Preparation of glucosamine hydrochloride

Details Preparation of glucosamine hydrochloride Preparation of glucosamine hydrochloride

2001-08-23

2002-11-26

Davis, Brian J. (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

C568S583000, C568S423000, C568S492000

Reexamination Certificate

active

06486307

ABSTRACT:

BACKGROUND OF INVENTION
The present invention relates to methods of preparing glucosamine hydrochloride from chitin or chitinaceous material.
Glucosamine hydrochloride (GHCl) is an amino sugar which is incorporated into the structure of body tissues. It comprises about 80% glucosamine, a compound helpful in maintaining joint health in individuals suffering from degenerative conditions such as arthritis. When orally ingested, it is selectively taken up by joint tissues to exert beneficial effects. Glucosamine may also have other therapeutic effects such as antiviral, anti-cancer, anti-aging, immune boosting or cholesterol lowering activity.
GHCl may be obtained by hydrolysis and deacetylation of chitin, a polymer of N-acetyl glucosamine or by the hydrolysis of chitosan with hydrochloric acid. It is desirable if such processes are efficient in both time and cost, and produce high-purity product with good yield. As well, it would be advantageous to provide a quick, simple and accurate method of assaying GHCl to be used in conjunction with a method of producing GHCl.
SUMMARY OF INVENTION
The present invention is directed to a method of producing glucosamine hydrochloride from chitin or chitinaceous material, said method comprising the steps of: (a) grinding the chitin or chitinaceous material to less than about −20 mesh; (b) digesting the chitin with prewarmed, concentrated HCl, by mixing the chitin with the HCl, and heating to about 95° C. to produce a slurry; (c) cooling the slurry to room temperature and filtering the precipitate; (d) dissolving the precipitate in water and with activated charcoal at room temperature; (e) filtering the solution and discarding the solids; (f) evaporating the solution to recover GHCl solids; (g) washing the solids with ethanol and filtering the solids/ethanol mixture to separately recover both the solids and the ethanol; and (h) drying the solids.
In another aspect, the invention may comprise a method of producing glucosamine hydrochloride from chitin or chitinaceous material, said method comprising the steps of: (a) hydrolysing the chitin in hydrochloric acid; (b) precipitating the glucosamine hydrochloride; (c) separating the precipitated glucosamine hydrochloride and redissolving it in water; and (d) assaying for GHCl by pHmetric titration.
In another aspect, the invention may comprise a method of assaying GHCl in solution comprising the step of measuring the amount of base necessary to raise the pH of the solution to a pre-determined value and corresponding the amount of base to an amount of GHCl. The base may be sodium hydroxide.


REFERENCES:
patent: 2884411 (1959-04-01), Heyns
Database CAPLUS on STN, Acc. No. 1975:410655, Ingle et al., ‘Production of D-glucosamine hydrochloride (GAH) from fish canning waste.’ Res. Ind. (1973), 18(2), pp. 54-56 (abstract).*
Database CAPLUS on STN, Acc. No. 1998:718206, CAO, ‘Preparation of glucosamine hydrochloride from chitin.’ Hauxue Shijie (1998), 39(5), pp. 250-253 (abstract).*
CAPLUS on STN, Acc. No. 2000:639481, Zhou et al., ‘Preparation and properties of glucosamine hydrochloride.’ Shuichan Xuebao (2000), 24(1), pp. 76-80 (abstract).*
Peters and Kowerski. Basic Chemical Principles, 2nded. Saunders College Publishing. 1994, 1998, pp. 417-421.*
Chen, et al.; Preparation of D-glucosamine hydrocholoride; Journal—Shipkin Kexue (Beijing); 2000 vol. 21, No. 9, pp. 34-36.
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CAO; Preparation of Glucosamine Hydrochloride from Chitin; Journal: Huaxue Shijie; date: 1998 vol. 39, No. 5; pp. 250-253.
V. Yu. Novikov; Kinetics of Formation of D(+)-Glucosamine by Acid Hydrolysis of Chitin; Russian Journ Applied Chemistry; vol. 72, No. 1, 1999 pp. 156-161.
Novikov, et al.; “Synthesis of D(+)-Glucosamine Hydrochloride” Russian Journal of Applied Chemistry; vol. 70, No. 9, 1997, pp. 1467-1470.

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