CA1157036A - Perfuming compositions comprised of 2-phenyl-1(2)- propen-1-yl carboxylate - Google Patents
Perfuming compositions comprised of 2-phenyl-1(2)- propen-1-yl carboxylateInfo
- Publication number
- CA1157036A CA1157036A CA000370743A CA370743A CA1157036A CA 1157036 A CA1157036 A CA 1157036A CA 000370743 A CA000370743 A CA 000370743A CA 370743 A CA370743 A CA 370743A CA 1157036 A CA1157036 A CA 1157036A
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- propen
- carboxylic acid
- product
- formula
- 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
Links
Classifications
-
- 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
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
The invention is directed to a perfumery composition consisting essentially of from about 1 to 50 percent by weight of 2-phenyl-1(2)-propen-1-yl carboxylic acid esters of the formula
The invention is directed to a perfumery composition consisting essentially of from about 1 to 50 percent by weight of 2-phenyl-1(2)-propen-1-yl carboxylic acid esters of the formula
Description
~lS7~36 PERFUMING COMPOSITIONS COMPRISED OF
2-PHENYI,-1(2)-PROPEN-l-YL CARBOXYLATE
This invention is directed to novel perfuming agents. More particularly, this invention is directed to the'use of 2-phenyl-1(2)-propen-1-yl carboxylic acid esters as perf~ming agents as well as perf~ming compositions containing such compounds.
..
It is an object of the invention to provide for the use'of 2-phenyl-1(2)-propen-1-yl carboxylic acid esters as perfuming agents.
It is also an object of the invention to provide perfuming compositionS based upo~ 2-phenyl-1(2)--propen-l-yl, carboxylic acid esters.
These'and other ob~ects of the'inventlon will' become'more apparent in the'discussion bel'ow~ '~
It has been found that 2-phenyl-lt2)-propen-1-yl carboxylic acid esters of the general formula O~R (I) .
.
-1- , 7~36 wherein R is an alkyl o~ from 1 to 4 carbon atoms, can advantayeously be used as perfuming agents with a vigorous, flowery scent. The 2-phenyl-1(2)-propen-l-yl carboxylic-acid esters of Formula (I) represent a mixture of the isomeric compounds of the formulas .
,, '` ' ' ' ~ I?
_. , ~, . .
and O~R (IVI
wherein R is as defined a~ove.
The 2-pheny~ 2)-propen-l-yl carboxylic . acid esters to be used as.perfuming agents according to ;~ the invention are prepared by conversion of 2-phenyl-1,-2-propane diol in the presence of an acid catalyst and -- excess car~oxylic anhydride of the formula ~RCO)20, wherein R is as defined above, with the dehydration of the tertiary hydroxyl group and simultaneous esterifi-cation of the primary hydroxyl group. The 2-phenyl---2-- .
'. ' - .- .' --. ~: ' .
, ~57C~36 .
1,2-propane diol used as starting material for the preparatiOn of theesters can be readily and cheaply prepared from ~-methylstyrene. The preparatiOn of the esters of Formula I proceeds according to the foIlowing reaction scheme- .
~ ' ' . .`., ":
~. '', . -` ' ;
. ~
',', :, ~ .,~,:, .
: .
. .' ~ -' ~ ' ' ' ' ' ':'.,; - . '' ' ` . '. ' ` - . ' : .
. . . . . ....
.. : ' : ,
This invention is directed to novel perfuming agents. More particularly, this invention is directed to the'use of 2-phenyl-1(2)-propen-1-yl carboxylic acid esters as perf~ming agents as well as perf~ming compositions containing such compounds.
..
It is an object of the invention to provide for the use'of 2-phenyl-1(2)-propen-1-yl carboxylic acid esters as perfuming agents.
It is also an object of the invention to provide perfuming compositionS based upo~ 2-phenyl-1(2)--propen-l-yl, carboxylic acid esters.
These'and other ob~ects of the'inventlon will' become'more apparent in the'discussion bel'ow~ '~
It has been found that 2-phenyl-lt2)-propen-1-yl carboxylic acid esters of the general formula O~R (I) .
.
