WO1979000588A1 - Esters aliphatiques polyinsatures et leur utilisation en tant qu'ingredients aromatisants et parfumants - Google Patents
Esters aliphatiques polyinsatures et leur utilisation en tant qu'ingredients aromatisants et parfumants Download PDFInfo
- Publication number
- WO1979000588A1 WO1979000588A1 PCT/CH1979/000006 CH7900006W WO7900588A1 WO 1979000588 A1 WO1979000588 A1 WO 1979000588A1 CH 7900006 W CH7900006 W CH 7900006W WO 7900588 A1 WO7900588 A1 WO 7900588A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hexa
- 3cis
- tant
- pour
- diene
- Prior art date
Links
- 239000004615 ingredient Substances 0.000 title abstract description 12
- 125000001931 aliphatic group Chemical group 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 claims description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 8
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 8
- 238000005899 aromatization reaction Methods 0.000 claims description 7
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 2
- 235000013361 beverage Nutrition 0.000 abstract 2
- 235000013305 food Nutrition 0.000 abstract 2
- 241000208125 Nicotiana Species 0.000 abstract 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000002304 perfume Substances 0.000 abstract 1
- 239000012437 perfumed product Substances 0.000 abstract 1
- -1 polyunsaturated aliphatic ester Chemical class 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229940070710 valerate Drugs 0.000 description 3
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 3
- 244000099147 Ananas comosus Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 244000290333 Vanilla fragrans Species 0.000 description 2
- 235000009499 Vanilla fragrans Nutrition 0.000 description 2
- 235000012036 Vanilla tahitensis Nutrition 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- 229960004063 propylene glycol Drugs 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 2
- 229960001860 salicylate Drugs 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- JRJBVWJSTHECJK-PKNBQFBNSA-N 3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one Chemical compound CC(=O)C(\C)=C\C1C(C)=CCCC1(C)C JRJBVWJSTHECJK-PKNBQFBNSA-N 0.000 description 1
- IKTHMQYJOWTSJO-UHFFFAOYSA-N 4-Acetyl-6-tert-butyl-1,1-dimethylindane Chemical compound CC(=O)C1=CC(C(C)(C)C)=CC2=C1CCC2(C)C IKTHMQYJOWTSJO-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- 241000195940 Bryophyta Species 0.000 description 1
- 240000004307 Citrus medica Species 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 description 1
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- PFHBCQFBHMBAMC-UHFFFAOYSA-N oct-4-enoic acid Chemical compound CCCC=CCCC(O)=O PFHBCQFBHMBAMC-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
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
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
- C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/24—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with monohydroxylic compounds
Definitions
- esters aliphatics polyinsatures et leur utilization en tant qu'ingredi ⁇ nts aromatisants et perfumeants
- the presente invention se rapporte au domaine des arömes et a check de la perfumeerie.
- a trait andhold à l'utilisation d'esters aliphatiques polyinsatures de formula
- dans lattle le symbols R represente un radical alkyle, lineaire ou ram licensed, ministert 1 à 5 atomes de carbone et dans lattle la double liaison à la position 3 possede la configuration eis, en tant qu'ingredients perfumeants pour la preparation de perfumes et wall parfurnes , and pour l'aromatization d'aliments, de boissons, de preparations pharmaceutiques et du tabac.
- the present invention is rapporte en outre a une composition perfumeante ou aromatisantecharacterisee en ce qu'ellehold en tant qu'ingredient actif un ester aliphatique polyinsature de formula (I).
- the composes de formula (I) thank des composes medical.
- La invention a ceremoniernent trait à l'utilisation d 'hexa-3cis, 5-diene-1-ol en tant qu'ingredient perfumeant pour la preparation de perfumes et wall parfurnes, et pour l'aromatisation d'aliments, de boissons, pharmaceutical preparations and tabac preparations.
- de l'invention peuvent etre utilises ä l'etat is ⁇ le ou, de preference, sous forme d'une composition en me- lang Malawi d' improving ingredients aromatisants.
