DE1793847C3 - Verwendung bestimmter Pyridincarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente - Google Patents

Verwendung bestimmter Pyridincarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente

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Publication number
DE1793847C3
DE1793847C3 DE1793847A DE1793847A DE1793847C3 DE 1793847 C3 DE1793847 C3 DE 1793847C3 DE 1793847 A DE1793847 A DE 1793847A DE 1793847 A DE1793847 A DE 1793847A DE 1793847 C3 DE1793847 C3 DE 1793847C3
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DE
Germany
Prior art keywords
note
pyridine
roasted
flavorings
taste
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
DE1793847A
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English (en)
Other versions
DE1793847B1 (de
Inventor
Fritz Dr. Commugny Waadt Gautschi
verstorben Max Dr. Confignon Genève Stoll
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
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Firmenich SA
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Publication date
Application filed by Firmenich SA filed Critical Firmenich SA
Publication of DE1793847B1 publication Critical patent/DE1793847B1/de
Application granted granted Critical
Publication of DE1793847C3 publication Critical patent/DE1793847C3/de
Expired legal-status Critical Current

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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
    • 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
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/32—Sulfur atoms
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
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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
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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
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    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D241/36—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
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    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
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    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D307/36—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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    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
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    • 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

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  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)
  • Fats And Perfumes (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
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Description

