(+/-)-Jasmonic acid-D5

Description

(±)-Jasmonic acid-d₅ is intended for use as an internal standard for the quantification of jasmonic acid by GC- or LC-MS. Jasmonic acid (JA) is a plant growth regulator and derivative of α-linolenic acid that can exist in four stereoisomeric forms.^1,2 (–)-3(R),7(R)-JA and (+)-3(S),7(S)-JA have the two side chains in the trans configuration, whereas (–)-3(S),7(R)-JA and (+)-3(R),7(S)-JA have the two side chains in the cis configuration, which can epimerize at C7 to the trans configuration via keto-enol tautomerization.²

References

1. Creelman, R.A., and Mullet, J.E. Biosynthesis and action of jasmonates in plants Annu. Rev. Plant Physiol. Plant Mol. Biol. 48,355-381(1997).
2. Holbrook, L., Tung, P., Ward, K., et al. Importance of the chiral centers of jasmonic acid in the responses of plants. Activities and antagonism between natural and synthetic analogs Plant Physiol. 114(2),419-428(1997).