sodium (2R)-1-[(2,3-dihydroxypropyl phosphonato)oxy]-3-(tetradecanoyloxy)propan-2-yl tetradecanoate

• ChemBase ID: 154533
• Molecular Formular: C34H66NaO10P
• Molecular Mass: 688.845371
• Monoisotopic Mass: 688.42912922
• SMILES: CCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC(CO)O)OC(=O)CCCCCCCCCCCCC.[Na+]
• Canonical SMILES: CCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCC)COP(=O)(OCC(CO)O)[O-].[Na+]
• InChI: InChI=1S/C34H67O10P.Na/c1-3-5-7-9-11-13-15-17-19-21-23-25-33(37)41-29-32(30-43-45(39,40)42-28-31(36)27-35)44-34(38)26-24-22-20-18-16-14-12-10-8-6-4-2;/h31-32,35-36H,3-30H2,1-2H3,(H,39,40);/q;+1/p-1/t31?,32-;/m1./s1
• InChIKey: QLNOOKSBAYIHQI-SKZICHJRSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2R)-1-[(2,3-dihydroxypropyl phosphonato)oxy]-3-(tetradecanoyloxy)propan-2-yl tetradecanoate
• IUPAC Traditional name: sodium (2R)-1-[(2,3-dihydroxypropyl phosphonato)oxy]-3-(tetradecanoyloxy)propan-2-yl tetradecanoate
• Synonyms: 1,2-Ditetradecanoyl-sn-glycero-3-phospho-(1′-rac-glycerol) sodium salt; L-α-Phosphatidyl-DL-glycerol, dimyristoyl sodium salt; L-α-Phosphatidyl-DL-glycerol, dimyristoyl; DMPG-Na; DMPG; PG(14:0/14:0); Tetradecanoic acid 1-[[[(2,3-dihydroxypropoxy)hydroxyphosphinyl]oxy]methyl]-1,2-ethanediyl ester monosodium salt; 1,2-Dimyristoyl-sn-glycero-3-phospho-rac-(1-glycerol) sodium salt

Database IDs

• CAS Number: 67232-80-8
• MDL Number: MFCD00056649
• PubChem SID: 24898765; 162248672
• PubChem CID: 46891824

CALCULATED PROPERTIES

• Acid pKa: 1.8907738
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 6.806963
• LogD (pH = 7.4): 6.7826962
• Log P: 9.158777
• Molar Refractivity: 175.7832 cm^3
• Polarizability: 71.16826 Å^3
• Polar Surface Area: 151.65 Å^2
• Rotatable Bonds: 36
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.0% (TLC); ≥99%
• Biological Source: from synthetic
• Linear Formula: C34H66O10PNa

DETAILS

Sigma Aldrich - 90998

Application
Prototype for the preparation of liposomes with negatively charged hydrophilic head groups. Phase transitions, close-packing ratios, and ion permeability are all strongly affected by the presence of a stoichiometric amount (1:2) of divalent cations.1

Sigma Aldrich - P6412

Application
Prototype for the preparation of liposomes with negatively charged hydrophilic head groups. Phase transitions, close-packing ratios, and ion permeability are all strongly affected by the presence of a stoichiometric amount (1:2) of divalent cations.1