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

• ChemBase编号: 155431
• 分子式: C20H32O3
• 平均质量: 320.46628
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (12S)-12-hydroxyicosa-5,8,10,14-tetraenoic acid
• IUPAC传统名: (12S)-12-hydroxyicosa-5,8,10,14-tetraenoic acid
• 别名: (S)-12-HETE; 12(S)-Hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoic acid

登记号

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

理论计算性质

• Acid pKa: 4.889631
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 4.6512523
• LogD (pH = 7.4): 2.8843422
• Log P: 5.35636
• 摩尔折射率: 101.4695 cm^3
• 极化性: 37.740055 Å^3
• 极化表面积: 57.53 Å^2
• 可自由旋转的化学键: 14
• 里宾斯基五规则: false

分子性质

理化性质

• 闪点: 14 °C; 57 °F

安全信息

• 欧盟危险性物质标志: 易燃性(Flammable) (F); 刺激性(Irritant) (Xi)
• 联合国危险货物编号: 1170
• 德国WGK号: 1
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 2
• 危险公开号: 11-36/37/38
• 安全公开号: 7-16-26-36
• RID/ADR: UN 1170 3/PG 2
• 保存温度: -20°C

产品相关信息

• 纯度: ≥95% (HPLC)
• 浓度: ~100 μg/mL in ethanol
• 运输包装: dry ice
• Empirical Formula (Hill Notation): C20H32O3

详细说明

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.
包装
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.