DE1793842C3 - Verwendung bestimmter Benzofuranverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente - Google Patents
Verwendung bestimmter Benzofuranverbindungen als Geschmacksstoffe oder GeschmacksstoffkomponenteInfo
- Publication number
- DE1793842C3 DE1793842C3 DE1793842A DE1793842A DE1793842C3 DE 1793842 C3 DE1793842 C3 DE 1793842C3 DE 1793842 A DE1793842 A DE 1793842A DE 1793842 A DE1793842 A DE 1793842A DE 1793842 C3 DE1793842 C3 DE 1793842C3
- Authority
- DE
- Germany
- Prior art keywords
- benzofuran
- taste
- note
- coffee
- connection
- 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
Links
Classifications
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
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- C—CHEMISTRY; METALLURGY
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- 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
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- C—CHEMISTRY; METALLURGY
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
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- 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
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- C—CHEMISTRY; METALLURGY
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- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—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
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- C—CHEMISTRY; METALLURGY
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
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- 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
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- C—CHEMISTRY; METALLURGY
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- 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
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- C—CHEMISTRY; METALLURGY
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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- C07D307/36—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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- C07D307/42—Singly bound oxygen atoms
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- C—CHEMISTRY; METALLURGY
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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- C07D307/78—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
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- C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/28—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
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- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
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Description
Gegenstand der Erfindung ist die Verwendung der im
verstehenden Anspruch 1 genannten Benzofuranverbindungen zur Veränderung der Geschmackseigenschaften fester oder flüssiger Nahrungs- und Genußmittel und von Getränken sowie als Geschmacksstoffskomponente in einem geschmacksverändernden Mittel.
Unter »geschmacksverändernd« sind alle Vorgänge oe'-r 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 dann, die Auswahl der bisher zur
Verfügung stehenden Geschmacksstoffe zu erweitern und dem Lebensmitteltcchniker 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 gesihrn.u kuchen 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 gewissen Gebieten des Erdballs entgegenzutreten.
Es wurde festgestellt, daß die erfindungsgemäß /u
verwendenden Verbindungen entweder einzeln oder in Form /weckentsprechender Mischungen dazu geeignet
sind, die Gesthmackseigenschaften 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. Mehle, Konfiseriewaren, Fleischprodukte,
Backwaren und Speiseeis, geschmacklich verändert
a. Benzofuran
b. 2-Methyl-benzofuran
c. 2-Äthyl-benzofuran
d. 2,3-Dimethyl-benzofuran
e. 2-VinyI-benzofuran
f. 2-lsopropenyl-benzofuran
g. 7-Methyl-benzofuran
h. 7-Äthyl-benzofuran
i. 2,7-Dimethyl-benzofuran
LH.
J. ehem. Soc.
(London) 1955,3689
73,754(1951)
J. ehem. Soc.
(London) 1955,3689
73,754(1951)
n.V.
J. ehem. Soc.
(London) 1920,1534
n.V.
no. 858 470
Die obenzitierten neuen Verbindungen können wie folgt erhalten werden:
f. 2-Isopropenyl-benzofuran
Nach der in J. Amer. ehem. Soc. 73. 754 (1951)
beschriebenen Methode wird 2-Acetyl-benzofuran mit Methyl-magnesiumbromid umgesetzt, worauf
das erhaltene 2-(2-Hydroxy-isopropyl)-benzofuran in das Acetat übergeführt wird. Durch Pyrolyse des
Acetats erhält man 2-Isopropenyl-benzofuran mit 4- Sdp.8l -83°C/0.001 mm Hg.
h. 7-Äthyl-benzofuran
wird nach der in J. ehem. Soc. (London) 1920, 1534.
beschriebenen Methode hergestellt, indem man o-Äthylphenol ansieile von o-Kresol verwendet.
