(12S)-12-hydroxyicosa-5,8,10,14-tetraenoic acid

• ChemBase ID: 155431
• Molecular Formular: C20H32O3
• Molecular Mass: 320.46628
• Monoisotopic Mass: 320.23514488
• SMILES: CCCCC/C=C/C[C@@H](/C=C/C=C/C/C=C/CCCC(=O)O)O
• Canonical SMILES: CCCCC/C=C/C[C@@H](/C=C/C=C/C/C=C/CCCC(=O)O)O
• InChI: 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)/t19-/m0/s1
• InChIKey: ZNHVWPKMFKADKW-IBGZPJMESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (12S)-12-hydroxyicosa-5,8,10,14-tetraenoic acid
• IUPAC Traditional name: (12S)-12-hydroxyicosa-5,8,10,14-tetraenoic acid
• Synonyms: (S)-12-HETE; 12(S)-Hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoic acid

Database IDs

• CAS Number: 54397-83-0
• MDL Number: MFCD00036916
• Beilstein Number: 2656104
• PubChem SID: 24895806; 162249569
• PubChem CID: 6442490

CALCULATED PROPERTIES

• Acid pKa: 4.889631
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.6512523
• LogD (pH = 7.4): 2.8843422
• Log P: 5.35636
• Molar Refractivity: 101.4695 cm^3
• Polarizability: 37.740055 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Flash Point: 14 °C; 57 °F

Safety Information

• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 1170
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-36/37/38
• Safety Statements: 7-16-26-36
• RID/ADR: UN 1170 3/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Concentration: ~100 μg/mL in ethanol
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C20H32O3

DETAILS

Sigma Aldrich - H7768

Biochem/physiol Actions
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.
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.
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.