FR2653766A1 - New butanethiol derivative, process for its preparation, its application especially in perfumery and the compositions containing it - Google Patents
New butanethiol derivative, process for its preparation, its application especially in perfumery and the compositions containing it Download PDFInfo
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- FR2653766A1 FR2653766A1 FR8914627A FR8914627A FR2653766A1 FR 2653766 A1 FR2653766 A1 FR 2653766A1 FR 8914627 A FR8914627 A FR 8914627A FR 8914627 A FR8914627 A FR 8914627A FR 2653766 A1 FR2653766 A1 FR 2653766A1
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- derivative
- methyl
- thiol
- ethoxy
- butane
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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
-
- 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
- A23L27/29—Fruit flavours
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/12—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Nutrition Science (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
La présente demande concerne un nouveau dérivé du butane thiol, son procédé de préparation, son application notamment en parfumerie et les compositions le renfermant. The present application relates to a new derivative of butane thiol, its preparation process, its application in particular in perfumery and the compositions containing it.
On connaît déjà le 1-méthoxy 3-méthyl 3-butane thiol isolé à partir de bourgeons de cassis. We already know 1-methoxy 3-methyl 3-butane thiol isolated from blackcurrant buds.
Ce dérivé est responsable de la composante olfactive dite "d'urine de chat" de l'arôme de cassis. This derivative is responsible for the so-called "cat urine" olfactory component of blackcurrant aroma.
La préparation par extraction d'un tel dérivé a été décrite notamment dans le brevet français N 85.14680. The preparation by extraction of such a derivative has been described in particular in French patent N 85.14680.
La Demanderesse a découvert que ltéthoxy-4 méthyl-2 butane thiol-2 est doté de propriétés interessantes : à dilution appropriée, il a une remarquable odeur de même qu'un seuil de perception olfactive très bas. The Applicant has discovered that 4-ethoxy-2-methyl-2-butane thiol-2 has interesting properties: at appropriate dilution, it has a remarkable odor as well as a very low olfactory perception threshold.
Rien dans l'art antérieur ne décrit ni ne suggère ltéthoxy-4 méthyl-2 butane thiol-2, d'autant que les dérivés homologues portant un radical propoxy ou butoxy sont dotés d'une note typique d'urine de chat/cassis beaucoup moins intense que celle de ltéthoxy-4 méthyl-2 butane thiol-2. De plus, le seuil de perception olfactive de ces homologues, est largement supérieur à celui dudit dérivé. Nothing in the prior art describes or suggests ltethoxy-2-methyl-2-butane thiol-2, especially since the homologous derivatives carrying a propoxy or butoxy radical are endowed with a typical note of cat urine / blackcurrant much less intense than that of 4-ethoxy-2-methyl-2-butane thiol. In addition, the threshold for olfactory perception of these counterparts is much higher than that of said derivative.
C'est pourquoi la présente demande a pour objet l'éthoxy-4 méthyl-2 butane thiol-2. This is why the subject of the present application is 4-ethoxy-2-methyl-2-butane thiol.
La présente demande a également pour objet un procédé de préparation de l'éthoxy-4 méthyl-2 butane thiol-2, caractérisé en ce que l'on fait réagir le sénécioate de méthyle avec le benzylmercaptan pour obtenir un dérivé de formule (II)
que l'on réduit pour obtenir un dérivé de formule (III)
que l'on fait réagir avec un halogénure d'éthyle pour obtenir le dérivé de formule (IV)
que l'on débenzyle pour obtenir l'éthoxy-4 méthyl-2 butane thiol-2 attendu.The present application also relates to a process for the preparation of 4-ethoxy-2-methyl-2-butane thiol, characterized in that the methyl senecioate is reacted with the benzylmercaptan to obtain a derivative of formula (II)
which is reduced to obtain a derivative of formula (III)
which is reacted with an ethyl halide to obtain the derivative of formula (IV)
debenzylated to obtain the 4-ethoxy-2-methyl-2-thiol butane expected.
