DE1793850B1 - Verwendung bestimmter Thiophanverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente - Google Patents
Verwendung bestimmter Thiophanverbindungen als Geschmacksstoffe oder GeschmacksstoffkomponenteInfo
- 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
- Authority
- DE
- 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
Links
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
- A23F5/00—Coffee; Coffee substitutes; Preparations thereof
- A23F5/46—Coffee flavour; Coffee oil; Flavouring of coffee or coffee extract
- A23F5/465—Flavouring with flavours other than natural coffee flavour or coffee oil
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/56—Flavouring or bittering agents
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/204—Aromatic compounds
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/205—Heterocyclic compounds
- A23L27/2054—Heterocyclic compounds having nitrogen as the only hetero atom
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- 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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- C07C45/67—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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- C07D213/24—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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- C07D333/04—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)
- Non-Alcoholic Beverages (AREA)
- Pyrrole Compounds (AREA)
- Furan Compounds (AREA)
- Bakery Products And Manufacturing Methods Therefor (AREA)
- Fats And Perfumes (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
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)
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.
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:
Aromatisierung von verdünnter Zuckersiruplösung1)
Verbindung Menge
(ppm*)
(ppm*)
Organoleptische Bewertung
2,0 - 3,0 verbrannt; knoblauchartig
1,5 - 2,5 grün; gerösteter Kaffee,
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).
* 1 g/ 100 1 = 10 ppm (parts per million).
Aromatisierung von Salzwasser1)
Verbindung Menge
(ppm)
(ppm)
Organoleptische Bewertung
Aromatisierung von löslichem Kaffee1)
Verbindung Meöge
(ppm*)
(ppm*)
Organoleptische Bewertung )
2,0 - 3,0 verbrannt; knoblauchartig,
geflügelfleischartig
geflügelfleischartig
1,0 - 2,0 verbrannt; Fleischboullion;
würzig; knoblauchartig
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).
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)
(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.
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)
(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
Thienylmercaptan
(I) Auswertung in Mineralwasser (Typ EVIAN)
Verbindung
Dosis Bemerkungen ppm*
Furfurylmercaptan 2,0 0,5
Thienylmercaptan
a
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
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)
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.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US45234265A | 1965-04-30 | 1965-04-30 | |
US54306966A | 1966-04-18 | 1966-04-18 |
Publications (2)
Publication Number | Publication Date |
---|---|
DE1793850B1 true DE1793850B1 (de) | 1980-04-24 |
DE1793850C2 DE1793850C2 (de) | 1980-12-11 |
Family
ID=27036753
Family Applications (12)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE1793845A Expired DE1793845C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung von Chinoxalin-Kohlenwasserstoffen als Geschmacksstoffe oder Geschmacksstoffkomponenten |
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 |
DE1793850A Expired DE1793850C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter Thiophan-Verbindungen 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 |
DE1793851A Expired DE1793851C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung von schwefelhaltigen Furanverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten und solche Verbindungen |
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 |
DE1793848A Expired DE1793848C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter aromatischer Thiole, Sulfide und Disulfide als Geschmacksstoffe oder Geschmacksstoff komponente |
DE1793849A Expired DE1793849C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung von schwefelhaltigen Ketonen als Geschmacksstoffe oder Geschmacksstoffkomponenten und Furfurylthioaceton |
DE1793842A Expired DE1793842C3 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter Benzofuranverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente |
DE1793843A Expired DE1793843C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter Pyridin-Kohlenwasserstoffe als Geschmacksstoffe oder Geschmacksstoffkomponente |
Family Applications Before (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE1793845A Expired DE1793845C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung von Chinoxalin-Kohlenwasserstoffen als Geschmacksstoffe oder Geschmacksstoffkomponenten |
