1101843-02-0

Basic information

• Product Name: Methyl JasMonate (Mixture of isoMers)
• Synonyms: Methyl Jasmonate (90%);MethylJasmonate(mixtureofisomers)>Jasmonic Acid Impurity 1（Methyl Jasmonate）;Cyclopentaneacetic acid, 3-oxo-2-(2Z)-2-penten-1-yl-, methyl ester
• CAS NO: 1101843-02-0
• Molecular Formula: C₁₃H₂₀O₃
• Molecular Weight: 224.2961
• EINECS: 254-705-5
• Mol File: 1101843-02-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 96°C/2.7mmHg(lit.)
• Flash Point: 156°C(lit.)
• Appearance: /
• Density: 1.003±0.06 g/cm3(Predicted)
• Refractive Index: 1.47
• CAS DataBase Reference: Methyl JasMonate (Mixture of isoMers)(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl JasMonate (Mixture of isoMers)(1101843-02-0)
• EPA Substance Registry System: Methyl JasMonate (Mixture of isoMers)(1101843-02-0)

Safety Data

• Hazardous Substances Data: 1101843-02-0(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 36884-25-0 3,4,4,6-tetramethyl-2-methylene-1,3-oxazine 
• 41031-88-3 (Z)-2-(2-pentenyl)-2-cyclopenten-1-one 
• 221682-41-3 (Z)-2-(2-(but-2-en-1-yl)-3-oxocyclopentyl)acetic acid 
• 55254-73-4 2-methoxycarbonyl-3-<(methoxycarbonyl)methyl>-2-<(Z)-2-pentenyl>cyclopentanone 
• 41653-95-6 (Z)-4-heptenoic acid 
• 41031-87-2 (Z)-4-oxodec-7-enal 
• 78078-51-0 cis-1,1-trimethylenedioxy-7-decen-4-one 
• 193155-33-8 3--2-(cis-2-pentenyl)cyclopentenone 
• 122248-46-8 (Z)-1-(p-toluenesulphonyloxy)pent-2-ene 
• 94517-95-0 (Z)-methyl 8-hydroxy-3-oxo-6-octenoate 
• 141621-65-0 methyl (Z)-8-hydroxy-3-oxo-2-<(Z)-2-pentenyl>-6-octenoate 
• 141621-66-1 methyl (Z)-7-formyl-3-oxo-2-<(Z)-2-pentenyl>-6-octenoate 
• 141621-67-2 3-<(formy)methyl>-2-methoxycarbonyl-2-<(Z)-2-pentenyl>cyclopentanone 

Downstream Products

• 66971-95-7 opt.-inakt. (Z)-5-Hydroxymethylen-3-methoxycarbonylmethyl-2-(pent-2-enyl)-cyclopentanon 
• 1211-29-6 Methyl jasmonate 
• 78609-06-0 (3S,7S)-methyl jasmonate 
• 221682-41-3 (Z)-2-(2-(but-2-en-1-yl)-3-oxocyclopentyl)acetic acid 
• 24851-98-7 methyl 3-oxo-2-pentylcyclopentaneacetate 
• 139435-18-0 C₁₃H₁₄⁽²⁾H₆O₃ 
• 139435-19-1 (+/-)-(10-2H,11-2H2,12-2H3)jasmonic acid 

Relevant articles and documents

Syntheses of methyl jasmonate and analogues

This account corresponds to the presentation given by the main author on the occasion of the 2nd Swiss Industrial Symposium in Basel (October 19th, 2018). After a short historical introduction to methyl-jasmonate and methyl-epijasmonate, it essentially focuses on the reported more promising industrial approaches devoted to the synthesis of these naturally occurring odorants isolated from jasmine flowers. Some attempts to simplify these approaches, as well as independent unreported strategies are also presented. Several asymmetric methodologies are also discussed such as Xie hydrogenation, Corey-CBS reduction, enzymatic resolution, and 1,4-addition.

Jasmonoid Synthesis from cis-4-Heptenoic Acid

Jesmonoids with cis-2-pentenyl side-chain such as cis-jasmone, methyl jasmonate, and jasmolone were easily synthesized from cis-4-heptenoic acid obtained by the ring opening reaction of β-propiolactone with di-cis-butenylcuprate.

METHODS FOR PREPARATION OF JASMONATE COMPOUNDS

This invention relates to methods for preparation of jasmonate compounds via a salt of jasmonic acid.

Process for the preparation of chiral epoxides

The invention describes novel malonates and a process for using said malonates for the preparation of chiral epoxides of formula having a cyclanic (1R) configuration, the group in position 2 having a transconfiguration and the epoxy group having a cis-configuration with respect to the substituent in position 1 and wherein R is an alkyl group from C1to C4, linear or branched, and R1is an alkyl or an alkenyl group from C2to C8, linear or branched. The above process comprises the rearrangement of malonate (VII) to malonate (VI) and the decarboxylation reaction of into an ester of formula followed by the stereoselective epoxidation of the thus-obtained compound.