20-HETE

Modify Date: 2024-01-03 08:51:23

20-HETE Structure
20-HETE structure
Common Name 20-HETE
CAS Number 79551-86-3 Molecular Weight 320.47
Density 1.0±0.1 g/cm3 Boiling Point 482.0±33.0 °C at 760 mmHg
Molecular Formula C20H32O3 Melting Point N/A
MSDS N/A Flash Point 259.4±21.9 °C
Symbol GHS02 GHS07
GHS02, GHS07
Signal Word Danger

 Use of 20-HETE


20-HETE(20-hydroxy Arachidonic Acid) is a potent vasoconstrictor produced in vascular smooth muscle (VSM) cells. It depolarizes VSM by blocking the open-state probability of Ca2+-activated K+-channels.IC50 Value:Target: 20-Hydroxyeicosatetraenoic acid (20-HETE) is a cytochrome P450-derived arachidonic acid metabolite that has been shown to increase smooth muscle contractions and proliferation, stimulate endothelial dysfunction and activation and promote hypertension. in vitro: Addition of 20-HETE to the bath (1-100 nM), reduced the frequency of opening of the large-conductance Ca(2+)-activated K+ channel recorded using cell-attached patches on VSM [1]. In kidney, 20-HETE induces diuresis by inhibiting Na+-K+-ATPase in proximal tubules and Na+/K+/Cl+ cotransporter in the thick ascending limb of Henle's loop [2].in vivo: In Cyp4a14(-/-) mice, which display androgen-driven and 20-HETE-dependent hypertension, treatment with20-HETE antagonist abolished remodeling of renal resistance arteries measured as media thickness (24±1 vs. 15±1μm) and M/L (0.29±0.03 vs. 0.17±0.01) [4]. The transgenic mice had overexpressed hepatic CYP4F2, high hepatic 20-HETE and fasting plasma glucose levels but normal insulin level. The GP activity was increased and the cAMP/PKA-PhK-GP pathway was activated in the transgenic mice compared with wild-type mice [5]. Clinical trial: Mechanisms of Response to Diesel Exhaust in Subjects With Asthma. Phase not specified

 Names

Name 20-hete
Synonym More Synonyms

 20-HETE Biological Activity

Description 20-HETE(20-hydroxy Arachidonic Acid) is a potent vasoconstrictor produced in vascular smooth muscle (VSM) cells. It depolarizes VSM by blocking the open-state probability of Ca2+-activated K+-channels.IC50 Value:Target: 20-Hydroxyeicosatetraenoic acid (20-HETE) is a cytochrome P450-derived arachidonic acid metabolite that has been shown to increase smooth muscle contractions and proliferation, stimulate endothelial dysfunction and activation and promote hypertension. in vitro: Addition of 20-HETE to the bath (1-100 nM), reduced the frequency of opening of the large-conductance Ca(2+)-activated K+ channel recorded using cell-attached patches on VSM [1]. In kidney, 20-HETE induces diuresis by inhibiting Na+-K+-ATPase in proximal tubules and Na+/K+/Cl+ cotransporter in the thick ascending limb of Henle's loop [2].in vivo: In Cyp4a14(-/-) mice, which display androgen-driven and 20-HETE-dependent hypertension, treatment with20-HETE antagonist abolished remodeling of renal resistance arteries measured as media thickness (24±1 vs. 15±1μm) and M/L (0.29±0.03 vs. 0.17±0.01) [4]. The transgenic mice had overexpressed hepatic CYP4F2, high hepatic 20-HETE and fasting plasma glucose levels but normal insulin level. The GP activity was increased and the cAMP/PKA-PhK-GP pathway was activated in the transgenic mice compared with wild-type mice [5]. Clinical trial: Mechanisms of Response to Diesel Exhaust in Subjects With Asthma. Phase not specified
Related Catalog
Target

Human Endogenous Metabolite

References

[1]. Zou AP, Fleming JT, Falck JR, 20-HETE is an endogenous inhibitor of the large-conductance Ca(2+)-activated K+ channel in renal arterioles. Am J Physiol. 1996 Jan;270(1 Pt 2):R228-37.

[2]. Schwartzman M, Ferreri NR, Carroll MA, Renal cytochrome P450-related arachidonate metabolite inhibits (Na+ + K+)ATPase. Nature. 1985 Apr 18-24;314(6012):620-2.

[3]. Ding Y, Wu CC, Garcia V, 20-HETE INDUCES REMODELING OF RENAL RESISTANCE ARTERIES INDEPENDENT OF BLOOD PRESSURE ELEVATION IN HYPERTENSION. Am J Physiol Renal Physiol. 2013 Jul 3. [Epub ahead of print]

[4]. Lai G, Wu J, Liu X, 20-HETE induces hyperglycemia through the cAMP/PKA-PhK-GP pathway. Mol Endocrinol. 2012 Nov;26(11):1907-16.

 Chemical & Physical Properties

Density 1.0±0.1 g/cm3
Boiling Point 482.0±33.0 °C at 760 mmHg
Molecular Formula C20H32O3
Molecular Weight 320.47
Flash Point 259.4±21.9 °C
Exact Mass 320.235138
PSA 57.53000
LogP 4.91
Vapour Pressure 0.0±2.7 mmHg at 25°C
Index of Refraction 1.515
Storage condition −20°C

 Safety Information

Symbol GHS02 GHS07
GHS02, GHS07
Signal Word Danger
Hazard Statements H225-H319
Precautionary Statements P210-P305 + P351 + P338-P370 + P378-P403 + P235
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes F: Flammable;Xi: Irritant;
Risk Phrases 11-36/37/38
Safety Phrases 16-26-36
RIDADR UN 1170 3/PG 2
WGK Germany 3

 Synthetic Route

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 Synonyms

20-hydroxy-5,8,11,14-eicosatetraenoic acid
20-HETE
20-Hydroxyicosatetraenoic acid
5,8,11,14-Eicosatetraenoic acid, 20-hydroxy-, (5Z,8Z,11Z,14Z)-
DSR-II-247-30
(5Z,8Z,11Z,14Z)-20-hydroxyicosa-5,8,11,14-tetraenoic acid
20-Hydroxyeicosatetraenoic acid
20-Hydroxyicosatetraenoate
20-Hydroxy arachidonic acid
(5Z,8Z,11Z,14Z)-20-Hydroxy-5,8,11,14-icosatetraenoic acid