Furanverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten und solche Verbindungen
DE1793850A Expired DE1793850C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Thiophan-Verbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente
DE1793848A Expired DE1793848C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter aromatischer Thiole, Sulfide und Disulfide als Geschmacksstoffe oder Geschmacksstoff komponente
DE1793845A Expired DE1793845C2 (de) 1965-04-30 1966-04-29 Verwendung von Chinoxalin-Kohlenwasserstoffen als Geschmacksstoffe oder Geschmacksstoffkomponenten
DE1695505A Expired DE1695505C3 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Alkylnaphthaline als Geschmacksstoffe oder Geschmacksstoffkomponenten
DE1793842A Expired DE1793842C3 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Benzofuranverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente
DE1793847A Expired DE1793847C3 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Pyridincarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente
DE1793849A Expired DE1793849C2 (de) 1965-04-30 1966-04-29 Verwendung von schwefelhaltigen Ketonen als Geschmacksstoffe oder Geschmacksstoffkomponenten und Furfurylthioaceton

Country Status (10)

Country Link
JP (6) JPS5231420B1 (de)
BR (1) BR6679143D0 (de)
CH (1) CH529516A (de)
DE (12) DE1793844C2 (de)
DK (1) DK139012B (de)
ES (1) ES326503A1 (de)
GB (1) GB1156472A (de)
NL (1) NL150316B (de)
NO (1) NO134889C (de)
SE (9) SE373731B (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3767429A (en) * 1971-12-06 1973-10-23 Procter & Gamble Lard flavor concentrate
NL8403748A (nl) * 1984-12-10 1986-07-01 Zaan Cacaofab Bv Cacaopoeder.
BR9204339A (pt) * 1991-11-08 1993-05-18 Unilever Nv Composicao de pertume,composicao detergente,composicao de condicionamento de tecido e processo para tratar texteis
BR0008351B1 (pt) 1999-04-20 2010-12-28 composição precursora de flavorizante, método para liberar o componente flavorizante a partir da composição precursora de flavorizante, e, composto de sulfeto.
JP2008079545A (ja) * 2006-09-28 2008-04-10 Sanei Gen Ffi Inc カフェオフランまたはその類縁体からなる乳含有飲食品用添加剤
JP5153195B2 (ja) * 2007-04-13 2013-02-27 長谷川香料株式会社 コーヒーの淹れたて感賦与剤
MY183958A (en) * 2007-11-13 2021-03-17 Nestec Sa Use of thioester flavors to improve the flavor quality of ready-to-drink coffee upon retorting and storage

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3076818A (en) * 1963-02-05 Production of benzofurans
US3033875A (en) * 1959-09-28 1962-05-08 Hills Bros Coffee Condensed ring heterocyclic disulfides and sulfides

Also Published As

Publication number Publication date
DE1793847C3 (de) 1981-04-02
BR6679143D0 (pt) 1973-09-11
DE1793848B1 (de) 1980-04-30
DE1793846C2 (de) 1981-01-15
DE1793852B1 (de) 1980-01-24
SE373733B (de) 1975-02-17
ES326503A1 (es) 1967-07-01
DE1793846B1 (de) 1980-04-30
DE1793849C2 (de) 1982-07-01
DE1793843B1 (de) 1980-04-30
SE373734B (de) 1975-02-17
JPS5412552B1 (de) 1979-05-23
DE1793851C2 (de) 1982-07-01
DE1695505C3 (de) 1979-11-29
DE1793845C2 (de) 1980-08-07
NL6605854A (de) 1966-10-31
NO134889C (de) 1977-01-05
SE377270B (de) 1975-06-30
DE1793842C3 (de) 1981-03-19
DE1793848C2 (de) 1981-01-15
SE373731B (de) 1975-02-17
DE1793850B1 (de) 1980-04-24
DE1793844B1 (de) 1979-10-31
DE1793850C2 (de) 1980-12-11
DE1695505A1 (de) 1970-12-23
SE377269B (de) 1975-06-30
DE1793852C2 (de) 1980-10-09
DE1695505B2 (de) 1979-04-05
DK139012B (da) 1978-12-04
DE1793847B1 (de) 1980-06-26
JPS5333667B1 (de) 1978-09-16
NO134889B (de) 1976-09-27
NL150316B (nl) 1976-08-16
DE1793842B1 (de) 1980-06-26
JPS499746B1 (de) 1974-03-06
JPS499747B1 (de) 1974-03-06
SE373735B (de) 1975-02-17
DE1793845B1 (de) 1979-10-31
CH529516A (de) 1972-10-31
SE335463B (de) 1971-05-24
SE373732B (de) 1975-02-17
DK139012C (de) 1979-05-14
JPS4821509B1 (de) 1973-06-29
JPS5231420B1 (de) 1977-08-15
SE373736B (de) 1975-02-17
GB1156472A (en) 1969-06-25
DE1793844C2 (de) 1980-07-24

