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

• ChemBase ID: 174710
• 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}benzoic acid
• IUPAC Traditional name: 2-{[(5-carboxy-2-ethylpentyl)oxy]carbonyl}benzoic acid
• Synonyms: 1,2-Benzenedicarboxylic Acid Mono(5-carboxy-2-ethylpentyl) Ester; MECPP; rac Mono(5-carboxy-2-ethylpentyl) Phthalate

Database IDs

• CAS Number: 40809-41-4
• PubChem SID: 164230620
• PubChem CID: 148386

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: 30.558773 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethyl Acetate; Methanol
• Apperance: White to Beige Gel

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Very Hygroscopic

DETAILS

Toronto Research Chemicals - M525550

Mono(5-carboxy-2-ethylpentyl) Phthalate is 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)