(4R)-2-oxo-1,3-thiazolidine-4-carboxylic acid

• ChemBase ID: 134190
• Molecular Formular: C4H5NO3S
• Molecular Mass: 147.1524
• Monoisotopic Mass: 146.99901403
• SMILES: C1[C@H](NC(=O)S1)C(=O)O
• Canonical SMILES: O=C1SC[C@H](N1)C(=O)O
• InChI: InChI=1S/C4H5NO3S/c6-3(7)2-1-9-4(8)5-2/h2H,1H2,(H,5,8)(H,6,7)/t2-/m0/s1
• InChIKey: BMLMGCPTLHPWPY-REOHCLBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-2-oxo-1,3-thiazolidine-4-carboxylic acid
• IUPAC Traditional name: (4R)-2-oxo-1,3-thiazolidine-4-carboxylic acid
• Synonyms: L-(-)-2-Oxothiazolidine-4-carboxylic acid; (R)-(-)-2-Oxothiazolidine-4-carboxylic acid; (R)-(-)-2-Oxothiazolidine-4-carboxylic acid; (-)-2-Oxo-4-thiazolidinecarboxylic acid; (4R)-2-oxo-1,3-thiazolidine-4-carboxylic acid

Database IDs

• CAS Number: 19771-63-2
• MDL Number: MFCD00066092
• Beilstein Number: 4179169
• PubChem SID: 24858227; 162228467; 24898032
• PubChem CID: 72390

CALCULATED PROPERTIES

• Acid pKa: 3.1925256
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -2.4582732
• LogD (pH = 7.4): -3.6207128
• Log P: -0.17396238
• Molar Refractivity: 31.346 cm^3
• Polarizability: 12.388509 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 167 - 169°C; 174 °C (dec.)(lit.)
• Optical Rotation: [α]19/D -60°, c = 1 in H2O; [α]20/D -60±3°, c = 1% in H2O
• Hydrophobicity(logP): -0.247

Safety Information

• RTECS: XJ5426650
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥97% (TLC); ≥97.0% (T); ≥98% (titration); 95%; 97%
• Grade: purum
• Empirical Formula (Hill Notation): C4H5NO3S

DETAILS

Sigma Aldrich - O6254

包装
5 g in glass bottle
Biochem/physiol Actions
2-Oxothiazolidine-4-carboxylic acid augments glutathione and cysteine production.

Sigma Aldrich - 302023

Packaging
1, 5 g in glass bottle
Application
An intermediate in the total synthesis of (+)-latrunculin A.1

Sigma Aldrich - 75951

Other Notes
Derivative of L-cysteine. Chiral building block1