A-122

Arachidonic acid

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

• 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
• UNSPSC Code: 12352211
• NACRES: NA.24
• PubChem Substance ID: 329770689
• MDL number: MFCD00004417
• Beilstein/REAXYS Number: 1713889

Properties

• Product Name: Arachidonic acid, 1.0 mg/mL in ethanol, certified reference material, Cerilliant^®
• 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-
• SMILES string: OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O
• InChI key: YZXBAPSDXZZRGB-DOFZRALJSA-N
• 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

Description

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 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.

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

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.

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

Safety Information

• pictograms: GHS02,GHS07
• signalword: Danger
• hcodes: H225,H319
• pcodes: P210 - P233 - P240 - P241 - P242 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Flam. Liq. 2
• Storage Class: 3 - Flammable liquids
• wgk: WGK 1
• flash_point_f: 57.2 °F - closed cup
• flash_point_c: 14.0 °C - closed cup