1211-29-6 Usage
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
Different sources of media describe the Chemical Properties of 1211-29-6 differently. You can refer to the following data:
1. Methyl jasmonate has a powerful, floral–herbaceous, sweet, persistent odor.
2. 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
Different sources of media describe the Uses of 1211-29-6 differently. You can refer to the following data:
1. (-)-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.
2. 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
Check Digit Verification of cas no
The CAS Registry Mumber 1211-29-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,2,1 and 1 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1211-29:
(6*1)+(5*2)+(4*1)+(3*1)+(2*2)+(1*9)=36
36 % 10 = 6
So 1211-29-6 is a valid CAS Registry Number.
InChI:InChI=1S/C13H20O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h4-5,10-11H,3,6-9H2,1-2H3
1211-29-6Relevant articles and documents
Lipase-catalyzed preparation of both enantiomers of methyl jasmonate
Kiyota, Hiromasa,Higashi, Emi,Koike, Takanori,Oritani, Takayuki
, p. 1035 - 1038 (2001)
Preparation of both enantiomeric methyl jasmonates 1 was achieved via lipase-catalyzed resolution of (±)-methyl 7-epicucurbate 3. Lipase P (Amano) provided good selectivity both for acylation of (±)-3 (E = 370) and hydrolysis of the corresponding acetate (E = 41). Resolution of (±)-methyl 6,7-diepicucurbate 2 gave poor results. It was found that the (6R,7S)-configuration was suitable for the selective enzymatic reaction and the C-(3) stereochemistry of the substrate did not influence the enzymatic reaction.
Identification of jasmonic acid and abscisic acid as senescencepromoting substances from Cleyera ochnacea DC
Ueda,Kato
, p. 1975 - 1976 (1982)
-
Investigation of synthetic lipase and its use in transesterification reactions
Kecili, Rustem,Say, Rdvan,Ers?z, Arzu,Hür, Deniz,Denizli, Adil
body text, p. 1981 - 1984 (2012/06/29)
A novel synthetic polymer selective for p-nitrophenylpalmitate was synthesized by molecular imprinting technique. We have combined the principle of molecular imprinting with the ability of histidine, glutamic acid and serine to form a catalytic cavity that can promote the catalytic degradation of p-nitrophenyl palmitate. For the creation of such catalytic sites we first synthesized appropriate monomers and used p-nitrophenyl palmitate as a template to synthesize the imprinted polymers and the binding characteristics of the polymers were evaluated. The optimum pH was determined by evaluating different pH values and the hydrolytic activity of synthetic lipase was evaluated in the framework of Micheaelis-Menten kinetics. In addition, the values of maximal rate: Vm (0.68 mM/min) and Michaelis-Menten constant, Km (1.4 × 10 -2 mM) were obtained from Lineweaver-Burk plots for the imprinted polymeric catalyst.
Asymmetric total synthesis of enantiopure (-)-methyl jasmonate via catalytic asymmetric intramolecular cyclopropanation of α-diazo-β-keto sulfone
Takeda, Hiroyuki,Watanabe, Hideaki,Nakada, Masahisa
, p. 8054 - 8063 (2007/10/03)
A new asymmetric total synthesis of enantiopure (-)-methyl jasmonate is described. This synthesis was accomplished starting from the new enantiopure building block prepared via the catalytic asymmetric intramolecular cyclopropanation (IMCP) of the α-diazo-β-keto 1-naphthyl sulfone, which was devised to give good selectivity both in the IMCP reaction and in the C-alkynylation of the intermediate required for the total synthesis of enantiopure (-)-methyl jasmonate.
Synthesis of methyl epijasmonate and cis-3-(2-oxopropyl)-2-(pent-2Z-enyl)-cyclopentan-1-one
Hailes, Helen C,Isaac, Ben,Hashim Javaid
, p. 10329 - 10333 (2007/10/03)
A novel and efficient synthesis of both (±)-methyl epijasmonate and (±)-cis-3-(2-oxopropyl)-2-(pent-2Z-enyl)-cyclopentan-1-one is described. The key step to establish the cis-stereochemistry on the 5-membered ring is an ionic Diels-Alder reaction, which is high yielding and highly regioselective. Subsequent key steps include oxidative cleavage of the six-membered ring, Wittig coupling and for the synthesis of epijasmonate, the haloform reaction.