Similar Documents

Publication Publication Date Title
DE60319231T2 (de) Schaumhaltemittel und verwendung davon
KR20010074679A (ko) 슈크랄로오스의 개선된 감미 전달 방법
DE1934651A1 (de) Mildes Suessmittel fuer Lebensmittel und Getraenke
DE1793843C2 (de) Verwendung bestimmter Pyridin-Kohlenwasserstoffe als Geschmacksstoffe oder Geschmacksstoffkomponente
EP1148794B1 (de) Brotaufstrich mit cola-aroma und verfahren zum herstellen eines solchen brotaufstrichs
DE2349672A1 (de) Fruchtprodukte, nahrungsmittel, genussmittel und getraenke mit fruchtaromasteigerndem zusatzstoff
EP4166006A1 (de) Verfahren zur verbesserung der beständigkeit des geschmacks eines lebensmittel-/getränkprodukts
Damir Utilization of sunflower seeds in tahina and halawa processing
DE3118810C1 (de) Aus Tuben abgabefaehige Zubereitung von zerkleinerten Frischzwiebeln und Verfahren zur Herstellung dieser Zubereitung
DE2515269A1 (de) Mittel zur verstaerkung des suessgeschmackes von produkten mit verringertem zuckergehalt
DE2558551A1 (de) Dinatriumitaconat und verfahren zur geschmacksverbesserung von nahrungs- und genussmitteln sowie von futtermitteln
US20090092734A1 (en) Use of extracts of pineapple as flavor intensifiers
DE2059790A1 (de) Maltobionsaeurehaltige Lebensmittel und Getraenke
DE3601582A1 (de) Gewuerzzubereitung fuer ein alkoholhaltiges getraenk
CH502070A (de) Verfahren zur Desodorierung von Nahrungsmitteln, Genussmitteln und Getränken und Desodorierungsmittel zur Ausführung des Verfahrens
US20120301593A1 (en) Use of extracts of pineapple as flavor intensifiers
Gindi et al. Optimizing the Acceptability of Jam From Baccaurea Angulata Fruit Peel
CH497136A (de) Verfahren zur Unterdrückung des bitteren Geschmackes von geniessbaren Substanzen
JP2022140350A (ja) 香気含有糖焙焼物
US1881158A (en) Grape juice composition and process of preparing the same
DE19619448A1 (de) Kaffeefreie Getränke mit anregender Wirkung
Ellen et al. Nickelgehalt verschiedener holländischer Lebensmittel
CH548167A (de) Verfahren, einem genuss- bzw. nahrungsmittel einen geschmack und geruch von geroesteter oder gebrannter note zu erteilen.
DE19856748A1 (de) Creme für den Lebensmittelbereich
DE1692809B2 (de) Verfahren zur erzeugung oder verstaerkung eines spargelaromas in lebensmitteln

Legal Events

Date Code Title Description
OI Miscellaneous see part 1
OI Miscellaneous see part 1
OD Request for examination
OI Miscellaneous see part 1
8339 Ceased/non-payment of the annual fee