(±)-Jasmonic Acid-Isoleucine

(±)-Jasmonic acid-isoleucine (JA-Ile) is a mixture that contains two of the four possible stereoisomers of JA-Ile: (1R,2R)- and (1S,2S)-JA-Ile. JA-Ile is a plant hormone formed by the conjugation of jasmonic acid (Cay-88300) and the amino acid isoleucine. JA-Ile signals through a co-receptor complex composed of the jasmonate ZIM-domain (JAZ) repressor proteins and an E1 ubiquitin ligase complex containing the F-box Coronatine Insensitive 1 (COI1). Activation of the COI1-JAZ complex directs the degradation of the JAZ protein, resulting in the release of transcription factors bound and inhibited by JAZ. JA-Ile contributes to several aspects of plant growth and development and levels increase under stress conditions leading to the production of defense compounds and inhibition of growth. The (-)-JA-Ile isomer is more active than the (+)-JA-Ile isomer at inducing gene expression of jasmonate-induced protein of 23 kDa (JIP-23) in barley.Formal Name: N-[2-[(1R,2R)-3-oxo-2-(2Z)-2-penten-1-ylcyclopentyl]acetyl]-L-isoleucine, N-[2-[(1S,2S)-3-oxo-2-(2Z)-2-penten-1-ylcyclopentyl]acetyl]-L-isoleucine. Synonyms: (±)-JA-Ile. Molecular Formula: C18H29NO4. Formula Weight: 323.4. Purity: >95% (mixture of isomers). Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 25 mg/ml, DMSO: 16 mg/ml, Ethanol: 30 mg/ml, PBS (pH 7.2): 3 mg/ml. SMILES: C[C@@H](CC)[C@@H](C(O)=O)NC(C[C@H]([C@H]1C/C=C\CC)CCC1=O)=O. InChi Code: InChI=1S/C18H29NO4/c1-4-6-7-8-14-13(9-10-15(14)20)11-16(21)19-17(18(22)23)12(3)5-2/h6-7,12-14,17H,4-5,8-11H2,1-3H3,(H,19,21)(H,22,23)/b7-6-/t12-,13+,14+,17?/m0/s1. InChi Key: IBZYPBGPOGJMBF-MAXRTEDRSA-N.