DE3225293A1 - 2-METHYL PENTANIC ACID ESTER WITH BRANCHED OR CARBOCYCLIC ALCOHOL RESIDUE, THEIR PRODUCTION AND USE AS A FRAGRANCE - Google Patents
2-METHYL PENTANIC ACID ESTER WITH BRANCHED OR CARBOCYCLIC ALCOHOL RESIDUE, THEIR PRODUCTION AND USE AS A FRAGRANCEInfo
- Publication number
- DE3225293A1 DE3225293A1 DE19823225293 DE3225293A DE3225293A1 DE 3225293 A1 DE3225293 A1 DE 3225293A1 DE 19823225293 DE19823225293 DE 19823225293 DE 3225293 A DE3225293 A DE 3225293A DE 3225293 A1 DE3225293 A1 DE 3225293A1
- Authority
- DE
- Germany
- Prior art keywords
- methylpentanoic acid
- branched
- ester
- formula
- carbocyclic
- 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.)
- Withdrawn
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
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
- C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Beans For Foods Or Fodder (AREA)
Abstract
Description
Henkel straße 67 ^ HENKEL KGaAHenkel street 67 ^ HENKEL KGaA
4ooo Dusseldorf, den 2. Juli 1982 ZR-FE/Patente4ooo Dusseldorf, July 2, 1982 ZR-FE / Patents
Dr. Bz/Et.Dr. Bz / Et.
Patentanmeldung ■ D 6545 Patent application ■ D 6545
"2-Methylpentansäureester mit verzweigtem oder carbocyclischen! Alkoholrest, deren Herstellung und Verwendung als Riechstoffe""2-methylpentanoic acid ester with branched or carbocyclic! Alcohol residue, its production and use as odoriferous substances "
Es wurde gefunden, daß 2-Methylpentansäureester der FormelIt has been found that 2-methylpentanoic acid esters of the formula
CHCH
worin R ein verzweigter oder carbocyclischer Rest der Formel R2 wherein R is a branched or carbocyclic radical of the formula R 2
ist mit R1 = H, CH3 is with R 1 = H, CH 3
R2 = H, CH3, C2H5 R 2 = H, CH 3 , C 2 H 5
R3 = C2H5, n-C3H7, CH(CH3)2, n-C4Hg 1 ? wobei nur einer der Reste R , R .= H sein kannR 3 = C 2 H 5 , nC 3 H 7 , CH (CH 3 ) 2 , nC 4 H g 1 ? where only one of the radicals R, R. = H can be
oder mit R1, R2 = (CH9). η = 3 oder 4
- cn or with R 1 , R 2 = (CH 9 ). η = 3 or 4
- cn
R-* = HR- * = H
wertvolle Riechstoffe mit blumiger, fruchtiger, würziger, holziger Note mit hervorragender Haftfestigkeit sind.valuable fragrances with floral, fruity, spicy, woody Grade with excellent adhesive strength are.
Die Herstellung der Verbindungen erfolgt durch Veresterung von 2-Methylpentansäure mit einem verzweigten oder carbocyclischen Alkohol entsprechend der vorstehenden allgemeinen Formel. Die Veresterungsreaktion erfolgt nach bekannten Verfahren der organischen Chemie. The compounds are produced by esterification of 2-methylpentanoic acid with a branched or carbocyclic alcohol corresponding to the above general formula. The esterification reaction takes place according to known methods of organic chemistry.
Sd 230/438539 5.08.81Sd 230/438539 5.08.81
Patentanmeldung D 6545 J HENKELKGaAPatent application D 6545 J HENKELKGaA
'*· " ZR-FE/Patentfi '* · "ZR-FE / Patentfi
Als alkoholische Komponente kommen vor allem folgende Verbindungen in Betracht: 2-Pentanol, 2-Methylbutanol, 2-Methylpentanol, 2-Ethylbutanol, 2,3-Dimethylbutanol, 2-Ethylhexanol, Cyclopentanon Cyclohexanol.The following compounds in particular are used as the alcoholic component into consideration: 2-pentanol, 2-methylbutanol, 2-methylpentanol, 2-ethylbutanol, 2,3-dimethylbutanol, 2-ethylhexanol, cyclopentanone Cyclohexanol.