- the method particuliére Seae pour la preparation desdits composes de f ⁇ rmule (I) est irrie ci-lingerie à titre d' provided. (Les sins109es thanktypical en degres centigrades) Butyrate d'hexa-3cis, 5-diena-1-yle
- Composition A (contr.) Composition B (test) Composition de base 100 100
- Salicylate de benzyle 100 Acetate de p-ter-butylcycl ⁇ hexyle 80
- Héliotropine 50 Hydr ⁇ xycitronellal synth. 50
- Isobutyrate de citronellyle 40 Formiate de cinnamyle 40 ⁇ -Dorinone® 10% * (1) 30
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)
- Manufacture Of Tobacco Products (AREA)
- Seasonings (AREA)
- Cosmetics (AREA)
Abstract
Esters aliphatiques polyinsatures de formule (FORMULE) dans laquelle le symbole R represente un radical alkyle, lineaire ou ramifie, contenant 1 a 5 atomes de carbone et dans laquelle la double liaison a la position 3 possede la configuration cis. La presente invention concerne egalement leur utilisation en tant qu'ingredients parfumants et aromatisants ainsi qu'une composition parfumante et aromatisante les contenant. L'invention concerne egalement un aliment ou une boisson contenant en tant qu'ingredient aromatisant un ester aliphatique polyinsature de formule (I). La presente invention a egalement pour objet l'utilisation d'hexa-3cis, 5-diene 1-01 en tant qu'ingredient parfumant pour la preparation de parfums et produits parfumes, et pour l'aromatisation d'aliments, de boissons, de preparations pharmaceutiques et du tabac.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH125978A CH627434A5 (fr) | 1978-02-06 | 1978-02-06 | Esters aliphatiques polyinsatures et leur utilisation en tant qu'ingredients aromatisants et parfumants. |
| CH1259/78 | 1978-02-06 | ||
| CH1263778 | 1978-12-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1979000588A1 true WO1979000588A1 (fr) | 1979-08-23 |
Family
ID=25687145
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/CH1979/000006 WO1979000588A1 (fr) | 1978-02-06 | 1979-01-24 | Esters aliphatiques polyinsatures et leur utilisation en tant qu'ingredients aromatisants et parfumants |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS599538B2 (fr) |
| CH (1) | CH641143A5 (fr) |
| GB (1) | GB2035799B (fr) |
| WO (1) | WO1979000588A1 (fr) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0034334A3 (en) * | 1980-02-13 | 1981-10-14 | Firmenich Sa | 1,3-dimethyl-but-3-en-1-yl esters, their use as perfuming or aromatizing constituents; perfuming or aromatizing composition containing at least one of these esters |
| US4613457A (en) * | 1983-02-25 | 1986-09-23 | Henkel Kommanditgesellschaft Auf Aktien | 2-methyl pentanoic acid esters and perfume compositions containing them |
| US5531910A (en) * | 1995-07-07 | 1996-07-02 | The Procter & Gamble Company | Biodegradable fabric softener compositions with improved perfume longevity |
| US5559088A (en) * | 1995-07-07 | 1996-09-24 | The Proctor & Gamble Company | Dryer-activated fabric conditioning and antistatic compositions with improved perfume longevity |
| WO2007057810A1 (fr) * | 2005-11-17 | 2007-05-24 | Firmenich Sa | Esters de sorbol en tant qu’ingredients de parfum |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6171164A (ja) * | 1984-09-13 | 1986-04-12 | Fanuc Ltd | 型締力自動調整装置 |
| JPS61125829A (ja) * | 1984-11-24 | 1986-06-13 | Fanuc Ltd | 射出成形機における型締方式 |
| JPS6278835A (ja) * | 1985-09-30 | 1987-04-11 | Mitsubishi Electric Corp | 半導体素子用樹脂封止装置 |
| JPS62154914U (fr) * | 1986-03-24 | 1987-10-01 | ||
| JPS636825U (fr) * | 1986-06-27 | 1988-01-18 |
-
1979
- 1979-01-24 JP JP54500312A patent/JPS599538B2/ja not_active Expired
- 1979-01-24 CH CH914179A patent/CH641143A5/fr not_active IP Right Cessation
- 1979-01-24 WO PCT/CH1979/000006 patent/WO1979000588A1/fr unknown
- 1979-01-24 GB GB7931972A patent/GB2035799B/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| No relevant documents have been disclosed. * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0034334A3 (en) * | 1980-02-13 | 1981-10-14 | Firmenich Sa | 1,3-dimethyl-but-3-en-1-yl esters, their use as perfuming or aromatizing constituents; perfuming or aromatizing composition containing at least one of these esters |
| US4613457A (en) * | 1983-02-25 | 1986-09-23 | Henkel Kommanditgesellschaft Auf Aktien | 2-methyl pentanoic acid esters and perfume compositions containing them |
| US5531910A (en) * | 1995-07-07 | 1996-07-02 | The Procter & Gamble Company | Biodegradable fabric softener compositions with improved perfume longevity |
| US5559088A (en) * | 1995-07-07 | 1996-09-24 | The Proctor & Gamble Company | Dryer-activated fabric conditioning and antistatic compositions with improved perfume longevity |
| WO2007057810A1 (fr) * | 2005-11-17 | 2007-05-24 | Firmenich Sa | Esters de sorbol en tant qu’ingredients de parfum |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS599538B2 (ja) | 1984-03-03 |
| GB2035799B (en) | 1982-10-20 |
| CH641143A5 (fr) | 1984-02-15 |
| JPS55500058A (fr) | 1980-02-07 |
| GB2035799A (en) | 1980-06-25 |
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Designated state(s): CH DE GB JP US |
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| RET | De translation (de og part 6b) |
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