D-Glucosamine hydrochloride
[CAS# 66-84-2]

Identification

• Classification: API >> Antipyretic analgesics >> Anti-gout medicine
• Name: D-Glucosamine hydrochloride
• Synonyms: 2-Amino-2-deoxy-D-glucopyranose hydrochloride
• Molecular Formula: C₆H₁₃NO₅.HCl
• Molecular Weight: 215.63
• CAS Registry Number: 66-84-2
• EC Number: 200-638-1
• SMILES: C([C@H]([C@H]([C@@H]([C@H](C=O)N)O)O)O)O.Cl

Properties

• Melting point: 190 - 194 °C (Decomposes) (Expl.)
• alpha: 72.5 ° (c=2, H2O, 5hrs.)
• Water solubility: soluble

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

D-Glucosamine hydrochloride is the hydrochloride salt of D-glucosamine, a naturally occurring amino sugar derived from the hydrolysis of chitin, the structural component found in the exoskeletons of crustaceans and insects, as well as in fungal cell walls. D-Glucosamine itself is an essential precursor in the biosynthesis of glycosaminoglycans, which are critical constituents of cartilage, skin, tendons, and ligaments. The hydrochloride form enhances the stability and solubility of glucosamine, making it more suitable for pharmaceutical and nutraceutical applications.

The discovery of D-glucosamine dates back to the late 19th century when Georg Ledderhose first isolated the compound in 1876 through the hydrolysis of chitin with concentrated hydrochloric acid. This process yielded D-glucosamine hydrochloride as a stable crystalline product. Early studies characterized the compound’s structure through careful chemical degradation and analysis, ultimately confirming the presence of an amino group at the 2-position of the glucose backbone.

D-Glucosamine hydrochloride has been widely studied for its biological significance and applications. It plays a vital role in the biosynthetic pathway leading to the formation of important macromolecules such as hyaluronic acid, keratan sulfate, and heparan sulfate. These glycosaminoglycans are critical for maintaining the structural integrity and function of connective tissues. In the human body, glucosamine is synthesized from fructose-6-phosphate via the enzyme glutamine-fructose-6-phosphate amidotransferase, indicating its endogenous importance.

The compound has gained prominence for its application in the management of osteoarthritis, a degenerative joint disease characterized by cartilage breakdown and inflammation. D-Glucosamine hydrochloride is widely marketed as a dietary supplement intended to support joint health. Numerous clinical studies have investigated its efficacy, with some reporting that supplementation can alleviate joint pain and improve mobility, although results vary depending on study design and patient population. It is generally considered to have a favorable safety profile, with mild gastrointestinal discomfort being the most commonly reported side effect.

In addition to its use in joint health, D-glucosamine hydrochloride serves as a starting material for the synthesis of a variety of biologically active compounds. It is a key intermediate in the production of N-acetyl-D-glucosamine, which has applications in cosmetics and dermatology due to its moisturizing and anti-aging properties. Furthermore, derivatives of glucosamine have been explored for their potential antimicrobial, antitumor, and anti-inflammatory activities, reflecting the versatility of this molecule in medicinal chemistry.

Industrial production of D-glucosamine hydrochloride typically involves the chemical hydrolysis of chitin under acidic conditions, followed by neutralization and crystallization to obtain the pure salt. Alternative biotechnological methods employing enzymatic hydrolysis have also been developed to improve efficiency and reduce environmental impact. Quality control during production is critical, as impurities such as heavy metals or residual proteins must be minimized to meet pharmaceutical-grade standards.

The compound’s chemical properties, including its high solubility in water and its reactive amino group, make it a useful reagent in carbohydrate chemistry. It can undergo various chemical modifications, such as acetylation, sulfation, and conjugation with other biomolecules, to create novel materials for biomedical applications, including drug delivery systems and tissue engineering scaffolds.

D-Glucosamine hydrochloride’s stability as a salt also facilitates its formulation into tablets, capsules, and powders for oral administration. Its compatibility with other commonly used joint supplements, such as chondroitin sulfate and methylsulfonylmethane (MSM), has led to the development of combination products aimed at enhancing therapeutic outcomes for individuals with joint disorders.

References

1973. Anomeric effects in Schiff bases of D-glucosamine with aromatic aldehydes. Journal of Applied Spectroscopy, 19(6).
DOI: 10.1007/bf00611086

2001. The Amadori and Heyns Rearrangements: Landmarks in the History of Carbohydrate Chemistry or Unrecognized Synthetic Opportunities? Topics in Current Chemistry, 215.
DOI: 10.1007/3-540-44422-x_6

2004. Surface properties of surfactants derived from natural products. Part 1: Syntheses and structure/property relationships—Solubility and emulsification. Journal of Surfactants and Detergents, 7(2).
DOI: 10.1007/s11743-004-0298-6