(2S)-2,3-dihydroxypropyl (9Z,12Z)-octadeca-9,12-dienoate

• ChemBase ID: 172323
• Molecular Formular: C21H38O4
• Molecular Mass: 354.52402
• Monoisotopic Mass: 354.2770097
• SMILES: OC[C@@H](COC(=O)CCCCCCC/C=C\C/C=C\CCCCC)O
• Canonical SMILES: CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](CO)O
• InChI: InChI=1S/C21H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-19-20(23)18-22/h6-7,9-10,20,22-23H,2-5,8,11-19H2,1H3/b7-6-,10-9-/t20-/m0/s1
• InChIKey: WECGLUPZRHILCT-GSNKCQISSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2,3-dihydroxypropyl (9Z,12Z)-octadeca-9,12-dienoate
• IUPAC Traditional name: (2S)-2,3-dihydroxypropyl (9Z,12Z)-octadeca-9,12-dienoate
• Synonyms: α-Linoleic Acid (2S)-2,3-Dihydroxypropyl Ester; (9Z,12Z)-9,12-Octadecadienoic Acid (2S)-2,3-Dihydroxypropyl Ester; 1-Linoleoyl-(2S)-glycerol

Database IDs

• CAS Number: 67968-46-1
• PubChem SID: 164228233
• PubChem CID: 6436630

CALCULATED PROPERTIES

• Acid pKa: 13.619246
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 5.247334
• LogD (pH = 7.4): 5.2473335
• Log P: 5.247334
• Molar Refractivity: 105.5427 cm^3
• Polarizability: 40.927094 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - L467955

(9Z,12Z)-9,12-Octadecadienoic Acid (2S)-2,3-Dihydroxypropyl Ester is a monoacylglycerol (MAG) based unsaturated fatty acid derivative.

REFERENCES

• Garcia, P. et al.: J. Sep. Sci., 34, 999 (2011)
• Takagi, T. et al.: LIpids, 25, 398 (2011)