'" Das Massenspektrum des erhaltenen Produktes weist Signale bei den Massenzahlen 131 (100%),
146 (38%) und 77 (10%) auf. Die eingeklammerten Werte sind die relativen Intensitäten.
v> Die geschmacksverändernden Mittel gemäß der
Erfindung werden zweckmäßigerweise in verdünnter Form. z. B. als verdünnte Lösungen in Alkohol. Triacetin
oder in anderen genießbaren Lösungsmitteln, verwendet, um die genaue Dosierung und die gleichmäßige
so Verteilung in den Lebensmitteln zu erleichtern.
Die erfindungsgemäBen geschmacksverändernden Mittel eignen sich insbesondere zur geschmacksverändernden Behandlung von sogenanntem löslichem
Pulverkaffee. Bei der Herstellung solcher Kaffeepulver
ίϊ aus gemahlenem geröstetem Kaffee gehen viele
Geschmacks- und Aromastoffe verloren. Die auf dem Markt angebotenen löslichen Kaffeeprodukte liefern
Getränke, die geschmacks- und aromaarm sind, wenn
man sie mit einem Kaffeegetrlnk vergleicht, das aus
frisch gerösteten Kaffeebohnen hergestellt wurde. Puren Verwendung der geschmacksverändernden Mittel gemäß der Erfindung ist es nun möglich, die
geschmackliche Qualität der löslichen Kaffeepulver s wesentlich zu verbessern und ein Aroma zu erzeugen,
das dem natürlichen Kaffeearoma viel näher kommt Die geschmacksverändernden Mittel können dem
löslichen Pulverkaffee beispielsweise durch Aufsprühen einverleibt werden. to
Die geschmacksverändernden Mittel gemäß der Erfindung sind nicht nur zur Verbesserung des
Geschmacks und Aromas von löslichem Pulverkaffee verwendbar, sondern eignen sich auch zur Herstellung
von künstlichen Kaffee-Essenzen und zur Erzeugung is
von anderen Aromen.
Die organoleptische Bewertung der obenzitierten
Verbindungen wurde mittels Prüfmethoden A und B durchgeführt Die Methode A diente dazu, den
Eigengeschmack d«*r einzelnen Substanzen zu ermitteln. >o
Die geschmacksvcTändernden Eigenschaften der Substanzen wurden mittels der Methode B ermittelt. Es
wurde insbesondere die geschmacksverändernde Wirkung der Prüfsubstanzen (im folgenden »Geschmacksstoffe« genannt) auf Kaffeeprodukte und speziell auf
sprühgetrocknete lösliche Kaffeepulver geprüft.
Methode A
Die Geschmacksstoffe wurden in einer 65%igen Zuckersirup-Lösung, bestehend aus Rohrzucker in ω
Leitungswasser, gekostet Die zu prüfenden Geschmacksstoffe wurden dem Sirup in Form von
Lösungen von 1 Gew.-% odtr 1 Ge ,.-%o in 96%igem
Alkohol zugegeben. Die Konzentration der Geschmacksstoffe im Zuckersirup sch- dnkte entspre-
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
eine Beschreibung des Geschmacks der einzelnen 4Π Geschmacksstoffe abgeben.
Methode B
Als Substrat für die Prüfung wurde ein Kaffeegetränk verwendet, das durch Auflösen eines im Handel Ό
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 ">o Kaffeegetränk in Form von Lösungen von 1 Gew.-°/o
oder 1 Gew.-%o in 96%:gem 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 r>
geführt und sofort in eine Reihe von Tassen für die organoleptische Prüfung gegossen. Das Kosten des
Getränkes wurde so rasch als möglich, auf jeden Fall nicht späler als 15 Minuten nach der Zubereitung
vorgenommen. Μ)
Die nur mit einer Kennzahl versehenen gefüllten Tassen wurden in einer Reihe aufgestellt, wobei die
erste Tasse eine nicht aromatisierle Vergleichsprobe des Kaffeegetränkes enthielt. Die Geschmacksprüfer
mußten feststellen, ob zwischen der Vergleichsprobe ws
und den anderen Proben geschmacklich ein Unterschied bestand oder nicht. Die Prüfer mußten ferner die
Geschmacksunterschiede beschreiben und charakterisieren.
