12-HETE

Modify Date: 2024-01-02 14:22:39

12-HETE Structure
12-HETE structure
Common Name 12-HETE
CAS Number 71030-37-0 Molecular Weight 320.466
Density 1.0±0.1 g/cm3 Boiling Point 487.7±45.0 °C at 760 mmHg
Molecular Formula C20H32O3 Melting Point N/A
MSDS N/A Flash Point 262.8±25.2 °C

 Use of 12-HETE


12-HETE, a major metabolic product of arachidonic acid using 12-LOX catalysis, inhibits cell apoptosis in a dose-dependent manner. 12-HETE promotes the activation and nuclear translocation of NF-κB through the integrin-linked kinase (ILK) pathway[1].12-HETE has both anti-thrombotic and pro-thrombotic effects[2]. 12-HETE is a neuromodulator[3].

 Names

Name (5Z,8Z,10E,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoic acid
Synonym More Synonyms

 12-HETE Biological Activity

Description 12-HETE, a major metabolic product of arachidonic acid using 12-LOX catalysis, inhibits cell apoptosis in a dose-dependent manner. 12-HETE promotes the activation and nuclear translocation of NF-κB through the integrin-linked kinase (ILK) pathway[1].12-HETE has both anti-thrombotic and pro-thrombotic effects[2]. 12-HETE is a neuromodulator[3].
Related Catalog
In Vitro 12-HETE participates in the inhibition of cell apoptosis by activating the ILK/NF-κB pathway, implying an important underlying mechanism that promotes the survival of ovarian cancer cells. 12-HETE facilitates cell survival by activating the integrin-linked kinase/NF-κB pathway in ovarian cancer. 12-HETE protects against cell apoptosis in ovarian cancer cells in a concentration-dependent manner. 12-HETE (1 µM) significantly decreases the activation of caspase-3 induced by serum deprivation (SD).12-HETE represses the increased activity of caspase-3 induced by SD in a concentration-dependent manner, with an IC50 value of 1.13 µM[1]. 12-HETE (1 µM) facilitates the activation and nuclear translocation of NF-κB via ILK in ovarian cancer cells[1]. 12-HETE inhibits insulin secretion, reduces metabolic activity and induces cell death in human islets. 12-HETE increases bovine platelet aggregation induced by thrombin and inhibits prostaglandin E1-induced elevation of intracellular cAMP levels. 12-HETE inhibits washed platelet (WP) aggregation[2]. The neuronal effects of 12-HETE include attenuation of calcium influx and glutamate release as well as inhibition of AMPA receptor (AMPA-R) activation[3]. Cell Viability Assay[1] Cell Line: Ovarian cancer OVCAR-3 and SKOV3 cells Concentration: 0, 0.2, 0.5, and 1 µM Incubation Time: 0, 24, 48, 72, and 96 hours Result: Inhibited the decrease in cell viability induced by SD in a dose-dependent manner. 1 µM 12-HETE treatment significantly mitigated the decrease in cell viability under conditions of SD. Western Blot Analysis[1] Cell Line: Ovarian cancer OVCAR-3 and SKOV3 cells Concentration: 1 µM Incubation Time: Result: Led to increased levels of NF-κB p65 phosphorylation. Caused a significant increase in the protein levels of nuclear NF-κB p65, which was accompanied by decreased levels of NF-κB p65 in the cytoplasm.
References

[1]. Qian Liu, et al. 12-HETE facilitates cell survival by activating the integrin-linked kinase/NF-κB pathway in ovarian cancer. Cancer Manag Res. 2018 Nov 16;10:5825-5838.

[2]. Benedetta Porro, et al. Analysis, physiological and clinical significance of 12-HETE: a neglected platelet-derived 12-lipoxygenase product. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Aug 1;964:26-40.

[3]. Aidan J Hampson, et al. 12-hydroxyeicosatetrenoate (12-HETE) attenuates AMPA receptor-mediated neurotoxicity: evidence for a G-protein-coupled HETE receptor. J Neurosci. 2002 Jan 1;22(1):257-64.

 Chemical & Physical Properties

Density 1.0±0.1 g/cm3
Boiling Point 487.7±45.0 °C at 760 mmHg
Molecular Formula C20H32O3
Molecular Weight 320.466
Flash Point 262.8±25.2 °C
Exact Mass 320.235138
PSA 17.07000
LogP 5.45
Vapour Pressure 0.0±2.8 mmHg at 25°C
Index of Refraction 1.514

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
JX3871000
CHEMICAL NAME :
5,8,10,14-Eicosatetraenoic acid, 12-hydroxy-, (E,Z,Z,Z)-
CAS REGISTRY NUMBER :
71030-37-0
LAST UPDATED :
199712
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C20-H32-O3
MOLECULAR WEIGHT :
320.52

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Human Cells - not otherwise specified
DOSE/DURATION :
20 umol/L
REFERENCE :
CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 45,561,1985

 Safety Information

HS Code 2918199090

 Synthetic Route

 Customs

HS Code 2918199090
Summary 2918199090 other carboxylic acids with alcohol function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

 Synonyms

(±)12-HETE
5,8,10,14-Eicosatetraenoic acid, 12-hydroxy-, (5Z,8Z,10E,14Z)-
12-Hydroxyeicosatetraenoic acid
(5Z,8Z,10E,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoic acid
(5Z,8Z,10E,14Z)-12-hydroxyicosatetraenoic acid
(5Z,8Z,10E,14Z)-12-Hydroxy-5,8,10,14-icosatetraenoic acid
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