zur Veränderung der Geschmackseigenschaften fester oder flüssiger Nahrungs- und Genußmittel und von Getränken, sowie als Geschmacksstoffkomponente in einem geschmacksverändernden Mittel.
2. Verwendung der in Anspruch 1 genannten Verbindungen zur Aromatisierung von löslichen Kaffeeprodukten.
Kaffee-, Tee-, Kakao- und Schokoladeprodukte, Getreideflocken, Mehle, Konfiseriewaren, Fleischprodukte, Backwaren und Speiseeis geschmacklich verändert 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 löslichen Kaffeeprodukten (im englischen
ι ο Sprachgebrauch als »instant coffee« bezeichnet).
Die erfindungsgemäß zu verwendenden Verbindungen a) bis 1) sind im Handel erhältlich.
Das 4-(y-Pyridyl)-butanon-(2) wurde wie folg ι hergestellt:
8 ml 2-n Natriumhydroxydlösung wurden einem Gemisch von 10,8 g (0,1 Mol) Pyridin-4-aldehyd, 100 ml Wasser und 10 ml Aceton bei 12 — 15°C zugesetzt Nach einer Reaktionszeit von 3 Minuten wurde das Reaktionsgemisch mit 10%iger wäßriger Essigsäure
neutralisiert, mit Kochsalz gesättigt und mit Äther extrahiert. Nach Abdampfen des Äthers wurde der Rückstand destilliert. Man erhielt 8,4 g 4-(y-Pyridyl)-buten-(3)-on-(2) als gelbes öl vom Sdp. 135-138° C/0,07 Torr. 5,24 g dieses Produktes wurden in 30 ml Äthanol gelöst und in Gegenwart von 4 g Nickel-Katalysator hydriert. Durch Destillation des Reaktionsproduktes erhielt man 4-(y-Pyridyl)-butanon-(2) vom Sdp. 83-85°C/0,05Torr;/7?/ = 1,047; π S' = 1,516.
Gegenstand der Erfindung ist die Verwendung der im vorstehenden Anspruch 1 genannten Pyridincarbonylverbindungcn 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 gewissen Gebieten des Erdballs entgegenzutreten.
Es wurde festgestellt, daß die erfindungsgemäß zu verwendenden Verbindungen entweder einzeln oder in Form zweckentsprechender Mischungen dazu geeignet sind, die Geschmackseigenschaften verschiedenster fester und flüssiger Nahrungs- und Genußmittel oder Getränke im gewünschten Sinne zu verändern. Mittels der vorliegenden Erfindung können beispielsweise Produkte wie Fruchtsäfte, Gemüsesäfte, Milchprodukte, Beispiele
1) Aromatisierung von verdünntem Zuckersirup*)
Ver
Dosis Bemerkungen
bindun8 ppm"
1,2
verleiht Röstnote; an Röstkaffee
erinnernd
Röstnote vom Schokoladentyp
verleiht eine verbrannte und
leicht tierische Note
verbrannte Note;
an Röstkaffee erinnernd
verleiht eine Karamellnote;
leicht fettig
verleiht einen fruchtigen
Geschmack
verleiht eine Karamellnote;
leicht fruchtig
*) 10% Zucker in Wasser.
·) 1 g/100 I; 10 ppm (Teile pro Mill.)
2) Aromatisierung von löslichem Kaffee**)
25
25
50
40
50
40
Ver Dosis Bemerkungen
bindung ppm**)
a 0,8 verstärkt die gesamte Röstkaffee-
note; leicht haselnußartig
b 11.8 starke verbrannte Note
C 30 verleiht eine starke verbrannte
Note vom tierischen Typ
d 75 verstärkt die Röstkaffeenote
Fortselzuiitt
Ver- Dosis Bemerkungen ppm**)
Ver- Dosis
bindu"S ppm
e 55 verstärkte die bitter-grüne Note
f 75 starke bittere Note vom
»Espresso«-Typ
h 40 karamellartig, leicht fruchtig
i 20 verstärkt die bitteren und erdigen
Noten
j 25 verstärkt die grüne Note;
leicht holzig ι ">
k 45 bitterer Geschmack
1 55 bitterer Geschmack, verstärkte
Röstkaffeenote m 30 verstärkt die erdige Note 2< >
*) hergestellt aus 2,5 g handelsüblichem löslichem Kaffee
und 200 ecm heißem Wasser. **) 1 g/100 1 = ppm.
Die Auswertung erfolgte durch ein Gremium von :> Aromaexperten nach Vergleich mit einem nicht-aromatisierten Getränk.
Vergleichstests
Die im folgenden genannten Verbindungen wurden mit dem bekannten Pyridin (vgl. US-PS 16 96 419) bezüglich ihrer Geschmackseigenschaften verglichen.
Verbindung ,.
a 2-Acetylpyridin
b 6-Methyl-2-acetylpyridin
c 3-Acetylpyridin
e Pyridin-2-aldehyd
h 6-Methylpyridin-2-aldehyd
(1) Auswertung in Mineralwasser (Typ EVlAN)
Ver- Dosis
bindun8 ppm
Bemerkungen
Pyridin 3,0 praktisch geschmacklos
10 typisch Pyridin, chemisch,
abstoßend
a 3,0 geröstelc Note, haselnußartig
b 20 geröstete Mandeln, »Praline«
c 10 geröstete Note von tierischem
Charakter
e 30 karamellartig, leicht fettig
h 30 karamellarlig
(2) Auswertung in Milch
Ver- Dosis
bindunS ppm
Bemerkungen*)
Pyridin 3,0
10
keine Wirkung
typisch Pyridin, chemisch,
abstoßend
Bemerkungen*)
3,0
20
geröstete Note, kakaoartig, haselnußartig
geröstete Mandeln, geröstete Haselnüsse
verbrannte Note, leicht fleischig karamell, cremig, fettig karamell, leicht fruchtig
*) durch ein Gremium von Aromaexperten nach Vergleich mit unaromatisierter Milch.
(3) Auswertung in salzhaltigem Wasser*)
C 15
e 30
h 30
Ver- Dosis Bemerkungen
dung ppm
Pyridin 3,0 keine Wirkung
10 typisch Pyridin, chemisch,
abstoßend
a 3,0 verbrannte Note, haselnußartig,
leicht fleischig
b 20 geröstete Note
C 15 verbrannte Note, fettig, tierisch
e 30 gebrannte Zuckernote, fettig
h 30 gebrannte Zuckernote
*) 0,5%ige Natriumchloridlösung in Wasser. (4) Auswertung in Pralinengrundlage*)
Ver- Dosis bindu"8 P!,m
Bemerkungen**)
Pyridin
3,0 10
keine Wirkung
chemische Note, abstoßend, unausgeglichenes Aroma
verstärkte geröstete Haselnußnole verstärktes »Praline«-Gesamtaroma verstärkte geröstete Note karamellartig, leicht fettige Note verstärkte gebrannte Zuckernote ) hergestellt aus 500 g Haselnüssen, 50 g Erdnüssen und g Zucker.
) durch ein Aromaexpertcngremium nach Vergleich mit der unaromatisierten Grundlage.
3,0 20 15 30 30
(5) Auswertung brühe*)
in handelsüblicher Rindfleisch-
Ver- Dosis Bemerkungen**) bindung
ppm
Pyridin 3,0 keine Wirkung chemische Note, typisch Pyridin
unausgeglichenes Aroma
.ι 3,0 verstärkte geröstete Note, runderes
Fleischaroma
5 6
l-'orlsL't/unii „ .
- Allgemeine Bemerkungen
Vcr- Dosis Bemerkungen«) Bej Verwendung in denselben Verhältnissen wie
bindung ppm 2-Acetylpyridin (Verbindung -i) verleiht Pyridin keinen
■ > besonderen Effekt. In höheren Verhältnissen (3- bis
b 20 verstärkte geröstete Fleischnote 5mal höher) zeigt Pyridin jedoch keinerlei positive
c 15 verstärkte geröstete Fleischnote Wirkung und verleiht immer eine charakteristische,
. . ... chemische und abstoßende Aromanote. Die getesteten
e 30 verbrannt, fettiger, tierisch Carbonylpyridinderivate zeigten diesen Nachteil jedoch
h 30 verbrannt, leicht karamell m nicht.
*) hergestellt aus 20 g handelsüblicher Rindfleischbrühe Die Verwertung der Erfindung kann durch gesetzli-
und 1 I Wasser. ehe Bestimmungen, insbesondere durch das Lebensmit-
**) durch ein Greniium von Aromaexperten nach Vcr- telgesetz,beschränkt sein.
gleich mit unsromatisierter Brühe.