Der 2-Methylpentansäure-2-methylpentylester laßt sich besonders vorteilhaft herstellen aus 2-Methylpentanal durch Umsetzung nach Claisen-Tischtschenko mit Aluminiumalkoholat als Katalysator unter Disproportionierung des Aldehyds zu Säure und Alkohol, wobei die Komponenten unmittelbar zu dem gewünschten Ester weiterreagieren. Die beanspruchten 2-Methylpentansäureester zeichnen sich durch interessante blumige, fruchtige, würzige, holzige Geruchsnoten aus. Sie besitzen eine außergewöhnliche Haftfestigkeit und lassen sich sehr gut mit üblichen Parfüminhaltsstoffen und anderen Riechstoffen zu neuartigen Kompositionen kombinieren, denen sie ebenfalls eine hohe Haftfestigkeit verleihen. Der Anteil der 2-Methylpentansäureester in den Riechstoffkompositionen beträgt im allgemeinen 1- 5o Gewichtsprozent. Derartige Kompositionen können zur Parfümierung von kosmetischen Präparaten, wie Cremes, Lotionen, Duftwässern, Aerosolen, Toiletteseifen, Mundpflegemitteln usw., sowie in der Extrait-Parfümerie verwendet werden. Sie können ferner zur Geruchsverbesserung technischer Produkte, wie Wasch- und Reinigungsmittel, Weichspüler, dienen. Es werden etwa o,o5 - 2 Gewichtsprozent an Komposition, bezogen auf das gesamte Produkt, eingesetzt.The 2-methylpentanoic acid 2-methylpentyl ester can be particularly advantageous produced from 2-methylpentanal by reaction according to Claisen-Tischtschenko with aluminum alcoholate as a catalyst with disproportionation of the aldehyde to acid and alcohol, the components reacting further directly to form the desired ester. The claimed 2-methylpentanoic acid esters are characterized by interesting floral, fruity, spicy, woody odor notes. They have exceptional adhesive strength and can be easily combined with common perfume ingredients and other fragrances to create new ones Combine compositions to which they also give high adhesive strength. The proportion of 2-methylpentanoic acid ester in the Fragrance compositions is generally 1-50 percent by weight. Such compositions can be used for perfuming cosmetic Preparations such as creams, lotions, fragrances, aerosols, toilet soaps, Oral care products etc., as well as in the Extrait perfumery. You can also use technical means to improve odor Products such as detergents and cleaning agents, fabric softeners, are used. About 0.05 - 2 percent by weight of composition, based on the entire product.
Die beanspruchten 2-Methylpentansäureester sind neue Verbindungen, mit Ausnahme des 2- Methylpentansäure-2-methylpentylesters. Letzterer ist in. Beilsteins Handbuch der Organischen Chemie, Bd. 2, E II, < Seite 943, beschrieben. Es wird jedoch keine Aussage über Geruchsqualität oder parfümistische Eignung gemacht. The claimed 2-methylpentanoic acid esters are new compounds, with the exception of 2-methylpentanoic acid-2-methylpentyl ester. The latter is described in Beilstein's Handbook of Organic Chemistry, Vol. 2, E II, < page 943. However, no statement is made about the quality of the smell or suitability for perfumery.
Aus DE-OS 25 3o 227 sind niedere Alkylester der 2-Methylpentensäure, gegebenenfalls im Gemisch mit niederen Alkylestern der 2-Methylpentansäure bekannt, die als Würzessenz für flüssige und feste Lebensmittel und dergleichen bzw. als Parfüm für kosmetische und hygienische Präparate dienen. Es warden jedoch weder die beanspruchten 2-Methylpentansäureester mit verzweigter oder carbocyclischer Alkoholkompnente, noch deren besondere Eigenschaften erwähnt.From DE-OS 25 3o 227 are lower alkyl esters of 2-methylpentenoic acid, optionally mixed with lower alkyl esters of 2-methylpentanoic acid known as a seasoning essence for liquid and solid foods and the like or as a perfume for cosmetic and hygienic Serving preparations. However, neither the claimed 2-methylpentanoic acid esters are used with branched or carbocyclic alcohol component, their special properties are also mentioned.
