EP0826763A2 - Use of 3-acylthioesters as flavouring or perfuming agents - Google Patents

Use of 3-acylthioesters as flavouring or perfuming agents Download PDF

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Publication number
EP0826763A2
EP0826763A2 EP97114062A EP97114062A EP0826763A2 EP 0826763 A2 EP0826763 A2 EP 0826763A2 EP 97114062 A EP97114062 A EP 97114062A EP 97114062 A EP97114062 A EP 97114062A EP 0826763 A2 EP0826763 A2 EP 0826763A2
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Prior art keywords
acetate
acetylthiohexyl
flavouring
compounds
ppb
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EP97114062A
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German (de)
French (fr)
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EP0826763B1 (en
EP0826763A3 (en
Inventor
Heinz-Jürgen Dr. Bertram
Jürgen Dr. Brüning
Matthias Dr. Güntert
Peter Dr. Werkhoff
Peter Wörner
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Dragoco Gerberding and Co GmbH
Symrise AG
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Haarmann and Reimer GmbH
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0007—Aliphatic compounds
    • C11B9/0011—Aliphatic compounds containing S

Definitions

  • 3-acylthiohexyl esters Although occasionally 3-acylthiohexyl esters have been described in the literature, the sensory relevance of these compounds has not been recognized to date.
  • 3-acryloylthiohexyl acetate was obtained as a by-product in the synthesis of 3-mercaptohexyl acetate (G. Heusinger and A. Mosandl in Tetrahedron Letters 25 , 507, 1984 and K.-H. Engel and R. Tressl in J. Agric. Food Chem 39 , 2251, 1991), the 3- (2-methyl-2-phenylthio) hexylacetate was prepared as an intermediate (G. Heusinger and A.
  • the compounds I according to the invention can be used both as racemic Mixture as well as in enantioselectively enriched or in optically pure form for Come into play.
  • 3-propionylthiohexylpropionate, 3-acetylthiohexylpropionate are particularly preferred, 3-propionylthiohexyl acetate and 3-acetylthiohexyl acetate.
  • Aroma compositions can be found in the entire food and beverage sector be used. They are particularly suitable for fruit preparations, fat masses, Baked goods, yogurt, ice cream, confectionery and fruit juice preparations are suitable.
  • the 3-acylthiohexyl esters to be used according to the invention can be used in amounts of 1 ppb to 1 wt .-%, preferably 5 ppb to 50 ppm, based on the ready to eat Food.
  • Connections to be used are also excellent for the Suitable for use in fragrance compositions.
  • the 3-acylthiohexyl esters to be used according to the invention act in one wide range of fragrances, for example those of the floral-rich type, advantageous. They can be used for the entire area of perfuming.
  • perfumery such as creams, lotions, aerosols, toilet soaps, technical perfumery items (air fresheners, diesel, petrol, heating oil, polyurethane foam, Latex, PVC, insecticides), fabric softeners, detergents, disinfectants and textile treatment agents are used.
  • the 3-acylthiohexyl esters I to be used according to the invention can be obtained, for example, by esterification of 3-mercaptohexanol or of 3-mercaptohexyl esters respectively.
  • the one-step esterification of 3-mercaptohexanol is particularly suitable for cases in which two identical acyl residues are desired.
  • the two-stage synthesis from 3-mercaptohexanol via the 3-mercaptohexyl ester as an intermediate stage will preferably be chosen if two different acyl radicals are desired; in this case, the hydroxyl group is first esterified, if appropriate, the by-products are freed from the ester obtained and then the mercapto group is esterified.
  • Suitable carboxylic acid derivatives for the esterification are especially acid chlorides and Anhydrides; the amounts are preferably 1 to 3 moles per mole of OH or SH component to be esterified.
  • acid chlorides one can Bases such as Add triethylamine, dimethylbenzylamine or pyridine as acid scavengers.
  • the esterifications can be organic in the presence or absence Solvents take place; preferred solvents include e.g. Ethers such as diethyl and Dibutyl ether, aromatics such as toluene and xylene and halogen aromatics such as Chlorobenzene.
  • Preferred reaction temperatures are in the range from 50 to 150 ° C.
  • the reaction mixtures can be worked up by customary methods.
  • a fruit aroma composition is made by mixing the following ingredients: Parts by weight Propylene glycol 490 Ethyl butyrate 200 Ethyl capronate 100 Hexyl capronate 75 Hexyl butyrate 50 Hexanol 40 3Z-hexenol 20th Caproic acid 10th Linalool 5 Benzyl acetate 5 Benzaldeyhd 2nd Damascenon 1 ⁇ -Damascon 1 ⁇ -decalactone 1 1000
  • a perfume composition is made by mixing the following components: Parts by weight 2-phenoxyethyl i-butyrate 200 Terpineol 150 Linalool 150 alpha amyl cinnamaldehyde 100 Orange oil 100 Triethyl citrate 65 Citronelly acetate 50 Hexyl salicylate 50 Bergamot oil 30th Ylang ylang oil 25th Ambrettia 25th Citral 20th Lilial 10th Pyroprunate 10th Aldehyde C16 so-called 5 Mandarin oil 5 Allylionone 2nd Vertocitral 2nd Farenal 1 1000

