ethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate

• ChemBase ID: 133043
• Molecular Formular: C22H36O2
• Molecular Mass: 332.52004
• Monoisotopic Mass: 332.27153039
• SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCC
• Canonical SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCC
• InChI: InChI=1S/C22H36O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24-4-2/h8-9,11-12,14-15,17-18H,3-7,10,13,16,19-21H2,1-2H3/b9-8-,12-11-,15-14-,18-17-
• InChIKey: SNXPWYFWAZVIAU-GKFVBPDJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
• IUPAC Traditional name: ethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
• Synonyms: (5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraenoic Acid Ethyl Ester; (all-Z)-5,8,11,14-Eicosatetraenoic Acid Ethyl Ester; Ethyl Arachidonate; 5,8,11,14-Eicosatetraenoic acid ethyl ester; Arachidonic acid ethyl ester; Ethyl arachidonate

Database IDs

• CAS Number: 1808-26-0
• MDL Number: MFCD00038340
• PubChem SID: 162227320; 24891398
• PubChem CID: 5367369

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 7.089873
• LogD (pH = 7.4): 7.089873
• Log P: 7.089873
• Molar Refractivity: 109.4717 cm^3
• Polarizability: 41.105614 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: liquid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.5% (GC)

DETAILS

Sigma Aldrich - A9135

Biochem/physiol Actions
Arachidonic acid (AA) is an unsaturated omega-6 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 p450-catalyzed metabolism. AA and its metabolites play important roles in a variety of biological processes, including signal transduction, contraction, chemotaxis, and cell proliferation, differentiation and apoptosis. AA has been demonstrated to bind to the α 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.
包装
Sealed ampule.

Toronto Research Chemicals - E899400

Arachidonic acid (AA) is an unsaturated omega-6 fatty acid constituent of the phospholipids of cell membranes. Phospholipase A2 releases AA from the membrane phospholipids in response to inflammation.

REFERENCES

• Peterson, J., et al.: J. Pediatr., 152, 788 (2008)
• Pichini, S., et al.: J. Pharm. Biomed. Anal., 48, 927 (2008)