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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

13(S)-HpODE

Cayman Chemical Item Number 48610

(CAS 33964-75-9)

13(S)-HpODE (CAS 33964-75-9)

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Description

13(S)-HpODE is produced by the oxidation of linoleic acid by lipoxygenase-1 (LO-1) in many plants including soybean, flaxseed, apples, and tea leaves,1,2 and by 15-LO in mammals.3 In plants, 13(S)-HpODE is the preferred substrate for the garlic bulb divinyl ether synthase.4 In mammalian tissues, 13(S)-HpODE is generally reduced to 13(S)-HODE (Catalog No. 38610), a compound which exhibits many biological activities.3 A direct action for 13(S)-HpODE has been demonstrated in Syrian hamster embryo cells where it stimulates EGF-dependent mitogenesis and up-regulation of EGF-dependent tyrosine phosphorylation.5 Membrane-esterified 13(S)-HpODE has been identified in human atherosclerotic plaques.6

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

2 Vick, B.A. Oxygenated fatty acids of the lipoxygenase pathway. 167-191 (1993).

3 Kühn, H. Biosynthesis, metabolization and biological importance of the primary 15-lipoxygenase metabolites 15-hydro(pero)xy-5Z,8Z,11Z,13E-eicosatetraenoic acid and 13-hydro(pero)xy-9Z,11E-octadecadienoic acid. Prog Lipid Res 35 203-226 (1996).

4 Grechkin, A.N., and Hamberg, M. Divinyl ether synthase from garlic (Allium sativum L.) bulbs: Sub-cellular localization and substrate regio- and stereospecificity. FEBS Lett 388 112-114 (1996).

5 Glasgow, W.C., Hui, R., Everhart, A.L., 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 272 19269-19276 (1997).

6 Folcik, V.A., Nivar-Aristy, R.A., Krajewski, L.P., et al. Lipoxygenase contributes to the oxidation of lipids in human atherosclerotic plaques. J Clin Invest 96 504-510 (1995).

Formal Name 13S-​hydroperoxy-​9Z,​11E-​octadecadienoic acid
CAS Number 33964-75-9
Molecular Formula C18H32O4
Formula Weight 312.4
Formulation A solution in ethanol
Purity >98%
λmax 234 nm
ε 23
Stability 6 months
Storage -80°C
Shipping Dry ice in continental US; may vary elsewhere
SMILES
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CCCCC[C@H]​(OO)​/C=C/C=C\CCCCCCCC(O)​=O

Background Reading

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

Vick, B.A. Oxygenated fatty acids of the lipoxygenase pathway. 167-191 (1993).

Buchanan, M.R., Haas, T.A., Lagarde, M., et al. 13-Hydroxyoctadecadienoic acid is the vessel wall chemorepellant factor, LOX. J Biol Chem 260 16056-16059 (1985).

Folcik, V.A., Nivar-Aristy, R.A., Krajewski, L.P., et al. Lipoxygenase contributes to the oxidation of lipids in human atherosclerotic plaques. J Clin Invest 96 504-510 (1995).

Kühn, H. Biosynthesis, metabolization and biological importance of the primary 15-lipoxygenase metabolites 15-hydro(pero)xy-5Z,8Z,11Z,13E-eicosatetraenoic acid and 13-hydro(pero)xy-9Z,11E-octadecadienoic acid. Prog Lipid Res 35 203-226 (1996).

Glasgow, W.C., Hui, R., Everhart, A.L., 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 272 19269-19276 (1997).

Grechkin, A.N., and Hamberg, M. Divinyl ether synthase from garlic (Allium sativum L.) bulbs: Sub-cellular localization and substrate regio- and stereospecificity. FEBS Lett 388 112-114 (1996).

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13(S)-HpODE is available in the following screening library:

Size Price Quantity Subtotal
50 µg $52.00 $0.00
100 µg $99.00 $0.00
500 µg $416.00 $0.00
1 mg $728.00 $0.00
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Cart Total $0.00

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Pricing updated 2012-02-12. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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(±)13-HpODE
13(S)-HODE
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