D-Galactosamine

HCID 24154

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

D-GalactosamineGALACTOSAMINE2-Amino-2-deoxy-D-galactopyranoseChondrosamineD-GalNgaln2-Amino-2-deoxy-D-galactoseDTXSID70438712-Deoxy-2-Amino-D-Galactopyranose2-amino-2-deoxy-galactose2-Deoxy-2-Amino-Galactose2-deoxy-2-amino-d-galactose
Show more names
C02262D-Chondrosamined-2-amino-2-deoxygalactoseD-Galactose, 2-amino-2-deoxy-2-Amino-2-deoxy-D-galactose-7535-00-4(2R,3R,4R,5R)-2-Amino-3,4,5,6-tetrahydroxyhexanal
CHEBI:28328CHEBI:603122-Amino-2-Deoxy-Galactopyranose2-Deoxy-2-Amino-Galactopyranose2-amino-2-deoxy-galactopyranoside2-Deoxy-2-Amino-Galactopyranoside2-amino-2-deoxy-d-galactopyranoside2-Deoxy-2-Amino-D-Galactopyranoside

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

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)

Safety & regulation

Safety data

Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H317-H319
Precautionary statements
P280-P305+P351+P338

Chemistry & industry

Applications · 1 item

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

湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
杭州璟皓生物科技有限公司(原河南辛迪加生物)17513242016 · [email protected]
湖北广奥生物科技有限公司027-02702759223056 18162699093 · [email protected]
北京秦岭医药科技有限公司010-61241352 18901327973 · [email protected]

Additional notes

DefinitionChEBI: The pyranose form of D-galactosamine.

Related reactions

10 records

Compound notes

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