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5,8,11,14-Eicosatetraenoic acid

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Name

5,8,11,14-Eicosatetraenoic acid

EINECS
CAS No. 7771-44-0 Density 0.928g/cm3
Solubility Melting Point
Formula C20H32O2 Boiling Point 407.4°Cat760mmHg
Molecular Weight 304.52 Flash Point 336.3°C
Transport Information Appearance
Safety A poison by Intraperitoneal Route. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors. Risk Codes
Molecular Structure Molecular Structure of 7771-44-0 (5,8,11,14-EICOSATETRAENOIC ACID			) Hazard Symbols
Synonyms

 

Chemistry

Molecule structure of 5,8,11,14-Eicosatetraenoic acid (CAS NO.7771-44-0) :

IUPAC Name: icosa-5,8,11,14-tetraenoic acid 
Molecular Weight: 304.46688 g/mol
Molecular Formula: C20H32O2
Density: 0.928 g/cm3
Melting Point: -4.95E+01 deg C
Boiling Point: 407.4 °C at 760 mmHg
Flash Point: 336.3 °C
Molar Volume: 327.7 cm3
Polarizability: 38.25*10-24 cm3
Surface Tension: 35.2 dyne/cm
Enthalpy of Vaporization: 72.34 kJ/mol
Vapour Pressure: 8.85E-08 mmHg at 25 °C 
log P (octanol-water): 8.070 (none) 
Atmospheric OH Rate Constant: 2.38E-10 cm3/molecule-sec at 25 °C
XLogP3-AA: 6.3
H-Bond Donor: 1
H-Bond Acceptor: 2
Rotatable Bond Count: 14
Exact Mass: 304.24023
MonoIsotopic Mass: 304.24023
Topological Polar Surface Area: 37.3
Heavy Atom Count: 22
Complexity: 362
Canonical SMILES: CCCCCC=CCC=CCC=CCC=CCCCC(=O)O
InChI: 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)
InChIKey: YZXBAPSDXZZRGB-UHFFFAOYSA-N
Synonyms of 5,8,11,14-Eicosatetraenoic acid (CAS NO.7771-44-0) : Arachidonic acid

Uses

 5,8,11,14-Eicosatetraenoic acid (CAS NO.7771-44-0) is a polyunsaturated fatty acid that is present in the phospholipids (especially phosphatidylethanolamine, phosphatidylcholine and phosphatidylinositides) of membranes of the body's cells, and is abundant in the brain and muscles. In addition to being involved in cellular signaling as a lipid second messenger involved in the regulation of signaling enzymes, such as PLC-δ and PKC-α, -β and -? isoforms, arachidonic acid is a key inflammatory intermediate.
 5,8,11,14-Eicosatetraenoic acid (CAS NO.7771-44-0) is one of the essential fatty acids required by most mammals. Some mammals lack the ability to—or have a very limited capacity to—convert linoleic acid into arachidonic acid, making it an essential part of their diet.

Production

 5,8,11,14-Eicosatetraenoic acid (CAS NO.7771-44-0) is freed from a phospholipid molecule by the enzyme phospholipase A2 (PLA2), which cleaves off the fatty acid, but can also be generated from DAG by Diacylglycerol lipase. 5,8,11,14-Eicosatetraenoic acid (CAS NO.7771-44-0) generated for signaling purposes appears to be derived by the action of a phosphatidylcholine-specific cytosolic phospholipase A2 (cPLA2, 85 kDa), whereas inflammatory arachidonic acid is generated by the action of a low-molecular-weight secretory PLA2 (sPLA2, 14-18 kDa).

Toxicity Data With Reference

1.    

dni-hmn-lym 20 µmol/L

    CNREA8    Cancer Research. 49 (1989),1138.
2.    

ipr-mus LD50:75 mg/kg

    NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD691-490 .

Safety Profile

A poison by Intraperitoneal Route. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.

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