DE1793852B1 - 4-Methyl-2-propionyl-und-butyrylthiazol und Verwendung von Thiazolcarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten - Google Patents

4-Methyl-2-propionyl-und-butyrylthiazol und Verwendung von Thiazolcarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten

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Publication number
DE1793852B1
DE1793852B1 DE1793852A DE1793852A DE1793852B1 DE 1793852 B1 DE1793852 B1 DE 1793852B1 DE 1793852 A DE1793852 A DE 1793852A DE 1793852 A DE1793852 A DE 1793852A DE 1793852 B1 DE1793852 B1 DE 1793852B1
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DE
Germany
Prior art keywords
taste
methyl
thiazole
propionyl
butyrylthiazole
Prior art date
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Granted
Application number
DE1793852A
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English (en)
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DE1793852C2 (de
Inventor
I Flament
F Gautschi
I M Goldman
M Stoll
M Winter
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Firmenich SA
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Firmenich SA
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Application filed by Firmenich SA filed Critical Firmenich SA
Publication of DE1793852B1 publication Critical patent/DE1793852B1/de
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Publication of DE1793852C2 publication Critical patent/DE1793852C2/de
Expired legal-status Critical Current

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    • 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
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    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/28—Halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D333/40—Thiophene-2-carboxylic acid