La réaction du sénécioate de méthyle avec le benzylmercaptan est réalisée de préférence en présence de
Triton B.The reaction of methyl senecioate with benzylmercaptan is preferably carried out in the presence of
Triton B.
La réduction du dérivé de formule (II) peut être réalisée par exemple par action d'un métal alcalin, de préférence le sodium dans un alcanol anhydre tel que l'éthanol, mais on utilise avantageusement un hydrure tel que 1 'hydrure d'aluminium-lithium. The reduction of the derivative of formula (II) can be carried out for example by the action of an alkali metal, preferably sodium in an anhydrous alkanol such as ethanol, but a hydride such as aluminum hydride is advantageously used. -lithium.
La réaction du dérivé de formule (III) avec l'halogénure d'éthyle est avantageusement réalisée après activation du dérivé de formule (III) par un hydrure alcalin, de préférence l'hydrure de sodium. The reaction of the derivative of formula (III) with ethyl halide is advantageously carried out after activation of the derivative of formula (III) with an alkaline hydride, preferably sodium hydride.
La débenzylation se fera avantageusement par action d'un métal alcalin, notamment le sodium, dans l'ammoniac liquide. Debenzylation will advantageously be carried out by the action of an alkali metal, in particular sodium, in liquid ammonia.
A dilution appropriée, l'éthoxy-4 méthyl-2 butane thiol-2 possède, de manière remarquable, la note typique dite d'urine de chat présente dans l'arôme de cassis -
Cette composante de l'odeur, ainsi que l'arôme de cassis peuvent trouver de remarquables applications, respectivement en parfumerie et dans l'aromatisation des aliments. When appropriately diluted, 4-ethoxy-2-methyl-2-butane thiol-2 has, remarkably, the typical note known as cat urine present in the aroma of blackcurrant -
This component of the smell, as well as the aroma of blackcurrant, can find remarkable applications, respectively in perfumery and in food flavoring.
C'est pourquoi la présente demande a pour objet l'application de l'éthoxy-4 méthyl-2 butane thiol-2 à titre d'agent parfumant. This is why the present application relates to the application of 4-ethoxy-2-methyl-2-butane thiol as a perfuming agent.
La présente demande a aussi pour objet l'application de ltéthoxy-4 méthyl-2 butane thiol-S, à titre d'agent aromatisant. The present application also relates to the application of 4-ethoxy-2-methyl-butane thiol-S, as a flavoring agent.
A titre d'agent parfumant ou aromatisant, ltéthoxy-4 méthyl-2 butane thiol-2 peut être incorporé à des compositions, selon le cas, parfumées ou parfumantes ou aromatisantes, telles que celles destinées à des boissons, gâteaux, desserts lactés, etc. As perfuming or flavoring agent, 4-ethoxy-2-methyl-2-butane thiol-2 can be incorporated into compositions, as the case may be, perfumed or perfuming or flavoring, such as those intended for drinks, cakes, dairy desserts, etc. .
C'est pourquoi la présente demande a également pour objet les compositions caractérisées en ce qu'elles renferment à titre d'agent parfumant l'éthoxy-4 méthyl-2 butane thiol-2. This is why the present application also relates to the compositions characterized in that they contain as perfuming agent 4-ethoxy-2-methyl-2-butane thiol.
La présente demande a enfin pour objet les compositions caractérisées en ce qu'elles renferment à titre d'agent d'aromatisation ltéthoxy-4 méthyl-2 butane thiol-2. Dans ces compositions, l'éthoxy-4 méthyl-2 butane thiol-2 sera généralement utilisé à une dose inférieure à 50 ppm et de préférence à la dose de 0,5 à 5 ppm. The present application finally relates to the compositions characterized in that they contain as ltethoxy-4-methyl-2-butane-thiol-2 flavoring agent. In these compositions, 4-ethoxy-2-methyl-2-butane thiol-2 will generally be used at a dose of less than 50 ppm and preferably at a dose of 0.5 to 5 ppm.
Les exemples qui suivent illustrent la présente invention sans toutefois la limiter. The examples which follow illustrate the present invention without however limiting it.
