α,ß-D-Glucose Pentaacetate

Chemical Name: 1,2,3,4,6-Penta-O-acetyl-α,β-D-glucopyranose

English Name: 1,2,3,4,6-Penta-O-acetyl-α,ß-D-glucopyranose; D-Glucose Pentaacetate

Molecular Formula: C₁₆H₂₂O₁₁

Molecular Weight: 390.34

CAS No.: α-:604-68-2, β-:604-69-3, α,β-:3891-59-6

EC No.: α-:210-073-2, β-:210-074-8, α,β-:223-439-1

Molecular Structure Formula:

Properties: This product is a white crystalline powder, insoluble in water, easily soluble in organic solvents such as ethanol and chloroform.

Uses: This product is mainly used for the synthesis of arbutin. It serves as a pharmaceutical intermediate and drug modifier, bioactive synthon, peroxide activator, additive for pharmaceuticals, food, and plastics, antisolvent crystallization for drugs, enzymes, and biomolecules, wood acetylation treatment, nanoporogen for polysilsesquioxane membranes, reference standard for acetyl determination, enzyme substrate for biological research, monitoring of human gluconeogenesis, and constructing molecular-sized pores in nanofilms formed by phospholipids and hydrophobic polymers. It is used in the synthesis of materials for biological research, glycoside-based liquid crystal materials, alkyl glucoside surfactants, low molecular weight gelators with sugar groups, chiral bidentate ligands, ionic liquids, amphiphilic sugar-containing polymers, biodegradable sugar-based polymers and copolymers, hydrophilic glucosyl prilocaine derivatives, glycopeptide oligomers, glycopeptide building blocks, various glycosylation donors and their derivatives, etc. Additionally, D-glucose pentaacetate, especially the α-form, can promote insulin secretion and is therefore expected to be a novel insulin secretagogue; it exhibits activity against more than ten types of bacteria including Shigella, Candida albicans, and Staphylococcus, making it a potential antibacterial agent. It has ovicidal activity against arthropods such as two-spotted spider mites and whiteflies, used for controlling arthropod pests. Glucose pentaacetate can effectively mimic plant lipid chitooligosaccharide signal transduction, leading to accelerated cell division and plant growth, hence used as a plant growth regulator.
As a pharmaceutical intermediate, it can synthesize the following drugs or active pharmaceutical ingredients: sterol glycoside toxins, licochalcone glycosides, diosgenin, glucosyl sapogenins such as hecogenin and hederagenin, and photodynamic therapeutic agents. Furthermore, glucosylated drugs like linsidomine, silybin, tocopherol (tocopheryl naphthoquinone), gallic acid, glibenclamide, and clopidol show improved bioavailability.

As a bioactive synthon, it can synthesize the following active compounds: Millingtonine A with antibacterial activity, triacetyl glucosyl-benzoxazinone, glucosyl-triazolotriazinone, curcumin, flavanone and nucleoside analogs, the alkaloid Iteamine, heptasaccharide phytoalexin elicitors, pentasaccharide vaccines, phenethyl trisaccharides with hepatoprotective and vasodilatory activity, oxadiazole glycosides and glucosyl retinoic acid with anti-human breast cancer activity, glycosyl dodecanoic acid adamantane inhibiting soluble epoxide hydrolase, natural active phenylpropanoid glycosides, triazole-alkyl glycosides with leukocytotoxic activity, 5-trifluoromethyl-2,4-dihydropyrazol-3-one nucleosides and Ipomoeassin F with anticancer activity, glucosyl ruscogenin with anti-cervical cancer activity, glucosyl acetylsalicylic acid inhibiting cancer cell proliferation, bicyclic sugar derivatives active against cytomegalovirus, flavivirus, bovine viral diarrhea virus, Trypanosoma brucei and Leishmania, glucosyl dithiocarbamate and its copper (zinc) conjugates with antiproliferative and antioxidant activity, Raphanuside with expectorant, antitussive, and antiasthmatic activity, quinazoline-thio-glucoside with analgesic and anti-inflammatory activity, (−)-Strictinin with anti-allergic and immunostimulatory activity, tannins with anti-HIV activity, isoverbascoside derivatives inhibiting β-amyloid peptide aggregation, diquinazolinyl glucoside inhibiting epidermal growth factor receptor activity, betulinic acid glucoside inhibiting human leukemia cells, acetylphenyl glucoside as a Class B UV absorber with antioxidant activity.

Peroxides such as sodium percarbonate used in sterilization, cold sterilization, and bleaching processes are often activated by glucose pentaacetate.

Glucose pentaacetate is an additive in powdered drugs like salmeterol xinafoate, artificial chocolate, and tobacco, particularly added to tobacco to reduce the pungent odor of cigarettes. Additionally, L-menthol glucoside synthesized from glucose pentaacetate is added to tobacco to impart a cool smoking taste. It serves as a bio-based plasticizer for polyvinyl chloride (PVC), cellulose acetate, and polylactic acid.

Due to its good affinity with carbon dioxide, it can be used as a phase-change solvent or absorbent for CO2; a solubilizer for organic compounds in supercritical CO2; for antisolvent crystallization of drug molecules, sugar-containing biomolecules, and enzymes, enabling selective separation and control of crystal morphology or habit.

Development of materials for biological research, such as graft polymers of polyhydroxyethyl methacrylate conjugated with glucose fixed on polypropylene surfaces, used for protein recognition and adsorption. Dendritic sugar-glycopeptide-colchicine conjugates for studying Hela cell cytotoxicity. Glycosyl-PCDA (10,12-pentacosadiynoic acid) biosensors. Brush-type polymers mimicking glycolipids.

Synthesis of branched alkyl, thioalkyl, p-phenol alkyl glucosides and sitosterol glucosides with liquid crystalline behavior. Organic semiconductor materials functionalized with biomolecules. Various glycosylation donors and their derivatives, such as tetraacetyl glucose, 1-chloro(bromo)-tetraacetyl glucose, etc.

Storage: Store tightly sealed in a cool, dry place.

Packaging: 25kg/drum or as per customer requirements.

Shelf Life: 2 years