(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(1H-imidazol-4-yl)propanoic acid

• ChemBase ID: 145025
• Molecular Formular: C14H15N3O4
• Molecular Mass: 289.2866
• Monoisotopic Mass: 289.10625598
• SMILES: c1ccc(cc1)COC(=O)N[C@@H](Cc1c[nH]cn1)C(=O)O
• Canonical SMILES: O=C(N[C@H](C(=O)O)Cc1c[nH]cn1)OCc1ccccc1
• InChI: InChI=1S/C14H15N3O4/c18-13(19)12(6-11-7-15-9-16-11)17-14(20)21-8-10-4-2-1-3-5-10/h1-5,7,9,12H,6,8H2,(H,15,16)(H,17,20)(H,18,19)/t12-/m0/s1
• InChIKey: WCOJOHPAKJFUDF-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(benzyloxy)carbonyl]amino}-3-(1H-imidazol-4-yl)propanoic acid; (2S)-2-{[(benzyloxy)carbonyl]amino}-3-(1H-imidazol-5-yl)propanoic acid
• IUPAC Traditional name: (2S)-2-{[(benzyloxy)carbonyl]amino}-3-(1H-imidazol-4-yl)propanoic acid; (2S)-2-{[(benzyloxy)carbonyl]amino}-3-(3H-imidazol-4-yl)propanoic acid
• Synonyms: Nα-Carbobenzyloxy-L-histidine; Nα-Z-L-Histidine; Z-His-OH; N-Cbz-L-histidine; (s)-2-benzyloxycarbonylamino-3-(3h-imidazol-4-yl)propionic acid; Nα-Z-L-组氨酸; Nα-苄氧羰基-L-组氨酸

Database IDs

• CAS Number: 14997-58-1
• EC Number: 239-084-0
• MDL Number: MFCD00065960
• Beilstein Number: 92342
• PubChem SID: 162239235; 24865575
• PubChem CID: 736313

CALCULATED PROPERTIES

• Acid pKa: 3.5476935
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.025239913
• LogD (pH = 7.4): -0.7382668
• Log P: -0.0023934664
• Molar Refractivity: 73.739 cm^3
• Polarizability: 28.423193 Å^3
• Polar Surface Area: 104.31 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 168 °C (dec.)(lit.)
• Optical Rotation: [α]20/D -24°, c = 1% in 6 M HCl

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 97%; 99%
• Empirical Formula (Hill Notation): C14H15N3O4

DETAILS

Sigma Aldrich - 408549

Packaging
5 g in glass bottle