(2S)-2-hydroxy-3-(1H-imidazol-5-yl)propanoic acid hydrate

• ChemBase ID: 171550
• Molecular Formular: C6H10N2O4
• Molecular Mass: 174.1546
• Monoisotopic Mass: 174.06405681
• SMILES: c1ncc([nH]1)C[C@H](O)C(=O)O.O
• Canonical SMILES: O[C@H](C(=O)O)Cc1cnc[nH]1.O
• InChI: InChI=1S/C6H8N2O3.H2O/c9-5(6(10)11)1-4-2-7-3-8-4;/h2-3,5,9H,1H2,(H,7,8)(H,10,11);1H2/t5-;/m0./s1
• InChIKey: LJUYTQBGWOQLKC-JEDNCBNOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-hydroxy-3-(1H-imidazol-5-yl)propanoic acid hydrate
• IUPAC Traditional name: (S)-3-(imidazol-5-yl)lactate hydrate
• Synonyms: Imidazole-4-lactic Acid Monohydrate; (S)-2-hydroxy-3-(1(3)H-imidazol-4-yl)propionic Acid Monohydrate; (αS)-α-Hydroxy-1H-imidazole-4-propanoic Acid Monohydrate; L-β-Imidazole Lactic Acid Monohydrate

Database IDs

• CAS Number: 220919-94-8
• PubChem SID: 164227460
• PubChem CID: 46781944

CALCULATED PROPERTIES

• Acid pKa: 3.3940573
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -2.0829282
• LogD (pH = 7.4): -2.8017657
• Log P: -2.061685
• Molar Refractivity: 36.4015 cm^3
• Polarizability: 13.939238 Å^3
• Polar Surface Area: 86.21 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Warm Water
• Apperance: White Solid
• Melting Point: 195-198°C

Safety Information

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

DETAILS

Toronto Research Chemicals - I355000

An intermediate in the synthesis of imidazole alkaloids (+)-pilocarpine and (+)-isopilocarpine.

REFERENCES

• Coote, J., et al.: Biochem. J., 111, 237 (1969)
• Kelley, J., et al.: J. Med. Chem., 20, 506 (1969)
• Tansini, C., et al.: Int. J. Dev. Neurosci., 22, 67 (1969)