Sd 230/438539 5. 08. 81Sd 230/438539 August 5, 81
Patentanmeldung D 6545 HENKELKGaA Patent application D 6545 HENKELKGaA
S ZR-FE/Patente S ZR-FE / patents
1. Allgemeine Herstellvorschrift 1. General manufacturing instructions
o,l Mol 2-Methylpentansäure, o,12 Mol verzweigter Alkohol, loo ml Cyclohexan und o,l g Paratoluolsulfonsäure werden zum Sieden erhitzt. Das freigesetzte Wasser wird azeotrop ausgekreist. Nach beendeter Umsetzung wird das auf Raumtemperatur abgekühlte Reaktionsgemisch zunächst mit Io %iger Natronlauge, danach mit gesättigter Natriumsulfatlösung neutral gewaschen, über Natriumsulfat getrocknet, im Vakuum eingeengt und über eine 2o cm FUl1-körperkolonne destilliert.0.1 mol of 2-methylpentanoic acid, 0.12 mol of branched alcohol, 100 ml of cyclohexane and 0.1 g of paratoluenesulfonic acid are heated to the boil. The released water is removed from the system azeotropically. To When the reaction has ended, the reaction mixture, which has been cooled to room temperature, is first mixed with 10% strength sodium hydroxide solution, then with saturated sodium sulfate solution, washed neutral, dried over sodium sulfate, concentrated in vacuo and passed through a 20 cm FUl1 body column distilled.
Ausbeute: 7o - 9o % d. Th.Yield: 70-90 % of theory Th.
Folgende Ester wurden nach dieser allgemeinen Herstellungsvorschrift hergestellt:The following esters were prepared according to this general manufacturing procedure manufactured:
la) 2-Methylpentansäure-2-pentylester Kp18 86 0C η20 1,414la) 2-methylpentanoic acid 2-pentyl ester bp 18 86 0 C η 20 1.414
NMR (CCl4) δ = 4,85 ppm IH mult.NMR (CCl 4 ) δ = 4.85 ppm IH mult.
2,3 ppm 1 H mult. Geruch: fruchtig, nach Banane2.3 ppm 1 H mult. Smell: fruity, like banana
Ib) 2-Metyh1 pen tan sä ure-2-methyl butyl ester Kp18 93 0C η20 1,419Ib) 2-Metyh1 pen tan acid-2-methyl butyl ester Kp 18 93 0 C η 20 1.419
NMR (CCl4) 6 = 3,85 ppm 2 H dubl .NMR (CCl 4 ) 6 = 3.85 ppm 2 H doubl.
2,3 ppm IH mult.2.3 ppm IH mult.
Geruch: Kamille-Note, würzigSmell: note of chamomile, spicy
ic) 2-Metyhlpentansäure-2-methylpentylester Kp28 113 0C n20 1,422 NMR (CDCl3) δ 3,9 ppm 2 H d.dubl .ic) 2-methylpentanoic acid-2-methylpentyl ester bp 28 113 0 C n 20 1.422 NMR (CDCl 3 ) δ 3.9 ppm 2 H d.dubl.
2,45 ppm 1 H mult.2.45 ppm 1 H mult.
Geruch: Apfel schale-Note , rosig, grünSmell: Apple peel note, rosy, green
Sd 230/438539 5.08.81Sd 230/438539 5.08.81
Patentanmeldung D 6545Patent application D 6545
ZR-FE/PatenteZR-FE / patents
ld) 2-Methylpentansäure-2-ethy! butyl esterld) 2-methylpentanoic acid-2-ethy! butyl ester
Kp16 99 UCKp 16 99 U C
1,4251.425
NMR (CDCl3) δ = 4,0 ppm 2 H dubl.NMR (CDCl 3 ) δ = 4.0 ppm 2 H doubl.
