DE1793851C2 - Verwendung von schwefelhaltigen Furanverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten und solche Verbindungen - Google Patents

Verwendung von schwefelhaltigen Furanverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten und solche Verbindungen

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Publication number
DE1793851C2
DE1793851C2 DE1793851A DE1793851A DE1793851C2 DE 1793851 C2 DE1793851 C2 DE 1793851C2 DE 1793851 A DE1793851 A DE 1793851A DE 1793851 A DE1793851 A DE 1793851A DE 1793851 C2 DE1793851 C2 DE 1793851C2
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Germany
Prior art keywords
compounds
taste
coffee
flavorings
flavor components
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Expired
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DE1793851A
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English (en)
Inventor
Ivon Dr. Petit-Lancy Flament
Fritz Dr. Commugny Gautschi
Max Dr. Confignon Stoll, (verstorben)
Max Dr. Vandoeuvres Winter, (verstorben)
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Firmenich SA
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Firmenich SA
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Publication of DE1793851C2 publication Critical patent/DE1793851C2/de
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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 OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • 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 OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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 OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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 OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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 OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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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    • 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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    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
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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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    • C07D213/02—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
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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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    • C07D241/12—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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    • 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Seasonings (AREA)
  • Tea And Coffee (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Bakery Products And Manufacturing Methods Therefor (AREA)
  • Furan Compounds (AREA)
  • Non-Alcoholic Beverages (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Fats And Perfumes (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Pyrrole Compounds (AREA)