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Description

worin Ri einen Alkylrest mit 1 bis 3 Kohlenstoffatomen und R2 ein Wasserstoffatom oder die Methylgruppe bedeutet als Geschmacksstoffe in Getränken, Nahrungs- und Genußmitteln oder als Geschmacksstoffkomponenten in geschmacksverändernden Mitteln.
3. Ausführungsform nach Anspruch 2, dadurch gekennzeichnet, daß man die Verbindungen der allgemeinen Formel I zum Aromatisieren von löslichen Kaffeeprodukten verwendet.
Die Erfindung betrifft die Verwendung von Thiazolcarbonylverbindungen der allgemeinen Formel
C=O
worin Ri einen Alkylrest mit 1 bis 3 Kohlenstoffatomen und R2 ein Wasserstoffatom oder die Methylgruppe bedeutet als Geschmacksstoffe in Getränken, Nahrungsund Genußmitteln oder als Geschmacksstoffkomponenten in geschmacksverändernden Mitteln.
Die Erfindung hat schließlich neue Thiazolcarbonylverbindungen zum Gegenstand, und zwar 4-Methyl-2-propionyl-thiazol und 4-Methyl-2-butyryl-thiazol.
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 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 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 gefunden, daß die oben beschriebenen Verbindungen entweder einzeln oder in Form zweckentsprechender Mischungen dazu geeignet sind, die Geschmackseigenschaften verschiedenster fester und flüssiger Nahrungs- und Genußmittel oder Getränke im gewünschten Sinne zu verändern. Mittels der Erfindung können beispielsweise Produkte wie Fruchtsäfte, Gemüsesäfte, Milchprodukte, Kaffee-, Tee-, Kakao- und Schokoladeprodukte, Getreideflocken, Mehle, Konfiseriewaren, Fleischprodukte, Backwaren und 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 der Geschmackseigenschaften von sogenannten löslichen Kafeeprodukten (im englischen Sprachgebrauch als »instant coffee« bezeichnet).
Anschließend folgen die unter die allgemeine Formel I fallenden Thiazolcarbonylverbindungen. 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. 4-Methyl-2-acetyl-thiazol
Bull. 20, 702 (1953)
b. 4-Methyl-2-propionyl-thiazol n.V.
c. 5-Methyl-2-acetyl-thiazol
Bull. 20, 702 (1953)
d. 4-Methyl-2-butyryl-thiazoI
n.V.
r>
Die neuen Verbindungen dieser Stoffklasse können wie folgt hergestellt werden:
(1) b. 4-Methyl-2-propionyl-thiazol wurde nach der in Bull. 20, 702 (1953) beschriebenen Methode hergestellt,
indem 4-Methyl-thiazol mit Äthylmagnesiumbromid umgesetzt und die als Zwischenprodukt gebildete Grignard-Verbindung mit Propionylchlorid acyliert wurde. Das Produkt wies einen Sdp. von 83—88° C/ 9 mm Hg auf.
(1) d. 4-Methyl-2-butyryl-thiazol wurde in der gleichen Weise wie die Verbindung (1) b. hergestellt, wobei jedoch Butyranhydrid als Acylierungsmittel verwendet wurde. Das Produkt wies einen Sdp. von 110 bis 115°C/8mmHgauf.
Die organoleptische Bewertung der oben definierten Verbindungen wurde mittels Prüfmethoden A und B durchgeführt Die Methode A diente dazu, den Eigengeschmack der einzelnen Substanzen zu ermitteln. Die geschmacksverändernden Eigenschaften der Substanzen wurden mittels der Methode B 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°/oigen Zuckersirup-Lösung, bestehend auf Rohrzucker in Leitungswasser, gekostet. Die zu prüfenden Geschmacksb5 stoffe 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 Geschmacks-
intensität 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 Geschmacksprüfung wurde eine l,35%ige Lösung eines im Handel erhältlichen, sprühgestrockneten 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 die Aromatisierung, verwendeten Gefäße und sonstigen Geräte wurden peinlichst gesäubert. Für die Geschmacksprüfung wurden mindestens 5 erfahrene Geschmacksprüfer eingesetzt. 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 bestand oder nicht. Die Prüfer mußten ferner die Geschmacksunterschiede beschreiben und charakterisieren.
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.
Tabelle
Ver- Verbin- such
dung
Menge Organoleptische Bewertung
a. A 2,0 anthranilisch, verbrannt
b. A 3,0 fruchtig, verbrannt
C. A 0,5 Geschmack verbrannter
Nüsse
C. B 0,034 toastartig; ungeröstete
Kaffeebohnen
d. A 3,0 grüner Grapefruitgeschmack
Die organoleptischen Eigenschaften weiterer Verbindungen der allgemeinen Formel I gehen aus dem folgenden Versuchsbericht hervor:
A) 2-Acetyl-thiazol