Die Resultate der organoleptischen Prüfungen sind in der nachfolgenden Tabelle zusammengefaßt In der
ersten Kolonne der Tabelle sind die Buchstaben der einzelnen Verbindungen innerhalb der genannten
Stoffklasse aufgeführt Die zweite Kolonne der Tabelle verweist auf die angewendete Prüfmethode. In der
dritten Kolonne sind die verwendeten Mengen der Prüfsubstanzen in g pro 100 Liter Getränk (Zuckertirup
oder Kaffeegetränk) angegeben.
Ver | Ver | Menge | Organoleptische Bewertung |
bin | such | ||
dung | |||
a. | A | 0,05 | styrolähnlich; aromatisch |
b. | A | 1-3 | leicht phenolisch; |
verbrannter Geschmack | |||
b. | B | 0.4 | Verstärkung der bitteren Note |
C. | A | 0,3 | salicylartiger Geschmack |
d. | A | 0,25 | erdige Geschmacksnote |
e. | A | 1,0 | verbrannt; Karamellen |
geschmack | |||
f. | A | 0,25 | phenolisch; safranartig |
g- | B | 0,12 | erdig; pilzartig; haselnußartig |
h. | B | 0,50 | verbrannt; grüner Geschmack |
B | 0,095 | erdige Geschmacksnote |
Obschon mehrere der in der vorangehenden Tabelle aufgezählten Stoffe einen mehr oder weniger unnatürlichen Eigengeschmack oder zumindest einen Geschmack aufweisen, der nicht unbedingt für die
Verwendung dieser Stoffe als Aromatisierungsmittel in Nahrungsmitteln oder Getränken spricht, haben sich
diese Stoffe dennoch als durchaus brauenbar erwiesen, wenn sie als Mischbestandteile zusammen mit anderen
Geschmacksstoffen in geeigneten Mischverhältnissen verwendet werden.
Die nachfolgenden Beispiele sollen zeigen, wie man
durch zweckmäßige Auswahl von gewissen Verbindungen bestimmte Geschmacksnoten von Nahrungs- und
Genußmitteln oder Getränken verändern, z. B. verstärken oder verbessern kann.
Vorbindungen | üewichtsleilc | 5 | - | 2 | I | Bei | 5 | Bei | I |
Bei | 2 | 4 | spiel 7 | 30 | spiel i | 4 | |||
spiel I | - | 3 | 4 | 6 | |||||
e. 2-Vinyl-benzofuran | 3 | - | 40 | 2 | 20 | 1.5 | |||
2-Methyl-3-äthyl-pyrazin | - | - | - | I | 0.5 | 2 | |||
2,3-Diäthyl-pyra/in | - | 4 | 80 | 7.5 | |||||
2-Methyl-3-isopropyl-pyra/in | - | 3 | 10 | ||||||
2-Acetyl-pyrazin | 4 | 2 | |||||||
2-MethyI-3-methylthio-pyra/in | 12 | 3 | |||||||
Essigsäure=furfurylthiolesler | 2 | - | |||||||
Furfuryl-methyl-sulfid | 4 | - | |||||||
2-Acetyl-thiophen | |||||||||
Furfuryl-propyl-sulfid | |||||||||
2,6-Dimethyl-thio-)>-pyron | |||||||||
2-Methoxyben7olthiol | |||||||||
2-Hydroxyphenyl-methyl-suind | |||||||||
3,4-Xylenol |
Fortsetzung
Verbindungen
Gewichtsteile
Bei- Beispiel I spiel 2
Beispiel 3
e. 2-Hydroxyacetophenon
4-Äthyl-2-methoxy-phenoI - 5 2,5
4-Äthyl-Dtieno! - - 0,5
Pyridin 20 30
4-Vinyl-l,2-dimethoxy-benzol - 40 -
Propionsäure-furfurylester - 50 -
Furfural - 100 -
Jedes der so erhaltenen, geschmacksgebende Mittel wurde einem Aufguß eines im Handel erhältlichen
15 Pulverkaffees zugesetzt. Dadurch wurden dem Kaffeegetränk
Geschmacksnoten verliehen, die in der Richtung des Geschmacks und Aromas eines aus frisch
gemahlenem geröstetem Kaffee zubereiteten Kaffeegetränks lagen.