2,45 ppm 1 H mult.2.45 ppm 1 H mult.
Geruch: fruchtigSmell: fruity
le) 2-Methylpentansäure-2,3-dimethyl butyl ester Kp21 98 0C nj·0 1,424 NMR (CDCl3) δ = 3,95 ppm 2 H d.dubl.le) 2-methylpentanoic acid-2,3-dimethyl butyl ester bp 21 98 0 C nj · 0 1.424 NMR (CDCl 3 ) δ = 3.95 ppm 2 H d.dubl.
2,4 ppm 1 H mult.2.4 ppm 1 H mult.
Geruch:würzig
Lf) 2-Methylpentansäure-2-ethylhexylesterSmell: spicy
Lf) 2-methylpentanoic acid 2-ethylhexyl ester
KpKp
123 0C123 0 C
1,4301.430
NMR (CDCl3) δ = 4,0 ppm 2 H d.dublNMR (CDCl 3 ) δ = 4.0 ppm 2 H double duplex
2,45 ppm 1 H mult.2.45 ppm 1 H mult.
Geruch: holzig, Guajak-NoteOdor: woody, guaiac note
Ig) 2-Methy1pentansäure-eye!open ty 1 ester Kp16 96 0C n^0 1,438 ■ NMR (CDCl3) δ = 5,1 ppm" IH mult.Ig) 2-methylpentanoic acid eye! Open ty 1 ester bp 16 96 0 C n ^ 0 1.438 ■ NMR (CDCl 3 ) δ = 5.1 ppm "IH mult.
2,4 ppm 1 H mult.2.4 ppm 1 H mult.
Geruch : würzi gOdor: spicy
lh) 2-Methylpentansäure-cyclohexylester Kp25 120 0C np° 1,444 NMR (CDCl3) δ = 4,8 ppm 1 H mult.lh) 2-methylpentanoic acid cyclohexyl ester bp 25 120 0 C np ° 1.444 NMR (CDCl 3 ) δ = 4.8 ppm 1 H mult.
2,4 ppm Geruch: Rosenoxid-Note2.4 ppm Odor: rose oxide note
1 H mult.1 H mult.
Sd 230/438539 5.08.81Sd 230/438539 5.08.81
Patentanmeldung D 6545 HENKELKGaAPatent application D 6545 HENKELKGaA
^ ZR-FE/Patente^ ZR-FE / Patents
-k--k-
2. Claisen-Tischtschenko-Reaktion mit 2-Methylpentanal zur Herstellung von 2-Methylpentansäure-2-methylpentylester2. Claisen-Tischtschenko reaction with 2-methylpentanal for production of 2-methylpentanoic acid-2-methylpentyl ester
loo g 2-Methylpentanal wurden unter Rühren tropfenweise bei Raumtemperatur mit 5 g eines Gemisches aus zwei Teilen Aluminiumisopropylat und einem Teil Aluminiumisobutyrat versetzt.100 g of 2-methylpentanal were added dropwise with stirring at room temperature 5 g of a mixture of two parts of aluminum isopropylate and one part of aluminum isobutyrate are added.
Nach Zugabe von ca. 1 g des Alkoholat-Gemisches trat eine exotherme Reaktion ein. Die Reaktionstemperatur wurde durch Kühlung des Kolbens mit Eiswasser unter 4o°C gehalten. Nach Zugabe von insgesamt 3 g des Alkoholat-Gemisches hielt sich die Reaktionstemperatur ohne äußere Kühlung bei 3o°C.After adding about 1 g of the alcoholate mixture, an exothermic occurred Response a. The reaction temperature was kept below 40 ° C. by cooling the flask with ice water. After adding a total of The reaction temperature was maintained at 30 ° C. for 3 g of the alcoholate mixture without external cooling.
Das klare, farblose Reaktionsgemisch wurde unter Kühlung mit 16 g Io %\ger Schwefelsäure versetzt und in 5oo ml Ether aufgenommen. Die wäßrige Phase wurde abgetrennt, die organische Phase mit Wasser neutral gewaschen, getrocknet und eingeengt.The clear, colorless reaction mixture was admixed with 16 g of 10% sulfuric acid with cooling and taken up in 500 ml of ether. The aqueous phase was separated off, and the organic phase was washed neutral with water, dried and concentrated.
