Hyaluronic acid
[CAS# 9004-61-9]

Identification

• Classification: Biochemical >> Enzymes and coenzymes
• Name: Hyaluronic acid
• Synonyms: HA
• Molecular Formula: (C₁₄H₂₁NO₁₁)_n
• Molecular Weight: ~25000
• CAS Registry Number: 9004-61-9
• EC Number: 232-678-0
• SMILES: N(C1C(OC(C(C1OC4OC(C(C(C4O)O)O)C(=O)O)O)CO)OC2C(OC(C(C2O)O)OC3C(C(OC(C3O)CO)O)NC(=O)C)C(=O)O)C(=O)C

Properties

• Solubility: DMSO: soluble (Expl.)

Discovory and Applicatios

Hyaluronic acid is a naturally occurring linear polysaccharide composed of repeating disaccharide units of D-glucuronic acid and N-acetyl-D-glucosamine linked by alternating β-1,4 and β-1,3 glycosidic bonds. It is widely distributed in connective tissues, epithelial tissues, and neural tissues of vertebrates. Hyaluronic acid plays a crucial role in maintaining the extracellular matrix structure and provides lubrication, hydration, and mechanical support in tissues.

The discovery of hyaluronic acid dates back to 1934 when Karl Meyer and John Palmer isolated it from the vitreous humor of bovine eyes. The name “hyaluronic” derives from “hyalos,” the Greek word for glass, reflecting its initial source, and “uronic acid,” referring to its sugar acid component. Since its identification, hyaluronic acid has been extensively studied for its biological functions and potential medical applications.

Hyaluronic acid is known for its remarkable ability to retain water, holding up to 1000 times its weight in water, which contributes to tissue hydration and elasticity. This property makes it essential in maintaining skin moisture and joint lubrication. It is a major component of synovial fluid, where it acts as a lubricant and shock absorber, facilitating smooth joint movement.

In medicine and cosmetics, hyaluronic acid is widely used for its biocompatibility and hydrating properties. It is a common ingredient in dermal fillers for aesthetic treatments to reduce wrinkles and restore facial volume. Additionally, it is employed in wound healing formulations, ophthalmic surgery as a viscoelastic agent, and osteoarthritis treatment through intra-articular injections to improve joint function and reduce pain.

Biotechnological advances have enabled the large-scale production of hyaluronic acid through bacterial fermentation, primarily using strains of Streptococcus species, providing a reliable and pure source for pharmaceutical and cosmetic use. The molecular weight of hyaluronic acid can vary, affecting its biological activity and clinical applications; higher molecular weights are typically used for joint treatments, while lower molecular weights are preferred in topical skin care products.

Research continues to explore the therapeutic potential of hyaluronic acid in drug delivery systems, tissue engineering, and regenerative medicine. Its unique physicochemical characteristics make it a promising candidate for developing advanced biomaterials that promote cell proliferation, migration, and differentiation.

References

2020. Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening. SLAS discovery : advancing life sciences R & D, 25(1).
DOI: 10.1177/2472555219873068

2019. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular Pharmacology, 96(5).
DOI: 10.1124/mol.119.115964

2011. Chemical Genomic Profiling for Antimalarial Therapies, Response Signatures, and Molecular Targets. Science (New York, N.Y.), 333(6043).
DOI: 10.1126/science.1205216