Exemple 1
Stade A : benylthio-3 méthyl-3 butyrate de méthyle
On agite pendant une heure 452 g de benzylmercaptan avec 831 g de sénécioate de méthyle en présence de 9 g de Triton B ; la température passe de 16"C à 45"C. On ajoute alors 9 g de Triton B supplémentaires, laisse sous agitation pendant 6 heures, extrait à I'hexane, lave jusqu'a neutralité, évapore le solvant et soumet le liquide brut obtenu à une distillation fractionnée sur colonne de
Vigreux de 20 cm.Example 1
Stage A: 3-benylthio-3-methyl-methyl butyrate
452 g of benzylmercaptan are stirred for one hour with 831 g of methyl senecioate in the presence of 9 g of Triton B; the temperature goes from 16 "C to 45" C. An additional 9 g of Triton B is then added, the mixture is stirred for 6 hours, extracted with hexane, washed until neutral, the solvent is evaporated off and the crude liquid obtained is subjected to fractional distillation on a column of
Vigrous 20 cm.
On obtient 843 g du produit attendu ; O eb. 843 g of the expected product are obtained; O eb.
-138 C (0,67 kPa). -138 C (0.67 kPa).
Stade B : Benzylthio-3 méthyl-3 butanol-1
On ajoute en 150 minutes une solution du produit obtenu au stade A dans un litre de tétrahydrofuranne à 80 g d'hydrure d'aluminium-lithium dans 1,5 litre de tétrahydrofuranne anhydre sous atmosphère inerte et en maintenant la température au-dessous de 25 C. Stage B: Benzylthio-3 methyl-3 butanol-1
A solution of the product obtained in Stage A in one liter of tetrahydrofuran is added over 150 minutes to 80 g of aluminum-lithium hydride in 1.5 liters of anhydrous tetrahydrofuran under an inert atmosphere and the temperature is kept below 25 vs.
On poursuit l'agitation å 250C pendant deux heures, refroidit à 100C, ajoute en une heure 160 g d'eau, laisse sous agitation pendant 30 minutes, ajoute une solution aqueuse d'acide chlorhydrique à 50 % sous forte agitation jusqu'a obtention de deux phases liquides se séparant facilement, extrait le produit attendu, lave, soumet à une distillation fractionnée dans une colonne de
Vigreux de 25 cm et obtient 746 g du produit attendu ; e eb. 145-156"C (0,67 kPa). Stirring is continued at 250C for two hours, cooled to 100C, added in one hour 160 g of water, left stirring for 30 minutes, add a 50% aqueous hydrochloric acid solution with vigorous stirring until obtaining of two easily separable liquid phases, extract the expected product, wash, subject to fractional distillation in a column of
Vigreux of 25 cm and obtains 746 g of the expected product; e eb. 145-156 "C (0.67 kPa).
Stade C : Benzvlthio-3 éthoxy-1 méthyl-3 butane
On ajoute sous agitation en 45 minutes, une solution de 315 g du produit obtenu au stade B dans 250 g de diméthylformamide a 54 g d'hydrure de sodium dans 1000 g de diméthylformamide sous atmosphère inerte, laisse sous agitation pendant deux heures à une température d'environ 47,50C, refroidit à 100C, ajoute 0,5 g d'iodure de potassium puis, en une heure environ, une solution de 245 g de bromure d'éthyle dans 250 g de diméthylformamide. Stage C: Benzvlthio-3 ethoxy-1 methyl-3 butane
Is added with stirring over 45 minutes, a solution of 315 g of the product obtained in stage B in 250 g of dimethylformamide to 54 g of sodium hydride in 1000 g of dimethylformamide under an inert atmosphere, left stirring for two hours at a temperature about 47.50C, cooled to 100C, added 0.5 g of potassium iodide then, in about an hour, a solution of 245 g of ethyl bromide in 250 g of dimethylformamide.
