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
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
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 ![External link](https://krackeler.com/images/sigma/ext-link.gif) |
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 |
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 |