Claims (1)

Patentansprüche:
1. Verwendung von
a. 2-Acetyl-pyridin
b. 6-Methy!-2-acetyl-pyridin
c. 3-Acetyl-pyridin
d. 4-Acetyl-pyridin
e. Pyridin-2-aldehyd
f. Pyridin-3-aldehyd
g. Pyridin-4-aldehyd
h. 6-Methyl-pyridin-2-aldehyd
L 2-Benzoyl-pyridin
j. 3-Benzoyl-pyridin
k. 4-Benzoyl-pyridin
1. 2,6-Diacetyl-pyridin
m. 4-(y-Pyridyl)-butanon-(2)
DE1793847A 1965-04-30 1966-04-29 Verwendung bestimmter Pyridincarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente Expired DE1793847C3 (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
DE1793847B1 DE1793847B1 (de) 1980-06-26
DE1793847C3 true DE1793847C3 (de) 1981-04-02

Family

ID=27036753

Family Applications (12)

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

Family Applications Before (3)

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

Country Status (10)

Country Link
JP (6) JPS499747B1 (de)
BR (1) BR6679143D0 (de)
CH (1) CH529516A (de)
DE (12) DE1793845C2 (de)
DK (1) DK139012B (de)
ES (1) ES326503A1 (de)
GB (1) GB1156472A (de)
NL (1) NL150316B (de)
NO (1) NO134889C (de)
SE (9) SE377270B (de)

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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.
EP0545556B1 (de) * 1991-11-08 1997-07-23 Quest International B.V. Parfumzusammenstellung
DE60018400T2 (de) 1999-04-20 2005-12-22 Ajinomoto Co., Inc. Zusammensetzungen von duftstoffvorstufen und verfahren zum hervorbringen von duftstoffen
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

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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
DE1695505A1 (de) 1970-12-23
DE1793851C2 (de) 1982-07-01
SE373734B (de) 1975-02-17
DE1793844B1 (de) 1979-10-31
DE1793850B1 (de) 1980-04-24
DE1793843C2 (de) 1981-01-15
SE335463B (de) 1971-05-24
NO134889C (de) 1977-01-05
SE377269B (de) 1975-06-30
DE1695505B2 (de) 1979-04-05
GB1156472A (en) 1969-06-25
SE373731B (de) 1975-02-17
JPS4821509B1 (de) 1973-06-29
JPS499746B1 (de) 1974-03-06
SE373733B (de) 1975-02-17
DK139012B (da) 1978-12-04
NL6605854A (de) 1966-10-31
DE1793844C2 (de) 1980-07-24
DE1695505C3 (de) 1979-11-29
JPS5412552B1 (de) 1979-05-23
CH529516A (de) 1972-10-31
DE1793850C2 (de) 1980-12-11
BR6679143D0 (pt) 1973-09-11
SE373735B (de) 1975-02-17
JPS5333667B1 (de) 1978-09-16
DK139012C (de) 1979-05-14
DE1793842C3 (de) 1981-03-19
SE373736B (de) 1975-02-17
DE1793848B1 (de) 1980-04-30
ES326503A1 (es) 1967-07-01
DE1793847B1 (de) 1980-06-26
DE1793843B1 (de) 1980-04-30
SE377270B (de) 1975-06-30
DE1793845C2 (de) 1980-08-07
SE373732B (de) 1975-02-17
DE1793842B1 (de) 1980-06-26
DE1793849C2 (de) 1982-07-01
DE1793846B1 (de) 1980-04-30
DE1793852C2 (de) 1980-10-09
DE1793848C2 (de) 1981-01-15
JPS499747B1 (de) 1974-03-06
JPS5231420B1 (de) 1977-08-15
DE1793846C2 (de) 1981-01-15
DE1793852B1 (de) 1980-01-24
NO134889B (de) 1976-09-27
NL150316B (nl) 1976-08-16
DE1793845B1 (de) 1979-10-31

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