DE1793845B1 - Verwendung von Chinoxalin-Kohlenwasserstoffen als Geschmacksstoffe oder Geschmacksstoffkomponenten - Google Patents
Verwendung von Chinoxalin-Kohlenwasserstoffen als Geschmacksstoffe oder GeschmacksstoffkomponentenInfo
- Publication number
- DE1793845B1 DE1793845B1 DE1793845A DE1793845A DE1793845B1 DE 1793845 B1 DE1793845 B1 DE 1793845B1 DE 1793845 A DE1793845 A DE 1793845A DE 1793845 A DE1793845 A DE 1793845A DE 1793845 B1 DE1793845 B1 DE 1793845B1
- Authority
- DE
- Germany
- Prior art keywords
- quinoxaline
- taste
- methyl
- flavors
- hydrocarbons
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- 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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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
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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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
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- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
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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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- C07D213/32—Sulfur atoms
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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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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- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
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- C07D213/00—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
- 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
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- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
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- C07D241/40—Benzopyrazines
- C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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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)
- Bakery Products And Manufacturing Methods Therefor (AREA)
- Furan Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Fats And Perfumes (AREA)
- Pyrrole Compounds (AREA)
Description
als Geschmacksstoffe in Getränken, Nahrungs- und Genußmitteln oder als Geschmacksstoffkomponenten
in geschmacksverändernden Mitteln.
2. Ausführungsform nach Anspruch 1, dadurch gekennzeichnet, daß die Verbindungen gemäß
Anspruch 1 zum Aromatisieren von löslichen Kaffeeprodukten verwendet werden.
3.2-Methyl-3-butyl-chinoxalin. 4.2-Methyl-3-isobutyl-chinoxalin.
Die Erfindung betrifft die Verwendung der in Anspruch 1 aufgeführten Chinoxalin-Kohlenwasserstoffe
als Geschmacksstoffe in Getränken, Nahrungs- und Genußmitteln oder als Geschmacksstoffkomponenten
in geschmacksverändernden Mitteln.
Die Erfindung hat auch neue Chinoxalin-Kohlenwasserstoffe zum Gegenstand, und zwar:
2-Methyl-3-butyl-chinoxalin und 2-Methyl-3-isobutyl-chinoxalin.
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 weiche der Geschmack von Nahrungsmitteln und
Getränken verstärkt, verbessert, überdeckt, unterdrückt oder sonstwie in einer bestimmten Geschmacksrichtung
verändert wird.
Die der vorliegenden Erfindung zugrunde liegende Aufgabe bestand darin, die Auswahl der bisher zur
Verfügung stehenden Geschmacksstoffe zu erweitern und dem Lebensmitteltechniker neue und verfeinerte
Mittel in die Hand zu geben, um die von der Natur
ίο 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
ι '■> 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 gefunden, daß die oben beschriebenen Verbindungen entweder einzeln oder in Form zweckentsprechender
Mischungen dazu geeignet sind, die Geschmackseigenschaften verschiedenster fester und
r·, 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 insbesondere zur Verbesserung oder Verstärkung des Geschmackes von konservierten
Lebensmitteln. Ganz besonders eignet sich die ErHndung zur Veränderung, Verbesserung oder Verstärkung
der Geschmackseigenschaften von sogenannten löslichen Kaffeeprodukten (im englischen Sprachgebrauch
als »instant coffee« bezeichnet).
Anschließend folgen die im Anspruch 1 aufgeführten Chinoxalin-Kohlenwasserstoffe. Neben dem chemischen Namen jeder Verbindung ist ein Literaturhinweis betreffend ein Herstellungsverfahren angegeben.
Anschließend folgen die im Anspruch 1 aufgeführten Chinoxalin-Kohlenwasserstoffe. Neben dem chemischen Namen jeder Verbindung ist ein Literaturhinweis betreffend ein Herstellungsverfahren angegeben.
