4-[(diethoxyphosphoryl)methyl]benzoic acid

• ChemBase ID: 118823
• Molecular Formular: C12H17O5P
• Molecular Mass: 272.234141
• Monoisotopic Mass: 272.08136027
• SMILES: P(=O)(Cc1ccc(C(=O)O)cc1)(OCC)OCC
• Canonical SMILES: CCOP(=O)(Cc1ccc(cc1)C(=O)O)OCC
• InChI: InChI=1S/C12H17O5P/c1-3-16-18(15,17-4-2)9-10-5-7-11(8-6-10)12(13)14/h5-8H,3-4,9H2,1-2H3,(H,13,14)
• InChIKey: BYKRBDLOUKSWNM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(diethoxyphosphoryl)methyl]benzoic acid
• IUPAC Traditional name: 4-[(diethoxyphosphoryl)methyl]benzoic acid
• Synonyms: 4-[(diethoxyphosphoryl)methyl]benzoic acid; α-Phosphono-p-toluic Acid P,P-Diethyl Ester; 4-Carboxyphenyl Phosphonate; 4-(Diethoxyphosphinylmethyl)benzoic Acid

Database IDs

• CAS Number: 28149-48-6
• MDL Number: MFCD00440869
• PubChem SID: 162098695
• PubChem CID: 13745801

CALCULATED PROPERTIES

• Acid pKa: 4.0659375
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.4650505
• LogD (pH = 7.4): -1.2311614
• Log P: 1.9117956
• Molar Refractivity: 67.6324 cm^3
• Polarizability: 26.6026 Å^3
• Polar Surface Area: 72.83 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Partition Coefficient: 1.6

Product Information

• Purity: 95+%

DETAILS

Toronto Research Chemicals - D441970

Used for the preparation of cholesterol acyltransferase-1 (ACAT-1) inhibitors suitable for use as antiarteriosclerotic and anticholesteremic agents.

REFERENCES

• Morioka, Y., et al.: Xenobiotica, 26, 853 (1996)
• Morioka, Y., et al.: Drug Metab. Dispos., 30, 301 (1996)