12(S)-HPETE Chemical Properties

Boiling point:

518.0±50.0 °C(Predicted)

Density 

1.013±0.06 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

0.1 M Na2CO3: 2 mg/ml; DMF: Miscible; DMSO: Miscible; Ethanol: Miscible; PBS pH 7.2: 0.8 mg/ml

form 

Liquid.

pka

4.75±0.10(Predicted)

12(S)-HPETE Usage And Synthesis

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. It activates human blood leukocyte 5-LO, resulting in the synthesis of 5(S)-HETE, leukotriene B₄ (LTB₄), and 5(S),12(S)-DiHETE. Rat lung metabolizes 12(S)-HpETE to 8,11,12- and 10,11,12-trihydroxyeicostrienoic acids. 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. It mediates the inhibitory synaptic response to FMRF-amide in Aplysia sensory neurons and inhibits Ca²⁺/calmodulin-dependent protein kinase II from rat brain cortex.

Uses

12(S)-HPETE is a fatty acid and an activator of human blood leukocyte 5-LO.

Definition

ChEBI: 12(S)-HPETE is the (S)-enantiomer of 12-HPETE. It has a role as a mouse metabolite. It is functionally related to an icosa-5,8,10,14-tetraenoic acid. It is a conjugate acid of a 12(S)-HPETE(1-). It is an enantiomer of a 12(R)-HPETE.

References

[1] J MACLOUF  P B  B F de Laclos. Stimulation of leukotriene biosynthesis in human blood leukocytes by platelet-derived 12-hydroperoxy-icosatetraenoic acid.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1982, 79 19: 6042-6046. DOI: 10.1073/pnas.79.19.6042
[2] KOJI KISHIMOTO . Suicide inactivation of porcine leukocyte 12-lipoxygenase associated with its incorporation of 15-hydroperoxy-5,8,11,13-eicosatetraenoic acid derivative[J]. Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism, 1996, 1300 1: Pages 56-62. DOI: 10.1016/0005-2760(95)00241-3
[3] C. PACE-ASCIAK B S E Granstr?m. 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]. The Journal of Biological Chemistry, 1983, 48 1: 6835-6840. DOI: 10.1016/s0021-9258(18)32298-1
[4] MAKOTO NISHIYAMA . Endothelium is required for 12-hydroperoxyeicosatetraenoic acid-induced vasoconstriction[J]. European journal of pharmacology, 1998, 341 1: Pages 57-63. DOI: 10.1016/s0014-2999(97)01353-8
[5] G N RAO. Role of hydroperoxyeicosatetraenoic acids in oxidative stress-induced activating protein 1 (AP-1) activity.[J]. The Journal of Biological Chemistry, 1996, 271 44: 27760-27764. DOI: 10.1074/jbc.271.44.27760
[6] D. PIOMELLI. Lipoxygenase metabolites of arachidonic acid as second messengers for presynaptic inhibition of Aplysia sensory cells[J]. Nature, 1987, 328 6125: 38-43. DOI: 10.1038/328038a0
[7] D PIOMELLI. Inhibition of Ca2+/calmodulin-dependent protein kinase II by arachidonic acid and its metabolites.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1989, 86 21: 8550-8554. DOI: 10.1073/pnas.86.21.8550

12(S)-HPETE(71774-10-2)Related Product Information

• 12(S)-HPETE LIPID MAPS
• 12(S)-HPETE [1-14C]
• 12(R)-HPETE
• (+/-)12-HPETE
• 12(S)-HPETE
• (+/-)12-HETE
• 12(S)-HETE
• 1,5-HEPTADIEN-4-OL
• 1.3.7-OCTATRIENE