(8Z,11Z,14Z)-icosa-8,11,14-trienoic acid

• ChemBase编号: 40
• 分子式: C20H34O2
• 平均质量: 306.48276
• 单一同位素质量: 306.25588033
• SMILES: OC(=O)CCCCCC/C=C\C/C=C\C/C=C\CCCCC
• Canonical SMILES: CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)O
• InChI: InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-
• InChIKey: HOBAELRKJCKHQD-QNEBEIHSSA-N

名称和登记号

名称

• IUPAC标准名: (8Z,11Z,14Z)-icosa-8,11,14-trienoic acid
• IUPAC传统名: dihomo-gamma-linolenic acid; gamma-homolinolenic acid
• 商标名: Tona-lean 1000 CLA (Action Labs); Star GLA (GNC)
• 别名: 顺式-8，11，14-二十烷三烯酸甲酯; 顺式-8,11,14-二十碳三烯酸; (8Z,11Z,14Z)-8,11,14-Eicosatrienoic Acid; 8,11,14-all-cis-Eicosatrienoic acid; Bishomo-γ-linolenic Acid; Dihomo-γ-linolenic Acid; Ro 12-1989; all-cis-8,11,14-Eicosatrienoic Acid; cis-8,cis-11,cis-14-Eicosatrienoic Acid; γ-Homolinolenic Acid; cis-8,11,14-Eicosatrienoic Acid; cis-8,11,14-Eicosatrienoic acid; Homo-γ-linolenic acid; (8E,11E,14E)-8,11,14-Icosatrienoic acid; 8,11,14-Eicosatrienoic Acid; (Z,Z,Z)-8,11,14-Eicosatrienoic acid; cis-8,11,14-Eicosatrienoic acid; DGLA; Dihomo-gamma-linolenic acid; Homo-gamma-linolenic acid; gamma-Homolinolenic acid

登记号

• CAS号: 1783-84-2
• EC号: 217-233-0
• MDL号: MFCD00065721
• Beilstein号: 1796533
• PubChem SID: 46508866; 160963503; 24894557
• PubChem CID: 5280581

理论计算性质

JChem

• Acid pKa: 4.8858237
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 6.24093
• LogD (pH = 7.4): 4.4736137
• Log P: 6.9490924
• 摩尔折射率: 98.8374 cm^3
• 极化性: 37.38399 Å^3
• 极化表面积: 37.3 Å^2
• 可自由旋转的化学键: 15
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 7.24
• LOG S: -6.6
• 溶解度: 7.71e-05 g/l

分子性质

理化性质

• 溶解度: chloroform: soluble50 mg/mL, clear, colorless
• 闪点: 143.6 °F; 62 °C
• 折射率: n20/D 1.478(lit.)
• 疏水性(logP): 6.8

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• 保存温度: -20°C

产品相关信息

• 纯度: ≥99%; ≥99.0% (GC); 99%
• 线性分子式: CH3(CH2)3(CH2CH=CH)3(CH2)6CO2H

详细说明

DrugBank - DB00154

• Drug Groups: approved; nutraceutical
• Description: A 20-carbon-chain fatty acid, unsaturated at positions 8, 11, and 14. It differs from arachidonic acid, 5,8,11,14-eicosatetraenoic acid, only at position 5. [PubChem]
• Indication: For nutritional supplementation, also for treating dietary shortage or imbalance
• Pharmacology: Dihomo gamma-linolenic acid or DHLA is an n-6 (omega-6) polyunsaturated fatty acid. It is comprised of 20 carbon atoms and three double bonds. DHLA is a byproduct of the 18 carbon gamma-linolenic acid (GLA). DHLA is then converted into prostaglandin E1 (PGE1). PGE1 inhibits platelet aggregation and also exerts a vasodilatory effect.
• Affected Organisms: Humans and other mammals
• External Links: PDRhealth

Sigma Aldrich - E4504

包装
100 mg in ampule
Sealed ampule.

Toronto Research Chemicals - E477930

cis-8,11,14-Eicosatrienoic acid is a fatty acid which has selective tumoricidal action.

参考文献

• Das, U., et al.: Cancer Lett., 56, 235 (1991)
• Rudra, P., et al.: Anticancer Res., 21, 29 (1991)
• Menendez, J., et al.: Breast Cancer Res. Treat., 72, 203 (1991)