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A-122

Supelco

Arachidonic acid

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

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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/REAXYS Number:
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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This Item
10931A3611A3631
vibrant-m

A-122

Arachidonic acid

vibrant-m

10931

Arachidonic acid

vibrant-m

A3611

Arachidonic acid

vibrant-m

A3631

Arachidic acid

format

single component solution

format

-

format

-

format

-

form

liquid

form

liquid

form

liquid

form

crystalline powder

feature

Snap-N-Spike®/Snap-N-Shoot®

feature

-

feature

-

feature

-

packaging

ampule of 1 mL

packaging

-

packaging

-

packaging

-

manufacturer/tradename

Cerilliant®

manufacturer/tradename

-

manufacturer/tradename

-

manufacturer/tradename

-

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 (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) .

Legal Information

CERILLIANT is a registered trademark of Merck KGaA, Darmstadt, Germany
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 Merck KGaA, Darmstadt, Germany

pictograms

FlameExclamation mark

signalword

Danger

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

57.2 °F - closed cup

flash_point_c

14.0 °C - closed cup


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