DE1695505C3 - Verwendung bestimmter Alkylnaphthaline als Geschmacksstoffe oder Geschmacksstoffkomponenten - Google Patents

Verwendung bestimmter Alkylnaphthaline als Geschmacksstoffe oder Geschmacksstoffkomponenten

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Publication number
DE1695505C3
DE1695505C3 DE1695505A DEF0049068A DE1695505C3 DE 1695505 C3 DE1695505 C3 DE 1695505C3 DE 1695505 A DE1695505 A DE 1695505A DE F0049068 A DEF0049068 A DE F0049068A DE 1695505 C3 DE1695505 C3 DE 1695505C3
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DE
Germany
Prior art keywords
taste
naphthalene
compound
flavor
dimethyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
DE1695505A
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English (en)
Other versions
DE1695505B2 (de
DE1695505A1 (de
Inventor
I Flament
F Gautschi
I M Goldman
M Stoll
M Winter
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Firmenich SA
Original Assignee
Firmenich SA
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Filing date
Publication date
Application filed by Firmenich SA filed Critical Firmenich SA
Publication of DE1695505A1 publication Critical patent/DE1695505A1/de
Publication of DE1695505B2 publication Critical patent/DE1695505B2/de
Application granted granted Critical
Publication of DE1695505C3 publication Critical patent/DE1695505C3/de
Expired legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/333—Radicals substituted by oxygen or sulfur atoms
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F5/00—Coffee; Coffee substitutes; Preparations thereof
    • A23F5/46—Coffee flavour; Coffee oil; Flavouring of coffee or coffee extract
    • A23F5/465—Flavouring with flavours other than natural coffee flavour or coffee oil
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/56—Flavouring or bittering agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/204—Aromatic compounds
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    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/205—Heterocyclic compounds
    • A23L27/2054—Heterocyclic compounds having nitrogen as the only hetero atom
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    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
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    • 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
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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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    • C07D213/02—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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    • C07D213/04—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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    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
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    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/28—Halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D333/40—Thiophene-2-carboxylic acid