Vergleichsversuche
Die erfindungsgemäßen Benzofuranderivate (Verbindungen a bis i) wurden mit den folgenden, bekannten
Verbindungen auf ihre Geschmackseigenschaften verglichen:
Bekannte Verbindungen
Furfurylmercaptan US-PS 16 96 419
Dibenzofurfuryldisulfid US-PS 30 33 875
(1) Auswertung in Mineralwasser (Typ EVIAN)
Verbindung | Dosis | Bemerkungen |
ppm*; | ||
Furfurylmercaptan | 2,0 | überverbrannt, schwefelig |
0,05 | verbrannt, Röstkafleenote | |
Dibenzofurfuryldisulfid | 10,0 | schwefelig, grün, metallische Note; |
an faule Eier und Gemüse erinnernd | ||
Verbindung a | 2,5 | starke verbrannte Note, phenolisch |
Verbindung b | 4,0 | verbrannt, phenolisch |
Verbindung c | 2,5 | phenolisch, salicylisch |
Verbindung d | 2,5 | erdig, phenolisch |
Verbindung e | 2,5 | verbrannt, karamellarcig |
Verbindung f | 2,5 | verbrannt, acetophenonartig, phenolisch |
Verbindung g | 2,5 | erdig, Haselnüsse, leicht kampferartig |
Verbindung h | 10,0 | verbrannt |
Verbindung i | 5,0 | erdig, phenolisch |
·) Teile pro Mill. | ||
(2) Auswertung in loslichem | Kaffee**) | |
Verbindung | Dosis | Bemerkungen**) |
ppm |
Furfurylmercaptan 0,05
Dibenzofurfuryldisulfid 5,0
Verbindung a 1,0
Verbindung b 2,0
Verbindung c 1,5
Verbindung d 1,0
Verbindung e 1,0
Verbindung f 1,5
verstärkte F östkaffeenote
schwefelig, metallische Note;
unausgeglichenes Aroma
unausgeglichenes Aroma
verstärkte verbrannte Note,
leicht pheno'isch
leicht pheno'isch
verstärkte verbrannte und bittere Noten
phenolisch, salicylisch
verstärkte erdige Note
phenolisch, salicylisch
verstärkte erdige Note
verstärkte verbrannte Note,
leicht karamellartig
leicht karamellartig
verstärkte verbrannte Note,
leicht nhenolisch
leicht nhenolisch
I OIImM/UML'
Ycrhin(luii|!
Dosis ppm
Bemerkungen"!
Verbindung g
Verbindung h
Verbindung i
Verbindung h
Verbindung i
1.5 5.0 2.5
verstärkte erdige Note. nuUartig
verbrannt
verstärkte erdige Note, leicht phenolisch
*) hergestellt aus 2.5 g handelsüblichem löslichem Kaffee und 2(Xl ecm Wasser.
**) durch ein Arnm.icvpc-ilcngrcmiiiMi nach Vergleich mil iin.irnmalisicrtcni kaffcegctrank
{}) Auswertung in Rindlleisclihrühe*)
[Wj.;
ppm
r ·'u rf u ry I nie reap Ui η
!■"urfurylmcrcaplan
!■"urfurylmcrcaplan
Dihcn/ofurfurvldisulfid
0.5 0.5
5.0
starke verbrannte Note, an geröstetem starke verbrannte Note, an gerösteten
Kaffee erinnernd: unausgeglichenes Λ ronia
schwei'elig. metallisch, an faule Hier
erinner >J
geröstete Note, leicht geräuchert verstärkte geröstete Flcischnote:
leicht geräuchert
verstärkte geröstete Note, anderes Aroma verbrannte Note, leicht geräuchert
*) hergestellt aus 20ji handelsüblicher Rindlleisehbrühc und I I Wasser.
