Arachidonic acid

SIAL/23401 - analytical standard

Synonym: cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid; Eicosa-5Z,8Z,11Z,14Z-tetraenoic acid; Immunocytophyte

CAS Number: 506-32-1
Empirical Formula (Hill Notation): C₂₀H₃₂O₂
Molecular Weight: 304.47
EC Number: 208-033-4
MDL Number: MFCD00004417
Linear Formula: CH₃(CH₂)₄(CH=CHCH₂)₄CH₂CH₂CO₂H
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-23401-50MG	50 mg	$215.00 1/EA	Add To Favorites

This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: 23401-50MG

Properties
Descriptions
Safety Info.
Basic Data

application(s)	food and beverages
assay	≥97.0% (GC)
biological source	synthetic
bp	169-171 °C/0.15 mmHg (lit.)
density	0.922 g/mL at 25 °C (lit.)
form	liquid
format	neat
functional group	carboxylic acid
grade	analytical standard
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
mp	−49 °C (lit.)
Quality Level	100
refractive index	n20/D 1.4872 (lit.)
shelf life	limited shelf life, expiry date on the label
SMILES string	OC(CCC/C=CC/C=CC/C=CC/C=CCCCCC)=O
storage temp.	2-8°C

Application:	Arachidonic acid for inflammation research studies: Research on gigantol, a natural compound, emphasized its anti-inflammatory properties. This study suggests a parallel with arachidonic acid′s known effects on inflammation pathways, providing a comprehensive view of its potential in pharmaceutical and biotechnological applications (Chowdhury et al., 2024 ). High-purity arachidonic acid for biochemical assays: A novel study on Yinhua Miyanling tablets for treating ulcerative colitis employed metabolomics and network pharmacology, highlighting arachidonic acid′s crucial role in understanding biochemical pathways in therapeutic contexts (Wang et al., 2024 ). Arachidonic acid as a signaling molecule in cell culture: A hepatoprotective study on cholic acid against liver injury used arachidonic acid for its significant roles in cellular signaling pathways, elucidating its mechanisms in medical research (Zhang et al., 2024 ).
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.
Biochem/physiol Actions:	Arachidonic acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .

RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	235.4 °F - closed cup
Flash Point(C)	113 °C - closed cup

Purity	≥97.0% (GC)
bp	169-171 °C/0.15 mmHg (lit.)
mp	−49 °C (lit.)
Density	0.922 g/mL at 25 °C (lit.)
Refractive Index	n20/D 1.4872 (lit.)
Storage Temp.	2-8°C
UNSPSC	85151701

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