DE1793845C2 - Verwendung von Chinoxalin-Kohlenwasserstoffen als Geschmacksstoffe oder Geschmacksstoffkomponenten - Google Patents

Verwendung von Chinoxalin-Kohlenwasserstoffen als Geschmacksstoffe oder Geschmacksstoffkomponenten

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Publication number
DE1793845C2
DE1793845C2 DE1793845A DE1793845A DE1793845C2 DE 1793845 C2 DE1793845 C2 DE 1793845C2 DE 1793845 A DE1793845 A DE 1793845A DE 1793845 A DE1793845 A DE 1793845A DE 1793845 C2 DE1793845 C2 DE 1793845C2
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DE
Germany
Prior art keywords
quinoxaline
methyl
taste
flavors
hydrocarbons
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
DE1793845A
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English (en)
Other versions
DE1793845B1 (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
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Firmenich SA
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Filing date
Publication date
Application filed by Firmenich SA filed Critical Firmenich SA
Publication of DE1793845B1 publication Critical patent/DE1793845B1/de
Application granted granted Critical
Publication of DE1793845C2 publication Critical patent/DE1793845C2/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
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    • 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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    • 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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    • C07D213/04—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
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    • 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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    • C07D213/04—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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    • C07D241/38—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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    • 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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  • Bakery Products And Manufacturing Methods Therefor (AREA)
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  • Pyrrole Compounds (AREA)
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Description

