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Methyl beta-D-glucopyranoside is used to study the specificity of fermented saccharomyces cerevisiae after carbohydrates have been removed.
Product Name | Methyl beta-D-glucopyranoside |
Apperance | White powder |
EINECS | 211-909-9 |
MF | C7H14O6 |
MW | 194.18 |
Assay | ≥98.0% |
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Product parameters | |
Cas number: | 709-50-2 |
Appearance: | White powder |
Purity: | 98.0%min |
Package details: | 100g/bag,1kg/bag or as you require |
Brand: | Fortunachem |
Methyl β-D-glucoside is a simple alkyl glucoside, a derivative of glucose in which the anomeric hydroxyl group (the one on carbon-1) is replaced by a methoxy group (-O-CH₃) in a specific spatial orientation (the beta configuration).
In simpler terms, it is a molecule where a glucose sugar is linked to a methyl group via a β-glycosidic bond. This makes it a non-reducing sugar because the anomeric carbon is no longer free to open into the aldehyde form, which is required for reduction reactions.
Structure: It is a white, crystalline solid at room temperature.
Solubility: It is highly soluble in water due to the presence of multiple hydroxyl (-OH) groups, which form hydrogen bonds with water molecules.
Stability: The β-glycosidic bond makes it relatively stable under neutral conditions but it can be hydrolyzed back to glucose and methanol by strong acids or specific enzymes (β-glucosidases).
Non-Reducing Sugar: Unlike its parent molecule, glucose, methyl β-D-glucoside does not give a positive test with Benedict's or Fehling's reagents because its anomeric carbon is blocked.
It is typically synthesized by the Fischer glycosidation, a classic acid-catalyzed reaction where D-glucose is refluxed in anhydrous methanol. This reaction produces a mixture of both the alpha and beta methyl glycosides, which can be separated due to their different crystallization properties.
Unlike the previous compounds discussed (PVP and PEG-20 Glyceryl Triisostearate), methyl β-D-glucoside is not a common industrial bulk ingredient. Its importance is primarily in scientific research and chemistry:
Model Compound and Chemical Intermediate:
Glycoscience Research: It is extensively used as a simple, stable model compound to study the structure, reactivity, and enzymatic hydrolysis of β-glycosidic bonds. Researchers use it to understand the behavior of more complex carbohydrates and celluloses.
Organic Synthesis: It serves as a protected form of glucose and a key starting material (building block) for the synthesis of more complex oligosaccharides, glycolipids, and other glycoconjugates. Its hydroxyl groups can be selectively modified to attach other molecules.
Surfactant Precursor: While not a surfactant itself, it belongs to the family of alkyl glucosides. Longer-chain alkyl glucosides (e.g., decyl glucoside, lauryl glucoside) are renowned as excellent, biodegradable, non-ionic surfactants derived from renewable resources (sugar and fatty alcohols). Methyl glucoside is a step towards understanding and producing these compounds.
Biological Studies: It is used in microbiology and plant science to study sugar transport and metabolism in cells and to investigate the activity and specificity of β-glucosidase enzymes.
Methyl β-D-glucoside is generally regarded as a low-toxicity, biodegradable compound. It is not a major industrial chemical of toxicological concern.
In essence, methyl β-D-glucoside is a fundamental research chemical. It is a simple, stable sugar derivative whose main value lies in its role as a:
Model compound for studying carbohydrate chemistry.
Building block for the synthesis of more complex sugar-based molecules.
Precursor to the family of benign, sugar-based surfactants.
Its significance is far greater in the laboratory than in commercial consumer products.
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