4-{[(benzyloxy)carbonyl]amino}butanoic acid

• ChemBase ID: 59961
• Molecular Formular: C12H15NO4
• Molecular Mass: 237.2518
• Monoisotopic Mass: 237.10010797
• SMILES: C(=O)(OCc1ccccc1)NCCCC(=O)O
• Canonical SMILES: OC(=O)CCCNC(=O)OCc1ccccc1
• InChI: InChI=1S/C12H15NO4/c14-11(15)7-4-8-13-12(16)17-9-10-5-2-1-3-6-10/h1-3,5-6H,4,7-9H2,(H,13,16)(H,14,15)
• InChIKey: STQMDRQJSNKUAW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[(benzyloxy)carbonyl]amino}butanoic acid
• IUPAC Traditional name: 4-{[(benzyloxy)carbonyl]amino}butanoic acid
• Synonyms: 4-(((benzyloxy)carbonyl)amino)butanoic acid; 4-(Benzyloxycarbonylamino)butanoic Acid; 4-(Benzyloxycarbonylamino)butyric Acid; 4-[(N-Carbobenzoxy)amino]butyric Acid; Carbobenzoxy-4-aminobutyric Acid; N-Benzyloxycarbonyl-γ-aminobutyric Acid; N-Carbobenzyloxy-γ-aminobutyric Acid; NSC 120007; N-Benzyloxycarbonyl-γ-aminobutyric Acid; 4-{[(Benzyloxy)carbonyl]amino}butanoic acid

Database IDs

• CAS Number: 5105-78-2
• MDL Number: MFCD00055835
• PubChem SID: 162064724
• PubChem CID: 21184

CALCULATED PROPERTIES

• Acid pKa: 4.042597
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.07217886
• LogD (pH = 7.4): -1.5933206
• Log P: 1.5408093
• Molar Refractivity: 61.1378 cm^3
• Polarizability: 23.83063 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Melting Point: 61 - 63°C
• Hydrophobicity(logP): 1.783

Safety Information

• Storage Warning: IRRITANT
• TSCA Listed: false

Product Information

• Purity: 95%; 95+%; 97%

DETAILS

Toronto Research Chemicals - B286075

γ-Aminobutyric acid (A602920) derivative. Antineoplastic agent. Suppresses electrical induced seizures.

REFERENCES

• Loeffler, L. et al.; J. Med. Chem. 20, 1584 (1977)
• Nishizawa, Y. et al.; J. Vitaminol. 14, 331 (1968).