20073-13-6

Basic information

• Product Name: Methyl Jasmonate
• Synonyms: methyl [1alpha,2beta(Z)]-(±)-3-oxo-2-(pent-2-enyl)cyclopentaneacetate;Jasmonicacidmethylester=MethylJasmonate;Cyclopentaneacetic acid, 3-oxo-2-(2Z)-2-pentenyl-, methyl ester, (1R,2 R)-rel-;Methyl-(+/-)Jasmonate=JasmonsreMethylester=JasmonicacidMethylester;trans-Methyl jasmonate;rac-trans JasMonic Acid Methyl Ester;(1R,2R)-rel-3-Oxo-2-(2Z)-2-penten-1-ylcyclopentaneacetic Acid Methyl Ester;(Z)-trans-(+/-)-
• CAS NO: 20073-13-6
• Molecular Formula: C₁₃H₂₀O₃
• Molecular Weight: 224.298
• EINECS: 243-497-1
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Chiral Reagents, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 20073-13-6.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 175 °C(Press: 0.08 Torr)
• Flash Point: 156°C
• Appearance: /
• Density: 1,02 g/cm3
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol
• CAS DataBase Reference: Methyl Jasmonate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl Jasmonate(20073-13-6)
• EPA Substance Registry System: Methyl Jasmonate(20073-13-6)

Safety Data

• Safety Statements: 23-24/25
• Hazardous Substances Data: 20073-13-6(Hazardous Substances Data)

Usage

Uses

Jasmonic acid (J210520) analog, a constituent of essential oil of Jasmine.

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

Upstream product

• 128777-72-0 β-Cucurbic acid methyl ester 
• 51388-61-5 [(1S,2S,3R)-3-Hydroxy-2-((Z)-pent-2-enyl)-cyclopentyl]-acetic acid methyl ester 
• 3572-65-4 jasmonic acid 
• 74-88-4 methyl iodide 
• 16400-32-1 1-bromo-pent-2-yne 
• 1117-71-1 methyl-4-bromo-2-butenoate 
• 57314-31-5 methyl (Z)-4,4-dimethoxy-2-butenoate 
• 63528-42-7 2-Acetyl-3-dimethoxymethyl-pentanedioic acid dimethyl ester 
• 51388-61-5 <1R*,2S*,3R*>-1-Hydroxy-2-<(3Z)-pentenyl>-3-methoxycarbonylmethylcyclopentane 
• 51388-61-5 [(1R,2S,3S)-3-Hydroxy-2-((Z)-pent-2-enyl)-cyclopentyl]-acetic acid methyl ester 
• 37435-88-4 3-(2-methoxycarbonylmethyl)-2-(2-pentyn-1-yl)cyclopentanone 
• 695-56-7 1,4-dioxaspiro[4.4]non-6-ene 
• 29119-44-6 2-(pent-2-ynyl)-cyclopent-2-enone 
• 37435-87-3 2-(pent-2-ynyl)-3-oxo-cyclopentyl acetic acid 

Downstream Products

• 3572-65-4 jasmonic acid 
• 1211-29-6 methyl (2-(2-pent-2Z-enyl)-3-oxocyclopentyl)acetate 
• 1211-29-6 methyl jasmonate 
• 67204-66-4 (+/-)-tetrahydrodicranenone 
• 98607-60-4 (2R,3S)-2-((Z)-Pent-2-enyl)-5-phenylselanyl-3-[8-(tetrahydro-pyran-2-yloxy)-oct-2-ynyl]-cyclopentanone 
• 98607-61-5 (2R,3S)-2-((Z)-Pent-2-enyl)-5-phenylselanyl-3-[8-(tetrahydro-pyran-2-yloxy)-octyl]-cyclopentanone 
• 120330-94-1 N-<(-)-jasmonoyl>-S-phenylalanine 
• 120330-97-4 N-<(-)-jasmonoyl>-R-phenylalanine 
• 120303-53-9 N-<(+)-jasmonoyl>-S-phenylalanine 
• 120330-96-3 N-<(+)-jasmonoyl>-R-phenylalanine 
• 488-10-8 cis-jasmone 
• 573703-57-8 (2R,3R)-3-(2-Hydroxy-ethyl)-2-((Z)-pent-2-enyl)-cyclopentanol 
• 1211-29-6 Methyl jasmonate 
• 903510-51-0 methyl (1-[(2Z)-5,5,5-2H3-pent-2-en-1-yl]-6,10-dioxa-8,8-dimethylspiro[4.5]dec-2-yl)acetate 

Relevant articles and documents

Synthesis of methyl epijasmonate and cis-3-(2-oxopropyl)-2-(pent-2Z-enyl)-cyclopentan-1-one

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.

Synthesis of (±)-methyl epijasmonate and (±)-methyl dihydroepijasmonate by diastereoselective protonation

The synthesis of (±)-methyl epijasmonate (1) was carried out by Michael addition of lithium diallylcuprate to enone 3 and diastereoselective enolate protonation with the chelating proton source 2-(methyliminomethyl)phenol (4; 85% ds), followed by ozonolysis, oxidation, esterification, and Lindlar hydrogenation. During the ozonisation, epimerization to the thermodynamically more stable trans-isomer takes place to some extent, so that 1 was isolated with a cis:trans ratio of 72:28. The analogous transformation of enone 7 with lithium diallylcuprate and 2-(methyliminomethyl)phenol (4) furnished ketone 8 with 94% ds; this was then transformed into (±)-methyl dihydroepijasmonate (2) with a cis:trans ratio of 91:9. The olfactory properties of this product are superior to those available from commercial sources.

Vitamin-B12-catalyzed C,C-bond formation: Synthesis of jasmonates via sequential radical reaction

The Cbl-catalyzed electroreduction of 3-(2'-bromo-1'-ethoxyethoxy)cyclopenten (1a) in presence of 1-cyanovinyl-acetate (8) gave, in a sequential radical reaction (5-exo-trig-cyclization of 1a following by addition to 8), 1-cyano-2-(2'-ethoxy-hexahydro-2'H-cyclopenta[b]furan-4'-yl)ethyl acetate (10a). This intermediate was transformed to methyl jasmonate (7; four steps) and epituberolide (9; three steps) in 20 and 31% yield, respectively, from cyclopent-2-en-1-ol.