-1- , 7~36 wherein R is an alkyl o~ from 1 to 4 carbon atoms, can advantayeously be used as perfuming agents with a vigorous, flowery scent. The 2-phenyl-1(2)-propen-l-yl carboxylic-acid esters of Formula (I) represent a mixture of the isomeric compounds of the formulas .
,, '` ' ' ' ~ I?
_. , ~, . .
and O~R (IVI
wherein R is as defined a~ove.
The 2-pheny~ 2)-propen-l-yl carboxylic . acid esters to be used as.perfuming agents according to ;~ the invention are prepared by conversion of 2-phenyl-1,-2-propane diol in the presence of an acid catalyst and -- excess car~oxylic anhydride of the formula ~RCO)20, wherein R is as defined above, with the dehydration of the tertiary hydroxyl group and simultaneous esterifi-cation of the primary hydroxyl group. The 2-phenyl---2-- .
'. ' - .- .' --. ~: ' .
, ~57C~36 .
1,2-propane diol used as starting material for the preparatiOn of theesters can be readily and cheaply prepared from ~-methylstyrene. The preparatiOn of the esters of Formula I proceeds according to the foIlowing reaction scheme- .
~ ' ' . .`., ":
~. '', . -` ' ;
. ~
',', :, ~ .,~,:, .
: .
. .' ~ -' ~ ' ' ' ' ' ':'.,; - . '' ' ` . '. ' ` - . ' : .
. . . . . ....
.. : ' : ,
-3- -.
., '.
~57~336 H H
H H H
--,'';'-~; - ~ ' `
C~=O . r ~--O
P~
._ ,, ~A~
~ .
0=~=0 i 1. 1 . ..
' \
~ ' , ' ' .
~57~36 The mixture of the three isomeric esters of Formulas II to IV, also represented ~y Formula I, can be used as a perfuming agent without further separation into indivi-dual components.
-The use of approximately 3 mols of carboxylic acid anhy-dride per moi of diol as well as the use of an elevated re-action temperature of from about 60 to 125 C are recommended for the complete conversion of 2-phenyl-1,2-propane diol , ~
into the desired esters. Suitable catalysts include acia catalysts such as, for example, sulfuric acid, p-toluene-sulfonic acid, and solid bed acid catalysts. The ratio of isomers in the mixture o 2-phenyl-1¢2)-propen-1-yl car-boxylic acid esters formed fluctuates somewhat with varia-tions in the reaction conditions, such as, for example, variation of the amount of anhydride, the reaction time, or the reaction temperature. ~owever, variations of the isomer ratio in the mixture have not been found to have a signifi-cant influence on the fragrance characteristics of the mix-ture.
The mixture 2-phenyl-1(2)-propen-1-yl acetate, which can be obtainea from 2 phenyl-1,2-propane diol, is of special significance due to its sweet, flowery scent remin-iscent of lilac, hyacinths, and ripe grain This ester mixture is particularly suitable for, for example, the for-mulation of interesting neroli and lilac compositions.
~$S7036 The product 2-phenyl-1(2)-propen-1-yl acetate is known from the literature and has been prepared by various methods without its suitability and importance as a per-fuming agent or as a component of perfuming compositions having been recogn~zea. For example, A. Wohl and E. ~
Berthold describe ~he preparation from hydratropaldehyde and acetic anhydride in the presence of hydrochloric acid in ~er~ 43:2184, 1910, and R. v~ Auwers describes the pre-paration from hydratropaldehyde and acetic anhydride in the presence of sodium acetate in Ann. 413:280, 1917.
A series of additional methods of preparation starting with ~-methylstyrene is described in more recent times, for example, by A. Kasahara, ~. Saito, and T. Izmi, Bull. chem.
~Soc. Ja~. 46:2610, 1973, and in Belgian Patent Specifica-tion No~ 630,862 of the General Electric Company.
