Jasmonic acid

Jasmonic acid
Jasmonic acid
Ball-and-stick model of jasmonic acid
Names
Preferred IUPAC name
{(1R,2R)-3-Oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl}acetic acid
Other names
Jasmonic acid
(−)-Jasmonic acid
JA
(1R,2R)-3-Oxo-2-(2Z)-2-pentenylcyclopentylethanoic acid
{(1R,2R)-3-Oxo-2-[(2Z)-2-penten-1-yl]cyclopentyl}acetic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C12H18O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h3-4,9-10H,2,5-8H2,1H3,(H,14,15)/b4-3-/t9-,10-/m1/s1 ☒N
    Key: ZNJFBWYDHIGLCU-HWKXXFMVSA-N ☒N
  • InChI=1/C12H18O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h3-4,9-10H,2,5-8H2,1H3,(H,14,15)/b4-3-/t9-,10-/m1/s1
    Key: ZNJFBWYDHIGLCU-HWKXXFMVBZ
  • CC/C=C\C[C@@H]1[C@H](CCC1=O)CC(=O)O
Properties
C12H18O3
Molar mass 210.27 g/mol
Density 1.1 g/cm3
Boiling point 160 °C (320 °F; 433 K) at 0.7 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Jasmonic acid (JA) is an organic compound found in several plants including jasmine. The molecule is a member of the jasmonate class of plant hormones. It is biosynthesized from linolenic acid by the octadecanoid pathway. It was first isolated in 1957 as the methyl ester of jasmonic acid by the Swiss chemist Édouard Demole and his colleagues.[1]

  1. ^ Demole, E.; Lederer, E.; Mercier, D. (1962). "Isolement et determination de la structure du jasmonate de methyle, constituent odorant characteristique de l'essence de jasmin" [Isolation and determination of the structure of methyl jasmonate, the aromatic constituent characteristic of jasmine essential oil]. Helvetica Chimica Acta (in French). 45 (2): 675–685. doi:10.1002/hlca.19620450233.