Die Erfindung betrifft die Verwendung der in Anspruch 1 aufgeführten Chinoxalin-Kohlenwasserstoffe als Geschmacksstoffe in Getränken, Nahrungs- und Geldmitteln oder als Geschmacksstoffkomponenten in geschmacksverändernden Mitteln.
Die Erfindung hat auch neue Chinoxalin-Kohlenwasserstof fe zum Gegenstand, und zwar:
2-Methyl-3-butyl-chinoxaIin und
2-Methyl-3-isobutyI-chinoxalia
Unter »geschmacksverändernd« sind alle Vorgänge oder Behandlungen zu verstehen, durch weiche geschmacksfreien bzw. geschmacksarmen Nahrungsmitteln und Getränken ein bestimmter Geschmack oder ein bestimmtes Aroma verliehen wird, oder durch
a. 5-Methyl-chinoxalin
b. 2-MethyI-chinoxalin
c. 6-Methyl-chinoxalin
d. 2,3-Dimethyl-chinoxalin
e. 2-Methyl-3-äthyl-chinoxalin
Γ. 2,3-Diäthyl-chinoxalin
g. 2-Methyl-3-propyl-chinoxalin h. 2<-MethyI-3*isopfopyI-chinoxalin welche der Geschmack von Nahrungsmitteln witi Getränken verstärkt, verbessert, pberdeckt, unterdrückt oder sonstwie in einer bestimmten Geschmacksrichtung verändert wird,
Die der vorliegenden Erfindung zugrunde liegende Aufgabe bestand darin, die Auswahl der bisher zm Verfügung stehenden Geschmacksstoffe zu erweitern und dem Lepensmitteltechiijker neue und verfeinerte Mittel in die Hand zu geben, um die von der Natui erzeugten Aromen auf synthetischem Wege bessei nachahmen zu können. Die Veränderung oder Verbesserung dei- geschmacklichen Eigenschaften von Nahrungsmitteln and Getränken durch Verwendung vor künstlichen Aromen mit genau reproduzierbarer
is Geschmackseigenschaften und -qualitäten nimmt in dei Lebensmittelindustrie mehr und mehr an Bedeutung zu seitdem für die Ernährung des Menschen neue, bishei nicht verwendete Rohstoffe erschlossen werden um dei drohenden Verknappung der Nahrungsmittel in gewis sen Gebieten des Erdballs entgegenzutreten.
Es wurde gefunden, daß die oben beschrieben« Verbindungen entweder einzeln oder in Form zweck entsprechender Mischungen dazu geeignet sind, di< Geschmackseigenschaften verschiedenster fester unc flüssiger Nahrungs-und Genußmittel oder Getränke in gewünschten Sinne zu verändern. Mittels der vorliegen den Erfindung können beispielsweise Produkte wie Fruchtsäfte, Gemüsesäfte, Milchprodukte, Kaffee-, Tee-Kakao- und Schokoladeprodukte, Getreideflocken Mehle, Konfiseriewaren, Fleischprodukte, Backwaren Speiseeis usw. geschmacklich verändert werden. Di< Erfindung eignet sich insbesondere zur Verbesserung oder Verstärkung des Geschmackes von konservierte: Lebensmitteln. Ganz besonders eignet sich die Erfin dung zur Veränderung, Verbesserung oder Verstärkung der Geschmackseigenschaften von sogenannten lösli
chen Kaffeeprodukten (im englischen Sprachgebraucl als »instant coffee« bezeichnet).
Anschließend folgen die im Anspruch 1 aufgeführtei
Chinoxalin-Kohlenwasserstoffe. Neben dem chemi sehen Namen jeder Verbindung ist ein Literaturhinwei betreffend ein Herstellungsverfahren angegeben.
Für die neuen Verbindungen (abgekürzt »n. V.«) sin< im Anschluß an die Aufzählung der Einzelverbindungei
Herstellungsmethoden angegeben.
j. 2-Methyl'3-isobutyl-chinoxalin k. 2-Melhyl-3-amyl-chinoxalin
I. 2-Äthyl-chinoxalin
Die oben zitierten neuen Verbindungen kennen wie folgt erhalten werden:
i. 2-Methyl-3-butyl-chinoxalin
wurde von o-Phenylendiamin und Heptandion-(23), wie in Ber. 40, 4852 (1907) beschrieben, Ann. 237, 336 (1887)
Org. Synth. 30, 86 (1950)
Ann. 237, 336 (1887)
Ber. 40,4852(1907)
Ber. 22,526(1889)
J.A.CS. 79, 1712(1957)
J. Chem. Soc. 1946, 54
J. Chem. Soc. 1953, 2822
n.V.
a V.
J. Chem. Soc 1943, 322
J, Chem, Soc, 1953,2822
hergestellt Die so erhaltene Verbindung besiu einen Siedepunkt von 153° C bei 12mbs (9 mm Hg).
2-Methyl'3-isobutyl'Chinoxalin
wurde von o-Phenylefldiäfflln und 5-Methyl-hexaf
di(23 wie hier oben beschrieben, hergestell
Die so erhaltene Verbindung besitzt einen Schmelzpunkt von 94-95"C
Pie organoleptische Bewertung der oben zitierten Verbindungen wurde mittels Prttfungsmethoden A, B und C durchgeführt Die Methode A diente dazu, den Eigengeschmack der einzelnen Substanzen zu bestimmen. Die geschmacksverändernden Eigenschaften der Substanzen wurden mittels der Methoden B und C 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 Leitungswasser, gekostet Die zu prüfenden Geschmacksstoffe wurden dem Sirup in Form von Lösungen von 1 G§*t.-% oder 1 Gew.-%o in 95%igem Alkohol zugegeben. Die Konzentration der Geschmacksstoffe im Zuckersirup schwankte entsprechend 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 meßte jeder Prüfer eine Beschreibung des Geschmackes der einzelnen Geschmacksstoffe abgebea
Methode B
Als Substrat für die Prüfung wurde ein Kaffeegetränk verwendet, das durch Auflösen eires 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.
Tabelle Nach Zugabe der abgemessenen Menge der Ge-
^schmack55tQfflö5ung wurde das Kaffeegetränk gut
gerührt 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 später als 15 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.
Methode C
Als Substrat für die Geschmacksprüfung wurde eine
l,35%ige Lösung eines im Handel erhältlichen, sprühgetrockneten Kaffeepulvers mit verhältnismäßig »flachem« Geschmack und Aroma in Queiiwasser verwendet Die einzelnen Geschmacksstoffe wurden je einer Portion des Kaffeegetränkes mittels einer Mikrospritze
in Mengen von 2 bis 150 Mikroliter zugegeben. Alle für die Zubereitung des Kaffeegetränkes sowie für die Aromatisierung verwendeten Gefäße und sonstigen Geräte wurden peinlichst gesäubert Für die Geschmacksprüfung wurden mindestens 5 erfahrene Geschmacksprüfer eingesetzt Im übrigen wurde gleich wie bei Methode B gearbeitet
Die Resultate der organoleptischen Prüfung sind in der nachfolgenden Tabelle zusammengefaßt In der ersten Kolonne der Tabelle sind die Buchstaben der einzelnen Verbindungen innerhalb der genannten Stoffklasse angeführt Die zweite Kolonne verweist auf die angewendete Prüfmethode. In der dritten Kolonne sind die verwendeten Mengen der Prüfsubstanzen in g pro 100 Liter Getränk (Zuckersirup oder Kaffeegetränk) angegeben.
Verbindung Versuch Menge Organoleptische Bewertung
a. A 1,0 verbrannte, geröstete Haselnüsse
a. C 0,27 toastartig
b. A 4,0 phenolisch, verbrannter Geschmack
C. A 4,0 verbrannter, erdiger Geschmack
d. B 2,5 astringierend, fettig, erdig
e. B 0,7 haselnußartig, bitter, geröstet
f. B 0,6 bitter, erdig
g. B 2,5 bitter, beißend, erdig
h. B 1,2 bitter, astringierend
i. B 2,5 bitter, sauer, holzig
j. B 1,2 bitter, erdig, holzig
k. B 1,2 bitter, erdig, fettig
I. B 2,0 grün, geröstet

