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23401

Supelco

Arachidonic acid

analytical standard

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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.24

biological source

synthetic

Quality Level

grade

analytical standard

Assay

≥97.0% (GC)

form

liquid

shelf life

limited shelf life, expiry date on the label

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.)

application(s)

food and beverages

format

neat

functional group

carboxylic acid

storage temp.

2-8°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
A3611A-122181198
Arachidonic acid analytical standard

Supelco

23401

Arachidonic acid

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

Sigma-Aldrich

A3611

Arachidonic acid

Arachidonic acid 1.0 mg/mL in ethanol, certified reference material, Cerilliant®

Supelco

A-122

Arachidonic acid

Arachidonic Acid Precursor for prostaglandins, prostacyclin, and thromboxane.

Sigma-Aldrich

181198

Arachidonic Acid

format

neat

format

-

format

single component solution

format

-

biological source

synthetic

biological source

non-animal source

biological source

-

biological source

-

assay

≥97.0% (GC)

assay

≥98.5% (GC)

assay

-

assay

≥99% (TLC and GC)

form

liquid

form

liquid

form

liquid

form

oil

shelf life

limited shelf life, expiry date on the label

shelf life

-

shelf life

-

shelf life

-

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) .

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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