On agite pendant deux heures à environ 37"C, refroidit à environ 15 C, ajoute sous agitation 100 g d'eau, laisse décanter, extrait, lave, soumet à une distillation fractionnée le produit obtenu au moyen d'une colonne de Vigreux de 25 cm et obtient 346 g du produit attendu ; O- eb. 127-130 C (0,67 kPa). The mixture is stirred for two hours at approximately 37 ° C., cooled to approximately 15 ° C., 100 g of water are added with stirring, the mixture is decanted, extracted, washed and the product obtained is subjected to fractional distillation by means of a Vigreux column. 25 cm and obtains 346 g of the expected product; O-eb. 127-130 C (0.67 kPa).
Spectre de RMN dans le chloroforme deutéré (CDCl3) 6 : 1.20 (3H, triplet), 1.35 (6H, singulet), 1.87 (2H > triplet), 3.45 (2H, quadruplet), 3.57 (2H, triplet), 3.72 (2H, singulet), 7.30 (5H, multiplet). NMR spectrum in deuterated chloroform (CDCl3) 6: 1.20 (3H, triplet), 1.35 (6H, singlet), 1.87 (2H> triplet), 3.45 (2H, quadruplet), 3.57 (2H, triplet), 3.72 (2H , singlet), 7.30 (5H, multiplet).
Stade D : éthoxy-4 méthyl-2 butane thiol-2
On ajoute progressivement 10 g de sodium sous forte agitation à 45,8 g du produit du stade C dans 900 ml d'ammoniac liquide, laisse sous agitation pendant une heure, après évaporation de l'ammoniac hydrolyse le mélange réactionnel sous atmosphère inerte par addition de 600 ml d'une solution aqueuse à 20 % d'acide chlorhydrique, extrait à l'éther éthylique, lave, concentre, soumet à une distillation fractionnée dans une colonne de Vigreux de 30 cm, 50 g du produit brut ainsi obtenu et obtient 23,5 g du produit attendu ; & ommat; eb. 77-79"C (2,7 kPa).Stage D: 4-ethoxy-2-methyl-2-butane thiol
10 g of sodium are added gradually with vigorous stirring to 45.8 g of the product of stage C in 900 ml of liquid ammonia, left stirring for one hour, after evaporation of the ammonia hydrolyses the reaction mixture under an inert atmosphere by addition of 600 ml of a 20% aqueous hydrochloric acid solution, extracted with ethyl ether, washed, concentrated, subjected to fractional distillation in a 30 cm Vigreux column, 50 g of the crude product thus obtained and obtained 23.5 g of the expected product; &ommat; eb. 77-79 "C (2.7 kPa).
Les spectres de masse, infrarouges et de RMN du produit obtenu sont annexés au présent mémoire, respectivement figures 1, 2 et 3. The mass, infrared and NMR spectra of the product obtained are annexed to this document, respectively Figures 1, 2 and 3.
Exemple A
En opérant comme indiqué à l'exemple 1, mais par réaction d'iodure de n-propyle, on a préparé le propoxy-4 méthyl-2 butane thiol-2 ; & ommat; # eb. 44 C (0,67 kPa). Example A
By operating as indicated in Example 1, but by reaction of n-propyl iodide, 4-propoxy-2-methyl-2-thiol-thiol was prepared; &ommat;# eb. 44 C (0.67 kPa).
Exemple B
En opérant comme indiqué à l'exemple 1, mais par réaction d'iodure de n-butyle, on a préparé le butoxy-4 méthyl-2 butane thiol-2 ; O eb. 108 C (9.,7 kPa).Example B
By operating as indicated in Example 1, but by reaction of n-butyl iodide, 4-butoxy-2-methyl-butane-2-thiol was prepared; O eb. 108 C (9., 7 kPa).
Exemple 2
Composition de parfumerie
On a préparé une composition å thème vertfloral a base principalement de - salicylate de benzyle - muguet M45 Spécialité - alcool phényléthylique - acétate de benzyle - HédioneR - jasmin fleur Spécialité - aldéhyde a-hexylcinnamique - galaxolide 50 % dans le
myristate dtisopropyle - autres dérivés
835,0 165,0
Lorsque l'on ajoute 15 ppm du dérivé de l'exemple 1, on perçoit un effet très agréable rappelant celui apporté par l'absolue de bourgeon de cassis, matière première particulièrement coûteuse, ou suggérant le zeste de pamplemousse.Example 2
Perfumery composition
We have prepared a composition with a floral theme based mainly on - benzyl salicylate - thrush M45 Specialty - phenylethyl alcohol - benzyl acetate - HédioneR - jasmine flower Specialty - a-hexylcinnamic aldehyde - 50% galaxolid
dtisopropyl myristate - other derivatives
835.0 165.0
When we add 15 ppm of the derivative of Example 1, we perceive a very pleasant effect recalling that provided by the absolute of blackcurrant bud, a particularly expensive raw material, or suggesting grapefruit zest.
