METHYL JASMONATE Chemical Properties

Boiling point:

110 °C0.2 mm Hg(lit.)

alpha 

D -76.5° (c = 3.4 in CH3OH)

Density 

1.03 g/mL at 25 °C(lit.)

FEMA 

3410 | METHYL JASMONATE

refractive index 

n20/D 1.474(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

Odor

at 100.00 %. floral fresh petal magnolia oily waxy

Odor Type

floral

JECFA Number

1400

LogP

2.12

CAS DataBase Reference

1211-29-6(CAS DataBase Reference)

EPA Substance Registry System

Cyclopentaneacetic acid, 3-oxo-2-(2Z)-2-pentenyl-, methyl ester, (1R,2R)- (1211-29-6)

Safety Information

WGK Germany 

3

Hazardous Substances Data

1211-29-6(Hazardous Substances Data)

MSDS

• Language:English Provider:SigmaAldrich

METHYL JASMONATE Usage And Synthesis

Description

Methyl jasmonate has a powerful, floral-herbaceous, sweet, persistent odor. Can be isolated from jasmine oil; or it may be prepared synthetically (probably in the trans-form) from muconic acid via the methyl-3-oxo-cyclopenthyl acetate.

Chemical Properties

Methyl jasmonate has a powerful, floral–herbaceous, sweet, persistent odor.

Chemical Properties

METHYL JASMONATE is a volatile component of jasmine flower absolute. It is a colorless to pale yellow liquid, bp0.125 kPa 116–118 °C, d20 20 1.022–1.028, n20 D 1.473–1.477, possessing an odor reminiscent of the floral heart of jasmine. Synthesis of the title compound is accomplished by reaction of (2Z)-2-buten-1-yl bromide with Li in the presence of copper-(I) iodide, and the product is treated with a mixture of 2-methylene- and 4-methylene-3-oxocyclopentylacetic acid methyl ester. The aforementioned ester mixture is obtained by reaction of methyl 3-oxocyclopentylacetate with formaldehyde.
An alternative route uses a palladium-catalyzed decarboxylation of the readily available substituted allyl 2-oxocyclopentanecarboxylates, which leads to the corresponding cyclopentenones. Addition of dimethylmalonate, with subsequent saponification/decarboxylation and, if necessary, (Z)-selective hydrogenation, yields methyl jasmonate:
Methyl jasmonate exists in an equilibrium mixture in which the trans-isomer dominates. But of all possible four enantiomeric isomers, chiefly the minor (+)-cis-isomer is responsible for the typical sensory properties of methyl jasmonate. Therefore, several approaches to obtain this material selectively have been developed either by directed syntheses or by enrichment using special isomerization distillation techniques.
Methyl jasmonate is used in fine fragrances where it provides rich, soft effects in jasmine and muguet compositions.

Occurrence

Reportedly identified in jasmine oil (Jasminum grandiflorum L.) and in Tunisian rosemary. Also found in lemon peel oil, peppermint oil and green and fermented tea

Uses

(-)-Jasmonic Acid Methyl Ester can be used in biological study where it can exert concn.-dependent effect on SE1 and upregulated SE1 expression in both young and mature leaves of Gynostemma pentaphyllum, with greater upregulation in young leaves than in mature leaves.

Uses

Methyl ester in perfumes.

Definition

ChEBI: A jasmonate ester that is the methyl ester of jasmonic acid.

Aroma threshold values

Detection: 5.7 ppm

Taste threshold values

Taste characteristics at 15 ppm: floral, fruity, green, waxy, seedy and melon-like

Trade name

Jasmoneige® (Nippon Zeon), Splendione® (Firmenich)

Synthesis

Can be isolated from jasmine oil; synthetically it can be prepared (probably in the trans-form) from muconic acid via the methyl-3-oxo-cyclopentyl acetate

METHYL JASMONATE(1211-29-6)Related Product Information

• (±)-JASMONIC ACID
• (-)-JASMONIC ACID
• Methyl-(+/-)Jasmonate=JasmonsreMethylester=JasmonicacidMethylester,trans-Methyl jasmonate
• Methyl JasMonate (Mixture of isoMers)
• Jasmonic Acid-d5 (Mixture of Diastereomers, (-)-trans major)
• N-[(-)-JASMONOYL]-(S)-ISOLEUCINE (JaIle)
• 3-oxo-2-pentylcyclopentaneacetic acid
• (+)-trans-Jasmonic Acid
• Methyl isocostate
• L-Isoleucine, N-[2-[(1R,2S)-3-oxo-2-(2Z)-2-penten-1-ylcyclopentyl]acetyl]-
• (±)-JASMONIC ACID METHYL ESTER (MeJA)
• CYCLOPENTYLACETIC ACID
• Jasmone
• CIS-2-PENTENE
• Methyl dihydrojasmonate
• METHYL JASMONATE 95+%
• (+/-)-JASMONIC ACID
• METHYL JASMONATE