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Fats And Perfumes (AREA)
  • Seasonings (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Furan Compounds (AREA)

Abstract

Flavouring and/or aromatic substances comprising compounds of formula (I) are new. R1, R2 = H, 1-6C alkyl and 5-12C aryl (including furyl and thienyl). Also claimed are (i) flavouring and aromatic substances containing at least one compound (I) and (ii) 3-propionyl thiohexyl propionate.

Description

Die Erfindung betrifft die Verwendung von 3-Acylthiohexylestern der Formel

Figure 00010001
worin

R1 und R2
unabhängig voneinander für Wasserstoff, C1-C6-Alkyl oder C5-C12-Aryl einschließlich Furyl und Thienyl stehen, als Aroma- und/oder Riechstoffe sowie diese Verbindungen enthaltende Aroma- und Riechstoffkompositionen.
The invention relates to the use of 3-acylthiohexyl esters of the formula
Figure 00010001
wherein
R 1 and R 2
independently of one another represent hydrogen, C 1 -C 6 -alkyl or C 5 -C 12 -aryl including furyl and thienyl, as aroma and / or fragrance substances and aroma and fragrance compositions containing these compounds.

Obwohl in der Literatur vereinzelt 3-Acylthiohexylester beschrieben worden sind, ist die sensorische Relevanz dieser Verbindungen bisher nicht erkannt worden. So ist das 3-Acryloylthiohexylacetat als Nebenprodukt bei der Synthese von 3-Mercaptohexylacetat angefallen (G. Heusinger und A. Mosandl in Tetrahedron Letters 25, 507, 1984 und K.-H. Engel und R. Tressl in J. Agric. Food Chem. 39, 2251, 1991), das 3-(2-Methyl-2-phenylthio)hexylacetat wurde als Zwischenprodukt hergestellt (G. Heusinger und A. Mosandl in Tetrahydron Letters 25, 507, 1984) und das 3-Butanoylthiohexylacetat wurde als Zwischenprodukt bei der Herstellung von 3-Mercaptohexylbutyrat erhalten. Außerdem wurden 3-Acetylthiohexylacetat, 3-Butanoylthiohexylbutanoat und 3-Hexanoylthiohexylhexanoat als Nebenprodukte bei Synthesen beschrieben (K.-H. Engel und R. Tressl in J. Agric. Food Chem. 39, 2251, 1991)Although occasionally 3-acylthiohexyl esters have been described in the literature, the sensory relevance of these compounds has not been recognized to date. For example, 3-acryloylthiohexyl acetate was obtained as a by-product in the synthesis of 3-mercaptohexyl acetate (G. Heusinger and A. Mosandl in Tetrahedron Letters 25 , 507, 1984 and K.-H. Engel and R. Tressl in J. Agric. Food Chem 39 , 2251, 1991), the 3- (2-methyl-2-phenylthio) hexylacetate was prepared as an intermediate (G. Heusinger and A. Mosandl in Tetrahydron Letters 25 , 507, 1984) and the 3-butanoylthiohexyl acetate was used as an intermediate obtained in the preparation of 3-mercaptohexyl butyrate. In addition, 3-acetylthiohexyl acetate, 3-butanoylthiohexylbutanoate and 3-hexanoylthiohexylhexanoate have been described as by-products in syntheses (K.-H. Engel and R. Tressl in J. Agric. Food Chem. 39 , 2251, 1991)

