(2S)-2-amino-3-(1H-imidazol-4-yl)propanoic acid dihydrochloride

• ChemBase ID: 102513
• Molecular Formular: C6H11Cl2N3O2
• Molecular Mass: 228.07644
• Monoisotopic Mass: 227.02283197
• SMILES: Cl.Cl.N[C@@H](Cc1c[nH]cn1)C(=O)O
• Canonical SMILES: N[C@H](C(=O)O)Cc1nc[nH]c1.Cl.Cl
• InChI: InChI=1S/C6H9N3O2.2ClH/c7-5(6(10)11)1-4-2-8-3-9-4;;/h2-3,5H,1,7H2,(H,8,9)(H,10,11);2*1H/t5-;;/m0../s1
• InChIKey: XEJCDBUNISUVGZ-XRIGFGBMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(1H-imidazol-4-yl)propanoic acid dihydrochloride
• IUPAC Traditional name: L-histidin dihydrochloride
• Synonyms: L-Histidine dihydrochloride; L-HISTIDINE DIHYDROCHLORIDE; (S)-2-Amino-3-(1H-imidazol-4-yl)propanoic acid dihydrochloride; L-组氨酸 二盐酸盐

Database IDs

• CAS Number: 1007-42-7; 6027-02-7
• EC Number: 213-754-2; 227-890-5
• MDL Number: MFCD00066569
• Beilstein Number: 6119230
• PubChem SID: 162088670; 24877959
• PubChem CID: 72609

CALCULATED PROPERTIES

• Acid pKa: 1.8547646
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -3.85503
• LogD (pH = 7.4): -3.2925096
• Log P: -3.293445
• Molar Refractivity: 37.4933 cm^3
• Polarizability: 14.774462 Å^3
• Polar Surface Area: 92.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 240-245 °C (dec.)
• Optical Rotation: [α]20/D +6.5±1°, c = 8% in H2O

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (AT); 95+%
• Ignition Residue: ≤0.1% (as SO4)
• Cation Traces: As: ≤0.1 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; NH4+: ≤500 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Zn: ≤5 mg/kg
• Antion Traces: sulfate (SO42-): ≤50 mg/kg
• Empirical Formula (Hill Notation): C6H9N3O2 · 2HCl

DETAILS

MP Biomedicals - 02101953

Dihydrochloride
Crystalline

Sigma Aldrich - 53340

Biochem/physiol Actions
L-Histidine is a natural proteinogenic α amino acid useful as a cell growth supplement that support protein and peptide biosynthesis. L-Histidine is studied in a wide range of applications that involve imidazole chemistry and biochemisty.
L-Histidine is a positively charged imidazole-side chain containing α amino acid. It is metabolized to histamine and is a precursor of the dipeptide carnosine. As one of the 22 proteinogenic amino acids L-His is incorporated into proteins by translation processes in vitro. L-Histidine is an essential amino acid added to cell culture media.