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Key Documents

SML1395

Sigma-Aldrich

Arachidonic acid sodium salt

from Mortierella alpina, ≥98.5% (GC), waxy solid, lipid precursor

同義詞:

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

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About This Item

經驗公式(希爾表示法):
C20H31O2Na
CAS號碼:
分子量::
326.45
分類程式碼代碼:
12352211
PubChem物質ID:
NACRES:
NA.77

product name

来自高山被孢霉的花生四烯酸钠盐, ≥98.5% (GC)

生物源

Mortierella alpina

品質等級

化驗

≥98.5% (GC)

形狀

waxy solid

顏色

white to off-white

溶解度

methanol: 50 mg/mL, clear, colorless to faintly yellow

運輸包裝

dry ice

儲存溫度

−20°C

SMILES 字串

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 密鑰

DDMGAAYEUNWXSI-XVSDJDOKSA-M

一般說明

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。

應用

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。

生化/生理作用

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需要消耗能量并且涉及涉及跨细胞质膜的蛋白质辅助转运。

注意

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。

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

235.4 °F - closed cup

閃點(°C)

113 °C - closed cup


分析證明 (COA)

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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
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
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
Arthur A Spector
Journal of lipid research, 50 Suppl, S52-S56 (2008-10-28)
Cytochrome P450 (CYP) epoxygenases convert arachidonic acid to four epoxyeicosatrienoic acid (EET) regioisomers, 5,6-, 8,9-, 11,12-, and 14,15-EET, that function as autacrine and paracrine mediators. EETs produce vascular relaxation by activating smooth muscle large-conductance Ca2+-activated K+ channels (BKCa). In addition
S Araki et al.
Pflugers Archiv : European journal of physiology, 441(5), 596-603 (2001-04-11)
Arachidonic acid activates isolated Rho-kinase and contracts permeabilized smooth muscle fibres. Various assays were carried out to examine the mechanism of this activation. Native Rho-kinase was activated 5-6 times by arachidonic acid but an N-terminal, constitutively-active fragment of Rho-kinase, expressed

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