sodium (2S,3S,4S,5R)-3,4,5-trihydroxy-6-(propan-2-ylsulfanyl)oxane-2-carboxylate

• ChemBase ID: 154051
• Molecular Formular: C9H15NaO6S
• Molecular Mass: 274.26657
• Monoisotopic Mass: 274.04870348
• SMILES: CC(C)SC1[C@@H]([C@H]([C@@H]([C@H](O1)C(=O)O[Na])O)O)O
• Canonical SMILES: [Na]OC(=O)[C@H]1OC(SC(C)C)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C9H16O6S.Na/c1-3(2)16-9-6(12)4(10)5(11)7(15-9)8(13)14;/h3-7,9-12H,1-2H3,(H,13,14);/q;+1/p-1/t4-,5-,6+,7-,9?;/m0./s1
• InChIKey: KBUAMHFDNNUCET-JYYOLFTLSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,3S,4S,5R)-3,4,5-trihydroxy-6-(propan-2-ylsulfanyl)oxane-2-carboxylate
• IUPAC Traditional name: sodium (2S,3S,4S,5R)-3,4,5-trihydroxy-6-(isopropylsulfanyl)oxane-2-carboxylate
• Synonyms: IPTGlcA · Na; Isopropyl β-D-thioglucuronic acid sodium salt; Isopropyl 1-thio-β-D-glucuronide sodium salt; Isopropyl β-D-thioglucuronic acid 钠盐; Isopropyl 1-thio-β-D-glucuronide 钠盐

Database IDs

• CAS Number: 208589-93-9
• PubChem SID: 162248190
• PubChem CID: 71311782

CALCULATED PROPERTIES

• Acid pKa: 12.421188
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.6377001
• LogD (pH = 7.4): -0.63770413
• Log P: -0.6377
• Molar Refractivity: 55.0004 cm^3
• Polarizability: 24.833408 Å^3
• Polar Surface Area: 96.22 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]/D -88.0±3.0°, c = 1 in H2O

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥97.0% (TLC)
• Empirical Formula (Hill Notation): C9H15NaO6S

DETAILS

Sigma Aldrich - 42897

Application
Isopropyl β-D-thioglucuronic acid (Isopropyl 1-thio-β-D-glucuronide) is closely related to the lac operon inducer, isopropyl 1-thio-β-D-glalactoside. Isopropyl β-D-thioglucuronic acid is used to induce β-D-glucosidase(s) for detection of bacteriophage via chromogenic assays.