i) 100 g 2-Aminothiazol wurden bei 00C zu 400 ecm 84%iger Phosphosäure zugefügt. Die Reaktionsmischung wurde auf -1O0C abgekühlt, und unter gründlichem Rühren wurden 180 ecm 65%ige Salpetersäure und anschließend 90 g Natriumnitrit in 120 ecm Wasser eingetropft. Die so erhaltene Reaktionsmischung wurde eine weitere Stunde bei - 1O0C gerührt und schließlich bei derselben Temperatur gehalten. Die obige Mischung sowie eine Lösung aus 268 g Natriumbromid in 250 ecm Wasser wurden dann gleichzeitig zu einer kalten (-50C) Lösung aus 325 g CuSO4-5 H2O in 600 ecm Wasser innerhalb von etwa 90 Minuten zugefügt und die Reaktionsmischung weitere 30 Minuten bei 00C gerührt. Dann wurde die obige Mischung mit einer 2O°/oigen wäßrigen Natriumhydroxidlösung auf pH 7 neutralisiert und schließlich zur Bildung von etwa 31 Destillat destilliert Das so erhaltene Material wurde mit Natriumchlorid gesättigt, mit Äther extrahiert, über wasserfreiem Natriumsulfat getrocknet, eingedampft und schließlich unter Bildung von 136 g (83% Ausbeute) 2-Bromthiazol mit einem Kp. 72—75°C/25 Torr destilliert.
ii) 135 g 2-Bromthiazol in 200 ecm wasserfreiem Äther wurden zu einer Lösung aus 553 g Butyllithium in 532 ecm Hexan und 300 ecm wasserfreiem Äther (auf —700C abgekühlt) innerhalb von etwa 45 Minuten zugefügt. Nach weiterem, 90 Minuten langem Rühren
wurden 363 g Äthylacetat in 400 ecm wasserfreiem Äther zugefügt. Nachdem die Reaktionsmischung 4 Stunden bei Zimmertemperatur gehalten worden war, wurde sie auf 00C abgekühlt, mit 500 ecm 10%iger wäßriger HCl angesäuert, mit Natriumchlorid gesättigt
und schließlich mit Äther extrahiert Nach Trocknen über wasserfreiem Natriumsulfat Eindampfen und Destillieren erhielt man 78,6 g (75% Ausbeute) 2-Acetylthiazol mit einem Kp. 74°C/11 Torr.
MS:M+= 127 (43);
Vy m/e = 112 (30), 99 (41), 85 (13), 84 (10), 58 (35), 57 (18), 43 (100).
B) 2-Propionylthiazol
13,5 g 2-Bromthiazol, 55,8 ecm einer 1.55N Lösung aus Butyllithium in Hexan und 42 g Äthylpropionat wurden wie oben umgesetzt und lieferten nach Reinigung 8,7 g (72% Ausbeute) 2-Propionylthiazol mit einem Kp. 84°C/10 Torr.
IR (flüssiger Film): 1686 cm-'
MS: M+= 141 (12);
m/e-114 (11), 113 (92), 112 (100), 86 (12), 85 (31), 84 (21), 59 (13), 58 (32), 57 (84), 45 (8), 29 (71).
C) 2-Butyrylthiazol
13,5 g 2-Bromthiazol, 55,8 ecm einer 1,55N Lösung aus Butyllithium in Hexan und 47,8 g Äthylbutyrat wurden wie oben umgesetzt und lieferten nach Reinigung 8,9 g (70% Ausbeute) 2-Butyrylthiazol mit einem Kp. 91 bis93°C/ll Torr.
IR (flüssiger Film): 1683 cm-1
MS: M+= 155 (33);
m/e= 140 (12), 127 (32), 113 (20), 112 (96), 99 (19), 86 (20), 85 (64), 84 (17), 71 (30), 59 (29), 58 (30), 57 (28), 43 (100).
Die folgenden drei Verbindungen wurden zur Durchführung verschiedener Aromatests verwendet:
Verbindung A = 2-Acetylthiazol
Verbindung B = 2-Propionylthiazol
Verbindung C = Butyrylthiazol
1) Organoleptische Auswertung in Wasser
Verb. Dosis Bemerkungen
(ppm)*)
2,0
2,0
2,0
Verb. Dosis
(ppm)
Bemerkungen
A 2,0
B 2,0
C 2,0
nüsse
leicht fruchtig; an bestimmte Aspekte des Kaffeegeschmacks erinnernd
3) Aromatisierung von Roastbeef-sauce, hergestellt aus 45 g handelsüblichem Roastbeefsaucenpulver und 300 ecm Wasser
Verb. Dosis
(ppm)
Bemerkungen*)
5) Verwendung der Verbindungen A, B und A als aromamodifizierende Bestandteile in einem Karamellaromapräparat
verbrannt, geröstet, Tiergeschmack;
an Haselnüsse erinnernd
geröstet; weniger Tiergeschmack und
stärker haselnußartig als A
frische Haselnüsse, fruchtiger Ge-
schmack
*) = Teile pro MiII.
2) Aromatisierung von Salzwasser, d.h. 0,5%ige Natriumchloridlösung in Wasser
Dosis
(ppm)
Bemerkungen*)
A 2,0 geröstete Haselnüsse; leicht tierisch B 2,0 geröstete Haselnüsse; kokosartig,
leicht tierisch
C 3,0 leicht fruchtig; butterartiger, cremiger
Geschmack
*) Diese Auswertung stammt von einem Gremium von Aromaexperten nach Vergleich mit einem unaromatisierten Material.
15
fleischiger Geschmack, an Roastbeefsauce erinnernd; geröstete Haselnüsse gerösteter Fleischgeschmack; Hasel-
JO
A 2,0 tierischer, fleischiger Geschmack; verstärkt den gerösteten Fleischcharakter
B 2,0 tierischer, fleischiger Geschmack; verstärkt den gerösteten Fleischcharakter
C 3,0 leicht fruchtig, sauer; verleiht einen butterartigen Geschmack
*) Diese Auswertung stammt von einem Gremium von Aromaexperten nach Vergleich mit einem unaromatisierten Material.
4) Aromatisierung von Milch
45
a) Karamellgrundlage Gew.-Teile
Heliotropin 30
Äthylvanillin 40
Vanillin 300
Muskatnußöl 5
Äthylbutyrat 5
Limonenöl 5
Diacetyl 5
Süßorangenöl 10
Rhumäther 250
Äthylalkohol, 95°/oig 350
Insgesamt 1000
b) Karamellaromapräparate
Nr. 1 Nr. 2 100 Nr. 3 25 , Nr. 4 35
Gew.-Teile 25 875 865
Karamellgrundl. 100 875 100 1000 100 1000
Verbindung A; 10%*) 1000
Verbindung B; 10%
Verbindung C; 10%
Äthylalkohol 95% 900
Insgesamt 1000
*) Lösung in Äthylalkohol.
Dann wurden die obigen vier Aromapräparate 1 bis 4 in einer Menge von 1 g Aromapräparat pro 1 verdünntem Zuckersirup zum Aromatisieren des letzteren verwendet und die so aromatisierten Sirupe von einem Gremium von Aromaexperten wie folgt bewertet:
50
Sirup, aromatisiert
mit Nr.
mit Nr.
mit Nr. mit Nr.
typisch karamell, fruchtig, butterartig
geröstete Mandeln, geröstete Haselnüsse und leicht kokosartig dieselbe Aromawirkung wie Nr. 2 fruchtig, an frische Haselnüsse erinnernd

