5346-85-0

Basic information

• Product Name: 1,5-anhydro-2-deoxy-4-O-beta-D-glucopyranosyl-D-arabino-hex-1-enitol
• Synonyms: D-arabino-Hex-1-enitol, 1,5-anhydro-2-deoxy-4-O-beta-D-glucopyranosyl-; Cellobial
• CAS NO: 5346-85-0
• Molecular Formula: C₁₂H₂₀O₉
• Molecular Weight: 308.2818
• Mol File: 5346-85-0.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 612°C at 760 mmHg
• Flash Point: 323.9°C
• Density: 1.61g/cm³
• Vapor Pressure: 1.55E-17mmHg at 25°C
• Refractive Index: 1.626
• CAS DataBase Reference: 1,5-anhydro-2-deoxy-4-O-beta-D-glucopyranosyl-D-arabino-hex-1-enitol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-anhydro-2-deoxy-4-O-beta-D-glucopyranosyl-D-arabino-hex-1-enitol(5346-85-0)
• EPA Substance Registry System: 1,5-anhydro-2-deoxy-4-O-beta-D-glucopyranosyl-D-arabino-hex-1-enitol(5346-85-0)

Safety Data

• Hazardous Substances Data: 5346-85-0(Hazardous Substances Data)

Usage

Description

1,5-anhydro-2-deoxy-4-O-beta-D-glucopyranosyl-D-arabino-hex-1-enitol, also known as D-allulose, is a rare monosaccharide sugar that is naturally found in small quantities in certain fruits and foods. It has potential health benefits, including its ability to act as a low-calorie sweetener with a similar taste to sugar but with fewer calories. Additionally, D-allulose has been studied for its potential in reducing blood sugar levels and improving insulin sensitivity, making it a promising option for individuals with diabetes. It is also being researched for its role in weight management and potential effects on gut health.
Used in Food Industry:
1,5-anhydro-2-deoxy-4-O-beta-D-glucopyranosyl-D-arabino-hex-1-enitol is used as a low-calorie sweetener for its similar taste to sugar but with fewer calories.
Used in Pharmaceutical Industry:
1,5-anhydro-2-deoxy-4-O-beta-D-glucopyranosyl-D-arabino-hex-1-enitol is used as a potential treatment for diabetes due to its ability to reduce blood sugar levels and improve insulin sensitivity.
Used in Weight Management:
1,5-anhydro-2-deoxy-4-O-beta-D-glucopyranosyl-D-arabino-hex-1-enitol is used as a supplement for weight management due to its potential role in reducing calorie intake and promoting weight loss.
Used in Gut Health Research:
1,5-anhydro-2-deoxy-4-O-beta-D-glucopyranosyl-D-arabino-hex-1-enitol is used in research for its potential effects on gut health and its role in maintaining a healthy gut microbiome.

Upstream product

• 51450-24-9 hexa-O-acetyl-D-lactal 
• 4753-07-5 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide 
• 3616-19-1 1,2,3,6,2',3',4',6'-octa-O-acetylmaltose 
• 4753-07-5 α-hepta-O-acetylmaltosyl bromide 
• 51450-24-9 hexa-O-acetyl-D-maltal 
• 3616-19-1 1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 
• 5160-10-1 2,3,6-tetra-O-acetyl-4-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-D-glucopyranosylbromide 
• 70223-97-1 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl bromide 
• 13265-84-4 D-glucal 
• 952585-00-1 uridine-5'-diphosphoglucose 
• 2906-23-2 CDP-glucose 
• 2956-16-3 uridine 5'-diphospho-D-galactose 

Downstream Products

• 132911-81-0 4-O-(3-O-benzyl-β-D-galactopyranosyl)-D-arabino-hex-1-enitol 
• 132911-82-1 4-O-(3,6-di-O-benzyl-β-D-galactopyranosyl)-D-arabino-hex-1-enitol 

Relevant articles and documents

Glycosyltransferase-catalysed Stereoselective Glycosidation of Monosaccharide-based Glycosidase Inhibitors: a New Approach to the Synthesis of Sequence-specific Glycosidase Inhibitors

β-1,4-Galactosyltransferase was used as catalyst for galactosidation of 5-thioglucose, glucal and 1-deoxynojirimycin to form the corresponding β-1,4-galactosides as potential sequence-specific glycosidase inhibitors.

Effect of ionic liquids as additives in the catalytic properties of different immobilized preparations of Rhizomucor miehei lipase in the hydrolysis of peracetylated lactal

The addition of small amount of different ionic liquids modified the activity and regioselectivity of different immobilized preparations of R. miehei lipase catalyzing the hydrolysis of hexa-O-acetyl lactal in aqueous media. ILs with [emim] as cation and different anions were first evaluated affecting in a different manner depending on the immobilized preparation used. The enzymatic activity of RML immobilized on octyl-agarose or CNBr-agarose decreased in the following order: NO3-≈ BF4- > MeOSO3- > PF6-, whereas when RML was immobilized on Q-Sepharose, the enzymatic activity decreased in a different order: MeOSO3- > PF6- > BF4- > NO3-. Using [bdmim], the activity of octyl-RML and CNBr-RML preparations resulted higher in the presence of PF6- than BF4-, 6-fold for octyl-RML and 2-fold for CNBr-RML if compared with the enzyme activity without additive. In both preparations the enzyme was completely regioselective in the presence of the IL hydrolyzing at C-3 position in 99% yield. The modification of the cation in the IL did not affect to the activity of Q-RML with BF4- or decreased the activity with PF 6-, although affected to the regioselectivity producing another undesired product, a bihydrolized product in 20-25% yield. In this case, the addition of [emim][MeOSO3] caused the best increment in the activity for this RML biocatalyst, 2-fold with only 8% of bihydrolized production.

A highly convergent synthesis of an N-linked glycopeptide presenting the H-type 2 human blood group determinant

The total synthesis of an H-type blood group determinant in a model biological setting is described. The construct is comprised of a high mannose core structure with projecting lactose spacers, culminating in a two-copy presentation of the H-type blood group determinant itself. Key reactions that were used in this construction include sulfonamidohydroxylation (see 15→18) and benzoate-directed glycosylation via an activated thiophenyl donor (see 34→36). Another key strategic element involved the epimerization of an interior core glucoside to reach the β-mannoside (see 37→38) required in the ring C sugar of the high mannose core.