2-{[(5-carboxy-2-ethylpentyl)oxy]carbonyl}(2H4)benzoic acid

• ChemBase ID: 174711
• Molecular Formular: C16H20O6
• Molecular Mass: 308.3264
• Monoisotopic Mass: 308.12598836
• SMILES: c1ccc(c(c1)C(=O)OCC(CCCC(=O)O)CC)C(=O)O
• Canonical SMILES: CCC(COC(=O)c1ccccc1C(=O)O)CCCC(=O)O
• InChI: InChI=1S/C16H20O6/c1-2-11(6-5-9-14(17)18)10-22-16(21)13-8-4-3-7-12(13)15(19)20/h3-4,7-8,11H,2,5-6,9-10H2,1H3,(H,17,18)(H,19,20)
• InChIKey: XFGRNAPKLGXDGF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[(5-carboxy-2-ethylpentyl)oxy]carbonyl}(^2H₄)benzoic acid
• IUPAC Traditional name: 2-{[(5-carboxy-2-ethylpentyl)oxy]carbonyl}(^2H₄)benzoic acid
• Synonyms: 1,2-Benzenedicarboxylic Acid-d4 Mono(5-carboxy-2-ethylpentyl) Ester; MECPP-d4; rac Mono(5-carboxy-2-ethylpentyl) Phthalate-d4

Database IDs

• PubChem SID: 164230621
• PubChem CID: 71750783

CALCULATED PROPERTIES

• Acid pKa: 3.0273447
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.48002794
• LogD (pH = 7.4): -3.228982
• Log P: 3.3366418
• Molar Refractivity: 79.1531 cm^3
• Polarizability: 30.581263 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M525552

Labelled analogue of Mono(5-carboxy-2-ethylpentyl) Phthalate, a metabolite of Bis(2-ethylhexyl) Phthalate (DEHP) (B433850).

REFERENCES

• Engel, S. et al.: NeuroToxicol., 30, 522 (2009)
• Hernandez-Diaz, S. et al.: Environ. Health Perspectives, 117, 185 (2009)
• Berman, T. et al.: Environ. Int., 35, 353 (2009)