(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol

• ChemBase ID: 1418
• Molecular Formular: C7H14O6
• Molecular Mass: 194.18246
• Monoisotopic Mass: 194.07903817
• SMILES: CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
• Canonical SMILES: CO[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C7H14O6/c1-12-7-6(11)5(10)4(9)3(2-8)13-7/h3-11H,2H2,1H3/t3-,4-,5+,6-,7-/m1/s1
• InChIKey: HOVAGTYPODGVJG-XUUWZHRGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol
• IUPAC Traditional name: methyl β-d-glucoside; O1-methyl-glucose
• Brand Name: Beta-methyl-d-glucoside; M0779_SIGMA; MGL; Methyl beta-d-glucopyranoside; Methyl beta-d-glucoside; Methyl-beta-d-glucopyranoside
• Synonyms: β-Methyl-D-glucoside hemihydrate; Methyl-β-D-glucopyranoside hemihydrate; Methyl β-D-glucoside; Methyl β-D-glucopyranoside; O1-Methyl-Glucose; 1-O-Methyl-β-D-glucopyranoside; NSC 403457; Methyl β-D-Glucopyranoside

Database IDs

• CAS Number: 709-50-2; 7000-27-3
• EC Number: 211-909-9
• MDL Number: MFCD00006602
• Beilstein Number: 81567
• PubChem SID: 160964878; 24896570; 24885055; 46507087
• PubChem CID: 445238

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.211393
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.2894127
• LogD (pH = 7.4): -2.2894194
• Log P: -2.2894127
• Molar Refractivity: 40.6746 cm^3
• Polarizability: 17.016506 Å^3
• Polar Surface Area: 99.38 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.49
• LOG S: 0.65
• Solubility (Water): 8.62e+02 g/l

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear, colorless; Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 103-105°C; 107-111 °C
• Optical Rotation: [α]20/D -33±1°, c = 10% in H2O

Safety Information

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

Product Information

• Purity: ≥99% (HPLC and GC); ≥99.0% (sum of enantiomers, HPLC)
• Empirical Formula (Hill Notation): C7H14O6 · 0.5H2O

DETAILS

DrugBank - DB01642

Drug information: experimental

Sigma Aldrich - 66950

Application
Methyl-β-D-glucopyranoside is used as a starting material for the biosynthesis of long-chain alkyl glucosides. Methyl-β-D-glucopyranoside is used as a substrate to identify, differentiate and characterize β-D-glucosidase(s).