Description

>o
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 welche der Geschmack von Nahrungsmitteln und Getränken verstärkt, verbessert, überdeckt, unterdrückt oder sonstwie in einer bestimmten Geschmacksrichtung verändert wird.
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.
Die Verwendung schwefelhaltiger Furanverbindungen als Geschmacksstoffe für Nahrungs- und Genußmittel ist bereits bekannt; vgl. US-PS 30 33 875 und Angewandte Chemie, 62. Jahrgang (1950), S. 292. Es besteht jedoch Bedarf an weiteren Geschmacksstoffen, die spezifische Aromanoten besitzen und deshalb dazu geeignet sind, die von der Natur erzeugten Aromen auf synthetischem Wege besser nachahmen zu können.
Aufgabe der Erfindung ist es daher, die Auswahl der bisher zur Verfügung stehenden Geschmacksstoffe zu verbreitern und dem Lebensmitteltechniker neue und verfeinerte Geschmacksstoffe zur Verfügung zu stellen, die Nahrungs- und Genußmitteln besondere bzw. bessere Aromanoten verleihen können.
Es wurde nun gefunden, daß die im Hauptanspruch genannten 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, Kaffee-, Tee-, Kakao- und Schokoladeprodukte, Getreideflocken, Mehle, Konfiseriewaren, Fleischprodukte, Backwaren, Speiseeis, usw., geschmacklich verändert werden. Die Erfindung eignet sich insgesondere zur Verbesserung oder Verstärkung des Geschmackes von konservierten Lebensmitteln. Ganz besonders eignet sich die Erfindung zur Veränderung, Verbesserung oder
30 Verstärkung der Geschmackseigenschaften von sogenannten löslichen Kaffeeprodukten (im englischen Sprachgebrauch als »instant coffee« bezeichnet).
Im folgenden ist die Herstellung der erfindungsgemäß verwendeten Verbindungen näher erläutert
a) Furfurylthioaceton (neue Verbindung)
Furfurylthioaceton wurde in der gleichen Weise wie Methylthioaceton (Verbindung c) nach der in JA.CS. 76, 114 (1954), beschriebenen Methode hergestellt, in dem 0,122MoI Chloraceton mit 0,11MoI Natriumfurfurylmercaptid kondensiert wurden. Das Reaktionsprodukt wurde nach üblichen Methoden isoliert und gereinigt Durch Destillation wurden 13,9 g reines Furfurylthioaceton erhalten, das die folgenden physikalischen Eigenschaften aufwies: Sdp. 115—177° C/ 10 Torr;
n2? = 1,5250; d2/= 1,150
b) l-Methylthiobutanon-(2)
(Comptes Rendus 255,728 (1962)
Die Verbindung wurde aus 0,122 Mol 1-Chlor-butan-2-on (Chem. Ber. 82, 229 (1949)) und 0,11MoI Natrium-methyl-mercaptid nach der in JA.GS. 76, 114 (1954), beschriebenen Methode hergestellt und wies folgende physikalische Eigenschaften auf: Sdp. 51-53°C/8Torr;
/Ji,' = 1,4700; d" = 0,9970.
c) Methylthioaceton
(J.A.C.S. 76,114(1954)
Die Verbindung wurde aus 0,122MoI Chloraceton und 0,11MoI Natrium-methyl-mercaptid nach der in J.A.C.S. 76, 114 (1954) beschriebenen Methode herge-
3-, stellt und wies folgende physikalische Eigenschaften auf. Sdp.53°C/20Torr:
„.. = 1,4714.
Die organoleptische Bewertung der oben zitierten Verbindungen wurde mittels Priifungsmethoden 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 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 I 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
wi 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-
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 ais möglich, auf jeden Fall nicht später aJs 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 135%ige Lösung eines im Handel erhältlichen, sprühgetrockneten Kaffeepulvers mit verhältnismäßig »flachem« Geschmack und Aroma in Quellwasser verwendet. Die einzelnen Geschmacksstoffe wurden je einer Portion des Kaffesgetränkes mittels einer Mikrospritze in Mengen von 2 bis 150 Mikroliter zugegeben. Alle für die Zubereitung des Karfeeget. änkes, sowie für die Aromatisierung; verwendeten Gefäße und sonstigen Geräte wurden peinlichst gesäujert. Für die Geschmacksprüfung wurden mindestens 5 erfahrene Ge schmacksprüfer 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 Prüfsubstarizen in g
ίο pro 100 Liter Getränk (Zuckersirup oder Kaffeegetränk) angegeben.
Tabelle
Vcr- Versuch Menge Organoleplischc Bewertung
bindung
a. A 1.0 verbrannter Kaffte
a. C 0.625 Mercaptannote b. B 0.025 grün, süß. fettig
b. C 0.027 erdige, pilzariige Note
c. Λ 1.0 kohlarlig: knoblauchartig
Vergleichsversuche Die erfindungsgemäß verwendeten Verbindungen
a) Furfurylthioaceton
b) l-Methylthiobutanon-(2) id c) Methylthioaceton
werden bezüglich ihrer Geschmackeigenschaften mit den folgenden bekannten Verbindungen verglichen:
υ Furfurylmercaptan US-PS 16 96 419
Bis(2-benzofurfuryl)-disulfid US-PS 30 33 875
(I) Auswertung in Mineralwasser (Typ HVIANl
Verbindung
Furfurylmercaptan
Bis-(2-bcnzol"iirfuryl)-disulfitl
Verbindung a
Verbindung b
Verbindung c
Oosi; ppm Bemerkungen
2.0 überv.-rbrannt. schwcfclig
0.05 \erhriinnl. Röstkal'feenote
10.0 schwcfclig. grün, metallisch: an verfaulte
Hier und Gemüse erinnernd
2.5 Röstkaffeenote
0.5 erdig. Kartoffel, grüner Pfeffer, verbrannt
2.5 schwefelig. Gemüse, knoblauchartig
(2) Auswertung in löslichem Kaffee*)
Verbindung
Furfurylmercaptan
i)is-(2-bcnzofiirfurylMlisiiind
Verbindung a
Verbindung b
Verbindung c
Dosis ppm Bemerkungen**)
0.05
5.0
0.5
0.2
0.5 verstärkte geröstete Note
schwcfclig. metallische Note: unausgeglichenes Aroma
stärkt geröstete Note vom ..Kspresso"'-Typ süßer, grüne Kaffeenole
starke verbrannte Note, k-ichl schwefclig
*) hergestellt aus 2.5 g handelsüblichem löslichem K ι flee und 200 ecm Wasser **) durch ein Aroninexpt'rtengremium nach Vergleich mil unaromaliMcrlein KiilTeegclriink
(3) Auswertung in Kartoffelpüree*)
Verbindung
Dosis ppm Bemerkungen**)
Furfurylmercaptan 0,1
Bis-(2-benzofurfuryl)-disul(ld 5,0
Verbindung b 2,5
starke RöstkafTeenote; unausgeglichenes
Aroma
schwefelig, grün, metallisch; an faule Eier
erinnernd
verstärkte erdige Note; an frische
Kartoffeln erinnernd
*) von handelsüblichem Ursprung
**) durch ein Aromaexpertengremium nach Vergleich mit unaromatisiertem Püree
(4) Auswertung in Gemüsesuppe*)
Verbindung
Dosis ppm Bemerkungen**)
Furfurylmercaptan 0,1
Bis-{2-bcp.zofurfury!}-disu!fid 5,0
Verbindung a 2,5
Verbindung b 1,0
Verbindung c 2,5
starke Röstkaffeenote unausgeglichenes
Aroma
schwefeüg, grün, metallisch, εα faules
Gemüse erinnernd
verbrannt und leicht schwefclige Note; an
gebratene Zwiebeln erinnernd
verstärkter grüner und Pflanzencharakter,
kartoffelartig
verstärkter Pflanzenscharakter, würzige
Note
*) hergestellt aus 20 g handelsüblicher Gemüseblühe und 1 1 Wasser **) durch ein Aromaexpertengremium nach Vergleich mit unaromatisierter Brühe
Beim Testen in löslichem Kaffee entwickeln die Verbindungen a und c ziemlich ähnliche Noten wie die von Furfurylmercaptan, während die durch die Verbindung b erreichte Geschmacksnote sehr verschieden war.
Beim Testen in anderen Lebensmitteln, insbesondere solchen, in denen keine gerösteten Noten gewünscht sind, wie z.B. Gemüsesuppe oder Kartoffelpüree, J5 erreicht Furfurylmercaptan keinerlei positiven Effekt (unausgeglichenes Aroma). Im Gegensatz dazu sind die Verbindungen a, b und c, die die Pflanzen- oder erdigen Noten derartiger Lebensmittel verstärken, für eine derartige Aromatisierung äußerst zweckmäßig.

