DE1793850B1 - Verwendung bestimmter Thiophanverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente - Google Patents

Verwendung bestimmter Thiophanverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente

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Publication number
DE1793850B1
DE1793850B1 DE1793850A DE1793850A DE1793850B1 DE 1793850 B1 DE1793850 B1 DE 1793850B1 DE 1793850 A DE1793850 A DE 1793850A DE 1793850 A DE1793850 A DE 1793850A DE 1793850 B1 DE1793850 B1 DE 1793850B1
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Germany
Prior art keywords
taste
coffee
compounds
certain
thiophane
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.)
Granted
Application number
DE1793850A
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English (en)
Other versions
DE1793850C2 (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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Application filed by Firmenich SA filed Critical Firmenich SA
Publication of DE1793850B1 publication Critical patent/DE1793850B1/de
Application granted granted Critical
Publication of DE1793850C2 publication Critical patent/DE1793850C2/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
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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
    • A23L27/2054—Heterocyclic compounds having nitrogen as the only hetero atom
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    • 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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    • 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
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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
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    • 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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Description

Gegenstand der Erfindung ist die Verwendung der im vorstehenden Anspruch 1 genannten Thiophanverbindungen 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 zu Grunde liegende Aufgabe bestand darin, die Auswahl der bisher zur Verfugung 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 obendefinierten Thiophanverbindungen, entweder einzeln oder in Form zweckentsprechender Mischungen dazu geeignet sind, die Geschmackseigenschaften verschiedenster fester und flüssiger Nahrungs- und Genußmittel oder Getränke im gewünschten Sinne zu verändern. Mittels der vorliegenden Erfindung können beispielsweise Produkte wie Fruchtsäfte, Gemüsesäfte, Milchprodukte, Kaffee-, Tee-, Kakao- oder Schokoladenprodukte, Getreideflocken, Mehle, Konfiseriewaren, Fleischprodukte, Backwaren und Speiseeis geschmacklich verändert werden. Die Erfindung eignet sich insbesonders 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 Sprachgebrauch als »instant coffee« bezeichnet). Nachstehend ist neben dem chemischen Namen der erfindungsgemäß zu verwendenden Verbindungen ein Literaturhinweis betreffend ein Herstellungsverfahren angegeben:
a. Thiophanon-(3)
I.Amer.Chem.Soc. 68,2229 (1946)
b. 2-Methyl-thiophanon-(3)
HeIv. chim. Aeta 27,124 (1944)
Die organoleptische Bewertung der obenzitierten Verbindungen wurde mittels Prüf methoden A, B und C durchgeführt. Die Methode A diente dazu, den Eigengeschmack der einzelnen Substanzen zu ermitteln. Die geschmacksverändernden Eigenschaften der Substanzen wurden mittels der Methoden B und C ermittelt. Es wurde insbesonders 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 Gew.-% oder 1 Gew.-%o in 96%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 mußte jeder Prüfer eine Beschreibung des Geschmackes der einzelnen Geschmacksstoffe abgeben.
Methode B
Als Substrat für die Prüfung wurde ein Kaffeegetränk verwendet, das durch Auflösen eines im Handel erhältlichen, sprühgetrockneten Kaffeepulvers in sie-
4(i dendem Wasser im Verhältnis von 1 g Pulver auf 80 ml Wasser hergestellt wurde. Für jeden zu prüfenden Geschmacksstoff wurde ein Gefäß mit Kaffeegetränk bereitgestellt. Die Geschmacksstoffe wurden dem Kaffeegetränk in Form von Lösungen von 1 Gew.-% oder 1 Gew.-%o in 96%igem Alkohol in Konzentrationen von 0,005 bis 5 g auf 100 Liter Getränk zugegeben. Nach Zugabe der abgemessenen Menge der Geschmacksstofflösung wurde das Kaffeegetränk gut gerührt und sofort in eine Reihe von Tassen für die organoleptische Prüfung gegossen. Das Kosten des Getränkes 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
ho bestand oder nicht. Die Prüfer mußten ferner die Geschmacksunterschiede beschreiben und charakteri-
sieren.
Methode C
h-5 Als Substrat für die Geschmacksprüfung wurde eine l,35°/oige Lösung eines im Handel erhältlichen, sprühgetrockneten Kaffeepulvers mit verhältnismäßig »flachem« Geschmack und Aroma in Quellwasser verwen-