Aussagen über die geruchlichen oder geschmacklichen Eigenschaften dieser Verbindungen wurden aber in keinem Fall gemacht. Aussagen über physikalische Eigenschaften finden sich nur für das 3-Acetylthiohexylacetat. Dieses wird als "leicht flüchtig und entfernbar mit dem Lösungsmittel" bezeichnet (G. Heusinger und A. Mosandl in Tetrahedron Letters 25, 507, 1984).No statements were made about the olfactory or taste properties of these compounds. Statements about physical properties can only be found for 3-acetylthiohexyl acetate. This is referred to as "readily volatile and removable with the solvent" (G. Heusinger and A. Mosandl in Tetrahedron Letters 25 , 507, 1984).

Es wurde nun überraschenderweise gefunden, daß die 3-Acylthiohexylester der Formel I interessante organoleptische Eigenschaften aufweisen, die sie zu wertvollen Aroma- und Riechstoffen machen. Die Verbindungen sind dabei deutlich haftfester und stabiler als die entsprechenden freien Thiole und zeichnen sich durch einen intensiven Geruch und Geschmack nach tropischen Früchten aus.It has now surprisingly been found that the 3-acylthiohexyl ester of Formula I have interesting organoleptic properties that make them valuable Make flavorings and fragrances. The connections are much stronger and more stable than the corresponding free thiols and are characterized by a intense smell and taste of tropical fruits.

Dabei können die erfindungsgemäßen Verbindungen I sowohl als racemisches Gemisch wie auch in enantioselektiv angereicherter oder in optisch reiner Form zum Einsatz kommen.The compounds I according to the invention can be used both as racemic Mixture as well as in enantioselectively enriched or in optically pure form for Come into play.

Besonders bevorzugt sind 3-Propionylthiohexylpropionat, 3-Acetylthiohexylpropionat, 3-Propionylthiohexylacetat und 3-Acetylthiohexylacetat.3-propionylthiohexylpropionate, 3-acetylthiohexylpropionate are particularly preferred, 3-propionylthiohexyl acetate and 3-acetylthiohexyl acetate.

Neben der spezifischen Typisierung in Richtung tropische Frucht sind die Verbindungen insbesondere geeignet, in Fruchtaromakompositionen die Fülle zu verstärken und abrundend zu wirken.In addition to the specific typing in the direction of tropical fruit, the Compounds particularly suitable for filling the fullness in fruit aroma compositions strengthen and round off.

Die unter Verwendung der erfindungsgemäß zu verwendenden Verbindungen hergestellten Aromakompositionen können im gesamten Nahrungs- und Genußmittelbereich eingesetzt werden. Insbesondere sind sie für Fruchtzubereitungen, Fettmassen, Backwaren, Joghurt, Speiseeis, Süßwaren und Fruchtsaftzubereitungen geeignet.The prepared using the compounds to be used according to the invention Aroma compositions can be found in the entire food and beverage sector be used. They are particularly suitable for fruit preparations, fat masses, Baked goods, yogurt, ice cream, confectionery and fruit juice preparations are suitable.

