Dimethylsilanol hyaluronate
[CAS# 135507-00-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Acid ester compound
• Name: Dimethylsilanol hyaluronate
• Synonyms: DSH-C; [(2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-(dimethyl-$l^{3}-silanyl)oxycarbonyl-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3
• CAS Registry Number: 135507-00-5
• SMILES: [C@H]1([C@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2[C@@H]([C@@H](CO)O[C@H]([C@@H]2NC(C)=O)O[C@@H]3[C@@H](C(=O)O[Si](C)C)O[C@H]([C@@H]([C@H]3O)O)O[C@H]4[C@@H]([C@@H](CO)O[C@H]([C@@H]4NC(C)=O)O)O)O)O)O)O)C(=O)O[Si](C)C

Discovory and Applicatios

Dimethylsilanol hyaluronate is a chemically modified derivative of hyaluronic acid, a naturally occurring linear polysaccharide composed of repeating disaccharide units of D-glucuronic acid and N-acetyl-D-glucosamine. As a member of the glycosaminoglycan family, hyaluronic acid is well known for its remarkable hygroscopic properties and biocompatibility, which have led to extensive applications in medical, pharmaceutical, and cosmetic fields. The functionalization of hyaluronic acid with organosilicon compounds such as dimethylsilanol represents a strategic approach to enhance its stability, bioactivity, and functional performance in specialized formulations.

The incorporation of dimethylsilanol groups into hyaluronate molecules involves the reaction of organosilicon agents, typically alkoxysilanes, with hydroxyl or carboxyl moieties on the hyaluronan backbone. Dimethylsilanol, characterized by the presence of two methyl groups attached to a silicon atom bearing a hydroxyl group, forms silanol esters with hyaluronan. The resulting dimethylsilanol hyaluronate retains the high water-retention capacity of the native polymer while introducing additional functionalities, such as improved skin adherence and enhanced film-forming capability. These modifications are especially valued in dermatological and cosmetic applications, where prolonged hydration and skin conditioning are essential.

The emergence of dimethylsilanol hyaluronate was driven in part by the demand for multifunctional ingredients in cosmeceutical formulations. Its film-forming properties enable it to create a breathable protective barrier on the skin's surface, helping to reduce trans-epidermal water loss and preserve skin elasticity. Furthermore, the presence of silanol groups is believed to contribute to skin restructuring and regenerative effects by facilitating collagen synthesis and stabilizing extracellular matrix components. These properties have made dimethylsilanol hyaluronate a common ingredient in anti-aging creams, moisturizing serums, and postoperative skin repair products.

On the molecular level, the stability of dimethylsilanol hyaluronate in aqueous systems has been studied to ensure its compatibility with common cosmetic excipients and pH conditions. The silanol linkage provides resistance to enzymatic degradation compared to unmodified hyaluronan, extending its residence time on the skin. This improved persistence, coupled with a favorable safety profile, has encouraged its use in formulations requiring extended skin contact, such as dermal fillers or leave-on topical treatments. Its non-irritating and non-sensitizing nature has been confirmed through in vitro and in vivo safety assessments, aligning with international cosmetic safety standards.

In terms of synthesis, modern functionalization protocols emphasize mild reaction conditions and one-pot strategies to avoid polymer degradation. The use of organosilanes under aqueous or low-temperature environments allows for controlled substitution while preserving the molecular weight distribution of the original polymer. Analytical characterization of dimethylsilanol hyaluronate typically involves techniques such as NMR spectroscopy, gel permeation chromatography, and FTIR to confirm the presence of Si–O–C linkages and evaluate the degree of substitution. These parameters are essential for quality control and reproducibility in industrial-scale production.

Beyond cosmetics, there is growing interest in the use of dimethylsilanol hyaluronate in biomedical applications, particularly in tissue engineering and wound healing. Its biocompatibility, combined with mechanical reinforcement imparted by silicon-based moieties, offers potential in scaffold materials and hydrogels for controlled drug release. Additionally, silanol-modified hyaluronan has demonstrated promise in ophthalmic formulations, where enhanced mucoadhesion and viscoelastic properties are desirable.

As regulatory frameworks continue to evolve, the safety and efficacy of modified hyaluronic acid derivatives like dimethylsilanol hyaluronate remain a focus of scientific investigation. Comprehensive toxicological evaluations and clinical trials contribute to the understanding of their long-term effects and support their inclusion in advanced therapeutic and cosmetic systems. The convergence of polymer chemistry and bioactive functionalization exemplified by dimethylsilanol hyaluronate highlights the ongoing innovation in designing biopolymers tailored for specific human health and skincare needs.