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Merck
CN

10929

花生四烯酸

puriss., ≥98.5% (GC)

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

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关于此项目

线性分子式:
CH3(CH2)4(CH=CHCH2)4CH2CH2CO2H
化学文摘社编号:
分子量:
304.47
EC Number:
208-033-4
UNSPSC Code:
12352211
MDL number:
Beilstein/REAXYS Number:
1713889
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grade

puriss.

assay

≥98.5% (GC)

refractive index

n20/D 1.4872 (lit.)

bp

169-171 °C/0.15 mmHg (lit.)

mp

−49 °C (lit.)

density

0.922 g/mL at 25 °C (lit.)

shipped in

dry ice

storage temp.

−20°C

SMILES string

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

Biochem/physiol Actions

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。
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 。

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Precursor of many potent biological mediators such as prostaglandins, thromboxanes, leukotrienes. Role of arachidonic acid in the metabolism of platelet-activating factor (PAF)


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Alkylacetylglycerols versus lyso-PAF as precursors in PAF biosynthesis and the role of arachidonic acid in PAF metabolism.
F Snyder et al.
Pharmacological research communications, 18 Suppl, 33-41 (1986-08-01)
Joy Hsu et al.
The Journal of allergy and clinical immunology, 131(4), 977-993 (2013-04-02)
The cause of chronic rhinosinusitis (CRS) remains unclear. Study of the genetic susceptibility to CRS might be a valuable strategy to understand the pathogenesis of this burdensome disorder. The purpose of this review is to critically evaluate the current literature
Luis Gil-de-Gómez et al.
Journal of immunology (Baltimore, Md. : 1950), 190(10), 5169-5177 (2013-04-10)
Activation of macrophages with stimuli of the innate immune response results in the intense remodeling of arachidonate-containing phospholipids, leading to the mobilization of large quantities of this fatty acid for conversion into biologically active eicosanoids. As a consequence of this



全球贸易项目编号

货号GTIN
298190-50G04061826657119
429406-25G04061838139672
429406-5G04061832105628