DE1793846C2 - Verwendung bestimmter Pyrazincarbonylverbindungen als Geschmacksstoffe und Geschmacksstoffkomponente - Google Patents

Verwendung bestimmter Pyrazincarbonylverbindungen als Geschmacksstoffe und Geschmacksstoffkomponente

Info

Publication number
DE1793846C2
DE1793846C2 DE1793846A DE1793846A DE1793846C2 DE 1793846 C2 DE1793846 C2 DE 1793846C2 DE 1793846 A DE1793846 A DE 1793846A DE 1793846 A DE1793846 A DE 1793846A DE 1793846 C2 DE1793846 C2 DE 1793846C2
Authority
DE
Germany
Prior art keywords
taste
coffee
pyrazine
note
flavorings
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
DE1793846A
Other languages
English (en)
Other versions
DE1793846B1 (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 DE1793846B1 publication Critical patent/DE1793846B1/de
Application granted granted Critical
Publication of DE1793846C2 publication Critical patent/DE1793846C2/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)
  • Non-Alcoholic Beverages (AREA)
  • Bakery Products And Manufacturing Methods Therefor (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Fats And Perfumes (AREA)
  • Furan Compounds (AREA)
  • Pyrrole Compounds (AREA)

Description

Gegenstand der Erfindung ist die Verwendung der im vorstehenden Anspruch 1 genannten Pyrazincarbonylverbindungen 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 welche 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 zu geben, um die von der Natur erzeugten Aromen auf synthetischem Wege besser nachahmen zu können. Die Veränderung oder Verbesserung der geschmacklichen Eigenschaften von Nahrungsmitteln und Getränken durch Verwendung von künstlichen Aromen mit genau reproduzierbaren Geschmackseigenschaften und -qualitäten nimmt in der Lebensmittelindustrie mehr und mehr an Bedeutung zu. seitdem für die Ernährung des Menschen neue, bisher nicht verwendete Rohstoffe erschlossen werden, um der drohenden Verknappung der Nahrungsmittel in gewiv sen Gebieten des Erdballs entgegenzutreten.
Es wurde festgestellt, daß die oben beschriebenen Verbindungen entweder einzeln oder in Form zweckentsprechender Mischungen dazu geeignet sind, die Geschmackseigenschaften verschiedenster fester und flüssiger Nahrungs- und Genußmittel oder Getränke im ü gewünschten Sinne zu verändern. Mittels der vorliegen den Erfindung können beispielsweise Produkte wie Fruchtsäfte. Gemüsesäfte. Milchprodukte. Kaffee-. Tee-, Kakao· und Schokoladeprodukie. Cietreideflocken. Mehle, Korifiseriewareri, Fleischprodükte, Backwaren und Speiseeis geschmacklich verändert iwerdem Die Erfindung eignet sich insbesondere zur Verbesserung oder Verstärkung des GesShmäckes Von konservierten Lebensmitteini Ganz besonders eignet sich die Erfiri' düng zur Veränderung, Verbesserung oder Verstärkung e> der Geschrhackseigenschaffen von sogenannten iösll· chen Kaffccproduklen (im englischeil Sprachgebrauch als »instant coffee« bezeichnet);
Die geschmacksverändernden Verbindungen gemäß der Erfindung werden zweckmäßigerweise in verdünnter Form, z. B. als verdünnte Lösungen in Alkohol, Glycerintriacetat oder in anderen genießbaren Lösungsmitteln, verwendet, um die genaue Dosierung und die gleichmäßige Verteilung in den Lebensmitteln zu erleichtern.
Die erfindungsgemäß zu verwendenden geschmacksverändernden Verbindungen eignen sich insbesondere zur geschmacksverändernden Behandlung von sogenanntem löslichen Pulverkaffee. Bei der Herstellung solcher Kaffeepulver aus gemahlenem geröstetem Kaffee gehen viele Geschmacks- und Aromastoffe verloren. Die auf dem Markt angebotenen löslichen Kaffeeprodukte liefern Getränke, die gesehmacks- und aromaarm sind, wenn man sie mit einem Kaffeegetränk vergleicht, das aus frisch gerösteten Kaffeebohnen hergestellt wurde. Durch Verwendung der geschmacksverändernden Verbindungen gemäß der Erfindung ist es nun möglich, die geschmackliche Qualität der löslichen Kaffeepulver wesentlich zu verbessern und ein Aroma zu erzeugen, das dem natürlichen Kaffeearoma viel näher kommt. Die gesehmacks verändernden Verbindungen können dem löslichen Pulverkaffee beispielsweise durch Aufsprühen einverleibt werden.
