66940
Methyl α-D-glucopyranoside
suitable for microbiology, ≥99.0%
Synonym(s):
alpha-Methyl D-glucose ether, Methyl glucose, Methyl alpha-D-glucoside, Methyl glucopyranoside, Methyl alpha-D-glucose, Methyl pyranoside, Methyl α-D-glucoside
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About This Item
Empirical Formula (Hill Notation):
C7H14O6
CAS Number:
Molecular Weight:
194.18
UNSPSC Code:
41106212
NACRES:
NA.74
PubChem Substance ID:
EC Number:
202-571-3
Beilstein/REAXYS Number:
81568
MDL number:
Quality Level
assay
≥99.0% (sum of enantiomers, HPLC), ≥99.0%
form
crystalline powder
optical activity
[α]20/D +157±3°, c = 10% in H2O
packaging
pkg of 100 g
storage condition
(Keep container tightly closed in a dry and well-ventilated place.)
color
colorless
mp
165-169 °C
application(s)
microbiology
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-ZFYZTMLRSA-N
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General description
Methyl α-D-glucopyranoside is a chemical compound that belongs to the category of methylated glucose derivatives. Methyl α-D- glucopyranoside is also known as Methyl alpha-D-glucoside or alpha-Methyl-glucoside. Methyl alpha-D-glucopyranoside is a natural product found in Pseudoceratina purpurea, Forsythia viridissima, and Quassia amara. It is a monosaccharide and is commonly used in scientific research as a non-metabolizable analog of glucose. By replacing a hydroxyl group on the glucose molecule with a methyl group (-CH3), it becomes resistant to metabolism while retaining structural similarity to glucose. This property allows to study glucose transport, metabolism, and related cellular processes without interference from normal glucose metabolism.
Application
Methyl α-D-glucopyranoside is used for the differentiation of Listeria species, Listeria monocytogenes, Listeria innocua, and Listeria welshimeri by the ability to ferment the sugar, producing acid which can be identified using an appropriate pH indicator. Methyl α-D-glucopyranoside finds applications in various fields, including biochemical research, cell culture, chemical synthesis, analytical chemistry, and pharmaceutical industry.Methyl α-D- glucopyranoside is a methylated sugar used as an inhibitor of lectin-conjugate binding. commonly used in protein purification for eluting glycoproteins and other glycoconjugates from affinity chromatography columns of agarose lectin.Different concentrations of methyl α-D-glucopyranoside were used to vary echo decay times in a study that assessed the effects of cryoprotection on the structure and activity of p21ras.
Storage Class
11 - Combustible Solids
wgk
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Mikkel G Jørgensen et al.
Journal of bacteriology, 191(4), 1191-1199 (2008-12-09)
Toxin-antitoxin (TA) loci are common in free-living bacteria and archaea. TA loci encode a stable toxin that is neutralized by a metabolically unstable antitoxin. The antitoxin can be either a protein or an antisense RNA. So far, six different TA
Miyuki Kimura et al.
Journal of bioscience and bioengineering, 112(2), 194-201 (2011-05-21)
We studied the effects of d-glucose on transgene expression in mammalian cells by a reporter gene assay using CV-1 cells and a CMV promoter-controlled EGFP gene. Treatment of CV-1 cells with 5% D-glucose unchanged the number of fluorescent cells in
Sirpa Vuorinen et al.
AAPS PharmSciTech, 10(2), 566-573 (2009-05-12)
Sugar end-capped poly-D,L-lactide (SPDLA) polymers were investigated as a potential release controlling excipient in oral sustained release matrix tablets. The SPDLA polymers were obtained by a catalytic ring-opening polymerization technique using methyl alpha-D-gluco-pyranoside as a multifunctional initiator in the polymerization.
Amy B Blodgett et al.
Diabetes technology & therapeutics, 13(7), 743-751 (2011-04-23)
Diabetes may alter renal glucose reabsorption by sodium (Na(+))-dependent glucose transporters (SGLTs). Radiolabeled substrates are commonly used for in vitro measurements of SGLT activity in kidney cells. We optimized a method to measure glucose uptake using a fluorescent substrate, 2-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-2-deoxyglucose
Zhenqian Zhu et al.
Rapid communications in mass spectrometry : RCM, 26(11), 1320-1328 (2012-05-05)
Differentiation of underivatized monosaccharides is essential in the structural elucidation of oligosaccharides which are closely involved in many life processes. So far, such differentiation has been usually achieved by electrospray ionization mass spectrometry (ESI-MS). As an alternative to ESI-MS, atmospheric
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