Claims (1)

  1. Patentansprüche:
    1. Verwendung von
    a) Furfurylthioaceton
    b) l-Methylthiobutanon-(2)
    c) Methylthioaceton
    zur Veränderung der Geschmackseigenschaften fester oder flüssiger Nahrungs- oder Genußmittel ι ο und von Getränken sowie als Geschmacksstoffkomponenten in einem geschmacksverändernden Mittel.
    Z Verwendung der in Anspruch 1 genannten Verbindungen zur Aromatisierung von löslichen Kaffeeprodukten.
    3. Furfurylthioaceton.
DE1793851A 1965-04-30 1966-04-29 Verwendung von schwefelhaltigen Furanverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten und solche Verbindungen Expired DE1793851C2 (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 (1)

Publication Number Publication Date
DE1793851C2 true DE1793851C2 (de) 1982-07-01

Family

ID=27036753

Family Applications (12)

Application Number Title Priority Date Filing Date
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
DE1793850A Expired DE1793850C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Thiophan-Verbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente
DE1793845A Expired DE1793845C2 (de) 1965-04-30 1966-04-29 Verwendung von Chinoxalin-Kohlenwasserstoffen als Geschmacksstoffe oder Geschmacksstoffkomponenten
DE1793844A Expired DE1793844C2 (de) 1965-04-30 1966-04-29 Verwendung von Pyrazin-Verbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten
DE1793852A Expired DE1793852C2 (de) 1965-04-30 1966-04-29 4-Methyl-2-propionyl-und-butyrylthiazol und Verwendung von Thiazolcarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten
DE1793849A Expired DE1793849C2 (de) 1965-04-30 1966-04-29 Verwendung von schwefelhaltigen Ketonen als Geschmacksstoffe oder Geschmacksstoffkomponenten und Furfurylthioaceton
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
DE1793846A Expired DE1793846C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Pyrazincarbonylverbindungen als Geschmacksstoffe und Geschmacksstoffkomponente
DE1793843A Expired DE1793843C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Pyridin-Kohlenwasserstoffe als Geschmacksstoffe oder Geschmacksstoffkomponente
DE1793851A Expired DE1793851C2 (de) 1965-04-30 1966-04-29 Verwendung von schwefelhaltigen Furanverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten und solche Verbindungen

Family Applications Before (11)

