Arachidonic acid
SIGMA/A3611 - from non-animal source, ≥98.5% (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
Representative of vacuum-sealed amber ampule packaging. Non-uniform tips are an inherent feature in this sealing process.
| assay | ≥98.5% (GC) |
| biological source | non-animal source |
| 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 | 300  |
| refractive index | n |
| shipped in | dry ice |
| SMILES string | OC(CCC/C=CC/C=CC/C=CC/ |
| storage temp. | −20°C |
| Application: | <ul> <li><strong>Molecular Mechanisms Associated with the Inhibitory Role of Long Chain n-3 PUFA in Colorectal Cancer:</strong> This study discusses the effects of long-chain polyunsaturated fatty acids, like arachidonic acid, on colorectal cancer mechanisms. The research focuses on the anti-inflammatory and cancer inhibitory roles through the modulation of lipid metabolism and signal transduction pathways (Jayathilake et al., 2024)  .</li><li><strong>Zhilining Formula alleviates DSS-induced colitis through suppressing inflammation and gut barrier dysfunction via the AHR/NF-Bp65 axis:</strong> This article presents arachidonic acid′s role in the suppression of inflammation and restoration of gut barrier function, crucial for understanding inflammatory diseases and developing therapeutic strategies (Zhou et al., 2024) .</li><li><strong>5,6-diHETE lactone (EPA-L) mediates hypertensive microvascular dilation by activating the endothelial GPR-PLC-IP(3) signaling pathway:</strong> Explores the cardiovascular implications of arachidonic acid metabolites, specifically their role in microvascular responses, which could influence hypertension treatment strategies (Asulin et al., 2024) .</li></ul> |
| 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 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. |
| 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 ampule |
| Packaging: | 10, 100 mg in ampule |
| Packaging: | Sealed ampule |
| 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 | ≥98.5% (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 |