(2S)-1-(hexadecanoyloxy)-3-hydroxypropan-2-yl hexadecanoate

• ChemBase ID: 132571
• Molecular Formular: C35H68O5
• Molecular Mass: 568.91142
• Monoisotopic Mass: 568.50667528
• SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](CO)OC(=O)CCCCCCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCCCC)CO
• InChI: InChI=1S/C35H68O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(37)39-32-33(31-36)40-35(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h33,36H,3-32H2,1-2H3/t33-/m0/s1
• InChIKey: JEJLGIQLPYYGEE-XIFFEERXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-(hexadecanoyloxy)-3-hydroxypropan-2-yl hexadecanoate
• IUPAC Traditional name: diacylglycerol
• Synonyms: DG(16:0/16:0/0:0); Hexadecanoic acid 1,1′-[(1S)-1-(hydroxymethyl)-1,2-ethanediyl] ester; NSC 269964; 1,2-Dipalmitoyl-sn-glycerol; (S)-1,2-Dipalmitin; (S)-Glycerol 1,2-dipalmitate; 1,2-Dihexadecanoyl-sn-glycerol

Database IDs

• CAS Number: 30334-71-5
• EC Number: 250-131-4
• MDL Number: MFCD00067471
• Beilstein Number: 1730209
• PubChem SID: 162226848; 24894256
• PubChem CID: 644078

CALCULATED PROPERTIES

• Acid pKa: 14.577784
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 12.003094
• LogD (pH = 7.4): 12.003094
• Log P: 12.003094
• Molar Refractivity: 167.6989 cm^3
• Polarizability: 67.347694 Å^3
• Polar Surface Area: 72.83 Å^2
• Rotatable Bonds: 34
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 66-69 °C

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ~99%; ≥99.0% (TLC)
• Impurities: 1,3-isomer, essentially free
• fatty acid homogeneity: ≥99% (GC, after transesterification)
• Empirical Formula (Hill Notation): C35H68O5

DETAILS

Sigma Aldrich - D9135

Preparation Note
Prepared by a modification of the procedure of Sowdon, J.C. and Fisher, H.O.l., J. Am. Chem. Soc., 63, 3244 (1941).

Sigma Aldrich - 42553

Biochem/physiol Actions
1,2-Dipalmitoyl-glycerol affects membrane structure in model membranes. It is used to study the relationship between membrane structure and protein kinase C activity 1.