2-[(4-nitrophenyl)methyl]butanedioic acid

• ChemBase ID: 175224
• Molecular Formular: C11H11NO6
• Molecular Mass: 253.20814
• Monoisotopic Mass: 253.05863708
• SMILES: c1c(ccc(c1)CC(CC(=O)O)C(=O)O)[N+](=O)[O-]
• Canonical SMILES: OC(=O)CC(C(=O)O)Cc1ccc(cc1)[N+](=O)[O-]
• InChI: InChI=1S/C11H11NO6/c13-10(14)6-8(11(15)16)5-7-1-3-9(4-2-7)12(17)18/h1-4,8H,5-6H2,(H,13,14)(H,15,16)
• InChIKey: DYDFGNHHYHDJLU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4-nitrophenyl)methyl]butanedioic acid
• IUPAC Traditional name: 2-[(4-nitrophenyl)methyl]butanedioic acid
• Synonyms: 2-[(4-Nitrophenyl)methyl]butanedioic Acid; D,L-(p-Nitrobenzyl)succinic Acid

Database IDs

• CAS Number: 56416-12-7
• PubChem SID: 164231134
• PubChem CID: 91846

CALCULATED PROPERTIES

• Acid pKa: 3.261504
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -1.3789978
• LogD (pH = 7.4): -4.3821616
• Log P: 1.6628602
• Molar Refractivity: 60.1322 cm^3
• Polarizability: 22.625185 Å^3
• Polar Surface Area: 120.42 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; DMF; DMSO; Ethyl Acetate
• Apperance: Off-hite Solid
• Melting Point: 149-151°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Store in Freezer

DETAILS

Toronto Research Chemicals - N495600

An intermediate in the synthesis of D,L-(p-aminobenzyl)succinic acid which has been used as a ligand for affinity chromatographic isolation of pancreatic carboxypeptidase A and B enzymes.See also: Cat. No. B29200

REFERENCES

• Bazzone, T., et al.: Biochem., 18, 4362 (1979)
• Narahashi, Y., et al.: Agric. Biol. Chem., 44, 1661 (1979)