4163-59-1

Basic information

• Product Name: 1,2,3,4,6-PENTA-O-ACETYL-ALPHA-D-GALACTOPYRANOSE
• Synonyms: 1,2,3,4,6-Penta-O-acetyl-α-D-galactopyranose ,98%;1,2,3,4,6-Penta-O-acetyl-alpha-D-galactose;2,3,4,6-Tetra-O-acetyl-alpha-D-galactopyranosyl acetate;alpha-D-Galactopyranose 1,2,3,4,6-pentaacetate;alpha-D-Galactopyranose pentaacetate;Penta-O-acetyl-a-D-galactopyranoside;ALPHA-D-GALACTOSE-PENTAACETATE;1,2,3,4,6-PENTA-O-ACETYL-ALPHA-D-GALACTOPYRANOSE
• CAS NO: 4163-59-1
• Molecular Formula: C₁₆H₂₂O₁₁
• Molecular Weight: 390.34
• EINECS: 1312995-182-4
• Mol File: 4163-59-1.mol
• Article Data: 301

Chemical Properties

• Melting Point: 95-96℃
• Boiling Point: 435℃
• Flash Point: 188℃
• Appearance: White to Off-white/Powder
• Density: 1.30
• Vapor Pressure: 9.23E-08mmHg at 25°C
• Refractive Index: 1.482
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Soluble in methanol at approximately 50mg/ml
• CAS DataBase Reference: 1,2,3,4,6-PENTA-O-ACETYL-ALPHA-D-GALACTOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4,6-PENTA-O-ACETYL-ALPHA-D-GALACTOPYRANOSE(4163-59-1)
• EPA Substance Registry System: 1,2,3,4,6-PENTA-O-ACETYL-ALPHA-D-GALACTOPYRANOSE(4163-59-1)

Safety Data

• Statements: 22
• Safety Statements: 36/37
• Hazardous Substances Data: 4163-59-1(Hazardous Substances Data)

Usage

Description

1,2,3,4,6-Penta-o-acetyl-alpha-d-galactopyranose is an O-acyl carbohydrate that consists of alpha-D-galactopyranose bearing five O-acetyl substituents. It is a white solid and is known for its role in the synthesis of complex carbohydrates and its involvement in various chemical reactions.

Uses

Used in Pharmaceutical Industry:
1,2,3,4,6-Penta-o-acetyl-alpha-d-galactopyranose is used as a building block for the synthesis of oligosaccharides containing internal and terminal Galβ1-3GlcNAcβ fragments. These oligosaccharides are essential components in the development of various pharmaceutical compounds, particularly those targeting specific biological receptors.
Used in Chemical Synthesis:
1,2,3,4,6-Penta-o-acetyl-alpha-d-galactopyranose is used as a key intermediate in acyl transfer reactions, which are crucial for the synthesis of a wide range of complex organic compounds. These reactions are essential in the development of new materials, pharmaceuticals, and other chemical products.

InChI:InChI=1/C16H22O11/c1-7(17)22-6-12-13(23-8(2)18)14(24-9(3)19)15(25-10(4)20)16(27-12)26-11(5)21/h12-16H,6H2,1-5H3/t12-,13+,14+,15-,16+/m1/s1

Upstream product

• 7322-31-8 β-D-mannose 
• 108-24-7 acetic anhydride 
• 5019-25-0 methyl 2,3,4,6-tetra-O-acetyl-β-D-mannopyranoside 
• 56-75-7 chloramphenicol 
• 4163-60-4 β-D-galactose peracetate 
• 530-26-7 D-Mannose 
• 492-62-6 alpha-D-glucopyranose 
• 20672-66-6 3,4,6-tri-O-benzyl-D-glucopyranose 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 2280-44-6 D-Glucose 
• 64-19-7 acetic acid 
• 127-08-2 potassium acetate 
• 54325-28-9 6-O-trityl-D-glucopyranose 
• 552-76-1 D-mannose 

Downstream Products

• 74590-42-4 o-cyanophenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 28619-26-3 p-cresyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 134698-99-0 phenylethyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 134698-98-9 p-phenylphenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 74590-40-2 p-cyanophenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 28619-25-2 p-chlorophenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 2872-72-2 phenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 52443-07-9 3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptonitrile 
• 18463-30-4 (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-phenoxytetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose 
• 73366-80-0 1,2,3,4-tetra-O-acetyl-α-D-galactopyranose 
• 70191-05-8 2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside 

Relevant articles and documents

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.

Selectivity of 1-O-Propargyl-D-Mannose Preparations

Thanks to their ability to bind to specific biological receptors, mannosylated structures are examined in biomedical applications. One of the most common ways of linking a functional moiety to a structure is to use an azide-alkyne click reaction. Therefore, it is necessary to prepare and isolate a propargylated mannose derivative of high purity to maintain its bioactivity. Three known preparations of propargyl-α-mannopyranoside were revisited, and products were analysed by NMR spectroscopy. The preparations were shown to yield by-products that have not been described in the literature yet. Our experiments showed that one-step procedures could not provide pure propargyl-α-mannopyranoside, while a three-step procedure yielded the desired compound of high purity.

Preparation and formulation optimization of methotrexate-loaded human serum albumin nanoparticles modified by mannose

Background: Methotrexate (MTX) is the representative drug among the dis-ease-modifying anti-rheumatic drugs. However, the conventional treatment with MTX showed many limitations and side effects. Objective: To strengthen the targeting ability and circulation time of MTX in the treatment of rheumatoid arthritis, the present study focused on developing a novel drug delivery system of methotrexate-loaded human serum albumin nanoparticles (MTX-NPs) modified by mannose, which are referred to as MTX-M-NPs. Methods: Firstly, mannose-derived carboxylic acid was synthesized and further modified on the surface of MTX-NPs to prepare MTX-M-NPs. The formulation of nanoparticles was optimized by the method of central composite design (CCD), with the drug lipid ra-tio, oil-aqueous ratio, and cholesterol or lecithin weight as the independent variables. The average particle size and encapsulation efficiency were the response variables. The response of different formulations was calculated, and the response surface diagram, con-tour diagram, and mathematical equation were used to relate the dependent and independent variables to predict the optimal formula ratio. The uptake of MTX-M-NPs by neu-trophils was studied through confocal laser detection. Further, MTX-M-NPs were subject-ed to assessment of the pharmacokinetics profile after intravenous injection with Sprague-Dawley rats. Results: This targeting drug delivery system was successfully developed. Results from Nuclear Magnetic Resonance and Fourier Transform Infrared Spectroscopy analysis can verify the successful preparation of this drug delivery system. Based on the optimized for-mula, MTX-M-NPs were prepared with a particle size of 188.17 ± 1.71 nm and an encapsulation rate of 95.55 ± 0.33%. MTX-M-NPs displayed significantly higher cellular uptake than MTX-NPs. The pharmacokinetic results showed that MTX-M-NPs could pro-long the in vivo circulation time of MTX. Conclusion: This targeting drug delivery system laid a promising foundation for the treatment of RA.