Jasmonic Acid

Title: Jasmonic Acid
CAS Registry Number: 6894-38-8
CAS Name: (1R,2R)-3-Oxo-2-(2Z)-2-penten-ylcyclopentaneacetic acid
Additional Names: (1S,2S)-3-oxo-2-(2¢-cis-pentenyl)cyclopentan-1-acetate; JA
Molecular Formula: C12H18O3
Molecular Weight: 210.27
Percent Composition: C 68.54%, H 8.63%, O 22.83%
Literature References: Naturally occurring plant growth inhibitor. Orginally isolated from jasmin flowers as the methyl ester, the major aroma component: E. Demole et al., Helv. Chim. Acta 45, 675 (1962). Isoln of the free acid from Lasiodiplodia theobromae: D. C. Aldridge et al., J. Chem. Soc. 1971, 1623; by fermentation: D. Broadbent et al., GB 1286266 (1972 to ICI). Occurrence in plants: A. Meyer et al., J. Plant Growth Regul. 3, 1 (1984). NMR characterization: A. Husain et al., J. Nat. Prod. 56, 2008 (1993). Quantification by GC/MS: M. J. Mueller, W. Brodschelm, Anal. Biochem. 218, 425 (1994). Resoln of racemate: R. Kramell et al., Phytochem. Anal. 7, 209 (1996). Review of role in plant development: Y. Koda, Int. Rev. Cytol. 135, 155-199 (1992); of biochemisty and physiology: G. Sembdner, B. Parthier, Annu. Rev. Plant Physiol. Plant Mol. Biol. 44, 569-589 (1993); of signaling in plants: P. Staswick, Curr. Top. Plant Physiol. 11, 14-23 (1993).
Properties: Colorless oil. nD23 1.486. [a]D25 -73° (c = 1 in CH3OH).
Optical Rotation: [a]D25 -73° (c = 1 in CH3OH)
Index of refraction: nD23 1.486
Derivative Type: Methyl ester
CAS Registry Number: 1211-29-6
Additional Names: (-)-Methyl cis-2-pent-2¢-enyl-3-oxocyclopentylacetate; JA-ME; MeJA; methyl jasmonate
Molecular Formula: C13H20O3
Molecular Weight: 224.30
Percent Composition: C 69.61%, H 8.99%, O 21.40%
Properties: Colorless liquid with a sharp persistent odor. nD21.8 1.4730. [a]D -76.5° (c = 3.4 in CH3OH). d422.6 1.021.
Optical Rotation: [a]D -76.5° (c = 3.4 in CH3OH)
Index of refraction: nD21.8 1.4730
Density: d422.6 1.021
Use: Methyl ester in perfumes.
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