Claims (4)

  1. Patentansprüche;
    !,Verwendung von
    a. 5-Methyl-chinoxaIin
    b. 2-Methyl-cbinoxalin
    c. 6-Methyl-chinoxalin
    d. 2^-Dimethyl-chinoxalin
    e. 2-MethyI-3-äthyl-chinoxaün
    f. 2,3-Diäthyl-chinoxalin
    g. 2-Methyl-3-propyl-ehinoxalin
    h. 2-Methyl-3-isopropyl-chinoxalin
    L 2-Methyl-3-butyI-chinoxalin
    j. 2-MethyI-3-isobutyI-chinoxalin
    k. 2-MethyI-3-amyl-chinoxalm
    L 2-Aethyl-chinoxalin
    als Geschmacksstoffe in Getränken, Nahrungs- und Genußmitteln oder als Geschmacksstoffkoraponenten in geschmacksverändernden Mitteln.
  2. 2. Ausführungsform nach Anspruch 1, dadurch gekennzeichnet, daß die Verbindungen gemäß Anspruch 1 zum Aromatisieren von löslichen Kaffeeprodukten verwendet werden.
  3. 3.2-Methyl-3-butyl-chinoxalin.
  4. 4.2-Methyl-3-isobutyl-chinoxalin.
DE1793845A 1965-04-30 1966-04-29 Verwendung von Chinoxalin-Kohlenwasserstoffen als Geschmacksstoffe oder Geschmacksstoffkomponenten Expired DE1793845C2 (de)

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US45234265A 1965-04-30 1965-04-30
US54306966A 1966-04-18 1966-04-18

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DE1793845B1 DE1793845B1 (de) 1979-10-31
DE1793845C2 true DE1793845C2 (de) 1980-08-07

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

Family Applications Before (7)

Application Number Title Priority Date Filing Date
DE1793844A Expired DE1793844C2 (de) 1965-04-30 1966-04-29 Verwendung von Pyrazin-Verbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten
DE1793843A Expired DE1793843C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Pyridin-Kohlenwasserstoffe als Geschmacksstoffe oder Geschmacksstoffkomponente
DE1793852A Expired DE1793852C2 (de) 1965-04-30 1966-04-29 4-Methyl-2-propionyl-und-butyrylthiazol und Verwendung von Thiazolcarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten
DE1793846A Expired DE1793846C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Pyrazincarbonylverbindungen als Geschmacksstoffe und Geschmacksstoffkomponente
DE1793851A Expired DE1793851C2 (de) 1965-04-30 1966-04-29 Verwendung von schwefelhaltigen Furanverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten und solche Verbindungen
DE1793850A Expired DE1793850C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Thiophan-Verbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente
DE1793848A Expired DE1793848C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter aromatischer Thiole, Sulfide und Disulfide als Geschmacksstoffe oder Geschmacksstoff komponente

