MilliporeSigma
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A-122

Supelco

Arachidonic acid

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

Synonym(s):
Immunocytophyte, Eicosa-5Z,8Z,11Z,14Z-tetraenoic acid, cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid
Linear Formula:
CH3(CH2)4(CH=CHCH2)4CH2CH2CO2H
CAS Number:
Molecular Weight:
304.47
Beilstein:
1713889
MDL number:
PubChem Substance ID:
NACRES:
NA.24

grade

certified reference material

form

liquid

feature

Snap-N-Spike®/Snap-N-Shoot®

packaging

ampule of 1 mL

manufacturer/tradename

Cerilliant®

concentration

1.0 mg/mL in ethanol

technique(s)

gas chromatography (GC): suitable
liquid chromatography (LC): suitable

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)

clinical testing

format

single component solution

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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General description

A Certified Spiking Solution® suitable for use in mass spectrometry-based fatty acid testing applications such as assessment of cardiovascular disease risk and fatty acid deficiency, and detection and quantification of arachidonic acid in nutraceuticals and dietary supplements. Arachidonic acid (cis-5,8,11,14), sometimes referred to as AA or ARA, is a polyunsaturated omega-6 fatty acid. Studies suggests that ARA as well as other fatty acids can serve as biomarkers for cardiovascular disease, and nutritional and metabolic disorders.

Biochem/physiol Actions

Arachidonic acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .
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.

Legal Information

CERILLIANT is a registered trademark of Cerilliant Corporation
CERTIFIED SPIKING SOLUTION is a registered trademark of Cerilliant Corporation
Snap-N-Shoot is a registered trademark of Cerilliant Corporation
Snap-N-Spike is a registered trademark of Cerilliant Corporation

Pictograms

FlameExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

57.2 °F - closed cup

Flash Point(C)

14.0 °C - closed cup

Certificate of Analysis

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Certificate of Origin

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