H7768
12(S)-Hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoic acid
~100 μg/mL in ethanol, ≥95% (HPLC)
Synonym(s):
(S)-12-HETE
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About This Item
Empirical Formula (Hill Notation):
C20H32O3
CAS Number:
Molecular Weight:
320.47
Beilstein/REAXYS Number:
2656104
EC Number:
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.77
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Quality Level
assay
≥95% (HPLC)
form
liquid
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.
signalword
Danger
hcodes
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 2
Storage Class
3 - Flammable liquids
wgk_germany
WGK 1
flash_point_f
55.4 °F
flash_point_c
13 °C
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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
MyungJa Ro et al.
Allergy, 73(2), 350-360 (2017-09-01)
As asthma progresses, the levels of IL-33 in serum are markedly increased and contribute to asthmatic development and exacerbation. Mast cells, one of the principal effector cells in the pathogenesis of asthma, express high levels of the IL-33 receptor ST2
Xiaofang Wang et al.
Journal of diabetes investigation, 10(3), 639-649 (2018-09-27)
Diabetes is an important risk factor for atherosclerotic disease. The initiating factor of atherosclerosis is local endothelial cell injury. The arachidonic acid metabolite, 12(S)-hydroxyeicosatetraenoic acid (12[S]-HETE), might be involved in this process. In recent years, some studies have discussed the
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
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
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