7535-00-4

Basic information

• Product Name: D-GALACTOSAMINE
• Synonyms: d-2-amino-2-deoxygalactose;D-GALACTOSAMINE;C02262;D-Chondrosamine;(2R,3R,4R,5R)-2-Amino-3,4,5,6-tetrahydroxyhexanal
• CAS NO: 7535-00-4
• Molecular Formula: C₆H₁₃NO₅
• Molecular Weight: 179.17
• Mol File: 7535-00-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 185 °C
• Boiling Point: 449.9°C at 760 mmHg
• Flash Point: 225.9°C
• Appearance: /
• Density: 1.563g/cm³
• Vapor Pressure: 5.53E-10mmHg at 25°C
• Refractive Index: 1.6
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 11.21±0.45(Predicted)
• CAS DataBase Reference: D-GALACTOSAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: D-GALACTOSAMINE(7535-00-4)
• EPA Substance Registry System: D-GALACTOSAMINE(7535-00-4)

Safety Data

• Hazardous Substances Data: 7535-00-4(Hazardous Substances Data)

Usage

Description

Galactosamine is a model hepatotoxicant, induces hepatitis characterized by neutrophilic infiltration, and kills the animal by fulminant hepatic failure. Galactosamine, an amino derivative of sugar galactose, has been used as a model hepatotoxicant since the first reports of hepatotoxicity in late 1970s by Keppler and associates. Galactosamine-induced hepatitis has been a model of choice to study various aspects of liver disease, including mechanisms of toxicant-induced apoptosis and necrosis, liver tissue repair, neutrophil infiltration and transmigration, and the role of endotoxin or lipopolysaccharide (LPS) in initiating liver injury. Humans and animals synthesize galactosamine in the body. Galactosamine (a type of hexosamine) is formed when an amino group replaces one of the hydroxy groups of a sixcarbon sugar, or hexose. The human body utilizes uridine diphosphate (UDP)-N-acetyl-D-glucosamine or glucosamine as a precursor to synthesize this compound, and is most often found in the form N-acetyl-D-galactosamine (often referred to as N-acetylgalactosamine). Most importantly, galactosamine is a constituent of hyaluronic acid, a powerful water-binding agent. Many different types of tissues in human body contain hyaluronic acid, which acts as a lubricating agent in the synovial fluid of joints and in connective tissues. Hyaluronic acid also acts as a lubricating agent in the vitreous humor of the eyeball. Hyaluronic acid has considerable medicinal value; it is often used in wound healing, burn dressings, osteoarthritis treatment, cataract or corneal transplantation surgery, and various types of plastic surgeries.

Definition

ChEBI: The pyranose form of D-galactosamine.

Toxicity evaluation

Galactosamine induces liver injury by interfering with the uridine pool in the cell, which is essential for RNA and protein synthesis. Galactosamine ismetabolized via the Leloir pathway of galactose metabolism, which leads to the generation of uridine derivatives of galactosamine. The two enzymes of the Leloir pathway, galactokinase and UDP-galactose uridyltransferase, convert galactosamine into galactosamine-1-phosphate and UDP-galactosamine, respectively,due to their lowsubstrate specificity.UDPgalactosamine blocks the final enzyme in Leloir pathway, the UDP-galactose-40 epimerase, resulting in the accumulation of UDP-galactosamine in the cells. This results in the depletion of uridine triphosphate (UTP), UDP, uridine monophosphate (UMP), and the sugar derivative of uridine such as UDP-glucose and UDP-galactose essential for RNA and protein synthesis. Orotate, a precursor of the hexosamine biosynthesis pathway, has been used as an antidote to galactosamine toxicity.