Die geschmacksverändernden Verbindungen gemäß der Erfindung sind nicht nur zur Verbesserung des Geschmackes und Aromas von löslichem Pulverkaffee verwendbar, sondern eignen sich auch zur Herstellung von künstlichen Kaffee-Essenzen und zur Erzeugung von anderen Aromen.
In der folgenden Aufstellung der erfindungsgemäß zu verwendenden Pyrazincarbonylverbindungen ist neben dem chemischen Namen jeder Verbindung ein Literaturhinweis betreffend ein Herstellungsverfahren angegeben:
a. 2-Formyl-pyrazin
b. 2-AcetyI-pyrazin
c. 2-Acetonyl-pyrazin
Chemical Abstracts
58,10180b (1963)
J. Amer. Chem. Soc.
75,3621(1952)
J. Org. Chem.
23,406(1958)
Die organoleptische Bewertung der erfindungsgemäß zu verwendenden Verbindungen wurde mittels der Prüfungsmethoden A und B durchgeführt. Die Methode A dieme dazu, den Eigengeschmack der einzelnen Substanzen zu ermitteln. Die geschmacksverändernden Eigenschaften der Substanzen wurden mittels der Methode B ermittelt. Es wurde insbesondere die geschmacksverändernde Wirkung der Prüfsubstanzen (im folgenden »Geschmacksstoffe« genann») auf Kaffeeprodukte und speziell auf sprühgeirocknete lösliche Kaffeepulver geprüft.
Methode A
Die Cieschmacksstoffe wurden in einer 65%igen Zuckersirup-Lösung, bestehend aus Rohrzucker in Leitungswasser, gekostctr Die zu prüfenden Ge-^ iSchtrlacksstoffe wUfden dem Sirup in; Form von Lösungen von I Gew.^/o oder 1 Gew.-%ö in SWoigem Alkohol zügegeben, Die Konzentration der Geschmacksstoffd im Zückersirup schwankte entsprechend der Geschmacksintensität zwischen 0,005 und 6 g pro i00 Liier Sirup. Proben des arofnatisieffen Sirups wurden einer öruppe von Geschmacksprüfern vorgelegt Nach deni Koslen der Proben mußte jeder Prüfer
eine Beschreibung des Geschmackes der einzelnen Geschmacksstoffe abgeben.
Methode B
Als Substrat für die Prüfung wurde ein Kaffeegetränk verwendet, das durch Auflösen eines im Handel erhältlichen, sprühgetrockneten Kaffeepulvers in siedendem Wasser 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.-% oder 1 Gew.-%o in 96%igem Alkohol in Konzentrationen von 0,005 bis 5 g auf 100 Liter 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 wuide so rasch als möglich, auf jeden Fall nicht später ais i5 Minuten nach der Zubereitung vorgenommen.
Die nur mit einer Kennzahl versehenen 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.
Die Resultate der org»nolepiicchen Prüfung sind in der nachfolgenden Tabelle 1 zusammengefaßt. In der ersten Kolonne der Tabelle sind Aie Buchstaben der einzelnen Verbindungen innerhalb der genannten Stoffklasse angeführt. Die zweite Kolonne verweist auf die angewendete Prüfmethode. In der dritten Kolonne »ind die verwendeten Mengen der Prüfsubstanzen in g pro 100 Liter Getränk (Zuckersirup oder Kaffeegetränk) angegeben.
Tabelle 1
Ver- Verbindung such
Menge Organoleptische Bewertung
a A 5,0 brotartiger Geschmack
a B 1,25 Röstnote
b B 0,2 haselnußartig;
Röstgeschmack;
karamellartige Note
c A 5,0 leicht haselnußartige Note
Obschon mehrere der in der vorangehenden Tabelle aufgezählten Stoffe einen mehr oder weniger unnatürlichen Eigengeschmack oder zumindest einen Gejchmack aufweisen, der nicht unbedingt für die Verwendung dieser Stoffe als Aromatisierungsmittel in Nahrungsmitteln und Getränken spricht, haben sich diese Stoffe dertfioch,als durchaus brauchbar; erwiesen, (wenn sie als Mischbeständteile zusammen mit anderen Geschiriäcksstöffen in geeigneten Mischverhältnissen Verwendet werden-
