(3R,4S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one

• ChemBase ID: 177522
• Molecular Formular: C5H8O5
• Molecular Mass: 148.11402
• Monoisotopic Mass: 148.03717336
• SMILES: [C@@H]1([C@H](C(=O)OC1CO)O)O
• Canonical SMILES: OCC1OC(=O)[C@@H]([C@@H]1O)O
• InChI: InChI=1S/C5H8O5/c6-1-2-3(7)4(8)5(9)10-2/h2-4,6-8H,1H2/t2?,3-,4-/m1/s1
• InChIKey: CUOKHACJLGPRHD-FJWSOENFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one
• IUPAC Traditional name: (3R,4S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one
• Synonyms: D-(+)-Ribonic Acid γ-Lactone; D-(+)-Ribonolactone; D-Ribono-1,4-lactone; NSC 1031; D-Ribonolactone

Database IDs

• CAS Number: 5336-08-3
• PubChem SID: 164233432
• PubChem CID: 45040368

CALCULATED PROPERTIES

• Acid pKa: 11.633838
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -2.1149385
• LogD (pH = 7.4): -2.1149635
• Log P: -2.1149383
• Molar Refractivity: 28.8163 cm^3
• Polarizability: 12.117866 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 85-87°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Stable

DETAILS

Toronto Research Chemicals - R416000

A sugar lactone as inhibitor of β-galactosidase of E. coli.

REFERENCES

• Zhang, B., et al.: Science, 284, 974 (1999)
• Zimmet, P., et al.: Nature, 414, 782 (1999)
• Verspohl, E., et al.: Planta Med., 68, 581 (1999)
• Thompson, K., et al.: Science, 300, 936 (1999)
• Thompson, K., et al.: J. Inorg. Biochem., 98, 683 (1999)