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Merck
CN

A9673

Sigma-Aldrich

花生四烯酸

from Porcine liver, ≥99% (GC), liquid

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别名:
二十碳-5Z,8Z,11Z,14Z-四烯酸, 全顺式-5,8,11,14-二十碳四烯酸, 花生四烯酸
线性分子式:
CH3(CH2)4(CH=CHCH2)4CH2CH2CO2H
CAS号:
分子量:
304.47
Beilstein:
1713889
EC 号:
MDL编号:
UNSPSC代码:
12352211
PubChem化学物质编号:

生物来源

Porcine liver

检测方案

≥99% (GC)

形式

liquid

颜色

clear colorless to very faintly yellow

折射率

n20/D 1.4872 (lit.)

bp

169-171 °C/0.15 mmHg (lit.)

mp

−49 °C (lit.)

溶解性

ethanol: ≥10 mg/mL (lit.)(lit.)

密度

0.922 g/mL at 25 °C (lit.)

应用

food and beverages

官能团

carboxylic acid

运输

dry ice

储存温度

−20°C

SMILES字符串

OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O

InChI

1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-

InChI key

YZXBAPSDXZZRGB-DOFZRALJSA-N

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生化/生理作用

花生四烯酸 (AA) 是一种 ω6 不饱和脂肪酸,是细胞膜磷脂的组分。在炎症反应中,水解磷脂酶 A2 可将 AA 从膜磷脂中释放出来。然后,AA 可被至少两种环加氧酶 (COX) 亚型代谢为前列腺素和血栓烷,被脂氧合酶代谢为白三烯和脂氧素,以及通过细胞色素 p450 催化代谢为环氧-二十碳三烯酸。AA 及其代谢产物在多种生物过程中发挥着重要作用,包括信号转导、平滑肌收缩、趋化性、细胞增殖和分化,以及细胞凋亡。已证实 AA 可与 G 蛋白的亚基结合,抑制 Ras GTP 酶激活蛋白 (GAP) 的活性。AA 的细胞摄取需要消耗能量并涉及跨细胞质膜的蛋白质辅助运输。
花生四烯酸可刺激MDA-MB-435人转移癌细胞与细胞外基质分子(胶原蛋白IV和玻连蛋白)的粘附 。

象形图

Exclamation mark

警示用语:

Warning

危险声明

危险分类

Eye Irrit. 2 - Skin Irrit. 2

WGK

WGK 3

闪点(°F)

closed cup

闪点(°C)

closed cup

个人防护装备

Eyeshields, Faceshields, Gloves, multi-purpose combination respirator cartridge (US)

法规信息

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Channels (Austin, Tex.), 7(2), 74-84 (2013-01-22)
Polyunsaturated fatty acids such as arachidonic acid (AA) exhibit inhibitory modulation of Kv4 potassium channels. Molecular docking approaches using a Kv4.2 homology model predicted a membrane-embedded binding pocket for AA comprised of the S4-S5 linker on one subunit and several
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Frontiers in cellular neuroscience, 8, 374-374 (2014-11-27)
Management of lipids, particularly signaling lipids that control neuroinflammation, is crucial for the regeneration capability of a damaged nervous system. Knowledge of pro- and anti-inflammatory signals after nervous system injury is extensive, most of them being proteins acting through well-known
Jingying Chen et al.
Scientific reports, 6, 26608-26608 (2016-05-21)
Definitive haematopoiesis occurs during the lifetime of an individual, which continuously replenishes all blood and immune cells. During embryonic development, haematopoietic stem cell (HSC) formation is tightly controlled by growth factors, signalling molecules and transcription factors. But little is known
William J Gault et al.
The Journal of cell biology, 207(6), 767-782 (2014-12-24)
Osmotic cues from the environment mediate rapid detection of epithelial breaches by leukocytes in larval zebrafish tail fins. Using intravital luminescence and fluorescence microscopy, we now show that osmolarity differences between the interstitial fluid and the external environment trigger ATP
Jesmond Dalli et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 27(7), 2573-2583 (2013-03-19)
Maresins are produced by macrophages from docosahexaenoic acid (DHA) and exert potent proresolving and tissue homeostatic actions. Maresin 1 (MaR1; 7R,14S-dihydroxy-docosa-4Z,8E,10E,12Z,16Z,19Z-hexaenoic acid) is the first identified maresin. Here, we investigate formation, stereochemistry, and precursor role of 13,14-epoxy-docosahexaenoic acid, an intermediate

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