D(+)-Galactosamine hydrochloride

D(+)-Galactosamine hydrochloride Basic information
Product Name:D(+)-Galactosamine hydrochloride
Synonyms:D-Galactosamine hydrochloride ,98.5%;D(+)-GalactosaMine hydrochloride, 99% 1GR;D(+)-GalactosaMine hydrochloride, 99% 5GR;D(+)-GalatosaMine hydrochloride;Galactosamine Hydrochloride (300 mg);D-GalactosaMine HC1;2-aMino-2-deoxy-L-idose;(3R,4R,5R,6R)-3-aMino-6-(hydroxyMethyl)tetrahydro-2H-pyran-2,4,5-triol hydrochloride
CAS:1772-03-8
MF:C6H14ClNO5
MW:215.63
EINECS:217-198-1
Product Categories:Dextrins、Sugar & Carbohydrates;aldehydes;Carbohydrates & Derivatives;Sugars, Carbohydrates & Glucosides;Carbohydrates;13C & 2H Sugars;Aminosugars;Biochemistry;Galactose;Sugars;amino
Mol File:1772-03-8.mol
D(+)-Galactosamine hydrochloride Structure
D(+)-Galactosamine hydrochloride Chemical Properties
Melting point 182-185 °C (dec.)(lit.)
alpha 96 º (589nm c=1,H2O,24 hrs)
density 1.3965 (rough estimate)
refractive index 96 ° (C=1, H2O)
storage temp. room temp
solubility H2O: 50 mg/mL, clear, colorless
form White solid
color White to Off-White
Water Solubility SOLUBLE
Sensitive Hygroscopic
Merck 14,4334
BRN 3697825
Stability:Moisture Sensitive
CAS DataBase Reference1772-03-8(CAS DataBase Reference)
EPA Substance Registry SystemD-Galactose, 2-amino-2-deoxy-, hydrochloride (1772-03-8)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 24/25-36/37/39-27-26
WGK Germany 3
RTECS LW5500000
3-10
TSCA Yes
HS Code 29329970
MSDS Information
ProviderLanguage
2-Amino-2-deoxy-D-galactose hydrochloride English
SigmaAldrich English
ACROS English
ALFA English
D(+)-Galactosamine hydrochloride Usage And Synthesis
Chemical PropertiesWhite Crystalline Solid
UsesD-(+)-Galactosamine hydrochloride has been used to:
  • induce livery injury
  • inflammatory liver injury
  • acute liver failure (ALF) in mice

UsesD-(+)-Galactosamine (D-chondrosamine) is used with lipopolysaccharides (LPS) to induce models of acute hepatic failure (LPS/D-GalN-induced liver injury, hepatitis) for therapeutic research to find new drugs.
UsesSpecifically inhibits COX-2 by preventing COX-2 N-glycosylation and by increasing COX-2 protein turnover in a proteasome-dependent manner.
General DescriptionPharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards
Biochem/physiol ActionsGalactosamine (D-GalN) is synthesized from galactose and is potential hepatotoxic agent. D-GalN in combination with lipopolysaccharide leads to the development of lethal liver injury and hepatic failure. It sensitizes cells to the toxic effects of the cytokine in particular the tumor necrosis factor(TNF).
SynthesisA preparation process of D-galactosamine hydrochloride, adding 500ml absolute ethanol into a 1000ml three-necked flask with a reflux condenser, a stirrer and a thermometer, stirring at room temperature and adding 100g of dimethyl dodecyl respectively Tetradecylamine and 500g of solid-supported silica were heated to 110°C within 30 minutes, kept in reflux for 5 hours and then lowered to 29°C, filtered and dried to obtain 589g of organic amine solid-supported catalyst. In a 1000ml three-necked flask with a stirrer and a thermometer, 190g of 5-methyltryptamine hydrochloride and 600ml of dimethylamide were respectively added, 59g of organic amine solid-supported catalyst and 150g of chloropropene were added, and the reaction was carried out for eight hours at room temperature. Liquid filtration, the obtained filtrate was evaporated to dryness and dissolved in 1150ml of isopropanol, and 89ml of 36wt% hydrochloric acid was added to hydrochloride to obtain 130.32g of white crystals of 2-amino-2-deoxy-D-galactose hydrochloride with a yield of 42.05%.
Purification MethodsDissolve the hydrochloride in a small volume of H2O. Then add three volumes of EtOH, followed by acetone until faintly turbid and keep overnight in a refrigerator. [Roseman & Ludoweig J Am Chem Soc 76 301 1954, Beilstein 4 IV 2024.]
D(+)-Galactosamine hydrochloride Preparation Products And Raw materials
4-AMINOPHENYL 2-ACETAMIDO-2-DEOXY-ALPHA-D-GALACTOPYRANOSIDE HYDROCHLORIDE 5-Bromo-4-chloro-3-indolyl-N-acetyl-beta-D-galactosaminide O-(2-Acetamido-2-O-acetyl-4,6-di-O-benzylidene-2-deoxy-alpha-D-galactopyranosyl) trichloroacetimidate GALACTOSAMINE HYDROCHLORIDE, D-, [1-14C] D-(+)-GALACTOSE 5-Bromo-4-chloro-3-indolyl-2-acetamido-2-deoxy-alpha-D-galactopyranoside O-(2-AZIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-BETA-D-GALACTOPYRANOSYL)-TRICHLORACETIMIDATE Topotecan hydrochloride ALTRENOGEST GALACTOSAMINE HYDROCHLORIDE, D-, [1-3H(N)] 3-BROMO-4-CHLORO-3-INDOLYL-N-ACETYL-D-GALACTOSAMINIDE D-[15N]GALACTOSAMINE HYDROCHLORIDE 3,4,6-TRI-O-ACETYL-2-AZIDO-2-DEOXY-ALPHA-D-GALACTOPYRANOSYL TRICHLOROACETIMIDATE D-Lactose monohy D-[1-13C]GALACTOSAMINE HYDROCHLORIDE 6-CHLORO-3-INDOXYL-N-ACETYL-BETA-D-GLUCOSAMINIDE 4-AMINOAZOBENZENE HYDROCHLORIDE AMINO ACIDS

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