*■*) durch ein Aromaexpcrtcngrcmiuni nach \'ergleich mit unaromatisierter Brühe.
Verbindung a | 2.5 |
Verbindung b | 5.0 |
Verbindung e | 2.5 |
Verbindung f | 2.5 |
\~tf .·\ u:>
Wu ι im i
l.iuiiUL)i;ui
\ erbindung | Dosis | Bemerkungen**) |
ppm | ||
iurfury !mercaptan | 0.5 | starke verbrannte Note. kalTeeartig: unausgeglichenes Aroma |
Dibcvofurfuryldisulfid | 5.0 | schwefelig, metallisch; an faule Eier erinnernd |
Verbindung b | 2,5 | verstärkte geröstete Erdnußnote |
Verbindung d | 2.5 | verstärkte erdige Note, an frische Erdnüsse erinnernd |
Verbindung e | 2.5 |
verstärkte verbrannte Note,
leicht karamellsrtig |
Verbindung g | 23 | verstärkte erdige Note, an frische Erdnüsse und Haselnüsse erinnernd |
Verbindung i | 2^ | verstärkte erdige Note, leicht phenoliseh |
*I von handelsüblichem Ursprung.
**) durch ein Aromaexpertengremium nach Vergleich mit unaromatisierter Butter.
(5) Auswertung in Milch mit Karamellaroma*)
10
Diacetyl
Dipropionyl
Triacetin
Gew.-Teile
50
30
35
25
850
Verbindung
Dosis
ppm
Furiurylmercaptan
Dibenzofurfuryldisulfid
Verbindung b
Verbindung e
0,1
1,0
0,5
0,5
überverbrannte Note, gerösteter KalTee,
unausgeglichenes Aroma
schwefelig, metallische Note;
unausgeglichenes Aroma
verstärkte verbrannte Zuckernote,
leicht geräuchert
verstärkte verbrannte Zuckernote,
runderes Aroma
·) hergestellt aus 0,2 g Karamellgrundlagc und I I Milch.
**) durch ein Aromaexpertengremium nach Vergleich mit einer nur mit der obigen Karamcllgrundlage aromatisierten Milch.
Wie aus den obigen Versuchen ersichtlich, unterscheiden sich die erfindungsgemäßen Verbindungen deutlich
von den bekannten Verbindungen, nämlich Furfurylmercaptan und Dibenzofurfuryldisulfid. Ersteres
entwickelt eine starke, für gerösteten Kaffee typische Aromanote und ist daher wohlbekannt; in Lebensmit-IeIn und Getränken, in denen jedoch andere Noten als
nach geröstetem Fleisch in Rindfleischbriihe oder nach
verbranntem Zucker in einem Getränk mit Karameltroma, kann es jedoch nicht in derselben, vorteilhaften
Weise verwendet werden. Seine typische Note nach geröstetem Kaffee ist immer spürbar und ergibt einen
insgesamt als »unausgeglichenes Aroma« bezeichneten Geschmacksgesamteffekt.
Die erfindungsgemäßen Verbindungen entwickeln nicht nur geröstete, sondern auch phenolische, karamelartige und erdige Noten, wobei letztere besonders zum
Aromatisieren von Nüssen oder Erdnüssen im Gegensatz zum genannten Furfurylmercaptan geeignet sind.
Dibenzofurfuryldisulfid entwickelte beim Testen in verschiedenen Lebensmitteln oder Getränken immer
eine typische schwefelige und metallische Note, die an f™!s Eisr oder OcfTiO?1? •frinncr*? R*?i 2Ü?n Tpstc wnrHp
der durch seine Verbindung erzielte Geschmacksgesamteffekt als »unausgeglichenes Aroma« qualifiziert.
Die Verwertung der Erfindung kann durch gesetzliche Bestimmungen, insbesondere durch das Lebensmittelgesetz, beschränkt sein.
