Methylglucoside

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Methylglucoside
Alpha-methylglucoside.svg
α-D-Methylglucoside
Beta-methylglucoside.svg
β-D-Methylglucoside
Names
IUPAC name
Methyl D-glucopyranoside
Other names
1-O-Methyl-D-glucopyranose
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.019.620 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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
    Key: HOVAGTYPODGVJG-WLDMJGECSA-N
  • InChI=1/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
    Key: HOVAGTYPODGVJG-WLDMJGECBG
  • O[C@@H]1[C@@H](O)[C@H](O)[C@H](OC1OC)CO
Properties
C7H14O6
Molar mass 194.183 g·mol−1
AppearanceWhite crystalline solid
Density 1.46 g/cm3 (α) [1]
Melting point 168 °C (334 °F; 441 K) (α) [1]
108 g/100 mL [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Methylglucoside is a monosaccharide derived from glucose. It can be prepared in the laboratory by the acid-catalyzed reaction of glucose with methanol. [2]

It is used as a chemical intermediate in the production of a variety of products including emollients, emulsifiers, humectants, moisturizers, thickening agents, plasticizers, surfactants, varnishes, and resins. The formation of methyl glycoside indicates that the structure of glucose is not open chain. [1] [3]

Related Research Articles

A glucoside is a glycoside that is chemically derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes.

Decyl glucoside is a mild non-ionic surfactant used in cosmetic formularies, including baby shampoo and in products for individuals with a sensitive skin. Many natural personal care companies use this cleanser because it is plant-derived, biodegradable, and gentle for all hair types.

<span class="mw-page-title-main">Lauryl methyl gluceth-10 hydroxypropyl dimonium chloride</span> Chemical compound

Lauryl methyl gluceth-10 hydroxypropyl dimonium chloride is an ingredient in some types of soaps and personal care products. It is used as a substantive conditioning humectant. This chemical is a type of methyl glucoside derivative, which has been modified by ethoxylation and quaternization. A synthetic pathway for lauryl methyl gluceth-10 hydroxypropyldimonium chloride and other methyl glucoside humectants has been outlined in trade literature.

<span class="mw-page-title-main">Lotaustralin</span> Chemical compound

Lotaustralin is a cyanogenic glucoside found in small amounts in Fabaceae austral trefoil, cassava, lima bean, roseroot and white clover, among other plants. Lotaustralin is the glucoside of methyl ethyl ketone cyanohydrin and is structurally related to linamarin, the acetone cyanohydrin glucoside also found in these plants. Both lotaustralin and linamarin may be hydrolyzed by the enzyme linamarase to form glucose and a precursor to the toxic compound hydrogen cyanide.

In enzymology, a sinapoylglucose---sinapoylglucose O-sinapoyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a cyanidin 3-O-rutinoside 5-O-glucosyltransferase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Flavonol 3-O-glucosyltransferase</span> Class of enzymes

In enzymology, a flavonol 3-O-glucosyltransferase is an enzyme that catalyzes the chemical reaction

Lauryl glucoside is a surfactant used in cosmetics and laundry detergents. It is a glycoside produced from glucose and lauryl alcohol.

<span class="mw-page-title-main">Petunidin</span> Chemical compound

Petunidin (Pt), like Europinidin and Malvidin, is derived from Delphinidin and is an O-methylated anthocyanidin of the 3-hydroxy type. It is a natural organic compound, a dark-red or purple water-soluble pigment found in many red berries including chokeberries, Saskatoon berries or different species of grape, and also part of the pigments responsible for the petal colors in many flowers. This pigment gives the Indigo Rose tomatoes the majority of their deep purple color when the fruits are exposed to sunlight. The name of the molecule itself is derived from the word Petunia.

