D-(+)-グルコサミン塩酸塩

外観

白色粉末～結晶

定義

本品は、グルコサミン(*)の塩酸塩であり、次の化学式で表される。
参照表示名称：グルコサミン

解説

グルコサミン,化学式 C6H13NO5 。ヘクソサミンの一種で，代表的な天然のアミノ糖。動植物，微生物の多糖類，特に糖蛋白質や糖脂質の構成成分であり，エビやカニの殻であるキチン質の構成単位である。キチン質を塩酸とともに煮沸すると塩酸塩として得られる。遊離のグルコサミンの結晶には2型ある。α体は融点 88℃。β体は針状晶，分解点 110℃。これらは水，熱メタノールに易溶，エーテル，クロロホルムに不溶である。

化粧品の成分用途

pH調整剤

効能

抗リウマチ薬

化学的特性

white powder

使用

Novel application of D-Glucosamine hydrochloride to prepare medical agent for treating vertigo. Found in chitin, in mucoproteins, and in mucopolysaccharides. Antiarthritic. Recent studies show that its chondroprotective activity is related to its antiapoptic properties.

一般的な説明

Glucosamine, an amino sugar is generated form glucose and glutamine and is naturally produced in the body. Glucosamine, a endogenous amino monosaccharide is the major source of glucosamine-6-phosphate and n-acetylglucosamine.

純化方法

Crystallise the hydrochloride from 3M HCl, water, and finally water/EtOH/acetone as for galactosamine hydrochloride. [Purchase & Braun Org Synth 26 36 1946, Stacey & Webber Methods in Carbohydrate Chemistry I 228 1962, Academic Press.] The salt has also been purified by dissolving in the minimum volume of boiling H2O (charcoal), filtering and adding a large excess of 95% EtOH (~4 volumes) and stirring vigorously for several hours. Collect the crystals after 4-6hours to give 
anomer which mutarotates ] D +100o to +72o (equilibrium, c 1, H2O). A large amount of the -anomer stays in solution. This can be precipitated from the filtrate by adding excess Et2O. The mixture of -plus -anomers has [] D +68.8o (c 4.75, H2O, mutarotating to +70.1o)[Leaback Biochemical Preparations 10 118 1963]. Note that if Et2NH is used instead of Et3N, conversion to the -anomer can be complete (see above). [Stacey et al. Methods in Carbohydrate Chemistry I 3061962, Academic Press; Beilstein 4 IV 2018.]