| Identification | Back Directory | [Name]
(5S,6Z,8E,10E,14Z)-5-hydroxy-12-oxoicosa-6,8,10,14-tetraenoic acid | [CAS]
136696-10-1 | [Synonyms]
12-Oxo-ltb4
12-oxoleukotriene B4
12-Keto-leukotriene B4
12-dehydro-leukotriene B4
SJVWVCVZWMJXOK-NOJHDUNKSA-N
(5S,6Z,8E,10E,14Z)-5-hydroxy-12-oxoicosa-6,8,10,14-tetraenoic acid
6,8,10,14-Eicosatetraenoic acid, 5-hydroxy-12-oxo-, (S-(E,Z,E,Z))-
6,8,10,14-Eicosatetraenoic acid, 5-hydroxy-12-oxo-, (5S,6Z,8E,10E,14Z)- | [Molecular Formula]
C20H30O4 | [MDL Number]
MFCD00065854 | [MOL File]
136696-10-1.mol | [Molecular Weight]
334.45 |
| Chemical Properties | Back Directory | [Boiling point ]
524.2±50.0 °C(Predicted) | [density ]
1.036±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -80°C,protect from light | [solubility ]
DMF: Miscible; DMSO: Miscible; Ethanol: Miscible; PBS (pH 7.2): > 1 mg/ml | [pka]
4.66±0.10(Predicted) |
| Hazard Information | Back Directory | [Description]
Leukotriene B4 (LTB4) is a dihydroxy fatty acid derived from arachidonic acid through the 5-LO pathway. It promotes a number of leukocyte functions including aggregation, stimulation of ion fluxes, enhancement of lysosomal enzyme release, superoxide anion production, chemotaxis, and chemokinesis. 12-oxo LTB4 is an initial metabolite of LTB4 formed via the LTB4 12-hydroxydehydrogenase pathway. It is rapidly converted to 10,11-dihydro-12-oxo-LTB4, followed by reduction of the 12-oxo group to give 10,11-dihydro-LTB4. 12-oxo-LTB4 (EC50 = 33 nM) is about 70-fold less potent than LTB4 (EC50 = 0.46 nM) at stimulating Ca2+ mobilization in human neutrophils. It is also significantly less potent than LTB4 at stimulating neutrophil migration with EC50 values of 170 and 2.7 nM for 12-oxo-LTB4 and LTB4, respectively. | [Uses]
12-oxo Leukotriene B4 in acetonitrile is a potent eicosanoid lipid mediators. | [Definition]
ChEBI: A long-chain fatty acid consisting of leukotriene B4 having a 12-keto group in place of the 12-hydroxy group. | [References]
[1] T. YOKOMIZO. Enzymatic inactivation of leukotriene B4 by a novel enzyme found in the porcine kidney. Purification and properties of leukotriene B4 12-hydroxydehydrogenase.[J]. The Journal of Biological Chemistry, 1993, 292 1: 18128-18135. DOI: 10.1016/s0021-9258(17)46820-7
[2] S. WAINWRIGHT W P. Mechanism for the formation of dihydro metabolites of 12-hydroxyeicosanoids. Conversion of leukotriene B4 and 12-hydroxy-5,8,10,14-eicosatetraenoic acid to 12-oxo intermediates.[J]. The Journal of Biological Chemistry, 1991, 43 1: 20899-20906. DOI: 10.1016/s0021-9258(18)54795-5
[3] P WHEELAN. Metabolism of leukotriene B4 by cultured human keratinocytes. Formation of glutathione conjugates and dihydro metabolites.[J]. The Journal of Biological Chemistry, 1993, 268 34: 25439-25448.
[4] W S POWELL. Effects of metabolites of leukotriene B4 on human neutrophil migration and cytosolic calcium levels.[J]. Journal of Pharmacology and Experimental Therapeutics, 1996, 276 2: 728-736.
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