A9135
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:
Molecular Weight:
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 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
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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
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
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)
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
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