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A9135

Sigma-Aldrich

Ethyl arachidonate

≥98.5% (GC), liquid

Synonym(s):

5,8,11,14-Eicosatetraenoic acid ethyl ester, Arachidonic acid ethyl ester

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About This Item

Empirical Formula (Hill Notation):
C22H36O2
CAS Number:
1808-26-0
Molecular Weight:
332.52
MDL number:
MFCD00038340
UNSPSC Code:
12352211
PubChem Substance ID:
24891398
NACRES:
NA.25

biological source

fungus

assay

≥98.5% (GC)

form

liquid

functional group

ester

lipid type

omega FAs

shipped in

ambient

storage temp.

−20°C

SMILES string

CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OCC

InChI

1S/C22H36O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24-4-2/h8-9,11-12,14-15,17-18H,3-7,10,13,16,19-21H2,1-2H3/b9-8-,12-11-,15-14-,18-17-

InChI key

SNXPWYFWAZVIAU-GKFVBPDJSA-N

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Biochem/physiol Actions

Arachidonic acid (AA) is an unsaturated omega-6 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 p450-catalyzed metabolism. AA and its metabolites play important roles in a variety of biological processes, including signal transduction, contraction, chemotaxis, and cell proliferation, differentiation and apoptosis. AA has been demonstrated to bind to the α 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.

Packaging

Sealed ampule.

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves

Certificates of Analysis (COA)

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D L Luthria et al.
Lipids, 28(9), 853-856 (1993-09-01)
Ethyl 5,8,11,14-eicosatetraenoate-19,19,20,20-d4 and ethyl 8,11,14-eicosatrienoate-19,19,20,20-d4 were synthesized by Grignard coupling of the methanesulfonyl ester of 2,5-undecadiyn-1-ol-10,10,11,11-d4 with 5,8-nonadiynoic acid and 8-nonynoic acid, respectively. The coupled products upon Lindlar reduction, followed by the preparation of their ethyl esters, yielded deuteriated ethyl
Majed A Refaai et al.
Clinical chemistry, 48(1), 77-83 (2001-12-26)
Fatty acid ethyl esters (FAEEs) are nonoxidative ethanol metabolites that have been implicated as mediators of alcohol-induced organ damage. FAEEs are detectable in the blood after ethanol ingestion, and on that basis have been proposed as markers of ethanol intake.
Kwang-Geun Lee et al.
Journal of agricultural and food chemistry, 51(24), 7203-7207 (2003-11-13)
The antioxidant activities of naturally occurring plant compounds were measured in a lipid peroxidation system consisting of ethyl arachidonate and Fenton's reagent. Inhibitory effects of 24 plant-derived flavonoids and 5 phenolic acids on malonaldehyde (MA) formation from ethyl arachidonate were
Yin Duan et al.
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP, 148(3), 244-249 (2008-07-05)
Recent investigations in our laboratory showed that voltage-gated sodium channels (VGSCs) in brain are sensitive to inhibition by various synthetic cannabinoids and endocannabinoids. The present experiments examined the effects of the cannabinoid-1 (CB1) receptor agonist CP-55,940 and ethyl arachidonate on
Xinyu Zhang et al.
Analytica chimica acta, 963, 68-75 (2017-03-25)
The importance of ethanol non-oxidative metabolites as the specific biomarkers of alcohol consumption in clinical and forensic settings is increasingly acknowledged. Simultaneous determination of these metabolites can provide a wealth of information like drinking habit and history, but it was
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