Glucosamin

Glucosamine Chemische Eigenschaften,Einsatz,Produktion Methoden

• Chemische Eigenschaften

  (β form.) Colorless needles. Mp 110C (decomposes). Very soluble in water; slightly soluble in methanol and ethanol; insoluble in ether and chloroform.

• Occurrence

  Glucosamine is found in mucopolysaccharides, chitin, and mucoproteins. Glucosamine is a naturally occurring substance; glucosamine sulfate is manufactured synthetically.

• Verwenden

  Pharmaceutic aid.

• Verwenden

  Glucosamine is an amino sugar that can regulate growth factor gene transcription. It is also widely touted as remedy for osteoarthritis (OA).

• Definition

  ChEBI: The open-chain form of D-glucosamine.

• Trademarks

  Adaxil;Antatril;Arthryl;Chitosamine;Corti-anartril;Dona 200-s;Dona compositum;Donna 200;Pona;Terramycin;Terrastatom;Tetracyn;Thiocondramine;Viartril.

• Weltgesundheitsorganisation (WHO)

  Glucosamine is found in chitin, mucoproteins and mucopolysaccharides. It is used as a pharmaceutical aid. Glucosamine sulfate has been used in the treatment of rheumatic disorders though it is not widely marketed for this purpose.

• Veterinary Drugs and Treatments

  These compounds may be useful in treating osteoarthritis or other painful conditions in domestic animals, but large, well-designed controlled clinical studies proving efficacy were not located. One study in dogs (McCarthy, O’Donovan et al. 2007) showed some positive effect, but this study was not placebo controlled and compared responses versus carprofen. Another placebo-controlled, blinded study in dogs (Moreau, Dupuis et al. 2003), did not demonstrate statistically significant improvement after 60 days of treatment.
  These compounds potentially could be of benefit in cats with FLUTD (feline lower urinary tract disease) because of the presence of glycosaminoglycans as part of the protective layer of the urinary tract. Controlled studies have shown some positive effects in some cats, but overall did not appear to make a significant difference.

• läuterung methode

  Crystallise the amines from MeOH. The free base has been obtained from the hydrochloride (21.5g, see below) in a mixture of Et3N (15mL) and EtOH (125mL) by shaking for 2days at room temperature, and the solid Et3N.HCl is filtered off and the process repeated with more Et3N (3-4 times) until the 
  D-glucosamine (15g) is free from Cl ions. It has m 88o , [] D20 +100o mutarotating to +47.5o (c 1, H2O). When Et2NH is used as base, the 
  to 
  conversion is complete giving 
  D-glucosamine. The pentaacetate is purified by dissolving in CHCl3, treating with charcoal, drying (MgSO4), evaporating the solvent, and adding a little dry Et2O to induce crystallisation. It has m 124-126o, [] D +113o (c 1, CHCl3) after 16hours in a desiccator. [Leaback Biochemical Preparations 10 118 1963.] The N-acetyl derivative, m 203-205o from MeOH/Et2O (dry in vacuum P2O5) has [] D +75o to +41o (c 2, H2O); this derivative can also be purified by dissolving in the minimum volume of H2O to which is added 7-8volumes of EtOH followed by Et2O until turbid and keeping at ~20o to crystallise. Wash the crystals with MeOH then Et2O and dry in vacuo over P2O5. [Horton Biochemical Preparations 11 1 1966.]

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