Für die neuen Verbindungen (abgekürzt »n. V.«) sind im Anschluß an die Aufzählung der Einzelverbindungen
Herstellungsmethoden angegeben.
a. 5-Methyl-chinoxalin | Ann. 237, 336(1887) |
b. 2-Methyl-chinoxalin | Org. Synth. 30, 86 (1950) |
c. 6-Methyl-chinoxalin | Ann. 237, 336 (1887) |
d. 2,3-Dimethyl-chinoxalin | Ber. 40, 4852(1907) |
e. 2-Methyl-3-äthyl-chinoxalin | Ber. 22, 526(1889) |
f. 2,3-Diäthyl-chinoxalin | J.A.CS. 79, 1712(1957) |
g. 2-Methyl-3-propyl-chinoxalin | J. Chem. Soc. 1946, 54 |
h. 2-Methyl-3-isopropyl-chinoxalin | J. Chem. Soc. 1953, 2822 |
i. 2-Methyl-3-butyl-chinoxalin | n.V. |
j. 2-Methyl-3-isobutyl-chinoxalin | n.V. |
k. 2-Methyl-3-amyl-chinoxalin | J. Chem. Soc. 1943, 322 |
1. 2-Äthyl-chinoxalin | J. Chem. Soc. 1953, 2822 |
Die oben zitierten neuen Verbindungen können wie folgt erhalten werden:
i. 2-Methyl-3-butyl-chinoxalin
wurde von o-Phenylendiamin und Heptandion-(2,3), wie in Ber. 40, 4852 (1907) beschrieben, hergestellt. Die so erhaltene Verbindung besitzt einen Siedepunkt von 153° C bei 12mbar (9 mm Hg).
wurde von o-Phenylendiamin und Heptandion-(2,3), wie in Ber. 40, 4852 (1907) beschrieben, hergestellt. Die so erhaltene Verbindung besitzt einen Siedepunkt von 153° C bei 12mbar (9 mm Hg).
2-MethyI-3-isobutyl-chinoxalin wurde von o-Phenylendiamin und 5-Methyl-hexandion-(2,3),
wie hier oben beschrieben, hergestellt.
10
15
Die so erhaltene Verbindung besitzt einen Schmelzpunkt von 94—95° C.
Die organoleptische Bewertung der oben zitierten Verbindungen wurde mittels Prüfungsmethoden A, B
und C durchgeführt. Die Methode A diente dazu, den Eigengeschmack der einzelnen Substanzen zu bestimmen.
Die geschmacksverändernden Eigenschaften der Substanzen wurden mittels der Methoden B und C
ermittelt. Es wurde insbesondere die geschmacksverändernde Wirkung der Prüfsubstanzen (im folgenden
»Geschmacksstoffe« genannt) auf Kaffeeprodukte und speziell auf sprühgetrocknete, lösliche Kaffeepulver
geprüft.
Methode A
Die Geschmacksstoffe wurden in einer 65%igen Zuckersirup-Lösung, bestehend aus Rohrzucker in
Leitungswasser, gekostet. Die zu prüfenden Geschmacksstoffe wurden dem Sirup in Form von
Lösungen von 1 Gew.-% oder 1 Gew.-%o in 95°/oigem 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 siedendem Wasser im Verhältnis von 1 g Pulver auf 80 ml
Wasser hergestellt wurde. Für jeden zu prüfenden Geschmacksstoff wurde ein Gefäß mit Kaffeegetränk
bereitgestellt. Die Geschmacksstoffe wurden dem Kaffeegetränk in Form von Lösungen von 1 Gew.-%
oder 1 Gew.-%o in 96°/oigem Alkohol in Konzentrationen von 0,005 bis 5 g auf 100 Liter Getränk zugegeben.
30
40 Nach Zugabe der abgemessenen Menge der Geschmacksstofflösung
wurde das Kaffeegetränk gut gerührt und sofort ;n eine Reihe von Tassen für die
organoleptische Prüfung gegossen. Das Kosten des Getränkes wurde so rasch als möglich, auf jeden Fall
nicht später als 15 Minuten nach der Zubereitung vorgenommen.
Die nur mit einer Kennzahl versehenen gefüllten Tassen wurden in einer Reihe aufgestellt, wobei die
erste Tasse eine nicht aromatisierte Vergleichsprobe des Kaffeegetränkes enthielt. Die Geschmacksprüfer
mußten feststellen, ob zwischen der Vergleichsprobe und den anderen Proben geschmacklich ein Unterschied
bestand oder nicht. Die Prüfer mußten ferner die Geschmacksunterschiede beschreiben und charakterisieren.
Methode C
Als Substrat für die Geschmacksprüfung wurde eine l,35°/oige Lösung eines im Handel erhältlichen, sprühgetrockneten
Kaffeepulvers mit verhältnismäßig »flachem« Geschmack und Aroma in Quellwasser verwendet.