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Description

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.
Die vorliegende Erfindung betrifft die Verwendung der folgenden Naphthalinderivate
Λ-Methyl-naphthalin
/J-Methyl-naphthalin
0-Äthyl-naphthalin
1,2-Dimethyl-naphthalin
1,3-Dimethyl-naphthalin
1,4-Dimethyl-naphthalin
1,5-Dimethyl-naphthalin
1,6-Dimethyl-naphthalin
i. 2,3-Dimethyl-naphthalin
j. 2,6-Dimethyl-naphthalin
k. 1,3,7-Trimethyl-naphthalin
1. 2,3,5-Trimethyl-naphthalin
m. 2,3,6-Trimethyl-naphthalin
Λ-Äthyl-naphthalin
,7-Dimethyl-naphthalin
2,7-Dimethyl-naphthalin
zu; 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 bze. 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 Verfügung 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 Getränke durch Verwendung von künstlichen Aromen mit genau reproduzierbaren Geschmackseigenschaften und -qualitäten gewinnt in der Lebensmittelindustrie mehr und mehr an Bedeutung, seitdem für die Ernährung des Menschen neue, bisher nicht verwendete Rohstoffe erschlosssen werden, um der drohenden Verknappung der Nahrungsmittel in gewissen Gebieten des Erdballs entgegenzutreten.
π Es wurde gefunden, daß die oben beschriebenen Verbindungen entweder einzeln oder in Form zweckentsprechender Mischungen dazu geeignet sind, die Geschmackseigenschaften verschiedensT fester 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 oder Speiseeis, geschmacklich verändert werden. Die Erfindung eignet sich insbesondere zur Verbesserung oder Verstärkung des Geschmackes von konservierten Lebensmitteln. Ganz besonders eignet sich die Erfindung zur Veränderung, Verbesserung oder Verstärkung
jo der Geschmackseigenschaften von sogennnten löslichen Kaffeeprodukten (im englischen Sprachgebrauch als »instant coffee« bezeichnet).
Die genannten Naphthalinderivate sind im Handel erhältlich bzw. nach üblichen Verfahren herstellbar.
j5 Die organoleptische Bewertung der obenzitierten Verbindungen wurde mittels der folgenden Prüfmethoden durchgeführt. Sie diente dazu, den Eigengeschmack der einzelnen Substanzen zu ermitteln.
Prüfmethode
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 Geschmacks der einzelnen GeschmackLjtoffe abgeben.
Tabelle
Ver- Menge
bindung
Organoleptische Bewertung
a. 0,05-0,1 grüner, muffiger
Geschmack
b. 0,1 ölig, aromatisch
c. 0,15 öliger Geschmack
el. 0,15 aromatischer Geschmack
e. 1,0 aromatischer Geschmack
Fortsetzung
(3) Handelsübliches Apfelmus
Verbindung
Menge
Organoleptische Bewertung
f. 0,25 muffiger, teerartjger
Geschmack
g. 1,0 muffiger, aromatischer
Geschmack
h. 0,25 aromatischer Geschmack
i. 1,0 erdiger Geschmack
j. 2,0 süßer, anis- und
honigartiger Geschmack
k. 0,5 erdbeerähniich
1. 0,25 erdiger Geschmack
m. 1 leicht fruchtig; trocken
n. 0,15 fettiger, erdiger Geschimack
o. 0,25—0,50 aromatischer Geschmack
p. 1,0 aromatischer, erdiger
Geschmack
Vergleichsversuche
A. Die folgenden vier Naphthalinverbindungen wurden als Geschmackszusätze für verschiedene Lebensmittel und Getränke verwendet:
Verbindung A: Naphthalin (Vergleich) Verbindung B: 1,3,7-TrimethylnaphthaIin Verbindung C: 23,5-Trimethylnaphthalin Verbindung D: 2,3,6-f rimeth'j (naphthalin
(1) 0,5gew.-%ige Lösung von Kochsalz in Quellwasser
Ver Menge Geschmacksbewertung
bin
dung Ppm
A 1 chemisch, bitterer Nachgeschmack
B 0,5 blumig, rosenähnlich, grün,
an geröstetes Fett erinnernd, erdig
C 0,5 fettig, ölig, leicht verbrannt
D 5 holzig, grün, gemüseähnlich,
an Fleisch erinnernd
Ver Menge Geschmacksbewertung
bin
dung ppm •
A 1 unausgeglichener Geschmack,
bitterer Nachgeschmack
B 0,3 süßer, fluchtiger, typischer als -das
unbehandelte Apfelmus
C 0,5 fruchtiger, grün, frischer als das
unbehandelte Apfelmus
B. 1) Die folgenden vier Naphthalinderivate wurden i-uerst organolepüsch bewertet:
Verbindung A: Naphthalin (Vergleich)
Verbindung B: a-Methylnaphthalin
Verbindung C: /7-Methylnaphthalin
Verbindung D: 1,4-DimethyInaphthalin
Für diesen Zweck wurde jeweils 1 ppm der Verbindung in reinem Wasser gelöst; die Ergebnisse der Bewertung sind nachstehend zusammengefaßt
Verbindung A: »chemischer« Geschmack, erinnert an Kohlenwasserstoffe (Kerosin), .bitterer Nachgeschmack;
Verbindung B: verbrannter, grüner und erdiger Geschmack;
Verbindung C: erdiger, etwas muffiger, verbrannter und grüner Geschmack;
Verbindung D: erdiger, verbrannter und grüner Geschmack.
(2) Angesäuerter Zuckersyrup (10Gew.-% Zucker + 0,2gew.-%ige Zitronensäurelösung in Quellwasser
Verbin
dung
Menge Geschmacksbewertung
ppm
A 1 chemisch, bitterer Nachgeschmack
