(2S,4S)-4-hydroxypyrrolidine-2-carboxylic acid hydrochloride

• ChemBase ID: 52644
• Molecular Formular: C5H10ClNO3
• Molecular Mass: 167.5908
• Monoisotopic Mass: 167.03492087
• SMILES: [C@@H]1(C[C@H](NC1)C(=O)O)O.Cl
• Canonical SMILES: O[C@@H]1CN[C@@H](C1)C(=O)O.Cl
• InChI: InChI=1S/C5H9NO3.ClH/c7-3-1-4(5(8)9)6-2-3;/h3-4,6-7H,1-2H2,(H,8,9);1H/t3-,4-;/m0./s1
• InChIKey: YEJFFQAGTXBSTI-MMALYQPHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S)-4-hydroxypyrrolidine-2-carboxylic acid hydrochloride
• IUPAC Traditional name: L-hydroxyproline hydrochloride
• Synonyms: (2S,4S)-4-Hydroxypyrrolidine-2-carboxylic acid hydrochloride; (2R,4S)-(+)-4-Hydroxy-D-proline Hydrochloride; 4-(S)-Hydroxypyrrolidine-2-(R)-carboxylic Acid Hydrochloride; D-Hydroxyproline Hydrochloride; D-trans-4-Hydroxyproline Hydrochloride; NSC 206273 Hydrochloride; trans-4-Hydroxy-D-proline Hydrochloride; (4S)-4-Hydroxy-D-proline Hydrochloride; trans-4-Hydroxy-D-proline Hydrochloride

Database IDs

• CAS Number: 142347-81-7; 441067-49-8
• MDL Number: MFCD09953187
• PubChem SID: 162057407
• PubChem CID: 23395895

CALCULATED PROPERTIES

• Acid pKa: 1.641382
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -3.7163465
• LogD (pH = 7.4): -3.7165344
• Log P: -3.7163188
• Molar Refractivity: 29.3822 cm^3
• Polarizability: 11.9828205 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 257°C (241°C)

Safety Information

• Storage Warning: IRRITANT
• TSCA Listed: false

Product Information

• Purity: 95%; 95+%

DETAILS

Toronto Research Chemicals - H952385

Hydroxyprolines can be used as chiral building blocks in the synthesis of pharmaceuticals.

REFERENCES

• Lawrence, C., et al.: Biochem. J., 313, 185 (1996)
• Mori, H., et al.: J. Bacteriol., 179, 5677 (1996)
• Clifton, I., et al.: Eur. J. Biochem., 268, 6625 (1996)