Claims (2)
- Patentansprüche:I.Verwendung von:a. Benzofuranb. 2-Methyl-benzofuranc. 2-Äthyl-benzofuran& 2>3-DimethyI-benzofurane. 2-VuiyI-benzofuranf. 2-Isopropenyl-benzofurang. 7-Methyl-benzofuran h. 7-Äthyl-benzofuranL 2,7-DimethyJ-benzofuranzur Veränderung der Geschmackseigenschaften fester oder flüssiger Nahrungs- und Genußmittel und von Getränken sowie als Geschmacksstoffskomponente in einem geschmacksverändernden Mittel.
- 2. Verwendung der in Anspruch 1 genannten Verbindungen zur Aromatisierung von löslichen Kaffeeprodukten.werden. Die Erfindung eignet sich insbesondere zur Verbesserung oder Verstärkung des Geschmacks von konservierten Lebensmitteln. Ganz besonders eignet sich die Erfindung zur Veränderung, Verbesserung oder Verstärkung der Geschmackseigenschaften von sogenannten lösüchen Kaffeeprodukten (im englischen Sprachgebrauch als »instant coffee« bezeichnet).In der folgenden Aufstellung der erfindungsgemäß zu verwendenden Benzofuranverbindungen ist neben demto chemischen Namen jeder Verbindung ein Literaturhinweis betreffend ein Herstellungsverfahren angegeben. Im Handel erhältliche Produkte sind mit der Abkürzung »L H.« bezeichnet Für die neuen Verbindungen (abgekürzt »n. V.«) sindι s im Anschluß an die Aufzählung der Einzelverbindungen Herstellungsmethoden angegeben.
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 |
---|---|
DE1793842B1 DE1793842B1 (de) | 1980-06-26 |
DE1793842C3 true DE1793842C3 (de) | 1981-03-19 |
Family
ID=27036753
Family Applications (12)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE1695505A Expired DE1695505C3 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter Alkylnaphthaline als Geschmacksstoffe oder Geschmacksstoffkomponenten |
DE1793852A Expired DE1793852C2 (de) | 1965-04-30 | 1966-04-29 | 4-Methyl-2-propionyl-und-butyrylthiazol und Verwendung von Thiazolcarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten |
DE1793843A Expired DE1793843C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter Pyridin-Kohlenwasserstoffe als Geschmacksstoffe oder Geschmacksstoffkomponente |
DE1793842A Expired DE1793842C3 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter Benzofuranverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente |
DE1793844A Expired DE1793844C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung von Pyrazin-Verbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten |
DE1793850A Expired DE1793850C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter Thiophan-Verbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente |
DE1793846A Expired DE1793846C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter Pyrazincarbonylverbindungen als Geschmacksstoffe und 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 |
DE1793849A Expired DE1793849C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung von schwefelhaltigen Ketonen als Geschmacksstoffe oder Geschmacksstoffkomponenten und Furfurylthioaceton |
DE1793847A Expired DE1793847C3 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter Pyridincarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente |
DE1793851A Expired DE1793851C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung von schwefelhaltigen Furanverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten und solche Verbindungen |
Family Applications Before (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE1695505A Expired DE1695505C3 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter Alkylnaphthaline als Geschmacksstoffe oder Geschmacksstoffkomponenten |
DE1793852A Expired DE1793852C2 (de) | 1965-04-30 | 1966-04-29 | 4-Methyl-2-propionyl-und-butyrylthiazol und Verwendung von Thiazolcarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten |
DE1793843A Expired DE1793843C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter Pyridin-Kohlenwasserstoffe als Geschmacksstoffe oder Geschmacksstoffkomponente |
Family Applications After (8)