det. 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 1 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 und Kaffeegetränk) angegeben.
Tabelle 1
Ver Versuch Menge 1,0 Organoleptische
bindung Bewertung
a. A o,i- 0,5 zwiebel-,
knoblauchartig
b. A 0,25- grüner Geschmack;
verbrannter Kaffee
b. B 0,4 aromatische Note
b. C 0,27 schwefelige Note
Die nachfolgenden Tabellen 2 bis 6 zeigen die Aromatisierung von verschiedenen weiteren Getränken und Speisen:
Tabelle 2
Aromatisierung von verdünnter Zuckersiruplösung1)
Verbindung Menge
(ppm*)
Organoleptische Bewertung
2,0 - 3,0 verbrannt; knoblauchartig
1,5 - 2,5 grün; gerösteter Kaffee,
knoblauchartig
') 10% Zucker in Wasser (vergl. Methode A).
* 1 g/ 100 1 = 10 ppm (parts per million).
Tabelle 3
Aromatisierung von Salzwasser1)
Verbindung Menge
(ppm)
Organoleptische Bewertung
Tabelle 4
Aromatisierung von löslichem Kaffee1)
Verbindung Meöge
(ppm*)
Organoleptische Bewertung )
2,0 - 3,0 verbrannt; knoblauchartig,
geflügelfleischartig
1,0 - 2,0 verbrannt; Fleischboullion;
würzig; knoblauchartig
') 0,5% Lösung von NaCl in Wasser.
3,0 - 4,0 verbrannt; schweflig
2,5 - 3,5 Röstkaffee; knoblauchartig
2,50 g eines handelsüblichen löslichen Kaffees in 200 ml heißem Wasser (vergl. Methode B). Diese Bewertungen wurden von einer Prüfungskommission von Geschmacksexperten nach Vergleich mit nichtaromatisiertem Kaffeegetränk abgegeben. * lg/1001 = lOppm (parts per million).
Tabelle 5
Aromatisierung von Fleischbrühe
a) Fleischbrühe (Menge in g pro 101) Handelsübliche Fleischbrühe
M ononatriumglutamat
Natrium-5-inosinat/Natriumguanylat (50/50)
Kochsalz
Milchsäure
100 10 0,05
80
Verbindung Menge
(ppm)
Organoleptische Bewertung )
2,5 verstärkter Gesamt
geschmack; Hühnerbrühe
b 1,5 gebratenes Fleisch
') Diese Bewertungen wurden von einer Prüfungskommission von Geschmacksexperten nach Vergleich mit nichtaromatisierter Brühe abgegeben.
Tabelle 6
Aromatisierung von Frikadellen
a) Frikadellengrundmasse
Zutaten
Gew.-Teile
Rinderhackfleisch
Brotbrösel
Kochsalz
700
290
10
Zu verschiedenen Mengen dieser Grundmasse wurden die Verbindungen a oder b vor dem Kochen zugegeben:
Verbindung Menge
(ppm)
Organoleptische Bewertung )
a 2,0 - 3,0 abgerundetes Aroma;
geflügelartig
b 1,0 - 2,0 verstärkte Note nach
gebratenem Fleisch
') Diese Bewertungen wurden von einer Prüfungskommission von Geschmacksexperten nach Vergleich mit nichtaromatisierten Frikadellen abgegeben.
Vergleichsversuche
Die Verbindungen a und b, d. h. Thiophanon-(3) bzw. 2-Methylthiophanon-(3), wurden mit den folgenden bekannten Verbindungen der US-PS 1 696 419 auf ihre Geschmackseigenschaften verglichen: Furfurylmercaptan
Thienylmercaptan
(I) Auswertung in Mineralwasser (Typ EVIAN)
Verbindung
Dosis Bemerkungen ppm*
Furfurylmercaptan 2,0 0,5
Thienylmercaptan
a
0,10 2,0
2,0
* Teile pro Mill.
(2) Auswertung in Rindfleischbrühe*
überverbrannt, schwefel ig
verbrannt, typisch für Röstkaffee
Röstkaffeenote
verbrannte Note, fleischig, leicht knoblauchartig
verbrannte Note, fleischig, an Roastbeef erinnernd, würzig
Verbindung
Dosis Bemerkungen** ppm
Furfurylmercaptan 0,5
starke verbrannte Note, an Röstkaffee erinnernd, unausgeglichenes Aroma
identischer Effekt; unausgeglichenes Aroma * vgl. obenstehende Tabelle
** durch ein Aromaexpertengremium nach Vergleich mit unaromatisierter Brühe.
Thienylmercaptan 0,5
(3) Auswertung in Frikadellen (Hamburgers)*
Verbindung
Dosis
ppm
Bemerkungen*
Furfurylmercaptan 0,5
Thienylmercaptan 0,5
stark verbrannt, Röstkaffeenote; unausgeglichenes Aroma
identischer Effekt; unausgeglichenes Aroma
* hergestellt aus 700g Rindfleischhack, 290gSemmelbröseln und 10g Natriumchlorid.
** durch ein Aromaexpertengremium nach Vergleich mit unaromatisierten Hamburgers.
Vergleiche demgegenüber obenstehende Tabellen 5 und 6.
Allgemeine Bemerkungen
Bekanntlich sind Furfurylmercaptan und Thienylmercaptan zur Reproduktion der für gerösteten Kaffee typischen Röstaromanote geeignet. Beim Test in einem löslichen Kaffee unterscheiden sich die erfindungsgemäßen Verbindungen von den obigen bekannten Verbindungen nicht wesentlich mit Ausnahme ihres Röstcharakters, der nicht so typisch für Kaffee ist, sondern auch an geröstete Getreide oder sogar geröstetes Fleisch erinnert. Bei Verwendung in Grundlagen, wie Rindfleischbrühe oder Frikadellen, wo andere Röstnoten als die von Kaffee notwendig sind, verstärkten die erfindungsgemäßen Verbindungen die geröstete Fleischnote und ergeben ein runderes Gesamtaroma, während die bekannten Verbindungen aufgrund ihrer typischen Röstkaffeenote ein »unausgeglichenes« Aroma entwickeln.
Die Verwertung der Erfindung kann durch gesetzliche Bestimmungen, insbesondere durch das Lebensmittelgesetz, beschränkt sein.

