Substance
ID:310635
Names and Identifiers
IUPAC Traditional name
arachidonic acid
IUPAC name
icosa-5,8,11,14-tetraenoic acid
Synonyms
Arachidonic acidcis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acidEicosa-5Z,8Z,11Z,14Z-tetraenoic acid全顺式-5,8,11,14-二十碳四烯酸花生四烯酸Immunocytophyte二十碳-5Z,8Z,11Z,14Z-四烯酸
Registration numbers
CAS Number
EC Number
Beilstein Number
MDL Number
Properties
Product Information
Linear Formula
CH3(CH2)4(CH=CHCH2)4CH2CH2CO2H
Purity
99%
Safety Information
German water hazard class
3
Risk Statements
19
RTECS
CE6675000
MSDS Link
Personal Protective Equipment
Eyeshields, Faceshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
Supplemental Hazard Statements
May form explosive peroxides.
Physical Property
Flash Point
113 °C
235.4 °F
Boiling Point
169-171 °C/0.15 mmHg(lit.)
Refractive Index
n20/D 1.4872(lit.)
Density
0.922 g/mL at 25 °C(lit.)
Melting Point
-49 °C(lit.)
Molecule Details
Other Notes
See Chem. Eng. News., 61(33), 2 (1983).
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 stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .
See Chem. Eng. News., 61(33), 2 (1983).
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 stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .
Molecular Spectra
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References
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