Die einzelnen Geschmacksstoffe wurden je einer Portion des Kaffeegetränkes mittels einer Mikrospritze
in Mengen von 2 bis 150 Mikroliter zugegeben. Alle für die Zubereitung des Kaffeegetränkes sowie für die
Aromatisierung verwendeten Gefäße und sonstigen Geräte wurden peinlichst gesäubert. Für die Geschmacksprüfung
wurden mindestens 5 erfahrene Geschmacksprüfer eingesetzt. Im übrigen wurde gleich
wie bei Methode B gearbeitet.
Die Resultate der organoleptischen Prüfung sind in der nachfolgenden Tabelle zusammengefaßt. In der
ersten Kolonne der Tabelle sind die Buchstaben der einzelnen Verbindungen innerhalb der genannten
Stoffklasse angeführt. Die zweite Kolonne verweist auf die angewendete Prüfmethode. In der dritten Kolonne
sind die verwendeten Mengen der Prüfsubstanzen in g pro 100 Liter Getränk (Zuckersirup oder Kaffeegetränk)
angegeben.
Verbindung | Versuch | Menge | Organoleptische Bewertung |
a. | A | 1,0 | verbrannte, geröstete Haselnüsse |
a. | C | 0,27 | toastartig |
b. | A | 4,0 | phenolisch, verbrannter Geschmack |
C. | A | 4,0 | verbrannter, erdiger Geschmack |
d. | B | 2,5 | astringierend, fettig, erdig |
e. | B | 0,7 | haselnußartig, bitter, geröstet |
f. | B | 0,6 | bitter, erdig |
g. | B | 2,5 | bitter, beißend, erdig |
h. | B | 1,2 | bitter, astringierend |
i. | B | 2,5 | bitter, sauer, holzig |
j· | B | 1,2 | bitter, erdig, holzig |
k. | B | 1,2 | bitter, erdig, fettig |
1. | B | 2,0 | grün, geröstet |
Claims (1)
1. Verwendung von
a. 5-Methyl-chinoxalin
b. 2-Methyl-chinoxalin
c. 6-Methyl-chinoxalin
d. 2,3-Dimethyl-chinoxalin
e. 2-Methyl-3-äthyl-chinoxalin
f. 2,3-Diäthyl-chinoxalin
g. 2-Methyl-3-propyl-chinoxalin
h. 2-Methyl-3-isopropyl-chinoxalin i. 2-Methyl-3-butyl-chinoxalin
j. 2-Methyl-3-isobutyl-chinoxalin k. 2-Methyl-3-amyl-chinoxalin
1. 2-Aethyl-chinoxalin
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 |
---|---|
DE1793845B1 true DE1793845B1 (de) | 1979-10-31 |
DE1793845C2 DE1793845C2 (de) | 1980-08-07 |
Family
ID=27036753
Family Applications (12)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
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 |
DE1793852A Expired DE1793852C2 (de) | 1965-04-30 | 1966-04-29 | 4-Methyl-2-propionyl-und-butyrylthiazol und Verwendung von Thiazolcarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten |
DE1793848A Expired DE1793848C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter aromatischer Thiole, Sulfide und Disulfide als Geschmacksstoffe oder Geschmacksstoff komponente |
DE1793846A Expired DE1793846C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter Pyrazincarbonylverbindungen als Geschmacksstoffe und Geschmacksstoffkomponente |
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 |
DE1793850A Expired DE1793850C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter Thiophan-Verbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente |
DE1793842A Expired DE1793842C3 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter Benzofuranverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente |
DE1793844A Expired DE1793844C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung von Pyrazin-Verbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten |
DE1793843A Expired DE1793843C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter Pyridin-Kohlenwasserstoffe als Geschmacksstoffe oder Geschmacksstoffkomponente |
DE1793845A Expired DE1793845C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung von Chinoxalin-Kohlenwasserstoffen als Geschmacksstoffe oder Geschmacksstoffkomponenten |
Family Applications Before (11)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
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 |
DE1793852A Expired DE1793852C2 (de) | 1965-04-30 | 1966-04-29 | 4-Methyl-2-propionyl-und-butyrylthiazol und Verwendung von Thiazolcarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten |
DE1793848A Expired DE1793848C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter aromatischer Thiole, Sulfide und Disulfide als Geschmacksstoffe oder Geschmacksstoff komponente |