Die erfindungsgemäß zu verwendenden 3-Acylthiohexylester können in Mengen von 1 ppb bis 1 Gew.-%, vorzugsweise 5 ppb bis 50 ppm, bezogen auf das verzehrfertige Lebensmittel, eingesetzt werden.The 3-acylthiohexyl esters to be used according to the invention can be used in amounts of 1 ppb to 1 wt .-%, preferably 5 ppb to 50 ppm, based on the ready to eat Food.

Aufgrund ihres guten Haftvermögens und ihrer guten Stabilität sind die erfindungsgemäß zu verwendenden Verbindungen darüber hinaus hervorragend für den Einsatz in Riechstoffkompositionen geeignet.Because of their good adhesion and their good stability, they are according to the invention Connections to be used are also excellent for the Suitable for use in fragrance compositions.

Die erfindungsgemäß zu verwendenden 3-Acylthiohexylester wirken sich in einer breiten Palette von Duftnoten, zum Beispiel solchen vom blumigen-fuchtigen Typ, vorteilhaft aus. Sie sind für den gesamten Bereich der Parfümierungen einsetzbar. Außer in der Feinparfümerie kommen derartige Kompositionen insbesondere zur Parfümierung von Kosmetika wie Cremes, Lotionen, Aerosolen, Toilettenseifen, technischen Parfümerieartikeln (Luftverbesserer, Diesel, Benzin, Heizöl, Polyurethanschaum, Latex, PVC, Insektizide), Weichspülern, Waschmittel, Desinfektionsmitteln und Textilbehandlungsmitteln zum Einsatz. The 3-acylthiohexyl esters to be used according to the invention act in one wide range of fragrances, for example those of the floral-rich type, advantageous. They can be used for the entire area of perfuming. In addition to fine perfumery, such compositions are particularly popular Perfuming cosmetics such as creams, lotions, aerosols, toilet soaps, technical perfumery items (air fresheners, diesel, petrol, heating oil, polyurethane foam, Latex, PVC, insecticides), fabric softeners, detergents, disinfectants and textile treatment agents are used.

Die erfindungsgemäß zu verwendenden 3-Acylthiohexylester I können beispielsweise durch Veresterung von 3-Mercaptohexanol

Figure 00030001
oder von 3-Mercaptohexylestern
Figure 00030002
erfolgen. Die einstufige Veresterung von 3-Mercaptohexanol bietet sich vor allem für die Fälle an, in denen zwei gleiche Acylreste erwünscht sind. Die zweistufige Synthese aus 3-Mercaptohexanol über den 3-Mercaptohexylester als Zwischenstufe wird man bevorzugt dann wählen, wenn zwei verschiedene Acylreste erwünscht sind; in diesem Fall wird man zunächst die Hydroxylgruppe verestern, gegebenenfalls den erhaltenen Ester von Nebenprodukten befreien und dann die Mercaptogruppe verestern.The 3-acylthiohexyl esters I to be used according to the invention can be obtained, for example, by esterification of 3-mercaptohexanol
Figure 00030001
or of 3-mercaptohexyl esters
Figure 00030002
respectively. The one-step esterification of 3-mercaptohexanol is particularly suitable for cases in which two identical acyl residues are desired. The two-stage synthesis from 3-mercaptohexanol via the 3-mercaptohexyl ester as an intermediate stage will preferably be chosen if two different acyl radicals are desired; in this case, the hydroxyl group is first esterified, if appropriate, the by-products are freed from the ester obtained and then the mercapto group is esterified.