Io4 g Rohprodukt wurden über eine 2o cm Füllkörperkolonne destilliert und ergaben 81,8 g des gewünschten Esters mit einem Siedepunkt von lo4°C bei 17 mbar. ■Io4 g of crude product were passed through a 20 cm packed column distilled and gave 81.8 g of the desired ester with a boiling point of lo4 ° C at 17 mbar. ■
Sd 230 3. 08.80Sd 230 August 3, 1980
Patentanmeldung ηPatent application η
(f HENKELKGaA(f HENKELKGaA
ZR-FE/PatenteZR-FE / patents
2-Methylpentansäure-2-methyIpenty1ester2-methylpentanoic acid-2-methylpentanoate
GalaxolidR (IFF) o-tert.-Butylcyclohexylacetat Myrcenylacetat Aldehyd C 14 sogen.Galaxolid R (IFF) o-tert-butylcyclohexyl acetate myrcenyl acetate aldehyde C 14 absorbed.
Amylbutyrat Isobornylacetat Maltol (5 %ig in DPG) Cyclovertal (Henkel) Pfefferminzöl Diethylphthalat 100 Gew.-TeileAmyl butyrate isobornyl acetate maltol (5% in DPG) Cyclovertal (Henkel) peppermint oil diethyl phthalate 100 parts by weight
1000 Gew.-Teile1000 parts by weight
. Holz-Base . Wood base
2-Methylpentansäui e-2-ethylhexylester Formaldehyd-methyl-cyclododecylacetal2-methylpentane acid e-2-ethylhexyl ester Formaldehyde-methyl-cyclododecyl acetal
ρ-tert.-Butylcyclohexylacetat Vetiverylacetat Sandel (Haarmann & Reimer) Methyljonon Cumarin Phenylethylalkohol 150 Gew.-Teile 400 " " 100 w M 100 " " 100 » " 50 " " 50 » " 50 " " Gew.-Teileρ-tert-butylcyclohexyl acetate vetiveryl acetate sandel (Haarmann & Reimer) methyljonon coumarin phenylethyl alcohol 150 parts by weight 400 "" 100 w M 100 "" 100 »" 50 "" 50 »" 50 "" parts by weight
Sd 230/438539 5. 08.81Sd 230/438539 08.08.81
Claims (5)
K = H5 CH^, CpHf-2
K = H 5 CH ^, CpHf-
Rd = H,or with R 1 , R 2 = (CHJ n , η = 3 or 4
R d = H,
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19823225293 DE3225293A1 (en) | 1982-07-07 | 1982-07-07 | 2-METHYL PENTANIC ACID ESTER WITH BRANCHED OR CARBOCYCLIC ALCOHOL RESIDUE, THEIR PRODUCTION AND USE AS A FRAGRANCE |
EP83710043A EP0098791B1 (en) | 1982-07-07 | 1983-06-29 | 2-methylpentanoic-acid esters with branched or carbocyclic alcohols, their preparation and use as perfuming agents |
AT83710043T ATE18352T1 (en) | 1982-07-07 | 1983-06-29 | 2-METHYLPENTAEUR ESTERS WITH A BRANCHED OR CARBOCYCLIC ALCOHOL REST, THEIR PRODUCTION AND USE AS FRAGRANCES. |
DE8383710043T DE3362425D1 (en) | 1982-07-07 | 1983-06-29 | 2-methylpentanoic-acid esters with branched or carbocyclic alcohols, their preparation and use as perfuming agents |
JP58121149A JPS5921645A (en) | 1982-07-07 | 1983-07-05 | 2-methylpentanoic acid ester having branched or carbon cyclic alcohol residue, manufacture and perfume |
ES523902A ES8403851A1 (en) | 1982-07-07 | 1983-07-06 | 2-Methylpentanoic-acid esters with branched or carbocyclic alcohols, their preparation and use as perfuming agents. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19823225293 DE3225293A1 (en) | 1982-07-07 | 1982-07-07 | 2-METHYL PENTANIC ACID ESTER WITH BRANCHED OR CARBOCYCLIC ALCOHOL RESIDUE, THEIR PRODUCTION AND USE AS A FRAGRANCE |
Publications (1)
Publication Number | Publication Date |
---|---|
DE3225293A1 true DE3225293A1 (en) | 1984-01-12 |
Family
ID=6167785
