20-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoic acid - CAS 79551-86-3
Catalog number: 79551-86-3
Category: Inhibitor
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Molecular Formula:
C20H32O3
Molecular Weight:
320.47
COA:
Inquire
Targets:
Others
Description:
20-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoic acid is a potent vasoconstrictor produced in vascular smooth muscle cells. Its EC50 value is < 10 nM. It is a cytochrome P450 metabolite. It induces diuresis by inhibiting Na+-K+-ATPase in proximal tubules and Na+/K+/Cl+ cotransporter in the thick ascending limb of Henle's loop in kidney. It is involved in the regulation of sodium, potassium, and chloride transport in the renal tubules. It is a vasoconstrictor that mediates pressure-induced autoregulatory vasoconstriction in rat cerebral microvessels. It is excreted mainly as the glucuronide conjugate. It can be further metabolized by cyclooxygenase to 20-hydroxy PGG2 and 20-hydroxy PGH2. It regulates blood pressure in a complex way. It sensitizes smooth muscle cells to the constrictor stimuli and promotes the proliferation of endothelial cells. It has the ability to induce proinflammatory changes. It blocked the 70 pS K+ channel localized in the apical membrane in TALH cells. It was found to be a potent vasoconstrictor through activating the kinase pathways that contribute to the vascular tone regulation including MAPK, PKC, rho kinase and src-type tyrosine kinase. It may similarly regulate blood pressure and contribute to the development of stroke and heart attacks.
Purity:
>98%
Appearance:
Solid powder
Synonyms:
20-HETE;20-Hydroxyarachlidonic acid;(5Z,8Z,11Z,14Z)-20-hydroxyicosa-5,8,11,14-tetraenoic acid;20-Hydroxyeicosatetraenoic acid;20-hydroxy-5,8,11,14-eicosatetraenoic acid
Solubility:
DMSO: ≥ 3.2 mg/mL
Storage:
-20°C Freezer
MSDS:
Inquire
Application:
20-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoic acid induces diuresis by inhibiting Na+-K+-ATPase in proximal tubules and Na+/K+/Cl+ cotransporter in the thick ascending limb of Henle's loop in kidney. It can be further metabolized by cyclooxygenase to 20-hydroxy PGG2 and 20-hydroxy PGH2. It regulates blood pressure in a complex way. It sensitizes smooth muscle cells to the constrictor stimuli and promotes the proliferation of endothelial cells. It has the ability to induce proinflammatory changes. It was found to be a potent vasoconstrictor through activating the kinase pathways that contribute to the vascular tone regulation including MAPK, PKC, rho kinase and src-type tyrosine kinase. It may similarly regulate blood pressure and contribute to the development of stroke and heart attacks.
Quality Standard:
In-house standard
Shelf Life:
2 month in rt, long time
Quantity:
Milligrams-Grams
Boiling Point:
482.0±33.0 °C | Condition: Press: 760 Torr
Density:
0.985±0.06 g/cm3 | Condition: Temp: 20 °C Press: 760 Torr
InChIKey:
NNDIXBJHNLFJJP-DTLRTWKJSA-N
InChI:
InChI=1S/C20H32O3/c21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20(22)23/h1,3-4,6-7,9-10,12,21H,2,5,8,11,13-19H2,(H,22,23)/b3-1-,6-4-,9-7-,12-10-
Canonical SMILES:
C(CCC=CCC=CCC=CCC=CCCCC(=O)O)CCO
1.Purification by silica gel chromatography using dialysis tubing and characterization of sophorolipids produced from Candida bombicola grown on glucose and arachidonic acid.
Shah S1, Prabhune A. Biotechnol Lett. 2007 Feb;29(2):267-72. Epub 2006 Nov 8.
The yeast Candida bombicola (ATCC 22214) grown on primary carbon source glucose (100 g l(-1)) and secondary carbon, arachidonic acid (2 g l(-1)) produced mixture of sophorolipids up to 1.44 g l(-1). The crude product was a heterogeneous mixture of sophorolipids, which are glycolipids of sophorose linked to the fatty acid through glycosidic bond between omega and omega-1 carbon of arachidonic acid. The derived sophorolipids were isolated by silica gel chromatography using dialysis tubing. The purified sophorolipids were characterized by ESI-MS and FT-IR. Acid hydrolysis of the resolved sophorolipids were characterized by ESI-MS for the presence of 20-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid (20-HETE) and 19-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid (19-HETE), compounds of pronounced pharmaceutical importance.
2.Activation of Na+-independent Mg2+ efflux by 20-hydroxyeicosatetraenoic acid in rat renal epithelial cells.
Ikari A1, Nakajima K, Suketa Y, Harada H, Takagi K. Jpn J Physiol. 2004 Aug;54(4):415-9.
Renal epithelial cells may have Mg(2+) transport pathways that regulate intracellular free Mg(2+) concentration ([Mg(2+)](i)) and reabsorption into the body. In mag-fura 2 fluorescent measurement, extracellular Mg(2+) removal induced a Na(+)-independent [Mg(2+)](i) decrease. The [Mg(2+)](i) decrease was suppressed by methyl arachidonyl fluorophosphonate, a cytosolic and Ca(2+)-independent phospholipase A(2) (iPLA(2)) inhibitor, and bromoenol lactone, an iPLA(2) inhibitor, but it was not suppressed by a secretory phospholipase A(2) inhibitor. On the contrary, the [Mg(2+)](i) decrease was enhanced by the addition of exogenous arachidonic acid (AA). Next, we examined the effect of AA metabolite inhibitors on the [Mg(2+)](i) decrease. 17-octadecynoic acid inhibited the [Mg(2+)](i) decrease, but indomethacin and nordihydroguaiaretic acid did not. In the 17-octadecynoic acid-treated cells, 20-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoic acid (20-HETE) recovered the [Mg(2+)](i) decrease.
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Chemical Structure

CAS 79551-86-3 20-Hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoic acid

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