The perfuming agents to be used according to the inven-tion are prepared by conversion of 2-phenyl~1,2-propane ; .
k' diol with acetic anhydride, propionic anhydride, butyric anhydride, o~ isovaleric anhydride in t~e presence of acid catalysts. Useful 2-phenyl-1~2)-propen-1-yl carboxylic acid esters according to the invention include 2-phenyl-1-(2)-propen-1-yl acetate, propionate, b~tyrate r and 3-~`~ methylbutyrate. ~ -, . r~
The 2-phenyl-1~2)-propen-1-yl carboxylic acid esters ~` of Formula I are valuable perfuming agents with vigorous, flowery perfume notes. A special advantage is that they combine readily into interesting fragrance nuances.
~57C~36 The 2-phenyl-1~2)-propen-1-yl carboxylic acid esters of Formula I can be ~ixed with other perfumes in various quantity ratios to provide new perfume com-positions. Generally, the content of the 2-phenyl-1~2)-propen-l-yl carboxylic acid esters in the perfume compo-sitions will range from about 1 to 50 percent by weight, based on the weight of the total composition. Such compo-sitions can sèrve directly as perfume or also as per~
fuming agents in cosmetics, such as creams, lotions, toilet waters, aerosols, mouth-care products, toilet soaps, and the like, Also, they may be used to improve the odor of industrial and commercial products such as detergents and cleansing agents, disinfectants, softeners, textile treatment agents, and the like. To perfume the various ~roducts, the perfume compositions containing the 2-phenyl-1(2)-propen-1-yl carboxylic acid esters to be used according to the invention are added to the products generally in concentrations of from about 0.05 to 2 per-cent by weight, based on the total weight of the products.
The following examples are intended to illustrate the invention in greater detail and are not to be c~nQtrued as limiting the inventio~ thereto.
..-. ..
- . ~ . .. . ' i .
':
.
-'.
~L57036 E X A M P L E S
. . xample 1 - Preparation of 2-phenyl-l(2)-propen l-yl carboxylic acid esters (a) 2-Phenyl-(2)-propen-1-yl Acetate One to two drops of concentratèd sulfuric acid were added with agitation and cooling to lS.2 gm ~0.1 mol) of 2-phenyl-1,2-propane diol and 30.6 gm ~0.3 mol) -of acetic anhydride. The temperature of ~he reaction solution rose, due to the onset of the strongly exo-thermic reaction, to 85C. The mixture was then agitated for two hours at 125C. Excess acetic anhydride and acetic acid fQrmed were distilled off, and the reaction mixture was neutralized with 20% sodium carbonate solu-.;.....
tion and extracted with ether. After drying over mag-nesium sulfate and removal of the solvent, the product was distilled under vacuum. An amount of 12.7 gm t86%
of theory) of 2-phenyl-1~2)-propen-1-yl acetate with a boiling point of 94-96C at 2.7 mbar and a refractive index of n20 ~ 1.5324, was obtained. The product had a sweet, flowery scent of lilac, hyacinth, and ripe grain.
. ., . ::
~b) 2-Phenyl-1(2)-propen-1-yl Propionate The above product was pr~pared from 2-phenyi-1,2-pxopane diol and propionic anhydride using a prooedure analo~ous to that for the preparation of product ta). ~he product obtalned had boiling point of 12~-131-C at .
.
:
5~036 .
~ mbar and a refractive index of n20 _ 1.52~1. The odor was very similar to that of product ~a~.
~c) 2-Phenyl-lt2)-Fropen-l-yl Butyrate .
The above product was prepared from 2-phenyl-1,2-pro-pane diol using a procedure analogous.to that for the . . .
preparation of product ~a). The product obtained had a boiling point of 78-80 C at 0.01 mbar and a refractive index of n20 = 1.5193. The fragrance was similar to that of product ~z),.but arier. -.
A typical perfume composition is set forth ~elow in - -~ ~5Example.2. The 2-phenyl-1(.2)-propen-1-yl carboxylic acid .. ester in the example could readily be replaced by a simi-. lar such compound within the scope of the invention.
:. - . - .
.. Ex2mple 2 - Hyacinth Complex -. ~ Amount Component ~par*s by we~ht) 2-Phenyl~ propen-l-yl ~ ` --acetate : lS0' -J~. ' Phenylethyl alcohol 200~
Benzyl salicylate . 200 ; .
. . . .