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 |
DE1793850A Expired DE1793850C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter Thiophan-Verbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente |
DE1793846A Expired DE1793846C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter Pyrazincarbonylverbindungen als Geschmacksstoffe und 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 |
DE1793849A Expired DE1793849C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung von schwefelhaltigen Ketonen als Geschmacksstoffe oder Geschmacksstoffkomponenten und Furfurylthioaceton |
DE1793847A Expired DE1793847C3 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter Pyridincarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente |
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) | JPS4821509B1 (de) |
BR (1) | BR6679143D0 (de) |
CH (1) | CH529516A (de) |
DE (12) | DE1695505C3 (de) |
DK (1) | DK139012B (de) |
ES (1) | ES326503A1 (de) |
GB (1) | GB1156472A (de) |
NL (1) | NL150316B (de) |
NO (1) | NO134889C (de) |
SE (9) | SE373734B (de) |
Families Citing this family (7)
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 |
US7011860B1 (en) | 1999-04-20 | 2006-03-14 | Ajinomoto Co., Inc. | Flavor precursor composition and method for releasing the flavor component |
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 |
US20110027436A1 (en) * | 2007-11-13 | 2011-02-03 | Nestec S.A. | Use of thioester flavors to improve the flavor quality of ready-to-drink coffee upon retorting and storage |
Family Cites Families (2)
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 |
-
1966
- 1966-04-29 SE SE6914960A patent/SE373734B/xx unknown
- 1966-04-29 DE DE1695505A patent/DE1695505C3/de not_active Expired
- 1966-04-29 SE SE6914961A patent/SE377270B/xx unknown
- 1966-04-29 DE DE1793852A patent/DE1793852C2/de not_active Expired
- 1966-04-29 DE DE1793843A patent/DE1793843C2/de not_active Expired
- 1966-04-29 DK DK221766AA patent/DK139012B/da unknown
- 1966-04-29 DE DE1793842A patent/DE1793842C3/de not_active Expired
- 1966-04-29 SE SE6914963A patent/SE373736B/xx unknown
- 1966-04-29 DE DE1793844A patent/DE1793844C2/de not_active Expired
- 1966-04-29 DE DE1793850A patent/DE1793850C2/de not_active Expired
- 1966-04-29 SE SE6914955A patent/SE377269B/xx unknown
- 1966-04-29 DE DE1793846A patent/DE1793846C2/de not_active Expired
- 1966-04-29 CH CH625166A patent/CH529516A/de not_active IP Right Cessation
- 1966-04-29 DE DE1793848A patent/DE1793848C2/de not_active Expired
- 1966-04-29 DE DE1793845A patent/DE1793845C2/de not_active Expired
- 1966-04-29 SE SE6914959A patent/SE373733B/xx unknown
- 1966-04-29 BR BR179143/66A patent/BR6679143D0/pt unknown
- 1966-04-29 ES ES0326503A patent/ES326503A1/es not_active Expired
- 1966-04-29 DE DE1793849A patent/DE1793849C2/de not_active Expired
- 1966-04-29 NO NO162820A patent/NO134889C/no unknown
- 1966-04-29 NL NL666605854A patent/NL150316B/xx not_active IP Right Cessation
- 1966-04-29 SE SE6914962A patent/SE373735B/xx unknown
- 1966-04-29 DE DE1793847A patent/DE1793847C3/de not_active Expired
- 1966-04-29 DE DE1793851A patent/DE1793851C2/de not_active Expired
- 1966-04-29 SE SE05878/66A patent/SE335463B/xx unknown
- 1966-04-29 SE SE6914958A patent/SE373732B/xx unknown
- 1966-04-29 SE SE6914956A patent/SE373731B/xx unknown
- 1966-05-02 GB GB09260/66A patent/GB1156472A/en not_active Expired
-
1971
- 1971-03-31 JP JP46019568A patent/JPS4821509B1/ja active Pending
- 1971-03-31 JP JP1957071A patent/JPS5333667B1/ja active Pending
- 1971-03-31 JP JP46019571A patent/JPS499747B1/ja active Pending
- 1971-03-31 JP JP46019575A patent/JPS5231420B1/ja active Pending
- 1971-03-31 JP JP46019569A patent/JPS499746B1/ja active Pending
-
1976
- 1976-12-09 JP JP14826376A patent/JPS5412552B1/ja active Pending
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C3 | Grant after two publication steps (3rd publication) | ||
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