Geeignete Carbonsäurederivate für die Veresterung sind vor allem Säurechloride und Anhydride; die Mengen betragen bevorzugt 1 bis 3 Mol pro Mol OH bzw. SH der zu veresternden Komponente. Bei der Verwendung von Säurechloriden kann man Basen, wie z.B. Triethylamin, Dimethylbenzylamin oder Pyridin, als Säurefänger zusetzen. Die Veresterungen können in An- oder Abwesenheit organischer Lösungsmittel stattfinden; bevorzugte Lösungsmittel umfassen z.B. Ether wie Diethyl- und Dibutylether, Aromaten wie Toluol und Xylol und Halogenaromaten wie Chlorbenzol. Bevorzugte Reaktionstemperaturen liegen im Bereich von 50 bis 150°C. Die Aufarbeitung der Reaktionsmischungen kann nach üblichen Methoden erfolgen. Suitable carboxylic acid derivatives for the esterification are especially acid chlorides and Anhydrides; the amounts are preferably 1 to 3 moles per mole of OH or SH component to be esterified. When using acid chlorides one can Bases such as Add triethylamine, dimethylbenzylamine or pyridine as acid scavengers. The esterifications can be organic in the presence or absence Solvents take place; preferred solvents include e.g. Ethers such as diethyl and Dibutyl ether, aromatics such as toluene and xylene and halogen aromatics such as Chlorobenzene. Preferred reaction temperatures are in the range from 50 to 150 ° C. The reaction mixtures can be worked up by customary methods.

BeispieleExamples A. Herstellung A. Manufacturing Herstellung von 3-PropionylthiohexylpropionatPreparation of 3-propionylthiohexylpropionate

1,2 Mol Propionsäureanhydrid werden vorgelegt und auf 90°C erhitzt. Anschließend werden 0,5 Mol 3-Mercaptohexanol zudosiert, und das Gemisch wird für weitere 2 Stunden auf 140°C erhitzt. Man läßt auf 50°C abkühlen, fügt 50 ml Methanol hinzu und rührt 1 Stunde bei dieser Temperatur. Es werden dann zunächst Methanol und Methylpropionat als Vorlauf abdestilliert, um dann das 3-Propionylthiohexylpropionat im Vakuum zu destillieren, Kp. (2,2 mbar): 113°C.1.2 mol of propionic anhydride are introduced and heated to 90 ° C. Then 0.5 mol of 3-mercaptohexanol are metered in, and the mixture is heated to 140 ° C for a further 2 hours. The mixture is allowed to cool to 50 ° C. add 50 ml of methanol and stir for 1 hour at this temperature. It methanol and methyl propionate are then first distilled off as a lead, then to distill the 3-propionylthiohexylpropionate in vacuo, bp. (2.2 mbar): 113 ° C.

Analog diesem Verfahren können beispielsweise die folgenden Verbindungen hergestellt werden:

  • 3-Acetylthiohexylacetat
  • 3-Acetylthiohexylpropionat
  • 3-Acetylthiohexylbutyrat
  • 3-Propionylthiohexylacetat
  • 3-Butyrylthiohexylacetat
  • 3-Butyrylthiohexylbutyrat
  • 3-Acetylthiohexylcapronat
  • 3-Hexylthiohexylacetat
  • 3-Hexylthiohexylcapronat
  • 3-Isobutyrylthiohexylacetat
  • 3-Acetylthiohexylisobutyrat
  • 3-Isobutyrylthiohexylisobutyrat
    • The following compounds can be prepared analogously to this process:
  • 3-acetylthiohexyl acetate
  • 3-acetylthiohexyl propionate
  • 3-acetylthiohexyl butyrate
  • 3-propionylthiohexyl acetate
  • 3-butyrylthiohexyl acetate
  • 3-butyrylthiohexyl butyrate
  • 3-acetylthiohexyl capronate
  • 3-hexylthiohexyl acetate
  • 3-hexylthiohexyl capronate
  • 3-isobutyrylthiohexyl acetate
  • 3-acetylthiohexyl isobutyrate
  • 3-isobutyrylthiohexyl isobutyrate

    • B. Sensorische Untersuchung B. Sensory examination

    Die von einem Testpanel aus 6 speziell geschulten Prüfern ermittelten Geschmacksbeschreibungen für einige der Verbindungen I bei ihrer Anwendung in 0,5 gew.-%iger wäßriger Zuckerlösung lauten:

  • 3-Acetylthiohexylacetat
    bei einem Zusatz von 100 ppb: tropisch, fruchtig, Passionsfrucht, Fülle
  • 3-Propionylthiohexylpropionat
    bei einem Zusatz von 100 ppb: tropisch, fruchtig, Passionsfrucht, Fülle
  • 3-Acetylthiohexylbutyrat
    bei einem Zusatz von 500 ppb: tropisch, süß, fruchtig
  • 3-Acetylthiohexylcapronat
    bei einem Zusatz von 500 ppb: tropisch, Passionsfrucht, haftfest
    • The taste descriptions for some of the compounds I determined by a test panel of 6 specially trained testers when used in 0.5% strength by weight aqueous sugar solution are as follows:
  • 3-acetylthiohexyl acetate
    with an addition of 100 ppb: tropical, fruity, passion fruit, fullness
  • 3-propionylthiohexyl propionate
    with an addition of 100 ppb: tropical, fruity, passion fruit, fullness
  • 3-acetylthiohexyl butyrate
    with an addition of 500 ppb: tropical, sweet, fruity
  • 3-acetylthiohexyl capronate
    with an addition of 500 ppb: tropical, passion fruit, firm

    • C. Anwendung C. Application Anwendungsbeispiel 1Application example 1

    Eine Fruchtaromakomposition wird durch Mischen der folgendenden Bestandteile hergestellt: Gewichtsteile Propylenglycol 490 Ethylbutyrat 200 Ethylcapronat 100 Hexylcapronat 75 Hexylbutyrat 50 Hexanol 40 3Z-Hexenol 20 Capronsäure 10 Linalool 5 Benzylacetat 5 Benzaldeyhd 2 Damascenon 1 α-Damascon 1 γ-Decalacton 1 1000 A fruit aroma composition is made by mixing the following ingredients: Parts by weight Propylene glycol 490 Ethyl butyrate 200 Ethyl capronate 100 Hexyl capronate 75 Hexyl butyrate 50 Hexanol 40 3Z-hexenol 20th Caproic acid 10th Linalool 5 Benzyl acetate 5 Benzaldeyhd 2nd Damascenon 1 α-Damascon 1 γ-decalactone 1 1000

    Durch Zugabe von 1-10 Gewichtsteilen 3-Propionylthiohexylpropionat bekommt das Aroma eine deutliche Geschmacksintensivierung in Richtung tropische Frucht.By adding 1-10 parts by weight of 3-propionylthiohexylpropionate that gets Aroma a clear intensification of taste towards tropical fruit.

    Anwendungsbeispiel 2Example of use 2

    Eine Parfümkomposition wird durch Mischen der folgenden Komponenten hergestellt: Gewichtsteile 2-Phenoxyethyl-i-butyrat 200 Terpineol 150 Linalool 150 alpha-Amylzimtaldehyd 100 Orangenöl 100 Triethylcitrat 65 Citronellylacetat 50 Hexylsalicylat 50 Bergamotteöl 30 Ylang Ylang-Öl 25 Ambrettia 25 Citral 20 Lilial 10 Pyroprunat 10 Aldehyd C16 sog. 5 Mandarinenöl 5 Allylionon 2 Vertocitral 2 Farenal 1 1000 A perfume composition is made by mixing the following components: Parts by weight 2-phenoxyethyl i-butyrate 200 Terpineol 150 Linalool 150 alpha amyl cinnamaldehyde 100 Orange oil 100 Triethyl citrate 65 Citronelly acetate 50 Hexyl salicylate 50 Bergamot oil 30th Ylang ylang oil 25th Ambrettia 25th Citral 20th Lilial 10th Pyroprunate 10th Aldehyde C16 so-called 5 Mandarin oil 5 Allylionone 2nd Vertocitral 2nd Farenal 1 1000

    Durch Zugabe von 1-10 Gewichtsteilen 3-Propionylthiohexylpropionat bekommt die Komposition eine deutliche Geruchsintensivierung in Richtung tropische Frucht. By adding 1-10 parts by weight of 3-propionylthiohexylpropionate the Composition a distinct intensification of smell towards tropical fruit.