Hydroxycitronellal 120 --Linalool 100 a-Hexylcinnamaldehyde 60 Phenylacetaldehyde dimethylacetal 5 Gexaniol, natural 30 Ylang-ylang oil 30 Phenylethyl acetate - 20 `, _g -~
, ` ~57g~36 .
Component Amount (parts by wei~ht~
Galbanum res. synth. . 20 Cyclamen aldehyde 10 Styrallyl acetate . 10 1000 . , ~ "
~ -:- .... ' -~ -Various modifications of the process and products of ~ `
the invention may be made without departing from the -spirit or scope thereof and it should be understood .. ..
that the irlvention is intended to be limited only as defined in the appended claims.
,` , . . .
: , .- ' , ' ~ :7r' ', - ' ' ' " ':
.. . . .
~,', . ' , ' , ' . ', ' . ' . . , `
'>'. ' ' ': , ' , . ,., . ~. '` ;', '':.
f . ' . . . '. , ~ . ` :. ' ~. . ' i - ,- ., ' '.
'. .: ~ ' . . . ' . `':
'. ~',' ~.
.~:, ' ' ' - ' '. ' . "'''', :. ,. ' ' .
- ' ' .:
--10-- .
` ' ..
.: .-. . . -
., '.
~57~336 H H
H H H
--,'';'-~; - ~ ' `
C~=O . r ~--O
P~
._ ,, ~A~
~ .
0=~=0 i 1. 1 . ..
' \
~ ' , ' ' .
~57~36 The mixture of the three isomeric esters of Formulas II to IV, also represented ~y Formula I, can be used as a perfuming agent without further separation into indivi-dual components.
-The use of approximately 3 mols of carboxylic acid anhy-dride per moi of diol as well as the use of an elevated re-action temperature of from about 60 to 125 C are recommended for the complete conversion of 2-phenyl-1,2-propane diol , ~
into the desired esters. Suitable catalysts include acia catalysts such as, for example, sulfuric acid, p-toluene-sulfonic acid, and solid bed acid catalysts. The ratio of isomers in the mixture o 2-phenyl-1¢2)-propen-1-yl car-boxylic acid esters formed fluctuates somewhat with varia-tions in the reaction conditions, such as, for example, variation of the amount of anhydride, the reaction time, or the reaction temperature. ~owever, variations of the isomer ratio in the mixture have not been found to have a signifi-cant influence on the fragrance characteristics of the mix-ture.
The mixture 2-phenyl-1(2)-propen-1-yl acetate, which can be obtainea from 2 phenyl-1,2-propane diol, is of special significance due to its sweet, flowery scent remin-iscent of lilac, hyacinths, and ripe grain This ester mixture is particularly suitable for, for example, the for-mulation of interesting neroli and lilac compositions.
~$S7036 The product 2-phenyl-1(2)-propen-1-yl acetate is known from the literature and has been prepared by various methods without its suitability and importance as a per-fuming agent or as a component of perfuming compositions having been recogn~zea. For example, A. Wohl and E. ~
Berthold describe ~he preparation from hydratropaldehyde and acetic anhydride in the presence of hydrochloric acid in ~er~ 43:2184, 1910, and R. v~ Auwers describes the pre-paration from hydratropaldehyde and acetic anhydride in the presence of sodium acetate in Ann. 413:280, 1917.
A series of additional methods of preparation starting with ~-methylstyrene is described in more recent times, for example, by A. Kasahara, ~. Saito, and T. Izmi, Bull. chem.
~Soc. Ja~. 46:2610, 1973, and in Belgian Patent Specifica-tion No~ 630,862 of the General Electric Company.
The perfuming agents to be used according to the inven-tion are prepared by conversion of 2-phenyl~1,2-propane ; .
k' diol with acetic anhydride, propionic anhydride, butyric anhydride, o~ isovaleric anhydride in t~e presence of acid catalysts. Useful 2-phenyl-1~2)-propen-1-yl carboxylic acid esters according to the invention include 2-phenyl-1-(2)-propen-1-yl acetate, propionate, b~tyrate r and 3-~`~ methylbutyrate. ~ -, . r~
The 2-phenyl-1~2)-propen-1-yl carboxylic acid esters ~` of Formula I are valuable perfuming agents with vigorous, flowery perfume notes. A special advantage is that they combine readily into interesting fragrance nuances.