B 0,5 fruchtig, mild und erdbeerähnlich,
süß, grün, an Äpfel und Birnen
erinnernd
C 0,5 holzig, fettig/mandarinenartig,
trocken, leicht an Himbeeren
erinnernd
D 5 süß, blumig, an Aprikosen und
Zitrusfrüchte erinnernd
Die Verbindungen A, B, C und D wurden nun als Geschmackszusätze in die nachstehenden Getränke gegeben:
2) Löslicher Kaffee
Es wurden 2,8 g eines handelsüblichen1 löslichen Kaffees in 200 ecm siedendem Wasser gelöst.
Die Verbindungen A bis D wurden in Mengen von jeweils 1 ppm in mehrere Portionen dieses Kaffeegetränks gegeben; die Geschmacksprüfung führte zu folgenden Ergebnissen:
Verbindung A: »chemischer« Geschmack, unausgeglichenes Kaffee-Aroma;
Verbindung B: schmeckte stärker geröstet als das nicht mit einem Zusatz versehene Kaffeegetränk;
Verbindung C: gleicher Eindruck wie bei Verbindung B;
Verbindung D: gleicher Eindruck wie bei Verbindung B.
3) Schokoladenmilch-Getränk
Es wurden 100 g eines handelsüblichen, löslichen Schokoladenmilchgetränke-Pulvjrs, das Kakao, Milchw) pulver und Zucker enthielt, in 600 ecm kaltem Wasser gelöst.
Die Verbindungen A bis D wurden in Mengen von jeweils 1 ppm in mehrere Portionen dieses Schokoladenmilch-Getränks gegeben, wobei folgende Ergebnishi se erzielt wurden:
Verbindung A: »chemischer« Geschmack, unausgeglichenes Schokoladen-Aroma;
Verbindung B: voller und runder im Aroma, schmeckte stärker geröstet als das Getränk ohne Zusatz;
Verbindung C: gleicher Eindruck wie bei Verbindung B;
Verbindung D: gleicher Eindruck wie bei Verbindung B.
Die Verbindungen B, C und D wurden nun zur Aromatisierung der folgenden Lebensmitterund künstlichen Aromastoffe verwendet
4) Roastbeef-Soße
Es wurden 45 g einer handelsüblichen, pulverförmigen Roastbeef-Soße in 300 ecm Wasser gelöst
Die Verbindungen B und C wurden in Mengen von jeweils 5 ppm und die Verbindung D in einer Menge von 7 ppm in diese Soße gegeben.
In allen drei Fällen schmeckte die Soße — verglichen mit der Soße ohne Zusatz — nach stärker gebratenem Fleisch.
5) Künstliches Rauch-Arom*,
Ein Grund-Aromastoff wurde hergestelit, indem man die folgenden Komponenten miteinander mischte:
Guajacol
p-Kresol
Phenol
o-Kresol
Triacetin
Gew.-Teile
30
15
10
942
1000
Verbindung B: im Vergleich zu dem Sirup ohne Zusatz, stärker ausgeprägter erdiger und holziger Geschmack, ähnlich wie bei chinesischem Zimt;
Verbindung C: gleicher Eindruck wie bei Verbindung B;
Verbindung D: gleicher Eindruck wie bei Verbindung B,
ι ° 7) Künstliches Walnuß-Aroma
Aus folgenden Komponenten wurde eine Aroma-Grundmischung hergestellt:
Gew.-Teile
Methylcyclopentenolon 50
Furfurylalkohol 50
Furfural 10
Diacetal 5
Acetylmethylcarbinol 30
Benzylalkohol 100
Propylenglykol 755
1000
Diese Grundmischung wurde dann mit Äthylalkohol zu einer l°/oigen Lösung verdünnt und die Lösung schließlich in Salzwasser (03 g NaCl auf 100 ecm Wasser) gegeben, und zwar in einer Menge von 100 g äthanolischer Lösung pro 1001 Salzwasser.
Dem so aromatisierten Salzwasser wurden nun jeweils 0,5 ppm der Verbindungen B und C bzw. 1 ppm der Verbindung D zugesetzt
Alle drei Verbindungen verliehen dor Aromalösung einen erdigen, verbrannten und leicht teerartigen Geschmack und rundeten das Aroma ab.
6) Zimt-Sirup
Mit künstlichem Aroma wurde eine Zimtsäurealdehyd in 1001 eines 10%igen Zuckersirups löste.
In diesen Sirup wurden die Verbindungen B, C und D in Mengen von jeweils 1 ppm gegeben, und es wurden folgende Ergebnisse erzielt:
Diese Grundmischung wurde in zwei gleiche Teile geteilt, und eine Hälfte wurde mit 5% der Verbindung B fa-Methylnaphthalin) angereichert Darauf wurden beide Hälften mit Propylenglykol zu 10%igen Lösungen verdünnt und zur Herstellung der folgenden Süßspeisen verwendet:
8) Pudding
Eine Mischung aus 60 g Zucker und 3 g Pektin wurde in 500 ecm heiße Milch eingerührt Man ließ die Mischung einige Sekunden aufkochen, setzte dann den Aromastoff zu und ließ die Mischung abkühlen.
9) Eis
Aus 1 1 Milch, 5 Eigelb und 250 g Zucker wurde Eis hergestellt. Die Milch wurde erhitzt und unter Rühren in den mit dem Eigelb vermischten Zucker gegeben. Das Rühren wurde fortgesetzt, bis die Masse dick wurde, und dann wurde der Aromastoff zugegeben. Man ließ die Mischung in üblicher Weise gefrieren.
In beiden Fällen wurde festgestellt daß die Speisen mit dem Aromastoff, der die Verbindung B (bc-Methylnaphthalin) enthielt einen abgerundeteren Walnußgeschmack zeigten. Die erdige Geschmacksnote wurde betont
Die Verwertung der Erfindung kann durch gesetzliche Bestimmungen, insbesondere durch das Lebensmittelgesetz, beschränkt sein.

