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SML1395

Sigma-Aldrich

Arachidonic acid sodium salt from Mortierella alpina

≥98.5% (GC)

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Synonym(s):
5,8,11,14-Eicosatetraenoic acid, Eicosa-5Z,8Z,11Z,14Z-tetraenoic acid, Sodium arachidonate, cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid sodium salt, 20:4
Empirical Formula (Hill Notation):
C20H31O2Na
CAS Number:
6610-25-9
Molecular Weight:
326.45
PubChem Substance ID:
329825843

biological source

Mortierella alpina

Quality Level

200

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

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

General description

Arachidonic acid (AA) is a polyunsaturated ϖ fatty acid constituent of the phospholipids of cell membranes. Structurally, it is a 20-carbon chain that contains four cis double bonds, which allow the free acid form of AA to be an insoluble oil; this can be converted to the water-soluble sodium salt form within the normal physiological pH range. Arachidonic acid is metabolized by multiple enzymes to yield various metabolites; 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.

Application

Arachidonic acid is used in assays to measure activity of oxidizing enzymes, such as cyclooxygenase, as well as in assays to determine platelet inhibition in whole blood. Arachidonic acid has been demonstrated to bind to the a subunit of G protein and inhibit the activity of Ras GTPase-activating proteins (GAPs), to have a role in the development and progression of prostate cancer, and to enhance formation of lipid bodies in human mast cells.

Biochem/physiol Actions

Released arachidonic acid (AA) reacts with molecular oxygen nonenzymatically, through oxidative stress, and enzymatically through the action of oxygenase enzymes. AA is oxidized 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. Cellular uptake of arachidonic acid is energy dependent and involves protein-facilitated transport across the plasma membrane.

Caution

The sodium salts of arachidonic acid are very sensitive to oxidation and will turn yellow and deteriorate rapidly in air. They are packaged under vacuum in sealed ampules. Once opened the product must be used quickly or transferred into an inert atmosphere (dry argon) as soon as possible.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

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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
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
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
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
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