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 |
Family Applications After (8)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE1793852A Expired DE1793852C2 (de) | 1965-04-30 | 1966-04-29 | 4-Methyl-2-propionyl-und-butyrylthiazol und Verwendung von Thiazolcarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten |
DE1793851A Expired DE1793851C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung von schwefelhaltigen Furanverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten und solche Verbindungen |
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 |
DE1793848A Expired DE1793848C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter aromatischer Thiole, Sulfide und Disulfide als Geschmacksstoffe oder Geschmacksstoff komponente |
DE1793849A Expired DE1793849C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung von schwefelhaltigen Ketonen als Geschmacksstoffe oder Geschmacksstoffkomponenten und Furfurylthioaceton |
DE1793842A Expired DE1793842C3 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter Benzofuranverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente |
DE1793843A Expired DE1793843C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter Pyridin-Kohlenwasserstoffe als Geschmacksstoffe oder Geschmacksstoffkomponente |
Country Status (10)
Country | Link |
---|---|
JP (6) | JPS499746B1 (de) |
BR (1) | BR6679143D0 (de) |
CH (1) | CH529516A (de) |
DE (12) | DE1793845C2 (de) |
DK (1) | DK139012B (de) |
ES (1) | ES326503A1 (de) |
GB (1) | GB1156472A (de) |
NL (1) | NL150316B (de) |
NO (1) | NO134889C (de) |
SE (9) | SE373732B (de) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3767429A (en) * | 1971-12-06 | 1973-10-23 | Procter & Gamble | Lard flavor concentrate |
NL8403748A (nl) * | 1984-12-10 | 1986-07-01 | Zaan Cacaofab Bv | Cacaopoeder. |
DE69221087T2 (de) * | 1991-11-08 | 1997-11-13 | Quest Int | Parfumzusammenstellung |
ID30544A (id) | 1999-04-20 | 2001-12-20 | Ajinomoto Kk | Komposisi prekursor citarasa dan metode untuk melepaskan komponen citarasa |
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 |
PT2219466E (pt) * | 2007-11-13 | 2012-03-29 | Nestec Sa | Utilização de sabores de tioéster para melhoramento da qualidade do sabor de café pronto a beber após esterilização e armazenagem |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3076818A (en) * | 1963-02-05 | Production of benzofurans | ||
US3033875A (en) * | 1959-09-28 | 1962-05-08 | Hills Bros Coffee | Condensed ring heterocyclic disulfides and sulfides |
-
1966
- 1966-04-29 DE DE1793845A patent/DE1793845C2/de not_active Expired
- 1966-04-29 SE SE6914958A patent/SE373732B/xx unknown
- 1966-04-29 NO NO162820A patent/NO134889C/no unknown
- 1966-04-29 DE DE1793846A patent/DE1793846C2/de not_active Expired
- 1966-04-29 DE DE1695505A patent/DE1695505C3/de not_active Expired
- 1966-04-29 DE DE1793850A patent/DE1793850C2/de not_active Expired
- 1966-04-29 SE SE6914962A patent/SE373735B/xx unknown
- 1966-04-29 DE DE1793852A patent/DE1793852C2/de not_active Expired
- 1966-04-29 SE SE6914959A patent/SE373733B/xx unknown
- 1966-04-29 DE DE1793851A patent/DE1793851C2/de not_active Expired
- 1966-04-29 DE DE1793847A patent/DE1793847C3/de not_active Expired
- 1966-04-29 SE SE05878/66A patent/SE335463B/xx unknown
- 1966-04-29 DE DE1793844A patent/DE1793844C2/de not_active Expired
- 1966-04-29 SE SE6914956A patent/SE373731B/xx unknown
- 1966-04-29 DE DE1793848A patent/DE1793848C2/de not_active Expired
- 1966-04-29 SE SE6914961A patent/SE377270B/xx unknown
- 1966-04-29 CH CH625166A patent/CH529516A/de not_active IP Right Cessation
- 1966-04-29 DE DE1793849A patent/DE1793849C2/de not_active Expired
- 1966-04-29 DK DK221766AA patent/DK139012B/da unknown
- 1966-04-29 SE SE6914960A patent/SE373734B/xx unknown
- 1966-04-29 ES ES0326503A patent/ES326503A1/es not_active Expired
- 1966-04-29 DE DE1793842A patent/DE1793842C3/de not_active Expired
- 1966-04-29 BR BR179143/66A patent/BR6679143D0/pt unknown
- 1966-04-29 SE SE6914963A patent/SE373736B/xx unknown
- 1966-04-29 NL NL666605854A patent/NL150316B/xx not_active IP Right Cessation
- 1966-04-29 DE DE1793843A patent/DE1793843C2/de not_active Expired
- 1966-04-29 SE SE6914955A patent/SE377269B/xx unknown
- 1966-05-02 GB GB09260/66A patent/GB1156472A/en not_active Expired
-
1971
- 1971-03-31 JP JP46019569A patent/JPS499746B1/ja active Pending
- 1971-03-31 JP JP46019575A patent/JPS5231420B1/ja active Pending
- 1971-03-31 JP JP46019571A patent/JPS499747B1/ja active Pending
- 1971-03-31 JP JP1957071A patent/JPS5333667B1/ja active Pending
- 1971-03-31 JP JP46019568A patent/JPS4821509B1/ja active Pending
-
1976
- 1976-12-09 JP JP14826376A patent/JPS5412552B1/ja active Pending
Non-Patent Citations (1)
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