Claims (1)

Patentansprüche:
1. Verwendung von
a. Λ-Methyl-naphthalin
b, ^-Methyl-napbthaün
c j3-ÄthyI-naphthaIin
d 1,2-Dimethyl-naphthalin
e. 1,3-Dimethyl-naphthalin
f. 1,4-DimethyI-naphthaün
g. 14-Dimethyl-naphthalin
h. 1,6-Dimethyl-naphthalin
L 23-DimethyI-naphthalin
j. 2,6-Dimethyl-naphthaIin
k. 1,3,7-Trimethyl-naphthalin
1. 2,3,5-Trimethyl-naphthaIin
m. 23,6-Trimethyl-naphthaIin
n. Λ-ÄthyI-naphthalin
o. 1,7-Dimethyl-naphthalin
p. 2,7-Dimethyl-naphthalin
DE1695505A 1965-04-30 1966-04-29 Verwendung bestimmter Alkylnaphthaline als Geschmacksstoffe oder Geschmacksstoffkomponenten Expired DE1695505C3 (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 (3)

Publication Number Publication Date
DE1695505A1 DE1695505A1 (de) 1970-12-23
DE1695505B2 DE1695505B2 (de) 1979-04-05
DE1695505C3 true DE1695505C3 (de) 1979-11-29

Family

ID=27036753

Family Applications (12)

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

Family Applications Before (1)

Application Number Title Priority Date Filing Date
DE1793846A Expired DE1793846C2 (de) 1965-04-30 1966-04-29 Verwendung bestimmter Pyrazincarbonylverbindungen als Geschmacksstoffe und Geschmacksstoffkomponente

Family Applications After (10)