    D. Physikalische Werte einiger Verbindungen D. Physical values of some compounds

    n 20 / Dn 20 / D Kp (°C / mb)Kp (° C / mb) 3-Acetylthiohexylacetat3-acetylthiohexyl acetate 1.46771.4677 90 / 490/4 3-Propionylthiohexylpropionat3-propionylthiohexyl propionate 1.46601.4660 113 / 2.2113 / 2.2 3-Acetylthiohexylbutyrat3-acetylthiohexyl butyrate 1.46511.4651 111 / 4111/4 3-Acetylthiohexylcapronat3-acetylthiohexyl capronate 1.46561.4656 120 / 0.7120 / 0.7

    E. IR-Spektren einiger Verbindungen E. IR spectra of some compounds

       (w = schwach, m = mittel, s = stark) 3-Acetylthiohexylacetat Wellenzahl Intensität 2959 m 2933 m 1737 s 1689 s 1426 w 1366 m 1250 s 1112 m 1038 m 957 w 3-Butyrylthiohexylacetat Wellenzahl Intensität 2962 m 2934 m 1738 s 1689 s 1467 w 1366 w 1250 s 1116 m 1038 m 990 w 3-Acetylthiohexylbutyrat Wellenzahl Intensität 2959 m 2933 m 1736 s 1689 s 1429 w 1366 m 1250 s 1112 m 1037 m 958 w 3-Propionylthiohexylacetat Wellenzahl Intensität 2958 m 2936 m 1737 s 1691 s 1460 w 1366 m 1250 s 1091 m 1036 m 939 s 3-Acetylthiohexylpropionat Wellenzahl Intensität 2958 m 2935 m 1736 s 1690 s 1464 w 1355 m 1187 s 1111 m 1036 w 960 w 3-Propionylthiohexylpropionat Wellenzahl Intensität 2958 m 2939 m 2874 m 1737 s 1693 s 1462 w 1186 m 1088 w 1021 w 939 m 3-Butyrylthiohexylbutyrat Wellenzahl Intensität 2961 s 2933 m 2873 m 1734 s 1688 s 1465 m 1362 m 1180 s 1114 m 989 m 3-Isobutyrylthiohexylacetat Wellenzahl Intensität 861 m 977 m 1037 m 1250 s 1365 m 1468 m 1688 s 1738 s 2934 m 2966 m 3-Acetylthiohexylisobutyrat Wellenzahl Intensität 1114 m 1161 s 1196 m 1353 m 1469 m 1690 s 1732 s 2874 m 2934 m 2961 m 3-Isobutyrylthiohexylisobutyrat Wellenzahl Intensität 861 m 976 m 1160 m 1193 m 1468 m 1689 s 1734 s 2874 m 2934 m 2970 m (w = weak, m = medium, s = strong) 3-acetylthiohexyl acetate Wavenumber intensity 2959 m 2933 m 1737 s 1689 s 1426 w 1366 m 1250 s 1112 m 1038 m 957 w 3-butyrylthiohexyl acetate Wavenumber intensity 2962 m 2934 m 1738 s 1689 s 1467 w 1366 w 1250 s 1116 m 1038 m 990 w 3-acetylthiohexyl butyrate Wavenumber intensity 2959 m 2933 m 1736 s 1689 s 1429 w 1366 m 1250 s 1112 m 1037 m 958 w 3-propionylthiohexyl acetate Wavenumber intensity 2958 m 2936 m 1737 s 1691 s 1460 w 1366 m 1250 s 1091 m 1036 m 939 s 3-acetylthiohexyl propionate Wavenumber intensity 2958 m 2935 m 1736 s 1690 s 1464 w 1355 m 1187 s 1111 m 1036 w 960 w 3-propionylthiohexyl propionate Wavenumber intensity 2958 m 2939 m 2874 m 1737 s 1693 s 1462 w 1186 m 1088 w 1021 w 939 m 3-butyrylthiohexyl butyrate Wavenumber intensity 2961 s 2933 m 2873 m 1734 s 1688 s 1465 m 1362 m 1180 s 1114 m 989 m 3-isobutyrylthiohexyl acetate Wavenumber intensity 861 m 977 m 1037 m 1250 s 1365 m 1468 m 1688 s 1738 s 2934 m 2966 m 3-acetylthiohexyl isobutyrate Wavenumber intensity 1114 m 1161 s 1196 m 1353 m 1469 m 1690 s 1732 s 2874 m 2934 m 2961 m 3-isobutyrylthiohexyl isobutyrate Wavenumber intensity 861 m 976 m 1160 m 1193 m 1468 m 1689 s 1734 s 2874 m 2934 m 2970 m

