β-D-Glucose Pentaacetate

Synonyms: α/β-D-glucose pentaacetate; 1,2,3,4,6-penta-O-acetyl-a, β-D-Glucopyranose; 1,2,3,4,6-penta-O-acetyl-D-glucopyranose; 1,2,3,4,6-penta-O-acetyl-α-D-glucopyranose; 1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose; acetyl 2,3,4,6-tetr-o-acetyl-D-glucopyranoside

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

FEMA No.: α,β-:2524

Molecular Structure:

α-D-Glucose Pentaacetate

β-D-Glucose Pentaacetate

Specification:

Item	α-	ß-	α, ß-	α, ß-(high a)	α, ß-(high ß)
Appearance	White crystalline powder
Assay(GC), %	≥98.0	≥98.0	≥98.0	α-D-Glucose Pentaacetate≥70.0	β-D-Glucose Pentaacetate≥70.0
Specific rotation  ,(C=1,CHCl3)	+100.0~+103.0	+4.0~+6.0	+50.0~+60.0	≥+70.0	≤+35.0
Melting point,℃	111.0~114.0	130.0~134.0	≥85.0	-	-
Water,%	≤1.0	≤1.0	≤1.0	≤1.0	≤1.0
Residue on ignition, %	≤0.10	≤0.10	≤0.10	≤0.10	≤0.10

 

Characteristics: It is a white crystalline powder. It’s soluble in water and easy soluble in ethanol, chloroform etc.

Uses: This product is mainly used for the synthesis arbutin. Used as medicine, pharmaceutical intermediates and its modification, synthon of bioactive materials, activators of peroxides, additive of medicine, food and plastic, antisolvent crystallizations of pharmaceutical, enzyme and biomolecule, acetylation treatment of wood, nona porogen of polysilsesquioxanes film, standard of determination acetyl group, enzyme substrate in bioresearch, monitoring human body gluconeogenesis, fabrication molecular size nanopores for nano-thin films of phospholipids-hydrophobic polymers, synthese of biomaterials, glycoside liquid crystal materials, alkyl glucoside surfactants, low-molecular-mass gelators with sugar-appended, chiral bidentate ligands and ionic liquids, sugar-base amphiphilic polymer, glycosyl-biodegradable polymer or copolymer, hydrophily glycosyl pulvinic acid derivatives, glycopeptide oligomers, building block of glycopeptide, various of glycosylation donor and its derivative, ect.. In addition, α-D-glucose pentaacetate has insulinotropic action and expected to be a new type insulin secretagogue. It also has certain antimicrobial activities including shigella dysenteriae, candida albicans, staphylococcus and more than 10 kinds of bacterias to be a potential antimicrobial agent. It has ovicidal effect on tetranychus urticae, whitefly to control arthropod pests. GPA is sufficiently similar to effectively mimic lipochitooligosaccharides (LCOs)-signal transduction, leading to cell division and enhanced plant growth, so used as plant growth regulators (PGRs).

As pharmaceutical intermediates it used to synthesis the following pharmaceutical or active ingredients: sterol glucoside toxins, echinatin glycosides, diosgenin, glucosyl saponin such as tigogenin and hederagenin saponins, photodynamic therapy. In addition, glycosylation the pharmaceuticals such as linsidomide, silibinin, tocopherol (naphthotocopherol), gallic acid, glibenclamide, clopidol can improve their bioavailability.

As synthon the following bioactive compounds can be synthesized: Millingtonine A, triacetyl glucosyl-benzoxazinone, glucosyl- triazolo-triazine-ones / curcumin / flavanones and nucleoside analogs with antimicrobial activity, alkaloid Iteamine, heptasaccharide phytoalexin elicitor, pentasaccharide as vaccines, phenylethyl trisaccharide with hepatoprotective and vasorelaxant activities, glycosyl oxadiazoles derivatives and retinoic acid with anti-tumor activities for MDA-MB-231, glucosyl-12-(3-adamantan-1-yl-ureido)dodecanoic acid with inhibitor the soluble epoxide hydrolase, natural active phenylpropanoid glycosides, triazole-linked alkyl glucopyranosides with cytotoxic effects on Jurkat cells, 5-trifluoromethyl-2,4-dihydropyrazol-3-one nucleoside and Ipomoeassin F with anti-cancer activity, glucolaxogenin with anti-cervical cancer, glucose-based acetylsalicylic with inhibition proliferation of cancer cells, bicyclic carbohydrate-based derivative with inhibitory activity against human cytomegalovirus, flaviviruses, bovine viral diarrhea viruses, trypanosoma brucei rhodiense and leishmania donovani, glycoconjugates of dithiocarbamates and Their copper(zinc) complexes with anti-proliferative and antioxidant, Raphanuside with expectorant, anti-cough and antiasthmatic, quinazoline-S-glucoside with anti inflammatory, (-)-Strictinin with antiallergy and immunostimulatory, tannins compounds with anti-HIV, isoacteoside derivative with inhibiting β-amyloid peptides accumulation, bis-quinazoline glycosides with epidermal growth factor receptor inhibition, betulinic acid glucosides anti human myeloid leukemia activities, and acetylphenyl-glycosides with antioxidant as UV-B light absorbents.

It used as activator for peroxide such as hydrogen peroxide, peracetic acid, sodium percarbonate, ect., which used in sterilization, cold sterilization, bleaching process.

It used as additive for salrneterol xinafoate dry powder inhalers, artificial chocolate and tobacco, and especially it can reduce the pungent smell of cigarettes. In addition, added L-Menthyl glucoside origin from glucose pentaacetate to the tobacco giving cigarettes a cool and refreshing scent.  The modification of glucose pentaacetate can reduce Release of phenol in mainstream cigarette smoke containing paper-cellulose acetate binary filter.  And as bioplasticizers for PVC, polylactide and cellulose acetate.

It used as phase-change physical solvent or absorbent for CO₂, solubilizer of some organic compounds in supercritical carbon dioxide and used in antisolvent crystallization of pharmaceuticals molecules, carbohydrate-containing biomolecules and enzymes to selective separation and modify their crystal morphology or crystal habit because of its CO₂-philes.

It used to develop biological research materials, for example, the graft polymer of poly (hydroxyethyl methacrylate) and glucose that is immobilized on the surface of polypropylene to recognition and adsorption protein. Glycopeptide dendrimer conjugates of colchicines and sugar to study Hela-cell Cytotoxicitys. PCDA(10,12-pentacoasdiynoic acid) biosensor, which is tagging carbohydrates with PCDA dye. Brush glycopolymers, a kind of glycolipid mimic.

It used to synthesis branched-chain alkyl glucosides, thioglucopyranosides, p-phenylethylglucoside and β-sitosteryl-β-D-glucopyranoside, which exhibit liquid crystal behavior. Synthesis of organic semiconductors functionalized with biological molecules. And synthesis various glycosylation donors and its derivatives, such as tetra-O-acetyl-D-glucose, 1-chloro(or bromo)-tetra-O-acetyl-D-glucose, etc.

Storage: Maintain in cool, dry containment.

Package: 25kg/drum or as customer require.

Expiration Date: 2 years.