Family Applications After (4)

Application Number Title Priority Date Filing Date
DE1695505A Expired DE1695505C3 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Alkylnaphthaline als Geschmacksstoffe oder Geschmacksstoffkomponenten
DE1793842A Expired DE1793842C3 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Benzofuranverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente
DE1793847A Expired DE1793847C3 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Pyridincarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente
DE1793849A Expired DE1793849C2 (de) 1965-04-30 1966-04-29 Verwendung von schwefelhaltigen Ketonen als Geschmacksstoffe oder Geschmacksstoffkomponenten und Furfurylthioaceton

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BR (1) BR6679143D0 (de)
CH (1) CH529516A (de)
DE (12) DE1793844C2 (de)
DK (1) DK139012B (de)
ES (1) ES326503A1 (de)
GB (1) GB1156472A (de)
NL (1) NL150316B (de)
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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.
BR9204339A (pt) * 1991-11-08 1993-05-18 Unilever Nv Composicao de pertume,composicao detergente,composicao de condicionamento de tecido e processo para tratar texteis
BR0008351B1 (pt) 1999-04-20 2010-12-28 composição precursora de flavorizante, método para liberar o componente flavorizante a partir da composição precursora de flavorizante, e, composto de sulfeto.
JP2008079545A (ja) * 2006-09-28 2008-04-10 Sanei Gen Ffi Inc カフェオフランまたはその類縁体からなる乳含有飲食品用添加剤
JP5153195B2 (ja) * 2007-04-13 2013-02-27 長谷川香料株式会社 コーヒーの淹れたて感賦与剤
MY183958A (en) * 2007-11-13 2021-03-17 Nestec Sa Use of thioester flavors to improve the flavor quality of ready-to-drink coffee upon retorting and storage

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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

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Publication number Publication date
DE1793847C3 (de) 1981-04-02
BR6679143D0 (pt) 1973-09-11
DE1793848B1 (de) 1980-04-30
DE1793846C2 (de) 1981-01-15
DE1793852B1 (de) 1980-01-24
DE1793843C2 (de) 1981-01-15
SE373733B (de) 1975-02-17
ES326503A1 (es) 1967-07-01
DE1793846B1 (de) 1980-04-30
DE1793849C2 (de) 1982-07-01
DE1793843B1 (de) 1980-04-30
SE373734B (de) 1975-02-17
JPS5412552B1 (de) 1979-05-23
DE1793851C2 (de) 1982-07-01
DE1695505C3 (de) 1979-11-29
NL6605854A (de) 1966-10-31
NO134889C (de) 1977-01-05
SE377270B (de) 1975-06-30
DE1793842C3 (de) 1981-03-19
DE1793848C2 (de) 1981-01-15
SE373731B (de) 1975-02-17
DE1793850B1 (de) 1980-04-24
DE1793844B1 (de) 1979-10-31
DE1793850C2 (de) 1980-12-11
DE1695505A1 (de) 1970-12-23
SE377269B (de) 1975-06-30
DE1793852C2 (de) 1980-10-09
DE1695505B2 (de) 1979-04-05
DK139012B (da) 1978-12-04
DE1793847B1 (de) 1980-06-26
JPS5333667B1 (de) 1978-09-16
NO134889B (de) 1976-09-27
NL150316B (nl) 1976-08-16
DE1793842B1 (de) 1980-06-26
JPS499746B1 (de) 1974-03-06
JPS499747B1 (de) 1974-03-06
SE373735B (de) 1975-02-17
DE1793845B1 (de) 1979-10-31
CH529516A (de) 1972-10-31
SE335463B (de) 1971-05-24
SE373732B (de) 1975-02-17
DK139012C (de) 1979-05-14
JPS4821509B1 (de) 1973-06-29
JPS5231420B1 (de) 1977-08-15
SE373736B (de) 1975-02-17
GB1156472A (en) 1969-06-25
DE1793844C2 (de) 1980-07-24

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