InChI:InChI=1/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4+,5-,6?/m1/s1

Upstream product

• 20229-59-8 O³,O⁴-isopropylidene-O²-methanesulfonyl-1,6-anhydro-β-D-galactopyranose 
• 52526-54-2 O²-methanesulfonyl-1,6-anhydro-β-D-galactopyranose 
• 52579-97-2 1,6-anhydro-3,4-O-isopropylidene-β-D-galactopyranose 
• 67-56-1 methanol 
• 87-81-0 D-tagatose 
• 7664-41-7 ammonia 
• 885458-66-2 2-amino-2-deoxy-D-galactononitrile 
• 61074-38-2 2-acetamido-1,6-anhydro-2-deoxy-β-D-galactopyranose 
• 459409-43-9 2-amino-1,6-anhydro-2-deoxy-β-D-galactopyranose 
• 6893-59-0 1,6:2,3-dianhydro-β-D-talopyranose 

Downstream Products

• 20706-37-0 2-amino-2-deoxy-D-galacticol 
• 85395-58-0 2-((Ξ)-4-nitro-benzylidenamino)-2-deoxy-D-galactose 
• 64449-12-3 2-(2,4-dinitro-anilino)-2-deoxy-D-galactose 
• 109514-99-0 2-((Ξ)-vanillylidenamino)-2-deoxy-D-galactose 
• 1114-34-7 D-lyxose 
• 134-61-2 N-acetylgalactosamine 
• 197663-12-0 phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thiol-D-galactopyranoside 
• 28876-38-2 2-acetamido-2-deoxy-D-galactono-1,4-lactone 
• 34044-52-5 2-acetylamino-O⁵,O⁶-isopropylidene-2-deoxy-D-galactonic acid-4-lactone 
• 14278-76-3 2-(2,4-dinitro-anilino)-2-deoxy-D-galactitol 

Relevant articles and documents

Structure and gene cluster of the O-antigen of Escherichia coli O102

The O-polysaccharide (O-antigen) of Escherichia coli O102 was studied by sugar analysis along with one- and two-dimensional 1H and 13C NMR spectroscopy. The following structure of the branched pentasaccharide repeating unit was estab

High-throughput determination of urinary hexosamines for diagnosis of mucopolysaccharidoses by capillary electrophoresis and high-performance liquid chromatography

Mucopolysaccharidoses (MPS) diagnosis is often delayed and irreversible organ damage can occur, making possible therapies less effective. This highlights the importance of early and accurate diagnosis. A high-throughput procedure for the simultaneous determination of glucosamine and galactosamine produced from urinary galactosaminoglycans and glucosaminoglycans by capillary electrophoresis (CE) and HPLC has been performed and validated in subjects affected by various MPS including their mild and severe forms, Hurler and Hurler-Scheie, Hunter, Sanfilippo, Morquio, and Maroteaux-Lamy. Contrary to other analytical approaches, the present single analytical procedure, which is able to measure total abnormal amounts of urinary GAGs, high molecular mass, and related fragments, as well as specific hexosamines belonging to a group of GAGs, would be useful for possible application in their early diagnosis. After a rapid urine pretreatment, free hexosamines are generated by acidic hydrolysis, derivatized with 2-aminobenzoic acid and separated by CE/UV in ～10 min and reverse-phase (RP)-HPLC in fluorescence in ～21 min. The total content of hexosamines was found to be indicative of abnormal urinary excretion of GAGs in patients compared to the controls, and the galactosamine/glucosamine ratio was observed to be related to specific MPS syndromes in regard to both their mild and severe forms. As a consequence, important correlations between analytical response and clinical diagnosis and the severity of the disorders were observed. Furthermore, we can assume that the severity of the syndrome may be ascribed to the quantity of total GAGs, as high-molecular-mass polymers and fragments, accumulated in cells and directly excreted in the urine. Finally, due to the high-throughput nature of this approach and to the equipment commonly available in laboratories, this method is suitable for newborn screening in preventive public health programs for early detection of MPS disorders, diagnosis, and their treatment.

Process for the preparation of cyclopropane carboxylic acid esters

3-(Halogenovinyl- or propenyl-)-2,2-dimethyl cyclopropane-1-carboxylic acid esters, which are precursors of, or may themselves be, pyrethroid insecticides, are prepared by the reaction of certain halogenopentadienes with an alkyl diazoacetate in the presence of a catalyst which is a transition metal complex of certain chiral Schiff bases, which catalysts tend to increase the yield of preferred cis IR isomer relative to the other possible isomers.