<span class="mw-page-title-main">Genistin</span> Chemical compound

Genistin is an isoflavone found in a number of dietary plants like soy and kudzu. It was first isolated in 1931 from the 90% methanol extract of a soybean meal, when it was found that hydrolysis with hydrochloric acid produced 1 mole each of genistein and glucose. Chemically it is the 7-O-beta-D-glucoside form of genistein and is the predominant form of the isoflavone naturally occurring in plants. In fact, studies in the 1970s revealed that 99% of the isoflavonoid compounds in soy are present as their glucosides. The glucosides are converted by digestive enzymes in the digestive system to exert their biological effects. Genistin is also converted to a more familiar genistein, thus, the biological activities including antiatherosclerotic, estrogenic and anticancer effects are analogous.

<span class="mw-page-title-main">Okanin</span> Chemical compound

Okanin is a chalconoid. It can be found in the plant Bidens pilosa.

Cryptococcus ater is a species of Cryptococcus that has some unique characteristics. When grown on agar it typically produces cream colonies, however when grown on neopeptone agar slants, the colonies turn olive green after approximately four weeks. This species also turns nearly black when grown on Diamalt agar slants and on Gorodkova agar after approximately three months. When grown in liquid media it develops sediment and a weak ring. On the microscopic level the cells appear globose to ovate and are capsulated. Occasionally the cells have been seen to create chains of four to five cells. When grown, it does not require vitamins, but its growth is weakened by the presence of ammonium sulfate. It is able to assimilate alpha-methyl-D-glucoside, Ca-2-keto-gluconate, cellobiose, D-arabinose, D-mannitol, D-sorbitol, D-xylose, galactose, glucose, K-5-keto-gluconate- K-gluconate, lactose, L-arabinose, L-rhamnose, maltose, melezitose, i-inositol, raffinose, salicin and trehalose. This species has been isolated from ulcers in a leg.

<span class="mw-page-title-main">Cycasin</span> Chemical compound

Cycasin is a carcinogenic and neurotoxic glucoside found in cycads such as Cycas revoluta and Zamia pumila. Symptoms of poisoning include vomiting, diarrhea, weakness, seizures, and hepatotoxicity. In metabolic conditions, cycasin is hydrolyzed into glucose and methylazoxymethanol (MAM), the latter of which dissociates into formaldehyde and diazomethane.

Delphinidin 3',5'-O-glucosyltransferase is an enzyme with systematic name UDP-glucose:delphinidin 3-O-(6-O-malonyl)-beta-D-glucoside 3'-O-glucosyltransferase. This enzyme catalyses the following chemical reaction

Candida keroseneae is a species of yeast in the genus Candida, family Saccharomycetaceae. Described as new to science in 2011, it was isolated from aviation fuel.

4-Hydroxybenzoic acid 4-<i>O</i>-glucoside Chemical compound

4-Hydroxybenzoic acid 4-O-glucoside is a glucoside of p-hydroxybenzoic acid. It can be found in mycorrhizal and non-mycorrhizal roots of Norway spruces.

Gliflozins are a class of drugs in the treatment of type 2 diabetes (T2D). They act by inhibiting sodium/glucose cotransporter 2 (SGLT-2), and are therefore also called SGLT-2 inhibitors. The efficacy of the drug is dependent on renal excretion and prevents glucose from going into blood circulation by promoting glucosuria. The mechanism of action is insulin independent.

Rhizobium binae is a gram-negative bacterium which was isolated from root nodules of lentils in Bangladesh.

Rhizobium lentis is a gram-negative bacterium which was isolated from root nodules of lentils in Bangladesh.

The PTSGlucose-Glucoside (Glc) family includes porters specific for glucose, glucosamine, N-acetylglucosamine and a large variety of α- and β-glucosides, and is part of the PTS-GFL superfamily.

References

  1. 1 2 3 4 Merck Index , 11th Edition, 5997
  2. B. Helferich and W. Schäfer (1926). "α-METHYL d-GLUCOSIDE". Organic Syntheses . 6: 64.
  3. "Methyl Glucoside Derivatives". Lubrizol. Archived from the original on April 14, 2014. Retrieved October 15, 2012.