L'effet global est une accentuation particulièrement nette du caractère naturel de la composition. The overall effect is a particularly clear accentuation of the natural character of the composition.
Exemple 3
Composition de parfumerie
On a préparé une composition à thème fleuriboisé, à base principalement de - dihydromyrcénol - salicylate de benzyle - alcool phényléthylique - jasmin fleur Spécialité - a-méthylionone - acétate de tert.-butyl-4
cyclohexyle - Vertofix Coeur (1) - galaxolide 50 % dans le
myristate d'éthyle - dipropylèneglycol
830,0
- autres dérivés 170,0
Lorsque l'on ajoute 5 ppm du produit de l'exemple 1, on note un effet intense qui rappelle nettement celui qui est rendu par l'essence de Bucchu, matière première onéreuse dont l'approvisionnement est, de plus, aléatoire.Example 3
Perfumery composition
A flower-themed composition was prepared, mainly based on - dihydromyrcenol - benzyl salicylate - phenylethyl alcohol - jasmine flower Specialty - a-methylionone - tert.-butyl-4 acetate
cyclohexyle - Vertofix Coeur (1) - galaxolide 50% in the
ethyl myristate - dipropylene glycol
830.0
- other derivatives 170.0
When 5 ppm of the product of Example 1 is added, an intense effect is noted which clearly recalls that which is rendered by the essence of Bucchu, an expensive raw material whose supply is, moreover, random.
On note également que certains effets de l'essence de Bucchu pouvant être considérés comme désagréables sont absents avec le dérivé de l'exemple 1. It is also noted that certain effects of the essence of Bucchu which can be considered unpleasant are absent with the derivative of Example 1.
ExemPle 4
Composition aromatique alimentaire
On a préparé une composition aromatique de type fruit tropical, particulièrement de type mangue, à base principalement de triacétine et d'alcool éthylique à 95 % (943,7/1000 parties) renfermant également notamment de l'ocimène naturel et du Furanéol^. EXAMPLE 4
Food flavor composition
An aromatic composition of tropical fruit type, particularly of mango type, was prepared, mainly based on triacetin and 95% ethyl alcohol (943.7 / 1000 parts) also containing in particular natural oximene and Furaneol.
Lorsque l'on ajoute 0,3 ppm du produit de l'exemple 1, l'odeur et le got obtenus suggèrent nettement l'arôme de la mangue à pleine maturité, alors qu'en l'absence de celui-ci, l'effet est celui de la mangue verte. When 0.3 ppm of the product of Example 1 is added, the odor and the taste obtained clearly suggest the aroma of the mango at full maturity, whereas in the absence of the latter, the effect is that of green mango.
Exemple 5
Composition aromatique alimentaire
On a préparé une composition aromatique alimentaire de type fruit rouge européen, notamment cassis, à base de propylèneglycol, d'absolue de bourgeon de cassis en solution à 10 % dans l'alcool et de (hydroxy-4-phényl)-4 butanone de vanilline renfermant également notamment du maltol, de l'acétate de menthyle et du butyrate d'éthyle.Example 5
Food flavor composition
A food aromatic composition of the European red fruit type, in particular blackcurrant, was prepared, based on propylene glycol, blackcurrant bud absolute in 10% solution in alcohol and (4-hydroxy-phenyl) -4 butanone. vanillin also containing in particular maltol, menthyl acetate and ethyl butyrate.