Die nachfolgenden Beispiele sollen zeigen, wie man durch zweckmäßige Auswahl Von gewissen Verbindung gen bestimmte Geschmäciksnoten Von Nahrungs- Und Genußfflitteln öder Getränken verändern, z. B, verstau ken oder verbessern, kann.
Verbindungen Bei Bei 10
spiel 1 spiel 2 20
Gewicbtsteile 0,5
b, 2-AcetyI-pyrazin 30 7,5
2-Methyl-3-äthylpyrazin 40 2
2,3-Diäthyl-pyrazin - 3
2-Methyl-3-isopropyl-pyrazin 5 -
2-Methyl-3-methylth io-pyrazi η - -
Essigsäure-furfurylthiolester 2 1
Furfuryl-methylsulOd 1 4
2-Acetyl-thiophen 80 6
Furfuryl-propyl-sulfid 3 1,5
2,6-DimethyI-thio-)^pyron 4 2
2-Methoxy-benzolthiol 12 5
2-HydroxyphenyI-methyl-suIfid 2 2,5
3,4-XylenoI 4 0,5
2-Hydroxy-acetophenon - 20
4-ÄthyI-2-methoxy-phenoI 5 4
4-ÄthyI-phenol - -
Pyridin 30 -
2-Vinyl-benzofuran 3 —
4-VinyI-l,2-dimethoxy-benzoI 40
Propionsäure-furiurylester 50
Furfural 100
Jedes der so erhaltenen, geschmacksgebende Mittel wurde einem Aufguß eines im Handel erhältlichen Pulverkaffees zugesetzt. Dadurch wurden dem Kaffeegetränk Geschmacksnoten verliehen, die in der Richtung des Geschmackes und Aromas eines aus frisch gemahlenem gerösteten Kaffee zubereiteten Kaffeegetränks lagen.
Die nachfolgenden Tabellen 2 bis 7 zeigen die Aromatisierung von verschiedenen weiteren Getränken und Speisen sowie eines Karamelgeschmacksstoffes mit dem erfindungsgemäß zu verwendenden Pyrazincarbonylverbindungen:
Tabelle 2
Aromatisierung von verdünntem Zuckersirup1)
Ver- Menge
bindung (ppm2)
Organoleptische Bewertung
a 50 brotartiger Geschmack
b 12,5 Röstnote
50 leicht haselnußartige Note
') 10% Zucker in Wasser (vergl. Methode A).
2) 1 g/100 1 = 10 ppm (parts per million).
Tabelle 3
Aromatisierung von Salzwasser1)
Ver- Menge
bindung (ppm)
Organoleptische Bewertung
a 5 leicht gerösteter, brotartiger
Geschmack
b 0,1=0,5 Röstnote, fleisdhäftig
C 5 leicht haselnußartige Note
') 0,5% Lösung von NaGI in Wasser,
I Tabelle 4 17 93 5 wurden in einer Prüfungskommission Milch PralinengrundstofT b) Vcr- Menge Gew.-Teile Grundstoff abgegeben. 5 846 6 Tabelle 7 Vergleichsversuche
I I Aromatisierung von von Geschmacksexperten nach Vergleith mit einem nicht- Organoleptische Bewertung1) a) PralinengrundstofT bindung (ppm) Verwendung von 2-Acetyl-pyrazin (Verbindung b) als Die folgenden Pvra/incarbonvlverbindunperi wurden
i I löslichem KalTee1) aromatisiertem Kaffeegetränk abgegeben. Zutaten a 1,0-2,0 500 aromatisierender Zusatz zu einem Karamelgeschmaeks- "ι * I W I \J I p^ \* 1 1 ^J *^ Il M Vl U **l I IWi* 1 U ^^ 1 IT I ■ W I U III ^A ΙΛ 11 f^\*A A TT \Λ A ^4\rfl 1
mit bekannten Verbindungen auf ihre Geschmacksei
ρ Ver- Menge Geschmack nach gekochter b 0,2 50 IO stoff genschaften verglichen:
Ί bindung (ppm) Organoleptische Bewertung2) Tabelle 5 Milch mit leicht brotartiger H-iselnüsse C 1,0-2,0 450 a) KaramelgrundstofT Verbidung a 2-Formyl'pyrazin
Verbindung b 2-Äcetylpyrazin
!i I a 5,0 Aromatisierung von Note Erdnüsse ') Diese Bewertungen Zutaten Gew.-Teile Verbindung c 2-Acetonylpyrazin
ι abgerundetes Aroma; Ver- Menge
bindung (ppm)		 Röstnote, haselnußartig, Zucker Bekannte Verbindungen der US-PS 16 96 419
b 1,0-2,0 leicht brotartige Note kakaoartig Organoleptische Bewertung1) 15 Methyl-cyclopentenolon 50 2-Methylpyrazin
c 5,0 Röstnote a 1.0-2,0 haselnußartige Note Acetyl-methyl-carbinol 30 2,5-Dimethylpyrazin
abgerundetes Aroma; besser abgerundetes Aroma Diacetyl 5 2,6'DiIiIeIhVIpVrBZIn
leicht haselnußartige Note wurden in einer Prüfungskommission geröstete haselnußartige
NnI ρ 		Dipropionyl 5
b 0,2 von Geschmacksexperten nach Vergleich mit nicht aroma- haselnußartige Note Furfurylalkohol 35
') 2,50 g von handelsüblichem löslichen Kaffee in 200 ml tisierter Much abgegeben. wurdiri in einer Prüfungskommis' 20 Furfurylaldehyd 25
heißem Wasser (vergl. Methode B). c 1,0-2,0 siön von Öeschmäcksexpeften nach Vergleich mit Glycerintriacetat 850
-) Diese Bewertungen nicht:! romrilisicrtem 1» ^c<i m t 1 liilfi
') Diese Bewertungen Tabelle 6 25 VjCbdlUl IUUU
