4049-33-6

Basic information

• Product Name: 1,2,3,4-TETRA-O-ACETYL-BETA-D-XYLOPYRANOSE
• Synonyms: BETA D-XYLOSE TETRAACETATE;1,2,3,4-TETRA-O-ACETYL-BETA-D-XYLOPYRANOSE;1,2,3,4-Tetra-O-acetyl-b-D-xylopyranose;1,2,3,4-TETRA-O-ACETYL-SS-D-XYLOPYRANOSE;beta-D-Xylopyranose tetraacetate;xylose tetraacetate;b-D-Xylopyranose,1,2,3,4-tetraacetate;1,2,3,4-Tetra-O-acetyl-D-xylopyranose(β forM)
• CAS NO: 4049-33-6
• Molecular Formula: C₁₃H₁₈O₉
• Molecular Weight: 318.28
• EINECS: 200-258-5
• Mol File: 4049-33-6.mol
• Article Data: 105

Chemical Properties

• Melting Point: 123-125 °C
• Boiling Point: 362.9 °C at 760 mmHg
• Flash Point: 157 °C
• Appearance: /
• Density: 1.29 g/cm³
• Vapor Pressure: 1.87E-05mmHg at 25°C
• Refractive Index: 1.475
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 1,2,3,4-TETRA-O-ACETYL-BETA-D-XYLOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-TETRA-O-ACETYL-BETA-D-XYLOPYRANOSE(4049-33-6)
• EPA Substance Registry System: 1,2,3,4-TETRA-O-ACETYL-BETA-D-XYLOPYRANOSE(4049-33-6)

Safety Data

• Hazardous Substances Data: 4049-33-6(Hazardous Substances Data)

Usage

General Description

1,2,3,4-Tetra-O-acetyl-beta-D-xylopyranose is a chemical compound belonging to the class of carbohydrates. It is a derivative of beta-D-xylopyranose, which is a five-membered ring sugar molecule. The compound is acetylated at all four hydroxyl groups of the xylose ring, making it more resistant to hydrolysis and more stable. It is commonly used as a reagent in organic synthesis and as a building block for the synthesis of various pharmaceutical compounds and natural products. The acetyl groups can be selectively removed, allowing access to the free hydroxyl groups for further chemical reactions. Overall, 1,2,3,4-Tetra-O-acetyl-beta-D-xylopyranose is a versatile chemical with applications in various industries, including pharmaceuticals, agrochemicals, and biotechnology.

InChI:InChI=1/C13H18O9/c1-6(14)19-10-5-18-13(22-9(4)17)12(21-8(3)16)11(10)20-7(2)15/h10-13H,5H2,1-4H3/t10-,11+,12-,13+/m1/s1

Upstream product

• 107-13-1 acrylonitrile 
• 1195726-04-5 trans-2-ethoxy-3,4-epoxytetrahydropyran 
• 108-24-7 acetic anhydride 
• 31080-85-0 trans-6-ethoxy-5-hydroxy-5,6-dihydro-2H-pyran 
• 10369-25-2 2,3,4-tri-O-acetyl-α,β-L-arabinopyranose 
• 87-72-9 L-(+)-arabinose 
• 127-09-3 sodium acetate 
• 5328-37-0 L-arabinose 
• 41546-21-8 L-ribose 
• 58-86-6 D-xylose 
• 6763-34-4 D-xylose 
• 87-72-9 D-Xylose 
• 64-19-7 acetic acid 
• 2460-44-8 β-D-xylopyranoside 

