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

• 58-86-6 D-xylose 
• 108-24-7 acetic anhydride 
• 87-72-9 D-Xylose 
• 75-36-5 acetyl chloride 
• 2460-44-8 β-D-xylopyranoside 
• 6763-34-4 D-xylose 
• 5328-37-0 L-arabinose 
• 1233-03-0 α-D-xylopyranose tetraacetate 
• 77217-81-3 1,2-di-O-acetyl-β-D-xylopyranose 
• 64-19-7 acetic acid 
• 68579-19-1 Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-(5,5-dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester 
• 10343-54-1 2,3,4-tri-O-acetyl-α-D-xylopyranosyl chloride 
• 127-09-3 sodium acetate 
• 87-72-9 L-(+)-arabinose 

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 
• 3068-31-3 1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose 

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.

Synthesis and biological evaluation of 3β-O-neoglycosides of caudatin and its analogues as potential anticancer agents

In order to study the structure–activity relationship (SAR) of C21-steroidal glycosides toward human cancer cell lines and explore more potential anticancer agents, a series of 3β-O-neoglycosides of caudatin and its analogues were synthesized. The results revealed that most of peracetylated 3β-O-monoglycosides demonstrated moderate to significant antiproliferative activities against four human cancer cell lines (MCF-7, HCT-116, HeLa, and HepG2). Among them, 3β-O-(2,3,4-tri-O-acetyl-β-L-glucopyranosyl)-caudatin (2k) exhibited the highest antiproliferative activity aganist HepG2 cells with an IC50 value of 3.11 μM. Mechanical studies showed that compound 2k induced both apoptosis and cell cycle arrest at S phase in a dose dependent manner. Overall, these present findings suggested that glycosylation is a promising scaffold to improve anticancer activity for naturally occurring C21-steroidal aglycones, and compound 2k represents a potential anticancer agent deserved further investigation.

Isolation and characterization of triterpenoid saponins from leaves of Aralia nudicaulis L

Three new oleanolic glycosides (1–3), along with seven known saponins from various plants (4–10) were isolated for the first time from the leaves of Aralia nudicaulis. Their structures were elucidated on the basis of spectroscopic evidence, including 1D and 2D NMR, and HRESIMS. Nudicauloside A and B (1–2) have shown moderate anti-inflammatory activity, as demonstrated by inhibition of LPS-induced NO production in raw 264.7 murine macrophages (IC50 = 74–101 μM).