Application Number Title Priority Date Filing Date
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
DE1793850A Expired DE1793850C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Thiophan-Verbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente
DE1793845A Expired DE1793845C2 (de) 1965-04-30 1966-04-29 Verwendung von Chinoxalin-Kohlenwasserstoffen als Geschmacksstoffe oder Geschmacksstoffkomponenten
DE1793844A Expired DE1793844C2 (de) 1965-04-30 1966-04-29 Verwendung von Pyrazin-Verbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten
DE1793852A Expired DE1793852C2 (de) 1965-04-30 1966-04-29 4-Methyl-2-propionyl-und-butyrylthiazol und Verwendung von Thiazolcarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten
DE1793849A Expired DE1793849C2 (de) 1965-04-30 1966-04-29 Verwendung von schwefelhaltigen Ketonen als Geschmacksstoffe oder Geschmacksstoffkomponenten und Furfurylthioaceton
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
DE1793846A Expired DE1793846C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Pyrazincarbonylverbindungen als Geschmacksstoffe und Geschmacksstoffkomponente
DE1793843A Expired DE1793843C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Pyridin-Kohlenwasserstoffe als Geschmacksstoffe oder Geschmacksstoffkomponente

Country Status (10)

Country Link
JP (6) JPS5231420B1 (de)
BR (1) BR6679143D0 (de)
CH (1) CH529516A (de)
DE (12) DE1793848C2 (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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* Cited by examiner, † Cited by third party
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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.
CA2082281C (en) * 1991-11-08 1999-02-23 John M. Behan Perfume composition
WO2000063328A1 (en) * 1999-04-20 2000-10-26 Ajinomoto Co., Inc. Perfume precursor compositions and method for expressing perfume components
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
MX2010005134A (es) * 2007-11-13 2010-06-02 Nestec Sa Uso de sabores de tioester para mejorar la calidad del sabor de cafe listo para beber tras la esterilizacion en retorta y el almacenamiento.

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3076818A (en) * 1963-02-05 Production of benzofurans
US3033875A (en) * 1959-09-28 1962-05-08 Hills Bros Coffee Condensed ring heterocyclic disulfides and sulfides

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Publication number Publication date
ES326503A1 (es) 1967-07-01
SE373736B (de) 1975-02-17
DE1793843B1 (de) 1980-04-30
SE373735B (de) 1975-02-17
DE1793847C3 (de) 1981-04-02
SE373734B (de) 1975-02-17
DE1793852B1 (de) 1980-01-24
DE1793848C2 (de) 1981-01-15
NO134889B (de) 1976-09-27
BR6679143D0 (pt) 1973-09-11
SE373733B (de) 1975-02-17
JPS5412552B1 (de) 1979-05-23
JPS499747B1 (de) 1974-03-06
DE1793844C2 (de) 1980-07-24
DK139012C (de) 1979-05-14
SE373732B (de) 1975-02-17
DE1695505A1 (de) 1970-12-23
NL6605854A (de) 1966-10-31
SE335463B (de) 1971-05-24
DE1793852C2 (de) 1980-10-09
DE1793850B1 (de) 1980-04-24
DE1793846B1 (de) 1980-04-30
JPS5231420B1 (de) 1977-08-15
DE1793850C2 (de) 1980-12-11
JPS5333667B1 (de) 1978-09-16
DE1793847B1 (de) 1980-06-26
DE1793848B1 (de) 1980-04-30
NL150316B (nl) 1976-08-16
GB1156472A (en) 1969-06-25
DE1793842B1 (de) 1980-06-26
DE1695505B2 (de) 1979-04-05
JPS4821509B1 (de) 1973-06-29
NO134889C (de) 1977-01-05
JPS499746B1 (de) 1974-03-06
DE1793846C2 (de) 1981-01-15
DE1793845C2 (de) 1980-08-07
DE1695505C3 (de) 1979-11-29
CH529516A (de) 1972-10-31
DE1793843C2 (de) 1981-01-15
DE1793845B1 (de) 1979-10-31
DE1793849C2 (de) 1982-07-01
SE373731B (de) 1975-02-17
DK139012B (da) 1978-12-04
SE377269B (de) 1975-06-30
DE1793844B1 (de) 1979-10-31
DE1793842C3 (de) 1981-03-19
SE377270B (de) 1975-06-30

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