Downstream Products

• 94921-62-7 (4-nitro-phenyl)-(tri-O-acetyl-β-L-arabinopyranoside) 
• 94921-63-8 (4-nitro-phenyl)-(tri-O-acetyl-α-L-arabinopyranoside) 
• 3456-62-0 2-methylphenyl-α-L-arabinopyranoside 
• 14227-90-8 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide 
• 3180-45-8 o-tolyl-(tri-O-acetyl-β-D-xylopyranoside) 
• 3180-47-0 (4-chloro-phenyl)-(tri-O-acetyl-β-D-xylopyranoside) 
• 38420-12-1 1.1-diphenyl-1-deoxy-D-xylitol 
• 84380-09-6 phenyl 2,3,4-tri-O-acetyl-α-D-xylopyranoside 
• 5041-91-8 Phenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside 
• 10300-18-2 (2,3,4-Tri-O-acetyl-β-D-xylopyranosyl) chloride 
• 10343-54-1 2,3,4-tri-O-acetyl-α-D-xylopyranosyl chloride 
• 1233-03-0 α-D-xylopyranose tetraacetate 
• 15356-53-3 (2,3,4-Tri-O-acetyl-β-D-xylopyranosyl)benzene 
• 118358-94-4 3-O-(2,3,4-Tri-O-acetyl-β-D-xylopyranosyl)-N-(fluorenylmethoxycarbonyl)-L-serin-benzylester 

Relevant articles and documents

Preparation of new β-D-xyloside- and β-D-xylobioside-based ionic liquids through chemical and/or enzymatic reactions

Several tetraalkylphosphonium and tetraalkylammonium salts containing xyloside- and xylobioside-based anionic moieties have been prepared. Two stereoselective routes have been developed: i) a chemical pathway in four steps from D-xylose, and ii) a chemoenzymatic pathway directly from biomass-derived xylans. These salts displayed interesting properties as ionic liquids. Their structures have been correlated to their thermal properties (melting, glass transition and decomposition temperatures).

Synthesis, surface properties, and biocompatibility of 1,2,3-triazole- containing alkyl β-D-xylopyranoside surfactants

We are interested in the development of surfactants derived from hemicellulosic biomass, as they are potential components in pharmaceuticals, personal care products, and other detergents. Such surfactants should exhibit low toxicity in mammalian cells. In this study we synthesized a series of alkyl or fluoroalkyl β-xylopyranosides from azides and an alkyne using the copper-catalyzed azide-alkyne (CuAAC) 'click' reaction in 4 steps from xylose. The purified products were evaluated for both their surfactant properties, and for their biocompatibility. Unlike other carbohydrate-based surfactants, liquid-crystalline behavior was not observed by differential scanning calorimetry. The triazole-containing β-xylopyranosides with short (6 carbons) and long (>12 carbons) chains exhibited no toxicity at concentrations ranging from 1 to 1000 μM. Triazole-containing β-xylopyranosides with 8, 10, or 12 carbons caused toxicity via apoptosis, with CC50 values ranging from 26-890 μM. The two longest chain compounds did form stable monolayers at the air-water interface over a range of temperatures, although a brief transition to an the unstable monolayer was observed.

Design, Synthesis, biological investigations and molecular interactions of triazole linked tacrine glycoconjugates as Acetylcholinesterase inhibitors with reduced hepatotoxicity

Tacrine is a known Acetylcholinesterase (AChE) inhibitors having hepatotoxicity as main liability associated with it. The present study aims to reduce its hepatotoxicity by synthesizing tacrine linked triazole glycoconjugates via Huisgen's [3 + 2] cycloaddition of anomeric azides and terminal acetylenes derived from tacrine. A series of triazole based glycoconjugates containing both acetylated (A-1 to A-7) and free sugar hydroxyl groups (A-8 to A-14) at the amino position of tacrine were synthesized in good yield taking aid from molecular docking studies and evaluated for their in vitro AChE inhibition activity as well as hepatotoxicity. All the hybrids were found to be non-toxic on HePG2 cell line at 200 μM (100 % cell viability) as compared to tacrine (35 % cell viability) after 24 h of incubation period. Enzyme kinetic studies carried out for one of the potent hybrids in the series A-1 (IC50 0.4 μM) revealed its mixed inhibition approach. Thus, compound A-1 can be used as principle template to further explore the mechanism of action of different targets involved in Alzheimer's disease (AD) which stands as an adequate chemical probe to be launched in an AD drug discovery program.

Protecting carbohydrates with ethers, acetals and orthoesters under basic conditions

Chlorinated ethyl and vinyl ethers are introduced at various positions of carbohydrates. Depending on the relative stereochemistry, vinylethers, acetals or orthoesters are formed under basic conditions. The products are stable, but are easily deprotected