b) KaramelgeschmacksstofTzusammensetzung
Aromatisierung von Zutaten A B
JO Gew.-Teile
Karamelgrundstoff 100 100
Äthylalkohol 900 875
2-Acetyl-pyrazin l%ig*) - 25
Gesamt 1000 1000
35
*) Losung in Äthylalkohol.
Die obengenannten Geschmacksstoffzusammenset
40 zungen (A und B) wurden für die Aromatisierung in
Milch in einer Menge von 200 g Geschmacksstüff pro
1001 Milch verv/endet und das aromatisierte Milchge
tränk sodann einer Geschmacksbewertung durch
Geschmacksexperten unterworfen, welche zu folgen
45 dem Resultat kamen:
Milch aromatisiert mit A:
50 Zeigt gut definierten karamellenartigen und butter
artigen Geschmack;
Milch aromatisiert mit B:
Zeigt besser abgerundetes Aroma und einen
55 gerösteten Geschmack nach Haselnüssen unJ
Kakao.
60
65
-*rv ι 1 , i - * 1" 7 17 93 Dosis Bemerkungen Dosis Bemerkungen**) Dosis Bemerkungen*) III 846
8 		I
ε
I
fr
1 Λ 		j \ (I) Auswertung in Miiieriilwasser (Typ IfVIAN) ppm*) ppm ppm H
ι
, \ ' 50 grün; erdig W'rhiMiliiifj! Dosis Hrmcrkuiiucn ι I
j Verbindung 50 grün^ erdig,
leicht fruchligi		 30 grün, erdige Note 40 grün, erdig, iipin
ι
J '		 I , j frische Nüsse 30 grün, erdig; leicht nußartig 2,5-Dinicthylpyrazin 40 grüht crdiu. I
ι 2-Mclhylpyrazin 50 grün, erdig, nuUnrtig,- die geröstete
Kaffeenote ist		 Ιΐ Ieichi rrtichiiji.
frische Nüsse		 I
a '■
»'		 2,5-Dimethylpyrazin karamcllartig abgeschwächt 2,f)-Diiuülhyinyrazih 40 jjrün^ erdige nuli;irliu. j
10 leicht verbrannt. 30 grün, erdig, nußartig; I
1 ; 2,6-Dimethylpyrazin brolarligcr die geröstete *) Durch ein Aroniacxperlengronmim lüich Vergleich mil B
ϊ'
t Geschmack Xatteennrp i«r 211 unaruniatisicrtcr Milch. f
/' ■·' ι ' I Röstnote, abgeschwächt f
ieichi fleischig. Vergleiche demgegenüber obenslehendc Tabelle 5. I
an ccröstctc llasel- handelsüblichem löslichem Kafiee I
ί S b nüsse erinnernd **) Durch ein Aromaexpertengremium nach Vergleich mit 25 I
10 leicht geröstet. unaromatisiertem KafTeegetränk. (4) Auswertung in l'ralincngrundlagc*) ft
haselnußartig
> Verbindung Dosis Bemerkungen**) I
C io ppm I
Fr
( Vergleiche demgegenüber obenstehende Tabelle 4. I
( I *) Teile pro Mill. (2) Auswertung in löslichem Kaffee*) I
ϊ &■ * ' 2-Methylpyrazin 30 grün, erdig,
frische Nüsse		 I
Verbindung 2,5-Dimethylpyrazin 30 grün, erdig. S
1 J5 frische Haselnüsse 1
(3) Auswertung in Milch 2,6-Dimethylpyrazin 30 grün, erdig, nußartig. [
2-Methylpyrazin karamellartig 1
2,5-Dimethylpyrazin Verbindung 40 I
*) Hergestellt aus 500 g Haselnüssen, 50 g Erdnüssen und I
450 g Zucker. I
2,6-Dimethylpyrazin 2-Methylpyrazin **) Durch ein Aromaexpertengremium nach Vergleich mit I
45 einer nicht aromatisierten Grundlage. I
Vergleiche demgegenüber obenstehende Tabelle 6. t'
iS
.·
ft
Allgemeine Bemerkungen I
*) Hergestellt aus 2,5 g
und 200 ecm Wasser.		 Zuerst ist festzustellen, daß die bekannten Pyrazinde-
50 fTvöic ucüiiich weniger wirksam siiiü als die criindungs- $■'!
gemäßen Verbindungen. Zur Erzielung vergleichbarer 4
Geschmackseffekte müssen höhere (5- und in bestimm
ten Fällen 20- bis 50mal höhere) Verhältnisse verwendet
werden.		 H
55 . Bezüglich des in verschiedenen Grundlagen entwik-
icelten Geschmackseffektes verleihen alle bekannten
Pyrazinderivate eine grüne, erdige Note, die mehr oder %>'
weniger an die von frischen Nüssen oder Haselnüsse'-i Pi
erinnert, im Gegensatz zu den erfindungsgemäßen ρ
Pyrazincarbonylen, die alle eine typische Röstnote
entwickeln, die im Fall von 2-Acetylpyrazin (Verbin
dung b) besonders deutlich ist Wo Röstiiö ten nötig sind,
wie z. B. in Kaffee oder Pralinen usw., sind die
erfindungsgemäßen Pyrazinderivate besonders zweck
mäßig zur Verstärkung dieser typischen Aromanote.
Die Verwertung der Erfindung kann durch gesetzli
che Bestimmungen, insbesondere durch das Lebensmit
telgesetz, beschränkt sein. i
i
ί
i
ί
030 263/14
Jas ■ -' ■ -"-- - ■ -—^"i^'*'''

