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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 Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Eiichiro Ishido et al.
Bioscience, biotechnology, and biochemistry, 66(1), 73-77 (2002-02-28)
Two polyunsaturated fatty acids (PUFAs) or their esters were mixed, and their oxidation processes were measured at 65 degrees C and ca. 0% relative humidity. Except when a PUFA ester was mixed with a free PUFA, the oxidation of the
O Holian et al.
Biochemical and biophysical research communications, 160(3), 1110-1116 (1989-05-15)
Purified rat pancreas protein kinase C (PKC) is activated by unsaturated free fatty acids (oleic and arachidonic). The ethyl esters of these fatty acids are ineffective as enzyme activators. However, when the ethyl esters are added in combination with a
The improvement in endotoxin-induced redistribution of organ blood flow by inhibition of thromboxane and prostaglandin synthesis.
G E Tempel et al.
Advances in shock research, 7, 209-218 (1982-01-01)
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.
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
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