Basic information
- CAS
7535-00-4- Standard SMILES
N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O- InChIKey
MSWZFWKMSRAUBD-GASJEMHNSA-N- Molecular formula
- C6H13NO5
- Average molar mass
- 179.17 g/mol
- Monoisotopic mass
- 179.07937252
Overview
2-amino-2-deoxy-D-galactopyranose is the pyranose form of D-galactosamine. It has a role as a toxin. It is a D-galactosamine and a primary amino compound. It is functionally related to a D-galactopyranose. It is a conjugate base of a 2-ammonio-2-deoxy-D-galactopyranose.
Names & identifiers
- Preferred name
- D-Galactosamine
- IUPAC
- (3R,4R,5R,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol
- English name
- D-Galactosamine
- Molecular formula
- C6H13NO5
- Molecular weight
- 179.17
Names & synonyms
Show more names
Database identifiers
- CAS
7535-00-4、90-76-6- PubChem CID
- 24154
- DTXSID
DTXSID7043871- ChEMBL
CHEMBL3304228- ChEBI
CHEBI:60312- Nikkaji
- J774.534F
Properties
Computed structural properties
- XLogP
- -2.8
- Topological polar surface area
- 116 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 1
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 155
Physicochemical properties
- Melting point
- 185 °C · 185 °C
- Boiling point
- 532.5 · 532.5±50.0 °C(Predicted)
- Density
- 1.491 · 1.491±0.06 g/cm3(Predicted)
- storage temp.
- 2 · under inert gas (nitrogen or Argon) at 2–8 °C
- solubility
- Soluble (water), slightly soluble (ethanol)
- pka
- 11.21 · 11.21±0.45(Predicted)
- optical activity
- 124 · Alpha form +124 → +93 Beta form +47 → +93
- FDA UNII
- 4 Y6R29688W · 4Y6R29688W
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 317 · H317-H319
- Precautionary statements
- 280 · P280-P305+P351+P338
Safety & regulation
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H317-H319
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Applications
DescriptionGalactosamine 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.
Suppliers14 total
Additional notes
DefinitionChEBI: The pyranose form of D-galactosamine.
Related reactions
Compound notes
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