Jasmonic acid

  • YES
  • (-)- Jasmonic
  • (1R, 2R )-3 -oxo-2 -pent- 2-enyl - cyclopentaneacetic acid
  • 6894-38-8 (-)- jasmonic
  • 3572-66-5 ( ±)- jasmonic acid
  • 77026-92-7 ( ±)- jasmonic acid
  • 62653-85-4 (± )-7 -epi jasmonic acid

Viscous oil

Liquid

125 ° C ( 0.13 Pa)

1.4885 (at 19 ° C)

Template: Infobox chemical / molecular formula search available

Jasmonic acid is a ubiquitous phytohormone and basic structure of the group of jasmonates, whose function is to regulate the growth and aging, especially of leaves and roots of plants. Jasmonic acid plays in a variety of plants a crucial role as elicitor signal in the defense against biotic and abiotic stress. The most important derivative is its methyl ester, methyl jasmonate the.

Stereochemistry

Jasmonic acid is a chiral compound, which contains two asymmetrically substituted carbon atoms. The compound may therefore exist in four stereochemical forms. The pairs (-) - / ( )- jasmonic acid ( 1a/1b ) and ( ) -epi- / (-) -epi- jasmonic acid ( 2a/2b ) in this case represent each mirror- image molecules, so there are enantiomers. The pairings ( 1a/2a ) and ( 1b/2b ) are diastereomers.

Of course, is primarily the (-)- jasmonic acid and its methyl ester, (-)- methyl jasmonate, above.

Biosynthesis

The biosynthetic pathway of jasmonates could Brady Vick and Don Zimmerman enlighten. So jasmonic acid from α -linolenic acid is formed. The synthesis is carried out in two spatially separate steps. The first step is catalyzed by the enzymes localized in the chloroplast membrane 13 -lipoxygenase (13 -LOX ), 13 - allene oxide synthase ( AOS - 13 ) and allene oxide cyclase (AOC). Here, the intermediate cis ( ) -12- oxophytodienoic acid ( OPDA ) is formed. OPDA or its CoA ester is transferred in the second step to the peroxisomes. There, the cyclopentane ring of OPDA is reduced. Subsequently, the enzymes of β - oxidation of fatty acids catalyze the carboxyl side of ODPA and there is ( )-7 -iso- jasmonic acid or the diastereomer (-)- jasmonic acid.

Reactions

By reduction, for example using sodium borohydride, jasmonic acid can be used for the synthesis of cucurbic. The reduction proceeds only with low diastereoselectivity.

CAS registry number PubChem
431748
de