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Merck

A9135

Sigma-Aldrich

Ethyl arachidonate

≥98.5% (GC), liquid

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C22H36O2
Número de CAS:
Peso molecular:
332.52
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.25

biological source

fungus

Quality Level

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


Certificados de análisis (COA)

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Enrique M Ostrea et al.
Alcoholism, clinical and experimental research, 30(7), 1152-1159 (2006-06-24)
Biomarkers of fetal exposure to alcohol are important to establish so that early detection and intervention can be made on these infants to prevent undesirable outcomes. The aim of this study was to analyze long-chain fatty acid ethyl esters (FAEEs)
Hao Wang et al.
Alcohol (Fayetteville, N.Y.), 83, 29-35 (2019-06-09)
Problems of stability were found for biomarkers of alcohol consumption: ethyl glucuronide (EtG), ethyl sulfate (EtS), phosphatidylethanols (PEths), and fatty acid ethyl esters (FAEEs) in whole blood. The purpose of this study was to establish a method for the determination
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)

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