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12(S)-HpETE Lipid Maps MS Standard

Cayman Chemical Item Number 10007258

(CAS 71774-10-2)

12(S)-HpETE Lipid Maps MS Standard (CAS 71774-10-2)

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Description

12(S)-HpETE is a monohydroperoxy polyunsaturated fatty acid (PUFA) produced by the action of platelet or leukocyte 12-lipoxygenase (12-LO) on arachidonic acid.1,2 It activates human blood leukocyte 5-LO, resulting in the synthesis of 5(S)-HETE, leukotriene B4 (LTB4), and 5(S),12(S)-DiHETE.1 Rat lung metabolizes 12(S)-HpETE to 8,11,12- and 10,11,12-trihydroxyeicostrienoic acids.3 12(S)-HpETE is the mediator of many biological functions, including induction of c-fos and c-jun, activation of AP-1, and endothelium-dependent vasoconstriction.4,5 It mediates the inhibitory synaptic response to FMRF-amide in Aplysia sensory neurons6 and inhibits Ca2+/calmodulin-dependent protein kinase II from rat brain cortex.7,6

1 Maclouf, J., Fruteau De Laclos, B., and Borgeat, P. Stimulation of leukotriene biosynthesis in human blood leukocytes by platelet-derived 12-hydroperoxy-eicosatetraenoic acid. Proc Natl Acad Sci USA 79 6042-6046 (1982).

2 Kishimoto, K., Nakamura, M., Suzuki, H., et al. Suicide inactivation of porcine leukocyte 12-lipoxygenase associated with its incorporation of 15-hydroperoxy-5,8,11,13-eicosatetraenoic acid derivative. Biochim Biophys Acta 1300 56-62 (1996).

3 Pace-Asciak, C.R., Granström, E., and Samuelsson, B. Arachidonic acid epoxides. Isolation and structure of two hydroxy epoxide intermediates in the formation of 8,11,12- and 10,11,12-trihydroxyeicosatrienoic acids. J Biol Chem 258 6835-6840 (1983).

4 Nishiyama, M., Okamoto, H., Watanabe, T., et al. Endothelium is required for 12-hydroperoxyeicosatetraenoic acid-induced vasoconstriction. Eur J Pharmacol 341 57-63 (1998).

5 Rao, G.N., Glasgow, W.C., Eling, T.E., et al. Role of hydroperoxyeicosatetraenoic acids in oxidative stress-induced activating protein 1 (AP-1) activity. J Biol Chem 271 27760-27764 (1996).

6 Piomelli, D., Volterra, A., Dale, N., et al. Lipoxygenase metabolites of arachidonic acid as second messengers for presynaptic inhibition of Aplysia sensory cells. Nature 328 38-43 (1987).

7 Piomelli, D., Wang, J.K.T., Sihra, T.S., et al. Inhibition of Ca2+/calmodulin-dependent protein kinase II by arachidonic acid and its metabolites. Proc Natl Acad Sci USA 86 8550-8554 (1989).

Formal Name 12S-​hydroperoxy-​5Z,​8Z10E,​14Z-​eicosatetraenoic acid
CAS Number 71774-10-2
Molecular Formula C20H32O4
Formula Weight 336.5
Formulation A solution in ethanol
Purity ≥98%
Stability 6 months
Storage -80°C
Shipping Dry ice in continental US; may vary elsewhere
SMILES
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CCCCC/C=C\CC(OO)​\C=C\C=C\C/C=C\CCCC(=O)​O

Background Reading

Nishiyama, M., Okamoto, H., Watanabe, T., et al. Endothelium is required for 12-hydroperoxyeicosatetraenoic acid-induced vasoconstriction. Eur J Pharmacol 341 57-63 (1998).

Maclouf, J., Fruteau De Laclos, B., and Borgeat, P. Stimulation of leukotriene biosynthesis in human blood leukocytes by platelet-derived 12-hydroperoxy-eicosatetraenoic acid. Proc Natl Acad Sci USA 79 6042-6046 (1982).

Rao, G.N., Glasgow, W.C., Eling, T.E., et al. Role of hydroperoxyeicosatetraenoic acids in oxidative stress-induced activating protein 1 (AP-1) activity. J Biol Chem 271 27760-27764 (1996).

Kishimoto, K., Nakamura, M., Suzuki, H., et al. Suicide inactivation of porcine leukocyte 12-lipoxygenase associated with its incorporation of 15-hydroperoxy-5,8,11,13-eicosatetraenoic acid derivative. Biochim Biophys Acta 1300 56-62 (1996).

Piomelli, D., Wang, J.K.T., Sihra, T.S., et al. Inhibition of Ca2+/calmodulin-dependent protein kinase II by arachidonic acid and its metabolites. Proc Natl Acad Sci USA 86 8550-8554 (1989).

Piomelli, D., Volterra, A., Dale, N., et al. Lipoxygenase metabolites of arachidonic acid as second messengers for presynaptic inhibition of Aplysia sensory cells. Nature 328 38-43 (1987).

Pace-Asciak, C.R., Granström, E., and Samuelsson, B. Arachidonic acid epoxides. Isolation and structure of two hydroxy epoxide intermediates in the formation of 8,11,12- and 10,11,12-trihydroxyeicosatrienoic acids. J Biol Chem 258 6835-6840 (1983).

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Size Price Quantity Subtotal
25 µg $117.00 $0.00
50 µg $222.00 $0.00
100 µg $421.00 $0.00
250 µg $936.00 $0.00
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Cart Total $0.00

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Pricing updated 2012-05-25. Prices are subject to change without notice.

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