66-84-2 Usage
Uses
Used in Pharmaceutical Industry:
D-Glucosamine hydrochloride is used as a medical agent for treating vertigo, an inner ear disorder that causes dizziness and balance problems. Its chondroprotective and antiarthritic properties make it a valuable component in the development of treatments for various joint and connective tissue disorders.
Used in Cosmetics Industry:
D-Glucosamine hydrochloride is used as a pH adjuster in cosmetic formulations, helping to maintain the optimal pH level for various skin and hair care products. Its anti-static and hair-conditioning properties contribute to improved product performance and user experience.
Used in Food Industry:
D-Glucosamine hydrochloride is used as a food ingredient and additive, providing health benefits such as joint support and promoting overall well-being.
Used in Nutraceutical Industry:
As a raw material for anti-cancer and antibiotic drugs, D-Glucosamine hydrochloride plays a crucial role in the development of novel therapeutic agents that target various diseases and conditions. Its potential as a chondroprotective and antiarthritic agent makes it a valuable component in the formulation of nutraceutical products aimed at improving joint health and reducing inflammation.
Biochem/physiol Actions
Glucosamine is preferred as a nutritional supplement?for individuals with osteoarthritis. It is used as a building block for the production of proteoglycans?and?glycosaminoglycans.
Purification Methods
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 66-84-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 6 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 66-84:
(4*6)+(3*6)+(2*8)+(1*4)=62
62 % 10 = 2
So 66-84-2 is a valid CAS Registry Number.
InChI:InChI=1/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/p+1/t2-,3-,4-,5-,6+/m1/s1
66-84-2Relevant articles and documents
Medicinal plants of Thailand. I structures of rheedeiosides A-D and cis-entadamide A β-D-glucopyranoside from the seed kernels of Entada rheedei
Sugimoto, Sachiko,Matsunami, Katsuyoshi,Otsuka, Hideaki
experimental part, p. 466 - 471 (2011/06/19)
Four new oleanane-type triterpene oligoglycosides, named rheedeiosides A, B, C and D, and one new thioamide glycoside, cis-entadamide A β-D-glucopyranoside, were isolated from the seed kernels of a Thai medicinal plant, Entada rheedei SPRENGEL. The rheedeiosides were found to contain N-acetylglucosamine as a sugar component. Their structures were elucidated based on spectral and chemical evidence.
Echinocystic acid 3,16-O-bisglycosides from Albizia procera
Miyase, Toshio,Melek,Ghaly,Warashina, Tsutomu,El-Kady,Nabil, Marian
experimental part, p. 1375 - 1380 (2011/05/17)
Three triterpene glycosides and two known ones were isolated from the bark of Albizia procera by using chromatographic techniques. The structures of the compounds were determined to be 3-O-β-d-xylopyranosyl-(1 → 2)-β-d-galactopyranosyl-(1 → 6)-2-acetamido-2-deoxy-β-d- glucopyranosyl echinocystic acid 16-O-β-d-glucopyranoside, 3-O-β-d-xylopyranosyl-(1 → 2)-α-l-arabinopyranosyl-(1 → 6)-2-acetamido-2-deoxy-β-d-glucopyranosyl echinocystic acid 16-O-β-d-glucopyranoside and 3-O-α-l-arabinopyranosyl-(1 → 2)-α-l-arabinopyranosyl-(1 → 6)-2-acetamido-2-deoxy-β-d- glucopyranosyl echinocystic acid 16-O-β-d-glucopyranoside. Their structures were determined by NMR techniques including HOHAHA, 1H-1H COSY, ROE, HMQC and HMBC experiments together with FABMS as well as acid hydrolysis. To the best of our knowledge, the new compounds are considered the first examples of echinocystic acid 3,16-O-bisglycosides. In contrast to other cytotoxic echinocystic acid glycosides with N-acetyl glucosamine unit, the new glycosides were found inactive when assayed by MTT method for their cytotoxicities against the human tumor cell lines HEPG2, A549, HT29 and MCF7. The results showed the importance of the free hydroxyl group at the aglycone C-16 for exhibiting cytotoxic properties.
