Arachidonic acid
SIGMA/10931 - >95.0% (GC)
Synonym: cis,cis,cis,cis-
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
| assay | >95.0% (GC) |
| biological source | fungus |
| bp | 169-171 °C/0.15 mmHg (lit.) |
| density | 0.922 g/mL at 25 °C (lit.) |
| form | liquid |
| functional group | carboxylic acid |
| InChI | 1S/C20H32O2/c1-2-3-4-5-6- |
| InChI key | YZXBAPSDXZZRGB-DOFZRALJSA |
| lipid type | omega FAs |
| mp | −49 °C (lit.) |
| Quality Level | 100  |
| refractive index | n |
| shipped in | dry ice |
| SMILES string | OC(CCC/C=CC/C=CC/C=CC/ |
| storage temp. | −20°C |
| Application: | Arachidonic acid has been used: • in calibration curve generation in Raman spectroscopy and atomic force microscopy (AFM) in normal and breast cancer samples • as a polyunsaturated fatty acid supplement to the reconstituted synthetic bile (RSB) in drug resistance analysis • for the activation of mechanistic target of rapamycin 1 (mTOR1) and mTOR2 |
| 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) . |
| Packaging: | 1 g in glass bottle |
| Packaging: | 250 mg in glass bottle |
| 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 | >95.0% (GC) |
| bp | 169-171 °C/0.15 mmHg (lit.) |
| mp | −49 °C (lit.) |
| Density | 0.922 g/mL at 25 °C (lit.) |
| Refractive Index | n |
| Storage Temp. | −20°C |
| UNSPSC | 12352211 |