13(S)-HpODE

• CAT Number: R067304
• CAS Number: 33964-75-9
• Molecular Formula: C18H32O4
• Molecular Weight: 312.4
• Purity: ≥95%
• Synonyms: 13S-hydroperoxy-9Z,11E-octadecadienoic acid
• Storage: -80°C
• InChI: InChI=1S/C18H32O4/c1-2-3-11-14-17(22-21)15-12-9-7-5-4-6-8-10-13-16-18(19)20/h7,9,12,15,17,21H,2-6,8,10-11,13-14,16H2,1H3,(H,19,20)/b9-7-,15-12+
• InChIKey: JDSRHVWSAMTSSN-BSZOFBHHSA-N
• SMILES: CCCCC[C@H](OO)/C=C/C=CCCCCCCCC(O)=O

13(S)-<wbr></wbr>HpODE is produced by the oxidation of linoleic acid by lipoxygenase-<wbr></wbr>1 (LO-<wbr></wbr>1) in many plants including soybean, flaxseed, apples, and tea leaves, and by 15-<wbr></wbr>LO in mammals. In plants, 13(S)-<wbr></wbr>HpODE is the preferred substrate for the garlic bulb divinyl ether synthase. In mammalian tissues, 13(S)-<wbr></wbr>HpODE is generally reduced to 13(S)-<wbr></wbr>HODE (Catalog No. 38610), a compound which exhibits many biological activities. A direct action for 13(S)-<wbr></wbr>HpODE has been demonstrated in Syrian hamster embryo cells where it stimulates EGF-<wbr></wbr>dependent mitogenesis and up-<wbr></wbr>regulation of EGF-<wbr></wbr>dependent tyrosine phosphorylation. Membrane-<wbr></wbr>esterified 13(S)-<wbr></wbr>HpODE has been identified in human atherosclerotic plaques.

Reference

1.Gardner, H.W. Soybean lipoxygenase-1 enzymically forms both (9S)- and (13S)-hydroperoxides from linoleic acid by a pH-dependent mechanism. Biochimica et Biophysica Acta 1001, 274-281 (1989).