13(S)-HPODE 

13(S)-HPODE is a linoleic acid metabolite found in several plants and mammals.

13(S)-HPODE can be produced by the oxidation of linoleic acid by lipoxygenase-1 in many plants^[1]. The dioxygenation catalyzed by a 15-lipoxygenase and a reduction of intermediate 13-HPODE by a glutathione-dependent peroxidase can form 13(S)-HODE^[2]. 13(S)-HPODE can stimulate EGF-dependent mitogenesis and up-regulation of EGF-dependent tyrosine phosphorylation by inhibiting the dephosphorylation of the EGFR^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

312.44

C₁₈H₃₂O₄

33964-75-9

Liquid

Colorless to light yellow

CCCCC[C@H](OO)/C=C/C=C\CCCCCCCC(O)=O

Room temperature in continental US; may vary elsewhere.

Solution, -20°C, 2 years

• [1]. Gardner HW, et al. Soybean lipoxygenase-1 enzymically forms both (9S)- and (13S)-hydroperoxides from linoleic acid by a pH-dependent mechanism. Biochim Biophys Acta. 1989 Feb 20;1001(3):274-81.  [Content Brief]

  [2]. Reinaud O, et al. Oxidative metabolism of linoleic acid by human leukocytes. Biochem Biophys Res Commun. 1989 Jun 15;161(2):883-91.  [Content Brief]

  [3]. Glasgow WC, et al. The linoleic acid metabolite, (13S)-hydroperoxyoctadecadienoic acid, augments the epidermal growth factor receptor signaling pathway by attenuation of receptor dephosphorylation. Differential response in Syrian hamster embryo tumor suppressor phenotypes. J Biol Chem. 1997 Aug 1;272(31):19269-76.  [Content Brief]