Claims (1)

Patentansprüche:
1. Verwendung von
a. 2-Formyl-pyrazin
b. 2-Acetyl-pyrazin
α 2-Acetonyl-pyrazin
zur Veränderung der Geschmackseigenschaften fester oder flüssiger Nahrungs- und Genußmittel und von Getränken sowie als Geschmacksstoffkomponente in einem geschmacksverändernden Mittel.
Z Verwendung der im Anspruch 1 genannten Verbindungen zur Aromatisierung von löslichen Kaffeeprodukten.
DE1793846A 1965-04-30 1966-04-29 Verwendung bestimmter Pyrazincarbonylverbindungen als Geschmacksstoffe und Geschmacksstoffkomponente Expired DE1793846C2 (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
DE1793846B1 DE1793846B1 (de) 1980-04-30
DE1793846C2 true DE1793846C2 (de) 1981-01-15

Family

ID=27036753

Family Applications (12)

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

Family Applications After (11)

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

Country Status (10)

Country Link
JP (6) JPS499747B1 (de)
BR (1) BR6679143D0 (de)
CH (1) CH529516A (de)
DE (12) DE1793846C2 (de)
DK (1) DK139012B (de)
ES (1) ES326503A1 (de)
GB (1) GB1156472A (de)
NL (1) NL150316B (de)
NO (1) NO134889C (de)
SE (9) SE373735B (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
ES2380760T3 (es) * 2007-11-13 2012-05-18 Nestec S.A. Uso de saborizantes de tioéster para mejorar la calidad del sabor de café listo para tomar tras el tratamiento térmico y el almacenamiento