~57C~36 The 2-phenyl-1~2)-propen-1-yl carboxylic acid esters of Formula I can be ~ixed with other perfumes in various quantity ratios to provide new perfume com-positions. Generally, the content of the 2-phenyl-1~2)-propen-l-yl carboxylic acid esters in the perfume compo-sitions will range from about 1 to 50 percent by weight, based on the weight of the total composition. Such compo-sitions can sèrve directly as perfume or also as per~
fuming agents in cosmetics, such as creams, lotions, toilet waters, aerosols, mouth-care products, toilet soaps, and the like, Also, they may be used to improve the odor of industrial and commercial products such as detergents and cleansing agents, disinfectants, softeners, textile treatment agents, and the like. To perfume the various ~roducts, the perfume compositions containing the 2-phenyl-1(2)-propen-1-yl carboxylic acid esters to be used according to the invention are added to the products generally in concentrations of from about 0.05 to 2 per-cent by weight, based on the total weight of the products.
The following examples are intended to illustrate the invention in greater detail and are not to be c~nQtrued as limiting the inventio~ thereto.
..-. ..
- . ~ . .. . ' i .
':
.
-'.
~L57036 E X A M P L E S
. . xample 1 - Preparation of 2-phenyl-l(2)-propen l-yl carboxylic acid esters (a) 2-Phenyl-(2)-propen-1-yl Acetate One to two drops of concentratèd sulfuric acid were added with agitation and cooling to lS.2 gm ~0.1 mol) of 2-phenyl-1,2-propane diol and 30.6 gm ~0.3 mol) -of acetic anhydride. The temperature of ~he reaction solution rose, due to the onset of the strongly exo-thermic reaction, to 85C. The mixture was then agitated for two hours at 125C. Excess acetic anhydride and acetic acid fQrmed were distilled off, and the reaction mixture was neutralized with 20% sodium carbonate solu-.;.....
tion and extracted with ether. After drying over mag-nesium sulfate and removal of the solvent, the product was distilled under vacuum. An amount of 12.7 gm t86%
of theory) of 2-phenyl-1~2)-propen-1-yl acetate with a boiling point of 94-96C at 2.7 mbar and a refractive index of n20 ~ 1.5324, was obtained. The product had a sweet, flowery scent of lilac, hyacinth, and ripe grain.
. ., . ::
~b) 2-Phenyl-1(2)-propen-1-yl Propionate The above product was pr~pared from 2-phenyi-1,2-pxopane diol and propionic anhydride using a prooedure analo~ous to that for the preparation of product ta). ~he product obtalned had boiling point of 12~-131-C at .
.
:
5~036 .
~ mbar and a refractive index of n20 _ 1.52~1. The odor was very similar to that of product ~a~.
~c) 2-Phenyl-lt2)-Fropen-l-yl Butyrate .
The above product was prepared from 2-phenyl-1,2-pro-pane diol using a procedure analogous.to that for the . . .
preparation of product ~a). The product obtained had a boiling point of 78-80 C at 0.01 mbar and a refractive index of n20 = 1.5193. The fragrance was similar to that of product ~z),.but arier. -.
A typical perfume composition is set forth ~elow in - -~ ~5Example.2. The 2-phenyl-1(.2)-propen-1-yl carboxylic acid .. ester in the example could readily be replaced by a simi-. lar such compound within the scope of the invention.
:. - . - .
.. Ex2mple 2 - Hyacinth Complex -. ~ Amount Component ~par*s by we~ht) 2-Phenyl~ propen-l-yl ~ ` --acetate : lS0' -J~. ' Phenylethyl alcohol 200~
Benzyl salicylate . 200 ; .
. . . .
Hydroxycitronellal 120 --Linalool 100 a-Hexylcinnamaldehyde 60 Phenylacetaldehyde dimethylacetal 5 Gexaniol, natural 30 Ylang-ylang oil 30 Phenylethyl acetate - 20 `, _g -~
, ` ~57g~36 .
