2-(acetyloxy)-3-hydroxypropyl (9Z)-octadec-9-enoate

• ChemBase ID: 175839
• Molecular Formular: C23H42O5
• Molecular Mass: 398.57658
• Monoisotopic Mass: 398.30322444
• SMILES: C(=C\CCCCCCCC)\CCCCCCCC(=O)OCC(CO)OC(=O)C
• Canonical SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)OCC(OC(=O)C)CO
• InChI: InChI=1S/C23H42O5/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)27-20-22(19-24)28-21(2)25/h10-11,22,24H,3-9,12-20H2,1-2H3/b11-10-
• InChIKey: PWTCCMJTPHCGMS-KHPPLWFESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(acetyloxy)-3-hydroxypropyl (9Z)-octadec-9-enoate
• IUPAC Traditional name: 2-(acetyloxy)-3-hydroxypropyl (9Z)-octadec-9-enoate
• Synonyms: 1-Oleoyl-2-acetyl-glycerol; 1-Oleoyl-2-acetylglycerol; (9Z)-9-Octadecenoic Acid 2-(Acetyloxy)-3-hydroxypropyl Ester; OAG; 1-Oleoyl-2-acetyl-sn-glycerol

Database IDs

• CAS Number: 86390-77-4
• PubChem SID: 164231749
• PubChem CID: 6437085

CALCULATED PROPERTIES

• Acid pKa: 14.577799
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 6.050381
• LogD (pH = 7.4): 6.0503807
• Log P: 6.050381
• Molar Refractivity: 113.5776 cm^3
• Polarizability: 44.997517 Å^3
• Polar Surface Area: 72.83 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol (20 mg/ml); Ethyl Acetate; Hexanes
• Apperance: Colourless to light yellow oil

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Temperature Sensitive. This compound can rearrange to the 1,

DETAILS

Toronto Research Chemicals - O526000

Activator of phospholipid-dependent protein kinase C; and stimulator of secretion and aggregation in blood platelets.

REFERENCES

• Nature, 306, 487 (1983)
• J. Biol. Chem., 258, 6701 (1983)
• Biochem. Biophys. Res. Comm., 115, 383 (1983)
• Benz, I., et al.: J. Membr. Biol., 130, 183 (1983)
• Haeffner, E.W., et al.: J. Lipid Mediat., 5, 237 (1983)
• Florin-Christensen, J., et al.: Biochem.