(5Z,8Z,11Z,13E,15S)-15-hydroxyicosa-5,8,11,13-tetraenoic acid

• ChemBase编号: 133784
• 分子式: C20H32O3
• 平均质量: 320.46628
• 单一同位素质量: 320.23514488
• SMILES: CCCCC[C@@H](/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O)O
• Canonical SMILES: CCCCC[C@@H](/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O)O
• InChI: InChI=1S/C20H32O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14+/t19-/m0/s1
• InChIKey: JSFATNQSLKRBCI-VAEKSGALSA-N

名称和登记号

名称

• IUPAC标准名: (5Z,8Z,11Z,13E,15S)-15-hydroxyicosa-5,8,11,13-tetraenoic acid
• IUPAC传统名: 15 hete
• 别名: (15S,5Z,8Z,11Z,13E)-15-Hydroxyeicosatetraenoic acid; (S)-15-HETE; 15(S)-HETE; 15(S)-Hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid

登记号

• CAS号: 54845-95-3
• MDL号: MFCD00063590
• Beilstein号: 2470466
• PubChem SID: 24895431; 162228061
• PubChem CID: 5280724

理论计算性质

• Acid pKa: 4.8197722
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 4.594384
• LogD (pH = 7.4): 2.8212519
• 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; 57.2 °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: 3
• 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
• GHS危险品标识: GHS02; GHS07
• GHS警示词: Danger
• GHS危险声明: H225-H315-H319-H335
• GHS警示性声明: P210-P261-P305 + P351 + P338
• 个人保护装置: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1170 3/PG 2
• 保存温度: -20°C

产品相关信息

• 纯度: ≥97.0% (HPLC)
• 浓度: ~150 μg/mL in ethanol
• 运输包装: dry ice

详细说明

Sigma Aldrich - H1142

Biochem/physiol Actions
Metabolite of arachidonic acid via the 15-lipoxygenase pathway that may be involved in pulmonary anti-inflammatory responses through the inhibition of 5-lipoxygenase. 15(S)-HETE suppresses the incorporation of thymidine and biosynthesis of prostaglandin E2 in tumor cell cultures. Treatment of colon cancer cells with 15(S)-HETE inhibited cell proliferation and induced apoptosis, which was preceded by an increase in TGF-beta-inducible early gene (TIEG) and a decrease in Bcl-2.