Jasmonic acid

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
CAS Number	6894-38-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:18292 ;
ChemSpider	4444606 ;
PubChem CID	5281166;
UNII	6RI5N05OWW ;
CompTox Dashboard (EPA)	DTXSID4037665 ;
	InChI 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 Key: ZNJFBWYDHIGLCU-HWKXXFMVSA-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;
	SMILES CC/C=C\C[C@@H]1[C@H](CCC1=O)CC(=O)O;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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]

^
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.
- Chapuis, Christian (December 2011). "The chemistry and creative legacy of methyl jasmonate and hedione". Perfumer & Flavorist. 36: 36–48.

[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.
Chapuis, Christian (December 2011). "The chemistry and creative legacy of methyl jasmonate and hedione". Perfumer & Flavorist. 36: 36–48.

[2] Chapuis, Christian (December 2011). "The chemistry and creative legacy of methyl jasmonate and hedione". Perfumer & Flavorist. 36: 36–48.

[1]

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
CAS Number	6894-38-8^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:18292^N
ChemSpider	4444606^N
PubChem CID	5281166
UNII	6RI5N05OWW^Y
CompTox Dashboard (EPA)	DTXSID4037665
InChI 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
SMILES CC/C=C\C[C@@H]1[C@H](CCC1=O)CC(=O)O
Properties
Chemical formula	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). N verify (what is ^YN ?) Infobox references