Claims (2)

Patentansprüche:
1. Verwendung von
a) Thiophanon-(3)
b) 2-Methyl-thiophanon-(3)
zur Veränderung der Geschmackseigenschaften fester oder flüssiger Nahrungs- und Genußmittel und von Getränken sowie als Geschmacksstoffkomponente in einem geschmacksverändernden Mittel.
2. Verwendung der im Anspruch 1 genannten Verbindungen zur Aromatisierung von löslichen Kaffeeprodukten.
DE1793850A 1965-04-30 1966-04-29 Verwendung bestimmter Thiophan-Verbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente Expired DE1793850C2 (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)

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DE1793850B1 true DE1793850B1 (de) 1980-04-24
DE1793850C2 DE1793850C2 (de) 1980-12-11

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

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DE1793846A Expired DE1793846C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Pyrazincarbonylverbindungen als Geschmacksstoffe und Geschmacksstoffkomponente
DE1695505A Expired DE1695505C3 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Alkylnaphthaline als Geschmacksstoffe oder Geschmacksstoffkomponenten
DE1793845A Expired DE1793845C2 (de) 1965-04-30 1966-04-29 Verwendung von Chinoxalin-Kohlenwasserstoffen als Geschmacksstoffe oder Geschmacksstoffkomponenten
DE1793842A Expired DE1793842C3 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Benzofuranverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente
DE1793852A Expired DE1793852C2 (de) 1965-04-30 1966-04-29 4-Methyl-2-propionyl-und-butyrylthiazol und Verwendung von Thiazolcarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten

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

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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
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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US3033875A (en) * 1959-09-28 1962-05-08 Hills Bros Coffee Condensed ring heterocyclic disulfides and sulfides

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DE1793847C3 (de) 1981-04-02
DE1793846C2 (de) 1981-01-15
ES326503A1 (es) 1967-07-01
SE377270B (de) 1975-06-30
DE1793842C3 (de) 1981-03-19
DE1793848B1 (de) 1980-04-30
DE1793845B1 (de) 1979-10-31
DE1793842B1 (de) 1980-06-26
DE1695505B2 (de) 1979-04-05
DE1793844C2 (de) 1980-07-24
DK139012C (de) 1979-05-14
JPS4821509B1 (de) 1973-06-29
GB1156472A (en) 1969-06-25
JPS5333667B1 (de) 1978-09-16
DE1793843C2 (de) 1981-01-15
SE373735B (de) 1975-02-17
DE1793852B1 (de) 1980-01-24
DE1793848C2 (de) 1981-01-15
NL150316B (nl) 1976-08-16
DE1793852C2 (de) 1980-10-09
JPS5412552B1 (de) 1979-05-23
JPS5231420B1 (de) 1977-08-15
CH529516A (de) 1972-10-31
SE373733B (de) 1975-02-17
DE1793846B1 (de) 1980-04-30
SE373732B (de) 1975-02-17
SE335463B (de) 1971-05-24
DE1695505A1 (de) 1970-12-23
NO134889C (de) 1977-01-05
SE373736B (de) 1975-02-17
JPS499746B1 (de) 1974-03-06
SE377269B (de) 1975-06-30
DE1793844B1 (de) 1979-10-31
SE373731B (de) 1975-02-17
DE1793849C2 (de) 1982-07-01
DE1793847B1 (de) 1980-06-26
DE1695505C3 (de) 1979-11-29
JPS499747B1 (de) 1974-03-06
NL6605854A (de) 1966-10-31
DE1793843B1 (de) 1980-04-30
BR6679143D0 (pt) 1973-09-11
DK139012B (da) 1978-12-04
NO134889B (de) 1976-09-27
DE1793845C2 (de) 1980-08-07
DE1793851C2 (de) 1982-07-01
DE1793850C2 (de) 1980-12-11
SE373734B (de) 1975-02-17

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