H7768

Sigma-Aldrich

12(S)-Hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoic acid

~100 μg/mL in ethanol, ≥95% (HPLC)

Synonym(s):
(S)-12-HETE
Empirical Formula (Hill Notation):
C20H32O3
CAS Number:
Molecular Weight:
320.47
Beilstein/REAXYS Number:
2656104
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥95% (HPLC)

concentration

~100 μg/mL in ethanol

shipped in

dry ice

storage temp.

−20°C

SMILES string

CCCCC\C=C/C[C@H](O)\C=C\C=C/C\C=C/CCCC(O)=O

InChI

1S/C20H32O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17,19,21H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-,17-14+/t19-/m0/s1

InChI key

ZNHVWPKMFKADKW-LQWMCKPYSA-N

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Biochem/physiol Actions

12(S)-HETE is a bioactive lipid implicated in angiogenesis, growth, and metastasic action in tumor cell lines and in animal models. Arachidonate 12-lipoxygenase (12-LOX) converts arachidonic acid to 12(S)-(HETE). Alteration in 12-LOX expression or activity has been reported in various carcinomas including prostate carcinoma.
Prometastatic metabolite of arachidonic acid via the 12-lipoxygenase pathway that is expressed in many tumor cell lines. It is produced in coronary microvasculature and is a potent inducer of relaxation and hyperpolarization of these microvessels. It activates large-conductance Ca2+-activated K+ currents in coronary microvascular smooth muscle.

Packaging

Packaged under Argon.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H7768.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Pictograms

FlameExclamation mark

Signal Word

Danger

Hazard Statements

Precautionary Statements

RIDADR

UN1170 - class 3 - PG 2 - Ethanol, solution

WGK Germany

WGK 1

Flash Point(F)

55.4 °F

Flash Point(C)

13 °C

Yuke Li et al.
Free radical biology & medicine, 134, 239-247 (2019-01-20)
This study was designed to investigate the neuroprotective effects of baicalein and the effect of the cortical 12/15-lipoxygenase (12/15-LOX) pathway on diabetic cognitive dysfunction. Our results showed that spatial learning and memory ability, as well as cortex neurons, were significantly...
Yan Qu et al.
Cancer management and research, 11, 8303-8313 (2019-10-02)
To clarify the effect of 12-lipoxygenase/12-hydroxyeicosatetraeonic acid (12-LOX/12-HETE) on progress of esophageal squamous cell carcinoma (ESCC) and the possible mechanism. We performed cell experiments including chemical treatment, transfection, Western blotting and transwell assay to investigate the function of 12-LOX/12-HETE. Slices...
Alicja Pakiet et al.
Lipids in health and disease, 18(1), 29-29 (2019-01-28)
Altered metabolism of lipids is currently considered a hallmark characteristic of many malignancies, including colorectal cancer (CRC). Lipids are a large group of metabolites that differ in terms of their fatty acid composition. This review summarizes recent evidence, documenting many...
K Viola et al.
British journal of cancer, 108(3), 564-569 (2012-10-25)
Many cancers spread through lymphatic routes, and mechanistic insights of tumour intravasation into the lymphatic vasculature and targets for intervention are limited. The major emphasis of research focuses currently on the molecular biology of tumour cells, while still little is...
C Vonach et al.
British journal of cancer, 105(2), 263-271 (2011-06-02)
The intravasation of breast cancer into the lymphendothelium is an early step of metastasis. Little is known about the mechanisms of bulky cancer invasion into lymph ducts. To particularly address this issue, we developed a 3-dimensional co-culture model involving MCF-7...

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