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66940

Millipore

Methyl α-D-glucopyranoside

≥99.0%, suitable for microbiology

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
Beilstein:
81568
EC Number:
MDL number:
UNSPSC Code:
41106212
PubChem Substance ID:
NACRES:
NA.74

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 Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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
Tiemin Liu et al.
American journal of physiology. Cell physiology, 295(1), C64-C72 (2008-05-02)
Investigation of the structure/function relationships of the sodium-glucose transporter (SGLT1) is crucial to understanding the cotransporter mechanism. In the present study, we used cysteine-scanning mutagenesis and chemical modification by methanethiosulfonate (MTS) derivatives to test whether predicted transmembrane IV participates in
J Antonio González et al.
Diabetes, 57(10), 2569-2576 (2008-07-02)
Glucose sensing by specialized neurons of the hypothalamus is vital for normal energy balance. In many glucose-activated neurons, glucose metabolism is considered a critical step in glucose sensing, but whether glucose-inhibited neurons follow the same strategy is unclear. Orexin/hypocretin neurons
Vojtech Spiwok et al.
Carbohydrate research, 344(12), 1575-1581 (2009-06-23)
Accurate modelling of rotamer equilibria for the primary hydroxyl groups of monosaccharides continues to be a great challenge of computational glycochemistry. The metadynamics technique was applied to study the conformational free energy surfaces of methyl alpha-D-glucopyranoside and methyl alpha-D-galactopyranoside, employing
Emily B Golden et al.
Biochimica et biophysica acta, 1794(11), 1643-1647 (2009-08-05)
Sweet almond beta-glucosidase is a retaining, family 1, glycohydrolase, catalyzing the highly efficient hydrolysis of a variety of glycosides. For example, the enzyme-catalyzed hydrolysis of methyl beta-D-glucopyranoside is approximately 4 x 10(15)-times faster than the spontaneous hydrolysis at 25 degrees

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Culture media provides a habitat with suitable nutrients, energy sources, and certain environmental conditions for the growth of microorganisms. The components of the culture media range from simple sugars to peptones, salts, antibiotics, and complex indicators.

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