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
UNSPSC Code:
12352106
NACRES:
NA.77
PubChem Substance ID:
EC Number:
200-578-6
Beilstein/REAXYS Number:
2656104
MDL number:
Quality Segment
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
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
WGK 1
flash_point_f
55.4 °F
flash_point_c
13 °C
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