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13(S)-HpODE

Catalog No.GC19474 Copy One-Click Copy Product Info

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.

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13(S)-HpODE Chemical Structure

Cas No.: 33964-75-9

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50µg
$99.00
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100µg
$187.00
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500µg
$885.00
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1mg
$1,471.00
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Sample solution is provided at 25 µL, 10mM.



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Description of 13(S)-HpODE

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,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

Reference:

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(3), 274-281 (1989).

2. Vick, B.A. Oxygenated fatty acids of the lipoxygenase pathway Lipid Metabolism in Plants 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 Progress in Lipid Research 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 Letters 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 The Journal of Biological Chemisty 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 Journal of Clinical Investigation 96, 504-510 (1995).

Chemical Properties of 13(S)-HpODE

Cas No. 33964-75-9 SDF
Chemical Name 13S-hydroperoxy-9Z,11E-octadecadienoic acid
Canonical SMILES CCCCC[C@H](OO)/C=C/C=C\CCCCCCCC(O)=O
Formula C18H32O4 M.Wt 312.4
Solubility DMF: >50 mg/ml (per Rao Maddipati),DMSO: >50 mg/ml (per Rao Maddipati),Ethanol: >50 mg/ml (per Rao Maddipati),PBS pH 7.2: >1 mg/ml (from 13(S)-HODE) Storage Store at -20°C, protect from light
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of 13(S)-HpODE

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1 mg 5 mg 10 mg
1 mM 3.201 mL 16.0051 mL 32.0102 mL
5 mM 640.2 μL 3.201 mL 6.402 mL
10 mM 320.1 μL 1.6005 mL 3.201 mL
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Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.

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3. All of the above co-solvents are available for purchase on the GlpBio website.

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Average Rating: 5 ★★★★★ (Based on Reviews and 25 reference(s) in Google Scholar.)

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