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66950

Sigma-Aldrich

Methyl-β-D-glucopyranoside hemihydrate

≥99.0% (sum of enantiomers, HPLC)

Synonym(s):

β-Methyl-D-glucoside hemihydrate

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About This Item

Empirical Formula (Hill Notation):
C7H14O6 · 0.5H2O
CAS Number:
Molecular Weight:
203.19
Beilstein/REAXYS Number:
81567
EC Number:
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.25

assay

≥99.0% (sum of enantiomers, HPLC)

optical activity

[α]20/D −33±1°, c = 10% in H2O

mp

107-111 °C

solubility

H2O: 0.1 g/mL, clear, colorless

SMILES string

CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

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

InChI key

HOVAGTYPODGVJG-XUUWZHRGSA-N

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).

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Methyl glucoside hydrolysis catalyzed by β-glucosidase.
Golden EB, Byers LD.
Biochimica et Biophysica Acta, 1794, 1643-1647 (2099)
S Aubert et al.
Journal of experimental botany, 55(406), 2179-2189 (2004-09-14)
Using (13)C-NMR, methyl-beta-D-glucopyranoside (MeG) was characterized as a major compound in the leaves of the alpine herb Geum montanum L. MeG continuously accumulated during the life span of G. montanum leaves, and accounted for up to 20% of the soluble
Mohd Younis Rather et al.
Bioresource technology, 107, 287-294 (2012-01-10)
In the present study, we have investigated the use of Pichia etchellsii whole cells for synthesis of long-chain alkyl glucosides. Methyl-β-d-glucopyranoside (MG) was used in reaction with fatty alcohols, n-hexanol, n-octanol, n-decanol and n-dodecanol to synthesize the respective alkyl glucosides.
Mohd Younis Rather et al.
Journal of biotechnology, 150(4), 490-496 (2010-10-12)
Octyl-β-D-glucopyranoside was synthesized by transglucosylation between p-nitrophenyl β-D-glucopyranoside (pNPG) and octanol as an acceptor using whole cells of thermo tolerant yeast Pichia etchellsii displaying cell wall bound β-glucosidase. Effect of several parameters such as glucosyl donor concentration, enzyme units and

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