Metyl-dihydrojasmonat

Produktnavn:

Methyl dihydrojasmonate

Synonymer:

3-okso-2-pentyl-cyklopentaneddiksyreametylester; Syklopentaneddikesyre, 3-okso-2-pentyl-, metylester; hedion; CEPIONATEA.K.A. METYL EPI-DIHYDROJASMONATE; (3-Oxo-2-pentyl-cyclopentyl) -eddiksyre-metylester; Methyl-dihydrojasmonat (cis- og trans-blanding); METYLDIHYDROJASMONATE HC; (2-Pentyl-3-oxocycyclopentyl) eddiksyre-metyl

CAS:

24851-98-7

MF:

C13H22O3

MW:

226.31

EINECS:

246-495-9

Product Categories:

Alfabetiske lister; Smaker og dufter; Som et aromakjemikalie for bruk av smak, duft og andre bruksområder; Hemmere; M-N

Mol File:

24851-98-7.mol

Kokepunkt

110 °C0.2 mm Hg(lit.)

density 

0.998 g/mL at 25 °C(lit.)

FEMA

3408 | METHYL DIHYDROJASMONATE

refractive index 

n20/D 1.459(lit.)

Fp

>230 °F

solubility 

H2O: uoppløselig

Vannløselighet

399.8mg/L(25 ºC)

JECFA-nummer

1898

Merck

14.6052

InChIKey

KVWWIYGFBYDJQC-GHMZBOCLSA-N

CAS DataBase Reference

24851-98-7(CAS DataBase Reference)

NIST Chemistry Reference

Syklopentaneddiksyre, 3-okso-2-pentyl-, metylester (24851-98-7)

EPA Substance Registry System

Metyl-3-okso-2-pentyl-cyklopentanacetat (24851-98-7)

Safety Statements 

23-24/25

WGK Tyskland

2

RTECS 

GY2453800

HS kode

29183000

Toxicity

LD50 (g / kg):> 5 oralt hos rotter; > 5 dermalt hos kaniner (Food Chem. Toxicol.)

Description

Methyl dihydrojasmonate has a powerful sweet-floral, jasminelike, somewhat fruity odor. This is the odoriferous component in jasmine oil (Jasminum gradiflorum L.). May be prepared by condensation of 2-pentyl-2-cyclopenten-l-one with ethyl malonate, followed by hydrolysis, decarboxylation, and methylation.

Kjemiske egenskaper

Methyldihydrojasmonate har en kraftig søtblomst, jasminlignende, noe fruktig lukt. Denne forbindelsen er lukt [1] iferøs komponent av jasminolje (Jasminum gradiflorum L.)

Kjemiske egenskaper

Methyl dihydrojasmonate is a jasmine fragrance that is closely related to methyl jasmonate, which occurs in jasmine oil. Methyl dihydrojasmonate has been identified in tea. It is a liquid with a typical fruity, jasmine-like blossom odor.
Metyldihydrojasmonat fremstilles ved Michael-tilsetning av malonsyreestere til 2-pentyl-2-cyklopenten-l-on, etterfulgt av hydrolyse og dekarboksylering av det resulterende (2-pentyl-3-oksocyklopentyl) malonat, og forestring av (2-pentyl-3 oksocyklopentyl) eddiksyre [304] .2-Pentyl-2-cyklopenten-1-on fremstilles ved en aldolkondensasjon mellom cyklopentanon og valeraldehyd og påfølgende isomerisering av den resulterende 2- pentylidensyklopentanon eller ved palladiumkatalyser-karboksylering av allyl 2-okso-1-pentan .
Dealkoxycarbonylation of the malonate can also be accomplished directly with water at elevated temperature.
Methyl dihydrojasmonate of the aforementioned quality consists of a 9 : 1 equilibrium mixture of the trans- and cis-isomers. However, methyl cisdihydrojasmonate is the much more intensive isomer, with a threshold about 20 times lower than that of the trans-isomer. Therefore, methyl dihydrojasmonate qualities with enriched portions of the cis-isomer are also marketed.
These “high-cis” products are colorless liquids with extremely powerful jasmine character.Thedifferent commercial qualities may contain different amounts of the cis-isomer.
High-cis methyl dihydrojasmonate is a valuable material in fine fragrances but suffers from stability problems due to its tendency to isomerize into the equilibrium mixture and, therefore, has only limited usage in other perfumery applications.
High-cis methyl dihydrojasmonate can be produced from the equilibrium mixture by special distillation techniques in which isomerization is effected by the action of sodium carbonate. A high proportion of cis methyl dihydrojasmonate can also be obtained by hydrogenation of methyl dehydrodihydrojasmonate, which is accessible from 1(2-furyl)-hexanol via rearrangement, isomerization, etherification, and condensation with dimethyl malonate.
For andre stereoselektive syntetiske tilnærminger, se gjennomgang.
Av alle mulige isomerer har (+) - (1R) -cis-isomeren den mest karakteristiske og intensive jasminlukten. Derfor er det utviklet en industriell gjennomførbar prosess for produksjon av et metyldihydrojasmonat med en høy del av denne isomeren. Fremgangsmåten omfatter katalytisk hydrogenering av den tilsvarende cyklopenteneddiksyre i nærvær av et ruthenium (II) -kompleks med chirale ligander og påfølgende forestring.
Methyl dihydrojasmonate is used in perfumery for blossom fragrances, particularly in jasmine types.

Forberedelse

Ved kondensering av 2-pentyl-2-cyklopenten-1-on med etylmalonat, etterfulgt av hydrolyse, dekarboksylering og metylering

Smakterskelverdier

Smakskarakteristika ved 20 ppm: søt, blomster, sitrus, fruktig og bær med tutti-frutti undernoter.

Trade name

Claigeon®, Cepionate®(Nippon Zeon),Hedione®,Hedione®HC (Firmenich), Kharismal® (IFF).

Råvarer

Cyclopentanone-->Valeraldehyde