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 FRAGRANCE

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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
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DE
Germany
Prior art keywords
methylpentanoic acid
branched
ester
formula
carbocyclic
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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.)
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DE19823225293
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German (de)
Inventor
Klaus Prof. Dr. 4150 Krefeld Bruns
Ulf-Armin Dr. 4000 Düsseldorf Schaper
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Priority to DE19823225293 priority Critical patent/DE3225293A1/en
Priority to DE8383710043T priority patent/DE3362425D1/en
Priority to AT83710043T priority patent/ATE18352T1/en
Priority to EP83710043A priority patent/EP0098791B1/en
Priority to JP58121149A priority patent/JPS5921645A/en
Priority to ES523902A priority patent/ES8403851A1/en
Publication of DE3225293A1 publication Critical patent/DE3225293A1/en
Withdrawn legal-status Critical Current

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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

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  • 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

1. Claims (for the Contracting States : BE, CH, DE, FR, GB, IT, LI, NL) The use of 2-methylpentanoic acid esters corresponding to the following formula see diagramm : EP0098791,P6,F3 in which R is a branched or carbocyclic radical corresponding to the formula see diagramm : EP0098791,P6,F4 wherein R**1 = H, CH3 R**2 = H, CH3 , C2 H5 R**3 = C2 H5 , n-C3 H7 , CH(CH3 )2 , n-C4 H9 with the proviso that only one of the radicals R**1 , R**2 can represent H, or wherein R**1 , R**2 = (CH2 )n , n = 3 or 4 R**3 = H as perfumes. 1. Claims (for the Contracting State AT) The use of 2-methylpentanoic acid esters corresponding to the following formula see diagramm : EP0098791,P7,F3 in which R is a branched or carbocyclic radical corresponding to the following formula see diagramm : EP0098791,P7,F4 wherein R**1 = H, CH3 R**2 = H, CH3 , C2 H5 R**3 = C2 H5 , n-C3 H7 , CH(CH3 )2 , n-C4 H9 with the proviso that only one of the radicals R**1 , R**2 can represent H, or wherein R**1 , R**2 = (CH2 )n , n = 3 or 4 R**3 = H as perfumes.

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

BeispieleExamples

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

HENKEL KGaAHENKEL KGaA

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

Apfel-KompositionApple composition

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

400400 IlIl IlIl 160160 IlIl IlIl 100100 IlIl IlIl 8585 titi IlIl 1515th titi IlIl 2020th titi IlIl 55 titi - η. -- η. - 33 IlIl IlIl 22 IlIl ηη 110110 ηη ηη

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)

Patentanmeldung D 6545 HENKEL KGuAPatent application D 6545 HENKEL KGuA ZR-FE/PatenteZR-FE / patents PatentansprücheClaims IJ Verwendung von 2-Methylpentansaureestern der FormelIJ Use of 2-methylpentanoic acid esters of the formula CH,CH, COORCOOR worin R ein verzweigter oder carbocyclischer Rest der Formel R2 wherein R is a branched or carbocyclic radical of the formula R 2 R1 R 1 ist mit R1 = H, CH, 9 ύ is with R 1 = H, CH, 9 ύ - ti, υπΛ, "p"c- ti, υπΛ, "p" c R3 = C2H5Zn-C3H7, CH(CH3)2, n-C4Hg R 3 = C 2 H 5 Zn-C 3 H 7 , CH (CH 3 ) 2 , nC 4 H g 11 wobei nur einer der Reste R , R .= H sein kann oder mit R1, R2 = (CH2Jn, η = 3 oderwhere only one of the radicals R, R. = H or with R 1 , R 2 = (CH 2 J n , η = 3 or R-J —14 — ΠR-J -14 - Π als Riechstoffe.as fragrances. 2. Riechstoffkomposition, dadurch gekennzeichnet, daß sie 2-Methylpentansäureester gemäß Anspruch 1 in einer Menge von 1 - 5o Gewichtsprozent, bezogen auf die gesamte Komposition, enthalten.2. Fragrance composition, characterized in that it is 2-methylpentanoic acid ester according to claim 1 in an amount of 1-5o percent by weight, based on the total composition. Sd 230 3. 08.80Sd 230 August 3, 1980 Patentanmeldung D 6545 I HENKEL KGaAPatent application D 6545 I HENKEL KGaA ZR-FE/PatenteZR-FE / patents 3. Verfahren zur Herstellung von 2-Methylpentansäureestern des Anspruchs 1 durch Veresterung von 2-Methylpentansäure mit einem der allgmeinen Formel entsprechenden verzweigten oder carbocyclischen Alkohol.3. Process for the preparation of 2-methylpentanoic acid esters of claim 1 by esterification of 2-methylpentanoic acid with a branched or carbocyclic acid corresponding to the general formula Alcohol. 4. Verfahren zur Herstellung von 2-Methylpentansäure-2-methylpentylester durch Umsetzung von 2-Methylpentanal nach Claisen-Tischtschenko mit Aluminiumalkoholat als Katalysator.4. Process for the preparation of 2-methylpentanoic acid-2-methylpentyl ester by converting 2-methylpentanal according to Claisen-Tischtschenko with aluminum alcoholate as a catalyst. 5. Neue 2-Methylpentansäureester der Formel5. New 2-methylpentanoic acid esters of the formula CH3 CH 3 ' worin R ein verzweigter oder carbocyclischer Rest der Formel'wherein R is a branched or carbocyclic radical of the formula R2 R 2 R1 R 1 ist, mit R1 = H, CH,is, with R 1 = H, CH, 2
K = H5 CH^, CpHf-2
K = H 5 CH ^, CpHf- R3 = C2H5, ID-C3H7, CH(CH3)2, n-C4Hg 1 2 wobei nur einer der Reste R , RR 3 = C 2 H 5 , ID-C 3 H 7 , CH (CH 3 ) 2 , nC 4 H g 1 2 where only one of the radicals R, R = H sein kann,= Can be H, oder mit R1, R2 = (CHJn, η = 3 oder 4
Rd = H,or with R 1 , R 2 = (CHJ n , η = 3 or 4
R d = H, mit Ausnahme des 2-Methylpentansäure-2-methy^penty^esterswith the exception of 2-methylpentanoic acid-2-methy ^ penty ^ ester Sd 230/438539 S. 08. SISd 230/438539 p. 08. SI
DE19823225293 1982-07-07 1982-07-07 2-METHYL PENTANIC ACID ESTER WITH BRANCHED OR CARBOCYCLIC ALCOHOL RESIDUE, THEIR PRODUCTION AND USE AS A FRAGRANCE Withdrawn DE3225293A1 (en)

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
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
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.
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
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)

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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

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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)

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EP (1) EP0098791B1 (en)
JP (1) JPS5921645A (en)
AT (1) ATE18352T1 (en)
DE (2) DE3225293A1 (en)
ES (1) ES8403851A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5141921A (en) * 1990-04-13 1992-08-25 Takasago International Corporation Perfume composition

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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

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US5141921A (en) * 1990-04-13 1992-08-25 Takasago International Corporation Perfume composition

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EP0098791B1 (en) 1986-03-05
ES523902A0 (en) 1984-04-01
ES8403851A1 (en) 1984-04-01
EP0098791A1 (en) 1984-01-18
JPS5921645A (en) 1984-02-03
ATE18352T1 (en) 1986-03-15
DE3362425D1 (en) 1986-04-10

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