| Identification | Back Directory | [Name]
12(S)-HPETE | [CAS]
71774-10-2 | [Synonyms]
12(S)-HPETE
12(S)HpETE,12(S) HpETE
ZIOZYRSDNLNNNJ-LQWMCKPYSA-N
12(S)-HpETE Lipid Maps MS Standard
12(S)-Hydroperoxy-eicosatetraenoic acid
12S-HYDROPEROXY-5Z,8Z,10E,14Z-EICOSATETRAENOIC ACID
(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoic acid
12(S)-HYDROPEROXYEICOSA-5Z,8Z,10E,14Z-TETRAENOIC ACID
(5Z,8Z,10Z,12S,14Z)-12-Hydroperoxy-5,8,10,14-icosatetraenoic acid
(5Z,8Z,10E,12S,14Z)-12-Hydroperoxy-5,8,10,14-icosatetraenoic acid
(5Z,8Z,10E,12S,14Z)-12-Hydroperoxyicosa-5,8,10,14-tetraenoic acid | [Molecular Formula]
C20H32O4 | [MDL Number]
MFCD00063585 | [MOL File]
71774-10-2.mol | [Molecular Weight]
336.47 |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [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 |
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