    Claims (3)

    Verwendung von Verbindungen der Formel
    Figure 00130001
    worin
    R1 und R2
    unabhängig voneinander für Wasserstoff, C1-C6-Alkyl oder C5-C12-Aryl einschließlich Furyl und Thienyl stehen, als Aroma- und/oder Riechstoffe.
    Use of compounds of the formula
    Figure 00130001
    wherein
    R 1 and R 2
    independently of one another represent hydrogen, C 1 -C 6 -alkyl or C 5 -C 12 -aryl including furyl and thienyl, as flavorings and / or fragrances.
    Aroma- und Riechstoffkompositionen, die mindestens eine Verbindung I nach Anspruch 1 enthalten.Aroma and fragrance compositions containing at least one compound I. Claim 1 included. 3-Propionylthiohexylpropionat3-propionylthiohexyl propionate
    EP97114062A 1996-08-27 1997-08-14 Use of 3-acylthioesters as flavouring or perfuming agents Expired - Lifetime EP0826763B1 (en)

    Applications Claiming Priority (2)

    Application Number Priority Date Filing Date Title
    DE19634520A DE19634520A1 (en) 1996-08-27 1996-08-27 Use of 3-acylthiohexyl esters as flavoring and fragrances
    DE19634520 1996-08-27

    Publications (3)

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    EP0826763A2 true EP0826763A2 (en) 1998-03-04
    EP0826763A3 EP0826763A3 (en) 2000-04-26
    EP0826763B1 EP0826763B1 (en) 2002-11-20

    Family

    ID=7803767

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    EP (1) EP0826763B1 (en)
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    JP4836181B2 (en) * 2006-02-07 2011-12-14 独立行政法人産業技術総合研究所 Acyl compound production method and apparatus
    JP4953341B2 (en) * 2006-02-07 2012-06-13 独立行政法人産業技術総合研究所 Process for producing polyacyl compound and apparatus therefor
    JP2007291096A (en) * 2006-03-31 2007-11-08 National Institute Of Advanced Industrial & Technology Selective sequential polyacylation and device therefor
    JP2007297338A (en) * 2006-04-28 2007-11-15 National Institute Of Advanced Industrial & Technology N-acyl compound, and method and device for producing the same
    JP5403875B2 (en) * 2007-03-01 2014-01-29 小林製薬株式会社 Fragrance composition
    WO2010042938A1 (en) * 2008-10-10 2010-04-15 Takasago International Corporation Thiol-containing fragrance and flavor materials
    EP3174561A4 (en) 2014-07-30 2019-07-24 GPCP IP Holdings LLC Air freshener dispensers, cartridges therefor, systems, and methods
    JP6971571B2 (en) * 2016-12-26 2021-11-24 キリンホールディングス株式会社 Umeshu and its manufacturing method

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    Also Published As

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    EP0826763B1 (en) 2002-11-20
    US5830846A (en) 1998-11-03
    JPH1087604A (en) 1998-04-07
    DE59708755D1 (en) 2003-01-02
    EP0826763A3 (en) 2000-04-26
    DE19634520A1 (en) 1998-03-05
    JP3711310B2 (en) 2005-11-02

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