oxiran-2-ylmethyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate

• ChemBase ID: 169738
• Molecular Formular: C23H34O3
• Molecular Mass: 358.51426
• Monoisotopic Mass: 358.25079495
• SMILES: C(C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)CC(=O)OCC1OC1
• Canonical SMILES: CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCC1CO1
• InChI: InChI=1S/C23H34O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(24)26-21-22-20-25-22/h3-4,6-7,9-10,12-13,15-16,22H,2,5,8,11,14,17-21H2,1H3/b4-3-,7-6-,10-9-,13-12-,16-15-
• InChIKey: INTHOQCNXQLKIE-JLNKQSITSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: oxiran-2-ylmethyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
• IUPAC Traditional name: oxiran-2-ylmethyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
• Synonyms: (all-Z)-5,8,11,14,17-Eicosapentaenoic Acid Glycidyl Ester; EPA Glycidyl Ester; Glycidyl Eicosapentaenoate

Database IDs

• PubChem SID: 162263870
• PubChem CID: 71317134

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 6.21241
• LogD (pH = 7.4): 6.21241
• Log P: 6.21241
• Molar Refractivity: 114.5844 cm^3
• Polarizability: 42.63717 Å^3
• Polar Surface Area: 38.83 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Colourless Liquid

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - G615650

A monoacylglycerol used in the preparation of triacylglycerols acylated with n-3 polyunsaturated fatty acids for nutritional applications.

REFERENCES

• Whitcutt, J.M., et al.: Biochem. J., et al.: 67, 60 (1957)
• Bazan, N.G., et al.: J. Ocul. Pharmacol., 10, 591 (1957)
• Makrides, M., et al.: Lipids, 31, 115 (1957)