Arachidonic acid

• Catalog No.: 233846
• CAS Number: 506-32-1
• M. F.: C20H32O2
• M. W.: 304.46688
• Purity: 99%

SYNONYMS

• Title: 花生四烯酸
• IUPAC name: icosa-5,8,11,14-tetraenoic acid
• IUPAC Traditional name: arachidonic acid
• Synonyms: Immunocytophyte; Eicosa-5Z,8Z,11Z,14Z-tetraenoic acid; 全顺式-5,8,11,14-二十碳四烯酸; cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid; 二十碳-5Z,8Z,11Z,14Z-四烯酸

DATABASE IDS

• EC Number: 208-033-4
• CAS Number: 506-32-1
• Beilstein Number: 1713889
• MDL Number: MFCD00004417

PROPERTIES

• Linear Formula: CH3(CH2)4(CH=CHCH2)4CH2CH2CO2H
• Purity: 99%
• Boiling Point: 169-171 °C/0.15 mmHg(lit.)
• Density: 0.922 g/mL at 25 °C(lit.)
• Flash Point: 113 °C
• Flash Point: 235.4 °F
• Melting Point: -49 °C(lit.)
• Refractive Index: n20/D 1.4872(lit.)
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Risk Statements: 19
• RTECS: CE6675000
• Supplemental Hazard Statements: May form explosive peroxides.
• German water hazard class: 3

DETAILS

Description (English)

Other Notes
See Chem. Eng. News., 61(33), 2 (1983).
Biochem/physiol Actions
Arachidonic acid (AA) is an unsaturated ω6 fatty acid constituent of the phospholipids of cell membranes. Phospholipase A2 releases AA from the membrane phospholipids in response to inflammation. AA is subsequently metabolized to prostaglandins and thromboxanes by at least two cyclooxygenase (COX) isoforms, to leukotrienes and lipoxins by lipoxygenases, and to epoxyeicosatrienoic acids via cytochrome p450-catalyzed metabolism. AA and its metabolites play important roles in a variety of biological processes, including signal transduction, smooth muscle contraction, chemotaxis, cell proliferation and differentiation, and apoptosis. AA has been demonstrated to bind to the a subunit of G protein and inhibit the activity of Ras GTPase-activating proteins (GAPs). Cellular uptake of AA is energy dependent and involves protein-facilitated transport across the plasma membrane.
Arachidonic acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .

Description (简体中文)

Other Notes
请参见 Chem. Eng. News., 61(33), 2 (1983)。
Biochem/physiol Actions
Arachidonic acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .
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。