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19823225293 Withdrawn DE3225293A1 (en) | 1982-07-07 | 1982-07-07 | 2-METHYL PENTANIC ACID ESTER WITH BRANCHED OR CARBOCYCLIC ALCOHOL RESIDUE, THEIR PRODUCTION AND USE AS A FRAGRANCE |
DE8383710043T Expired DE3362425D1 (en) | 1982-07-07 | 1983-06-29 | 2-methylpentanoic-acid esters with branched or carbocyclic alcohols, their preparation and use as perfuming agents |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE8383710043T Expired DE3362425D1 (en) | 1982-07-07 | 1983-06-29 | 2-methylpentanoic-acid esters with branched or carbocyclic alcohols, their preparation and use as perfuming agents |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0098791B1 (en) |
JP (1) | JPS5921645A (en) |
AT (1) | ATE18352T1 (en) |
DE (2) | DE3225293A1 (en) |
ES (1) | ES8403851A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5141921A (en) * | 1990-04-13 | 1992-08-25 | Takasago International Corporation | Perfume composition |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1889641A1 (en) * | 2006-08-18 | 2008-02-20 | Cognis IP Management GmbH | Cosmetic compositions containing an ester obtained from 2-ethylbutanol |
EP1905419A1 (en) * | 2006-09-20 | 2008-04-02 | Cognis IP Management GmbH | Cosmetic composition and cosmetic oil substances |
JP5080776B2 (en) * | 2006-10-06 | 2012-11-21 | 花王株式会社 | Ester compound |
CN102942480B (en) * | 2012-11-12 | 2014-11-19 | 金溪县鑫润香料实业有限公司 | Production process of matricaria ester |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1006848B (en) * | 1956-02-07 | 1957-04-25 | Basf Ag | Process for the continuous production of acid-free esters of low molecular weight aliphatic carboxylic acids |
CH435420A (en) * | 1965-06-01 | 1967-05-15 | Bbc Brown Boveri & Cie | Stator earth fault protection device for generators in block connection |
NL7002359A (en) * | 1970-02-19 | 1971-08-23 | ||
US3714236A (en) * | 1970-08-07 | 1973-01-30 | Eastman Kodak Co | Process for producing mixed esters from aldehydes |
CH551361A (en) * | 1971-02-26 | 1974-07-15 | Givaudan & Cie Sa | PROCESS FOR MANUFACTURING A NEW (ALPHA) METHYL BUTTERIC ACID ESTER. |
US3907718A (en) * | 1974-07-22 | 1975-09-23 | Int Flavors & Fragrances Inc | 2-Methyl-4-pentenoic acid ester fragrance |
DE2530227C3 (en) * | 1974-07-22 | 1980-05-29 | Int Flavors & Fragrances Inc | 2-methyl-substituted pentenoic acid esters, 2-methyl-cis-3-pentenoic acid, and their acid and ester mixtures, their production process and use |
DE2626142A1 (en) * | 1976-06-11 | 1977-12-22 | Henkel Kgaa | USE OF ALIPHATIC 2-METHYL-2-ALKYL ALKANOIC ACID ESTERS AS FRAGRANCE SUBSTANCES AND FRAGRANCE COMPOSITIONS CONTAINING THEM |
-
1982
- 1982-07-07 DE DE19823225293 patent/DE3225293A1/en not_active Withdrawn
-
1983
- 1983-06-29 DE DE8383710043T patent/DE3362425D1/en not_active Expired
- 1983-06-29 EP EP83710043A patent/EP0098791B1/en not_active Expired
- 1983-06-29 AT AT83710043T patent/ATE18352T1/en not_active IP Right Cessation
- 1983-07-05 JP JP58121149A patent/JPS5921645A/en active Pending
- 1983-07-06 ES ES523902A patent/ES8403851A1/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5141921A (en) * | 1990-04-13 | 1992-08-25 | Takasago International Corporation | Perfume composition |
Also Published As
Publication number | Publication date |
