(4S,5S,6R)-6-methyloxane-2,4,5-triol

• ChemBase ID: 158513
• Molecular Formular: C6H12O4
• Molecular Mass: 148.15708
• Monoisotopic Mass: 148.07355886
• SMILES: C[C@@H]1[C@H]([C@H](CC(O1)O)O)O
• Canonical SMILES: OC1C[C@H](O)[C@@H]([C@H](O1)C)O
• InChI: InChI=1S/C6H12O4/c1-3-6(9)4(7)2-5(8)10-3/h3-9H,2H2,1H3/t3-,4+,5?,6-/m1/s1
• InChIKey: FDWRIIDFYSUTDP-WGDKFINWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,5S,6R)-6-methyloxane-2,4,5-triol
• IUPAC Traditional name: (4S,5S,6R)-6-methyloxane-2,4,5-triol
• Synonyms: 2,6-Dideoxy-D-ribohexose; D-(+)-Digitoxose

Database IDs

• CAS Number: 527-52-6
• MDL Number: MFCD00006621
• Beilstein Number: 1721555
• PubChem SID: 162252649
• PubChem CID: 2723626

CALCULATED PROPERTIES

• Acid pKa: 12.309899
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.98499125
• LogD (pH = 7.4): -0.9849965
• Log P: -0.9849912
• Molar Refractivity: 32.869 cm^3
• Polarizability: 13.731559 Å^3
• Polar Surface Area: 69.92 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 98-100 °C
• Optical Rotation: [α]20/D +48±2°, c = 1% in H2O

Safety Information

• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (TLC)
• Empirical Formula (Hill Notation): C6H12O4

DETAILS

Sigma Aldrich - 37040

Biochem/physiol Actions
The natural glycoside digitoxin contains a trisaccharide component made up of digitoxose monosaccharides. A modified monosaccharide digitoxin (with a single digitoxose moiety) was found to have greater anti-proliferative effects on various human non-small cell lung cancer cell lines than intact digitoxin. 1