SML1395
Arachidonic acid sodium salt
from Mortierella alpina, ≥98.5% (GC), waxy solid, lipid precursor
别名:
5,8,11,14-二十碳四烯酸, 二十碳-5Z,8Z,11Z,14Z-四烯酸, 花生四烯酸钠, 顺,顺,顺,顺-5,8,11,14-二十碳四烯酸钠，20:4
产品名称
来自高山被孢霉的花生四烯酸钠盐, ≥98.5% (GC)
SMILES string
O=C(O[Na])CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC
InChI
1S/C20H32O2.Na/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);/q;+1/p-1/b7-6-,10-9-,13-12-,16-15-;
InChI key
DDMGAAYEUNWXSI-XVSDJDOKSA-M
biological source
Mortierella alpina
assay
≥98.5% (GC)
form
waxy solid
color
white to off-white
solubility
methanol: 50 mg/mL, clear, colorless to faintly yellow
shipped in
dry ice
storage temp.
−20°C
Quality Level
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相关类别
General description
花生四烯酸（AA）是细胞膜磷脂的多不饱和ϖ脂肪酸成分。在结构上，它是一种含有四个 顺式 双键的20碳链，因此，AA的游离酸形式是不溶性油状物；它在正常生理pH范围内可转化为水溶性钠盐形式。 花生四烯酸可被多种酶代谢，产生各种代谢物；AA及其代谢物在多种生物过程中具有重要作用，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。
Application
花生四烯酸被用于测定氧化酶（如环加氧酶）活性，以及用于测定全血中的血小板抑制。 花生四烯酸已被证明能够与G蛋白的α亚基结合，并抑制Ras GTP酶活化蛋白（GAP）的活性，从而在前列腺癌的发展进程中发挥作用，并增强人肥大细胞中的脂质体形成。
Biochem/physiol Actions
花生四烯酸（ARA）是生物细胞膜的重要组成部分，为其提供所有细胞功能所需的流动性和柔韧性，尤其是在神经系统、骨骼肌和免疫系统中。游离ARA通过激活和抑制来调节离子通道、各种受体和酶的活性。ARA在细胞膜内经历再酰化/去酰化循环，将其浓度保持在低水平并限制其可用于氧化的量。ARA氧化产生的代谢物不会引发炎症，但会导致炎症，更重要的是，它们会产生对消退炎症和促进伤口愈合至关重要的介质。释放的花生四烯酸（AA）与分子氧在氧化应激作用下发生非酶促反应，并在加氧酶催化下发生酶促反应。AA可在至少两种环加氧酶（COX）亚型作用下被氧化成前列腺素和血栓素，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。花生四烯酸的细胞摄取是能量依赖性的，并且涉及蛋白质促进的跨质膜转运。
Disclaimer
花生四烯酸钠盐对氧化非常敏感，在空气中会很快地变黄和变质。它们在真空环境下包装在密封安瓿瓶中。产品一旦打开须尽快使用或尽快转移至惰性气体氛围（干燥氩气）中。
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
235.4 °F - closed cup
flash_point_c
113 °C - closed cup
P C Calder et al.
European journal of clinical nutrition, 56 Suppl 3, S14-S19 (2002-07-27)
Consumption of n-6 polyunsaturated fatty acids greatly exceeds that of n-3 polyunsaturated fatty acids. The n-6 polyunsaturated fatty acid arachidonic gives rise to the eicosanoid family of inflammatory mediators (prostaglandins, leukotrienes and related metabolites) and through these regulates the activities
Olga Bondarenko et al.
FEBS letters, 593(14), 1735-1750 (2019-05-23)
During spermatogenesis, fatty acids play an important role both as structural components and messengers that trigger male germ cell line differentiation. The spontaneous oxidation of fatty acids causes a decrease in mammalian fertility. Here, we examine the effects of nonenzymatically
L B Klickstein et al.
The Journal of clinical investigation, 66(5), 1166-1170 (1980-11-01)
The predominant lipoxygenase products of arachidonic acid were extracted and purified from synovial fluid and sonicates of synovial tissue of patients with rheumatoid arthritis (RA), spondyloarthritis (SA), or a noninflammatory arthropathy (NIA). The concentration of 5(S),12(R)-dihydroxy-6,8,10-(trans/trans/cis)-14-cis-eicosatetraenoic acid (leukotriene B4) in
J A Badwey et al.
The Journal of biological chemistry, 256(24), 12640-12643 (1981-12-25)
Arachidonate stimulates the production of large quantities of superoxide by human neutrophils: 93.8 +/- 12.5 S.D. nmol of O2(-)/min/10(7) cells. This rate is comparable to that observed with the most effective neutrophil-stimulating agents previously reported. Other cis-unsaturated fatty acids are
Arachidonic acid as a bioactive molecule.
A R Brash
The Journal of clinical investigation, 107(11), 1339-1345 (2001-06-08)
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