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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:
Molecular Weight:
304.47
Beilstein:
1713889
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

biological source

non-animal source

Quality Level

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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This Item
73500010931181198
Arachidonic acid from non-animal source, ≥98.5% (GC)

Sigma-Aldrich

A3611

Arachidonic acid

Arachidonic acid >95.0% (GC)

Sigma-Aldrich

10931

Arachidonic acid

Arachidonic Acid Precursor for prostaglandins, prostacyclin, and thromboxane.

Sigma-Aldrich

181198

Arachidonic Acid

assay

≥98.5% (GC)

assay

≥98% (CP)

assay

>95.0% (GC)

assay

≥99% (TLC and GC)

form

liquid

form

liquid

form

liquid

form

oil

refractive index

n20/D 1.4872 (lit.)

refractive index

-

refractive index

n20/D 1.4872 (lit.)

refractive index

-

bp

169-171 °C/0.15 mmHg (lit.)

bp

169-171 °C/0.15 mmHg (lit.)

bp

169-171 °C/0.15 mmHg (lit.)

bp

-

mp

−49 °C (lit.)

mp

-49 °C (lit.)

mp

−49 °C (lit.)

mp

-

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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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
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Maresins are produced by macrophages from docosahexaenoic acid (DHA) and exert potent proresolving and tissue homeostatic actions. Maresin 1 (MaR1; 7R,14S-dihydroxy-docosa-4Z,8E,10E,12Z,16Z,19Z-hexaenoic acid) is the first identified maresin. Here, we investigate formation, stereochemistry, and precursor role of 13,14-epoxy-docosahexaenoic acid, an intermediate
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Evidence is accumulating that a dietary supply of long-chain polyunsaturated fatty acids (LC-PUFAs) enhances the development of attention and efficient information processing in infants. However, it is uncertain whether LC-PUFAs in infancy influence cognitive development in later childhood. The objective

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