DE1793846A Expired DE1793846C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter Pyrazincarbonylverbindungen als Geschmacksstoffe und Geschmacksstoffkomponente |
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 |
DE1793850A Expired DE1793850C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter Thiophan-Verbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente |
DE1793842A Expired DE1793842C3 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter Benzofuranverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponente |
DE1793844A Expired DE1793844C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung von Pyrazin-Verbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten |
DE1793843A Expired DE1793843C2 (de) | 1965-04-30 | 1966-04-29 | Verwendung bestimmter Pyridin-Kohlenwasserstoffe als Geschmacksstoffe oder Geschmacksstoffkomponente |
Country Status (10)
Country | Link |
---|---|
JP (6) | JPS5231420B1 (de) |
BR (1) | BR6679143D0 (de) |
CH (1) | CH529516A (de) |
DE (12) | DE1793851C2 (de) |
DK (1) | DK139012B (de) |
ES (1) | ES326503A1 (de) |
GB (1) | GB1156472A (de) |
NL (1) | NL150316B (de) |
NO (1) | NO134889C (de) |
SE (9) | SE373731B (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. |
EP0545556B1 (de) * | 1991-11-08 | 1997-07-23 | Quest International B.V. | Parfumzusammenstellung |
JP4613421B2 (ja) | 1999-04-20 | 2011-01-19 | 味の素株式会社 | 香気前駆体組成物および香気成分発現方法 |
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 |
RU2497366C2 (ru) * | 2007-11-13 | 2013-11-10 | Нестек С.А. | Применение тиоэфирных вкусоароматических добавок для улучшения вкусоароматических свойств готового к употреблению кофе после автоклавирования и хранения |
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 DE1793851A patent/DE1793851C2/de not_active Expired
- 1966-04-29 ES ES0326503A patent/ES326503A1/es not_active Expired
- 1966-04-29 SE SE6914956A patent/SE373731B/xx unknown
- 1966-04-29 SE SE6914961A patent/SE377270B/xx unknown
- 1966-04-29 DK DK221766AA patent/DK139012B/da unknown
- 1966-04-29 DE DE1793847A patent/DE1793847C3/de not_active Expired
- 1966-04-29 DE DE1793852A patent/DE1793852C2/de not_active Expired
- 1966-04-29 SE SE6914959A patent/SE373733B/xx unknown
- 1966-04-29 BR BR179143/66A patent/BR6679143D0/pt unknown
- 1966-04-29 NO NO162820A patent/NO134889C/no unknown
- 1966-04-29 SE SE6914962A patent/SE373735B/xx unknown
- 1966-04-29 DE DE1793848A patent/DE1793848C2/de not_active Expired
- 1966-04-29 NL NL666605854A patent/NL150316B/xx not_active IP Right Cessation
- 1966-04-29 DE DE1793846A patent/DE1793846C2/de not_active Expired
- 1966-04-29 SE SE05878/66A patent/SE335463B/xx unknown
- 1966-04-29 DE DE1793849A patent/DE1793849C2/de not_active Expired
- 1966-04-29 SE SE6914958A patent/SE373732B/xx unknown
- 1966-04-29 SE SE6914960A patent/SE373734B/xx unknown
- 1966-04-29 DE DE1695505A patent/DE1695505C3/de not_active Expired
- 1966-04-29 CH CH625166A patent/CH529516A/de not_active IP Right Cessation
- 1966-04-29 SE SE6914963A patent/SE373736B/xx unknown
- 1966-04-29 DE DE1793850A patent/DE1793850C2/de not_active Expired
- 1966-04-29 DE DE1793842A patent/DE1793842C3/de not_active Expired
- 1966-04-29 DE DE1793844A patent/DE1793844C2/de not_active Expired
- 1966-04-29 DE DE1793843A patent/DE1793843C2/de not_active Expired
- 1966-04-29 DE DE1793845A patent/DE1793845C2/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 JP46019575A patent/JPS5231420B1/ja active Pending
- 1971-03-31 JP JP46019569A patent/JPS499746B1/ja active Pending
- 1971-03-31 JP JP46019568A patent/JPS4821509B1/ja active Pending
- 1971-03-31 JP JP46019571A patent/JPS499747B1/ja active Pending
- 1971-03-31 JP JP1957071A patent/JPS5333667B1/ja active Pending
-
1976
- 1976-12-09 JP JP14826376A patent/JPS5412552B1/ja active Pending
Non-Patent Citations (1)
Title |
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None * |
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