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A3611

Sigma-Aldrich

Arachidonic acid

from non-animal source, ≥98.5% (GC)

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Synonym(s):
cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid, Eicosa-5Z,8Z,11Z,14Z-tetraenoic acid, Immunocytophyte
Linear Formula:
CH3(CH2)4(CH=CHCH2)4CH2CH2CO2H
CAS Number:
506-32-1
Molecular Weight:
304.47
Beilstein:
1713889
EC Number:
208-033-4
MDL number:
MFCD00004417
PubChem Substance ID:
329770839
NACRES:
NA.25

biological source

non-animal source

Quality Level

300

Assay

≥98.5% (GC)

form

liquid

refractive index

n20/D 1.4872 (lit.)

bp

169-171 °C/0.15 mmHg (lit.)

mp

−49 °C (lit.)

density

0.922 g/mL at 25 °C (lit.)

functional group

carboxylic acid

lipid type

omega FAs

shipped in

dry ice

storage temp.

−20°C

SMILES string

OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O

InChI

1S/C20H32O2/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)/b7-6-,10-9-,13-12-,16-15-

InChI key

YZXBAPSDXZZRGB-DOFZRALJSA-N

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Biochem/physiol Actions

Arachidonic acid (AA) is an unsaturated ω6 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 cytochrome p450-catalyzed metabolism. 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. AA has been demonstrated to bind to the a 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.
Arachidonic acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .

Packaging

Sealed ampule

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

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Abdulaziz M S Alsaad et al.
Drug metabolism reviews, 45(2), 173-195 (2013-04-23)
A plethora of studies have demonstrated the expression of cytochrome P450 (CYP) and soluble epoxide hydrolase (sEH) enzymes in the heart and other cardiovascular tissues. In addition, the expression of these enzymes is altered during several cardiovascular diseases (CVDs), including
Alma M Astudillo et al.
Biochimica et biophysica acta, 1821(2), 249-256 (2011-12-14)
The development of mass spectrometry-based techniques is opening new insights into the understanding of arachidonic acid (AA) metabolism. AA incorporation, remodeling and release are collectively controlled by acyltransferases, phospholipases and transacylases that exquisitely regulate the distribution of AA between the
Tamás Decsi et al.
The American journal of clinical nutrition, 98(2), 543S-548S (2013-07-05)
We summarize data on the potential interaction of trans isomeric fatty acids [trans fatty acids (TFAs)] with the availability of long-chain polyunsaturated fatty acids (LC-PUFAs) in the perinatal period. Today, TFA intakes in pregnant and lactating women can be estimated
Kenneth D'Souza et al.
Biochimica et biophysica acta, 1838(6), 1501-1508 (2013-10-15)
There are six major species of phospholipids in eukaryotes, each of which plays unique structural and functional roles. One species, phosphatidylinositol (PI) only contributes about 2-10% of the total phospholipid pool. However, they are critical factors in the regulation of
Jean-Claude Honoré et al.
Arteriosclerosis, thrombosis, and vascular biology, 33(5), 954-961 (2013-03-23)
Nitro-oxidative stress exerts a significant role in the genesis of hypoxic-ischemic (HI) brain injury. We previously reported that the ω-6 long chain fatty acids, transarachidonic acids (TAAs), which are nitrative stress-induced nonenzymatically generated arachidonic acid derivatives, trigger selective microvascular endothelial
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