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Merck

A8798

Sigma-Aldrich

Natrium arachidonat aus Schweineleber

from Porcine liver, ≥99% (capillary GC), waxy solid

Synonym(e):

Arachidonsäure Natriumsalz, cis,cis,cis,cis-5,8,11,14-Eicosatetraensäure Natriumsalz, 20:4

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About This Item

Empirische Formel (Hill-System):
C20H31O2Na
CAS-Nummer:
Molekulargewicht:
326.45
MDL-Nummer:
UNSPSC-Code:
12352200
PubChem Substanz-ID:

Biologische Quelle

Porcine liver

Assay

≥99% (capillary GC)

Form

waxy solid

Farbe

white to off-white

Löslichkeit

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

Versandbedingung

dry ice

Lagertemp.

−20°C

SMILES String

[Na+].CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC([O-])=O

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-;

InChIKey

DDMGAAYEUNWXSI-XVSDJDOKSA-M

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Allgemeine Beschreibung

Arachidonic acid (AA) is a polyunsaturated ω6 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.[1] AA 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.

Anwendung

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. AA has been demonstrated to bind to the α 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.[2]

Biochem./physiol. Wirkung

Released arachidonic acid (AA) reacts with molecular oxygen nonenzymatically, through oxidative stress, and enzymatically through the action of oxygenase enzymes.[1] 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 AA is energy dependent and involves protein-facilitated transport across the plasma membrane.

Vorsicht

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.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

235.4 °F - closed cup

Flammpunkt (°C)

113 °C - closed cup

Persönliche Schutzausrüstung

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges


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