---|---|
JPS5921645A (en) | 1984-02-03 |
EP0098791B1 (en) | 1986-03-05 |
EP0098791A1 (en) | 1984-01-18 |
ES523902A0 (en) | 1984-04-01 |
ES8403851A1 (en) | 1984-04-01 |
ATE18352T1 (en) | 1986-03-15 |
DE3362425D1 (en) | 1986-04-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0033928B1 (en) | Use of alkyl-substituted 1,3-dioxolanes as perfumes, and perfume compositions containing them | |
DE2455761C2 (en) | Use of hydrogenated methyl ionones and their derivatives as fragrances, processes for their preparation and new hydrogenated methyl ionone derivatives | |
EP0168415A1 (en) | Utilization of salicylic acid esters as perfuming substances, perfuming compositions containing them and new salicylic acid esters. | |
DE2910579C2 (en) | ||
EP0098791B1 (en) | 2-methylpentanoic-acid esters with branched or carbocyclic alcohols, their preparation and use as perfuming agents | |
DE2729121C3 (en) | Use of cyclopentane derivatives as fragrances and new cyclopentane derivatives | |
EP0021356B1 (en) | 4(5)-acetyl-7,7,9(7,9,9)-trimethyl-bicyclo(4.3.0)non-1-ene, its preparation and use as perfume, and perfume compositions containing it | |
EP0022460B1 (en) | Aliphatic ethers of hydroxymethylcyclododecane and their utilization in the preparation of odorant compositions | |
DE3622600A1 (en) | NEW ALIPHATIC ALDEHYDE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A FRAGRANCE | |
DE1593442A1 (en) | Process for the preparation of cyclic compounds | |
DE2363535C2 (en) | 2,7-Dimethyl-5,7-octadien-2-ol, its methyl ether and its acetic acid ester, process for their preparation and their use | |
EP0025869B1 (en) | 3-methyl-cyclohexadecen-5-one-1, process for its preparation, and its use as odorant | |
EP0120274B1 (en) | Esters of 2-methylpentanoic acid, their preparation and use as flavouring compounds, and flavouring compositions containing these compounds | |
CH628809A5 (en) | SMELL COMPOSITION. | |
EP0022462B1 (en) | 2-alkoxyethyl-cycloalkyl-ethers, compositions containing these, and their utilization for the preparation of odorant compositions | |
DE3045373A1 (en) | Use of 3-hydroxy-2,2-di:methyl-propionate ester(s) as fragrances - including new propyl ester | |
EP0043507A2 (en) | 2,4-Dioxa-7,10 methano-spiro(5,5)undecanes, their preparation as well as perfume compositions containing them | |
DE602004009814T2 (en) | 3-isopropyl-1-methylcyclopentyl derivatives and their use in perfumery applications | |
EP0291849B1 (en) | 4-methyl-4-phenyl-pentan-1-als, their preparation and application as aroma chemicals | |
DE68906256T2 (en) | Tricyclic ketones, processes for their preparation and their use as fragrances. | |
EP0120290B1 (en) | Oxaspirododecane compounds, their preparation and their use as perfumes, and perfume compositions containing them | |
EP0051240B1 (en) | Acetylcycloundecane and acetylcycloundecene, their application and perfumed compositions containing them | |
DE2757559A1 (en) | USE OF THE 3,5,5-TRIMETHYLHEXANIC ACID ESTERS AS FRAGRANCES AND THESE FRAGRANCING COMPOSITIONS | |
DE1802121A1 (en) | Fragrance compositions | |
DE2407817A1 (en) | NEW FRAGRANCES |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
8139 | Disposal/non-payment of the annual fee |