Component Amount (parts by wei~ht~
Galbanum res. synth. . 20 Cyclamen aldehyde 10 Styrallyl acetate . 10 1000 . , ~ "
~ -:- .... ' -~ -Various modifications of the process and products of ~ `
the invention may be made without departing from the -spirit or scope thereof and it should be understood .. ..
that the irlvention is intended to be limited only as defined in the appended claims.
,` , . . .
: , .- ' , ' ~ :7r' ', - ' ' ' " ':
.. . . .
~,', . ' , ' , ' . ', ' . ' . . , `
'>'. ' ' ': , ' , . ,., . ~. '` ;', '':.
f . ' . . . '. , ~ . ` :. ' ~. . ' i - ,- ., ' '.
'. .: ~ ' . . . ' . `':
'. ~',' ~.
.~:, ' ' ' - ' '. ' . "'''', :. ,. ' ' .
- ' ' .:
--10-- .
` ' ..
.: .-. . . -
Claims (5)
1. A perfumery composition consisting essen-tially of from about 1 to 50 percent by weight of 2-phenyl-1(2)-propen-1-yl carboxylic acid esters of the formula wherein R is an alkyl of from 1 to 4 carbon atoms, and the remainder of customary constituents of perfumery compositions.
2. The perfumery composition of Claim 1, wherein R is a methyl radical.
3. A method of imparting a pleasant odor to a product comprising the step of adding to said product a sufficient amount of the perfumery composition of Claim 1 to provide the desired degree of odor.
4. The method of Claim 3 wherein the amount of perfumery composition added consists of from about 0.05 to 5 percent by weight, based on the weight of the total product.
5. A method of the preparation of the 2-phenyl-1(2)-propen-l-yl carboxylic acid esters of the formula of Claim 1 which comprises reacting 2-phenyl-1,2-propane diol with an excess of a carboxylic acid anhydride o the formula (RCO)2O, wherein R is as defined in Claim 1, in the presence of an acid catalyst at a temperature of from about 60° to 125°C and then recovering the product.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3007232.3 | 1980-02-27 | ||
| DE19803007232 DE3007232A1 (en) | 1980-02-27 | 1980-02-27 | USE OF 2-PHENYL-2 (2) -PROPEN-1-YL-CARBONIC ACID ESTERS AS A FRAGRANCE, THEIR PRODUCTION AND THEIR COMPOSITIONS CONTAINING THIS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1157036A true CA1157036A (en) | 1983-11-15 |
Family
ID=6095602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000370743A Expired CA1157036A (en) | 1980-02-27 | 1981-02-12 | Perfuming compositions comprised of 2-phenyl-1(2)- propen-1-yl carboxylate |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0035183A3 (en) |
| JP (1) | JPS56133211A (en) |
| BR (1) | BR8101174A (en) |
| CA (1) | CA1157036A (en) |
| DE (1) | DE3007232A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4772583A (en) * | 1987-09-03 | 1988-09-20 | International Flavors & Fragrances Inc. | Beta-alkylidene phenethyl alcohol esters and ethers, organoleptic uses thereof and processes for preparing same |
| DE10348062A1 (en) * | 2003-10-16 | 2005-05-19 | Symrise Gmbh & Co. Kg | Short chain enol esters as perfume precursors |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH571484A5 (en) * | 1972-10-17 | 1976-01-15 | Givaudan & Cie Sa |
-
1980
- 1980-02-27 DE DE19803007232 patent/DE3007232A1/en not_active Withdrawn
-
1981
- 1981-02-12 CA CA000370743A patent/CA1157036A/en not_active Expired
- 1981-02-20 EP EP81101199A patent/EP0035183A3/en not_active Withdrawn
- 1981-02-26 BR BR8101174A patent/BR8101174A/en unknown
- 1981-02-26 JP JP2621781A patent/JPS56133211A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP0035183A2 (en) | 1981-09-09 |
| JPS56133211A (en) | 1981-10-19 |
| EP0035183A3 (en) | 1982-02-03 |
| BR8101174A (en) | 1981-09-01 |
| DE3007232A1 (en) | 1981-09-10 |
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