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

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JP (6) JPS499747B1 (de)
BR (1) BR6679143D0 (de)
CH (1) CH529516A (de)
DE (12) DE1793846C2 (de)
DK (1) DK139012B (de)
ES (1) ES326503A1 (de)
GB (1) GB1156472A (de)
NL (1) NL150316B (de)
NO (1) NO134889C (de)
SE (9) SE373735B (de)

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US3767429A (en) * 1971-12-06 1973-10-23 Procter & Gamble Lard flavor concentrate
NL8403748A (nl) * 1984-12-10 1986-07-01 Zaan Cacaofab Bv Cacaopoeder.
BR9204339A (pt) * 1991-11-08 1993-05-18 Unilever Nv Composicao de pertume,composicao detergente,composicao de condicionamento de tecido e processo para tratar texteis
BR0008351B1 (pt) 1999-04-20 2010-12-28 composição precursora de flavorizante, método para liberar o componente flavorizante a partir da composição precursora de flavorizante, e, composto de sulfeto.
JP2008079545A (ja) * 2006-09-28 2008-04-10 Sanei Gen Ffi Inc カフェオフランまたはその類縁体からなる乳含有飲食品用添加剤
JP5153195B2 (ja) * 2007-04-13 2013-02-27 長谷川香料株式会社 コーヒーの淹れたて感賦与剤
ES2380760T3 (es) * 2007-11-13 2012-05-18 Nestec S.A. Uso de saborizantes de tioéster para mejorar la calidad del sabor de café listo para tomar tras el tratamiento térmico y el almacenamiento

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US3076818A (en) * 1963-02-05 Production of benzofurans
US3033875A (en) * 1959-09-28 1962-05-08 Hills Bros Coffee Condensed ring heterocyclic disulfides and sulfides

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Publication number Publication date
DE1793847C3 (de) 1981-04-02
DE1793846C2 (de) 1981-01-15
ES326503A1 (es) 1967-07-01
SE377270B (de) 1975-06-30
DE1793842C3 (de) 1981-03-19
DE1793848B1 (de) 1980-04-30
DE1793845B1 (de) 1979-10-31
DE1793850B1 (de) 1980-04-24
DE1793842B1 (de) 1980-06-26
DE1695505B2 (de) 1979-04-05
DE1793844C2 (de) 1980-07-24
DK139012C (de) 1979-05-14
JPS4821509B1 (de) 1973-06-29
GB1156472A (en) 1969-06-25
JPS5333667B1 (de) 1978-09-16
DE1793843C2 (de) 1981-01-15
SE373735B (de) 1975-02-17
DE1793852B1 (de) 1980-01-24
DE1793848C2 (de) 1981-01-15
NL150316B (nl) 1976-08-16
DE1793852C2 (de) 1980-10-09
JPS5412552B1 (de) 1979-05-23
JPS5231420B1 (de) 1977-08-15
CH529516A (de) 1972-10-31
SE373733B (de) 1975-02-17
DE1793846B1 (de) 1980-04-30
SE373732B (de) 1975-02-17
SE335463B (de) 1971-05-24
DE1695505A1 (de) 1970-12-23
NO134889C (de) 1977-01-05
SE373736B (de) 1975-02-17
JPS499746B1 (de) 1974-03-06
SE377269B (de) 1975-06-30
DE1793844B1 (de) 1979-10-31
SE373731B (de) 1975-02-17
DE1793849C2 (de) 1982-07-01
DE1793847B1 (de) 1980-06-26
JPS499747B1 (de) 1974-03-06
NL6605854A (de) 1966-10-31
DE1793843B1 (de) 1980-04-30
BR6679143D0 (pt) 1973-09-11
DK139012B (da) 1978-12-04
NO134889B (de) 1976-09-27
DE1793845C2 (de) 1980-08-07
DE1793851C2 (de) 1982-07-01
DE1793850C2 (de) 1980-12-11
SE373734B (de) 1975-02-17

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