Claims (2)

Patentansprüche:
1. 4-Methyl-2-propionyl-thiazol und 4-Methyl-2-butyryl-thiazol.
2. Verwendung von Thiazolcarbonylverbindungen der allgemeinen Formel
C=O
DE1793852A 1965-04-30 1966-04-29 4-Methyl-2-propionyl-und-butyrylthiazol und Verwendung von Thiazolcarbonylverbindungen als Geschmacksstoffe oder Geschmacksstoffkomponenten Expired DE1793852C2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US45234265A 1965-04-30 1965-04-30
US54306966A 1966-04-18 1966-04-18

Publications (2)

Publication Number Publication Date
DE1793852B1 true DE1793852B1 (de) 1980-01-24
DE1793852C2 DE1793852C2 (de) 1980-10-09

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Family Applications (12)

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

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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

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

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BR (1) BR6679143D0 (de)
CH (1) CH529516A (de)
DE (12) DE1793844C2 (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)

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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
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Publication number Publication date
DE1793847C3 (de) 1981-04-02
BR6679143D0 (pt) 1973-09-11
DE1793848B1 (de) 1980-04-30
DE1793846C2 (de) 1981-01-15
DE1793843C2 (de) 1981-01-15
SE373733B (de) 1975-02-17
ES326503A1 (es) 1967-07-01
DE1793846B1 (de) 1980-04-30
DE1793849C2 (de) 1982-07-01
DE1793843B1 (de) 1980-04-30
SE373734B (de) 1975-02-17
JPS5412552B1 (de) 1979-05-23
DE1793851C2 (de) 1982-07-01
DE1695505C3 (de) 1979-11-29
DE1793845C2 (de) 1980-08-07
NL6605854A (de) 1966-10-31
NO134889C (de) 1977-01-05
SE377270B (de) 1975-06-30
DE1793842C3 (de) 1981-03-19
DE1793848C2 (de) 1981-01-15
SE373731B (de) 1975-02-17
DE1793850B1 (de) 1980-04-24
DE1793844B1 (de) 1979-10-31
DE1793850C2 (de) 1980-12-11
DE1695505A1 (de) 1970-12-23
SE377269B (de) 1975-06-30
DE1793852C2 (de) 1980-10-09
DE1695505B2 (de) 1979-04-05
DK139012B (da) 1978-12-04
DE1793847B1 (de) 1980-06-26
JPS5333667B1 (de) 1978-09-16
NO134889B (de) 1976-09-27
NL150316B (nl) 1976-08-16
DE1793842B1 (de) 1980-06-26
JPS499746B1 (de) 1974-03-06
JPS499747B1 (de) 1974-03-06
SE373735B (de) 1975-02-17
DE1793845B1 (de) 1979-10-31
CH529516A (de) 1972-10-31
SE335463B (de) 1971-05-24
SE373732B (de) 1975-02-17
DK139012C (de) 1979-05-14
JPS4821509B1 (de) 1973-06-29
JPS5231420B1 (de) 1977-08-15
SE373736B (de) 1975-02-17
GB1156472A (en) 1969-06-25
DE1793844C2 (de) 1980-07-24

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