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
ES326503A1 (es) 1967-07-01
SE377270B (de) 1975-06-30
DE1793842C3 (de) 1981-03-19
DE1793848B1 (de) 1980-04-30
DE1793845B1 (de) 1979-10-31
DE1793850B1 (de) 1980-04-24
DE1793842B1 (de) 1980-06-26
DE1695505B2 (de) 1979-04-05
DE1793844C2 (de) 1980-07-24
DK139012C (de) 1979-05-14
JPS4821509B1 (de) 1973-06-29
GB1156472A (en) 1969-06-25
JPS5333667B1 (de) 1978-09-16
DE1793843C2 (de) 1981-01-15
SE373735B (de) 1975-02-17
DE1793852B1 (de) 1980-01-24
DE1793848C2 (de) 1981-01-15
NL150316B (nl) 1976-08-16
DE1793852C2 (de) 1980-10-09
JPS5412552B1 (de) 1979-05-23
JPS5231420B1 (de) 1977-08-15
CH529516A (de) 1972-10-31
SE373733B (de) 1975-02-17
DE1793846B1 (de) 1980-04-30
SE373732B (de) 1975-02-17
SE335463B (de) 1971-05-24
DE1695505A1 (de) 1970-12-23
NO134889C (de) 1977-01-05
SE373736B (de) 1975-02-17
JPS499746B1 (de) 1974-03-06
SE377269B (de) 1975-06-30
DE1793844B1 (de) 1979-10-31
SE373731B (de) 1975-02-17
DE1793849C2 (de) 1982-07-01
DE1793847B1 (de) 1980-06-26
DE1695505C3 (de) 1979-11-29
JPS499747B1 (de) 1974-03-06
NL6605854A (de) 1966-10-31
DE1793843B1 (de) 1980-04-30
BR6679143D0 (pt) 1973-09-11
DK139012B (da) 1978-12-04
NO134889B (de) 1976-09-27
DE1793845C2 (de) 1980-08-07
DE1793851C2 (de) 1982-07-01
DE1793850C2 (de) 1980-12-11
SE373734B (de) 1975-02-17

Similar Documents

Publication Publication Date Title
DE60021541T2 (de) Herstellung von hochloeslichen und stabilen mineralstoffergaenzungen
DE602005005845T2 (de) Verzehrbares produkt mit antioxidantien
EP0099557B1 (de) Instant-Getränke und Instant-Tees sowie Verfahren zu ihrer Herstellung
RU2246847C2 (ru) Способ получения мороженого и композиция мороженого
DE2349672C2 (de) Verwendung von L-Asparagyl-L-phenylalaninmethylester als Mittel zur Steigerung des Geschmacks und Aromas
DE1793846C2 (de) Verwendung bestimmter Pyrazincarbonylverbindungen als Geschmacksstoffe und Geschmacksstoffkomponente
RU2651282C1 (ru) Способ производства карамели на патоке крахмальной
DE4103209C1 (de) Aufbrühbares Kaffee-Extrakt-Pulver für die Zubereitung eines Kaffee-Getränks mit Cappuccino-Geschmack
DE2843322A1 (de) Molkematerial als aromastoff oder aromastreckmittel
KR20110030028A (ko) 흑마늘 초콜렛
DE19536097A1 (de) Flüssige Lebensmittelzubereitung sowie Verfahren zu deren Herstellung
RU2618338C1 (ru) Безалкогольный напиток
RU2372799C1 (ru) Безалкогольный напиток
RU2075953C1 (ru) Композиция из сухих ягод для приготовления напитка и способ ее получения
DE1812256A1 (de) Verfahren zur Herstellung von Lebensmittel-Aromen und Gewuerzen
RU2163080C1 (ru) Напиток газированный безалкогольный
Abdollahzadeh et al. The effect of honey and ginger powder on the quality characteristics of instant coffee mix
RU2496389C1 (ru) Способ получения взвара
RU2179577C2 (ru) Способ производства аперитива
RU2581227C1 (ru) Безалкогольный напиток
CH563725A5 (en) Synthetic flavour - modifying agents for coffee and other beverages and foods
DE1101118B (de) Verfahren zum Haltbarmachen von Gemuese und Fruechten
DE2852783A1 (de) Aromapraeparat, seine herstellung und verwendung
DD205605A1 (de) Verfahren zur herstellung eines kakaoaromahaltigen pulvers
CH548167A (de) Verfahren, einem genuss- bzw. nahrungsmittel einen geschmack und geruch von geroesteter oder gebrannter note zu erteilen.

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