(3S,4S,5S,6S)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol

• ChemBase ID: 132050
• Molecular Formular: C6H12O6
• Molecular Mass: 180.15588
• Monoisotopic Mass: 180.0633881
• SMILES: C([C@H]1[C@H]([C@@H]([C@@H](C(O1)O)O)O)O)O
• Canonical SMILES: OC[C@@H]1OC(O)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3+,4-,5-,6?/m0/s1
• InChIKey: WQZGKKKJIJFFOK-QRXFDPRISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4S,5S,6S)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
• IUPAC Traditional name: L-gulopyranose
• Synonyms: L-(+)-Gulose; L-Gulose

Database IDs

• CAS Number: 6027-89-0
• EC Number: 227-897-3
• MDL Number: MFCD00136022
• PubChem SID: 162226327; 24880019
• PubChem CID: 10130220

CALCULATED PROPERTIES

• Acid pKa: 11.298101
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -2.93254
• LogD (pH = 7.4): -2.932594
• Log P: -2.9325392
• Molar Refractivity: 35.9234 cm^3
• Polarizability: 15.155883 Å^3
• Polar Surface Area: 110.38 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]/D +23.0±2°, 24 hr, c = 0.5% in H2O

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C6H12O6

DETAILS

Sigma Aldrich - 56224

Application
L-(+)-Gulose, a rare aldohexose sugar C-3 epimer of galactose, is used in the development of various drugs and to glycosylate alginates. L-(+)-Gulose is a substrate of GDP-mannose 3′,5′-epimerase in plants and may be a precursor of L-ascorbic acid in plants.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 56224.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.