H7768

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: 54397-83-0
• Molecular Weight: 320.47
• Beilstein: 2656104
• EC Number: 200-578-6
• MDL number: MFCD00036916
• UNSPSC Code: 12352106
• PubChem Substance ID: 24895806
• NACRES: NA.77

Properties

• Quality Level: 200
• 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

Description

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.

Safety Information

• Pictograms: GHS02,GHS07
• Signal Word: Danger
• Hazard Statements: H225,H319
• Precautionary Statements: P210 - P233 - P240 - P241 - P242 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Flam. Liq. 2
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 1
• Flash Point(F): 55.4 °F
• Flash Point(C): 13 °C