En l'absence d'éthoxy-4 méthyl-2 butane thiol-2 en solution à I"/oo dans le propylèneglycol, l'arôme est décrit comme cassis doucement fruité, alors qu'en ajoutant 5 ppm seulement de ce produit, l'effet est spectaculaire : la composition se voit conférer un caractère net de jus de cassis frais que l'on peut observer par ailleurs dans d'autres applications de ce genre du type fraises, framboises, groseilles, etc.In the absence of 4-ethoxy-2-methyl-2-butane thiol-2 in solution at I "/ oo in propylene glycol, the flavor is described as sweetly fruity blackcurrant, whereas by adding only 5 ppm of this product, l 'effect is spectacular: the composition is given a clean character of fresh blackcurrant juice that can be observed in other applications of this kind such as strawberries, raspberries, currants, etc.
Exemple 6
Le produit de l'exemple 1 possède une note typique de cassis beaucoup moins intense que celle obtenue avec l'exemple 1, ainsi qu'un seuil de perception olfactive notablement plus élevé que celui de ce dernier produit. Le produit de l'exemple B n'a pas la note typique de cassis et, de plus, possède un seuil de perception olfactive encore plus élevé que celui du dérivé de l'exemple A.Example 6
The product of Example 1 has a typical blackcurrant note much less intense than that obtained with Example 1, as well as a significantly higher olfactory perception threshold than that of the latter product. The product of example B does not have the typical blackcurrant note and, moreover, has an even higher odor perception threshold than that of the derivative of example A.
Certains des produits ci-dessus cités sont d'origine notamment des sociétés suivantes : IFF
Firmenich, Henkel, Givaudan et Robertet S.A. Some of the products mentioned above are original, in particular from the following companies: IFF
Firmenich, Henkel, Givaudan and Robertet SA
Claims (7)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8914627A FR2653766B1 (en) | 1989-11-02 | 1989-11-02 | NEW DERIVATIVE OF BUTANE THIOL, ITS PREPARATION PROCESS, ITS APPLICATION IN PARTICULAR IN PERFUMERY AND THE COMPOSITIONS CONTAINING IT. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8914627A FR2653766B1 (en) | 1989-11-02 | 1989-11-02 | NEW DERIVATIVE OF BUTANE THIOL, ITS PREPARATION PROCESS, ITS APPLICATION IN PARTICULAR IN PERFUMERY AND THE COMPOSITIONS CONTAINING IT. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2653766A1 true FR2653766A1 (en) | 1991-05-03 |
| FR2653766B1 FR2653766B1 (en) | 1993-07-02 |
Family
ID=9387188
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8914627A Expired - Lifetime FR2653766B1 (en) | 1989-11-02 | 1989-11-02 | NEW DERIVATIVE OF BUTANE THIOL, ITS PREPARATION PROCESS, ITS APPLICATION IN PARTICULAR IN PERFUMERY AND THE COMPOSITIONS CONTAINING IT. |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2653766B1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006282627A (en) * | 2005-04-04 | 2006-10-19 | Takasago Internatl Corp | Stable composition for hair dye |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2179162A1 (en) * | 1972-04-06 | 1973-11-16 | Polak Frutal Works | |
| EP0217719A2 (en) * | 1985-10-03 | 1987-04-08 | INSTITUT NATIONAL DE LA RECHERCHE AGRONOMIQUE, Etablissement public dit: | Derivative of butane thiol found in the fragrance of black currant buds, process for its preparation and use of this derivative as a fragrance |
-
1989
- 1989-11-02 FR FR8914627A patent/FR2653766B1/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2179162A1 (en) * | 1972-04-06 | 1973-11-16 | Polak Frutal Works | |
| EP0217719A2 (en) * | 1985-10-03 | 1987-04-08 | INSTITUT NATIONAL DE LA RECHERCHE AGRONOMIQUE, Etablissement public dit: | Derivative of butane thiol found in the fragrance of black currant buds, process for its preparation and use of this derivative as a fragrance |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006282627A (en) * | 2005-04-04 | 2006-10-19 | Takasago Internatl Corp | Stable composition for hair dye |
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| Publication number | Publication date |
|---|---|
| FR2653766B1 (en) | 1993-07-02 |
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