(3R,4S,5S,6R)-6-methyloxane-2,3,4,5-tetrol

• ChemBase ID: 132497
• Molecular Formular: C6H12O5
• Molecular Mass: 164.15648
• Monoisotopic Mass: 164.06847348
• SMILES: C[C@@H]1[C@H]([C@@H]([C@H](C(O1)O)O)O)O
• Canonical SMILES: O[C@@H]1[C@@H](C)OC([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3-,4+,5-,6?/m1/s1
• InChIKey: SHZGCJCMOBCMKK-GASJEMHNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5S,6R)-6-methyloxane-2,3,4,5-tetrol
• IUPAC Traditional name: quinovose
• Synonyms: D-Isorhamnose; Epifucose; Quinovose; 6-Deoxy-D-glucose

Database IDs

• CAS Number: 7658-08-4
• EC Number: 231-622-2
• MDL Number: MFCD00061627
• Beilstein Number: 1723317
• PubChem SID: 162226774; 24858809; 24894327
• PubChem CID: 439746

CALCULATED PROPERTIES

• Acid pKa: 11.30218
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.8856299
• LogD (pH = 7.4): -1.8856835
• Log P: -1.8856293
• Molar Refractivity: 34.3797 cm^3
• Polarizability: 14.43744 Å^3
• Polar Surface Area: 90.15 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble10 mg/mL, clear, colorless

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: ≥98% (HPAE or TLC); ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C6H12O5

DETAILS

Sigma Aldrich - D9761

Analysis Note
Identity: Consistent with structure by IR or H-NMR
Application
6-deoxy-D-glucose is used to study the role of the carbon 6 hydroxyl group in the biological functions of glucose.
Biochem/physiol Actions
A structral homolog of D-glucoose that is lacking a hydroxyl group at carbon 6 position.

Sigma Aldrich - 31065

Other Notes
Mechanism of glucose-mediated cAMP increase in yeast1