Abstract
Retinyl palmitate (RP) is a derivative of Vitamin A and widely applied as the active component in the fields of cosmetic and pharmaceutics. RP can easily lose its physiological activity under UV irradiation due to its photosensitivity. In this work, it was found that the activity of RP remained 75% after 80 min of UVA irradiation when RP was entrapped in supramolecular gels formed by self-assembly of sorbitol-based gelators. By contrast, the activity of RP in conventional hydroxyethyl cellulose gels only remained 10% under the same conditions. These results showed that the supramolecular gels exhibited a significant protective effect on the photostability of RP. UV spectra of RP in supramolecular gels and corresponding solutions showed no distinct differences, indicating no change of the physicochemical properties of RP. The images of field-emission scanning electron microscopy and fluorescent optical microscopy suggested that the protection by supramolecular gels on the photostability of RP may be attributed to the three-dimensional network structure formed by the self-assembly of the gelators, which reduced the molecular collisions and the degradation process of the photoactivated RP. The present results showed that this protection can be influenced by the structures and the concentration of gelators as well as by the solvent composition.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Fu P P, Xia Q, Yin J J, et al. Photodecomposition of Vitamin A and photobiological implications for the skin. Photochem Photobiol, 2007, 83: 409–424
Eskandar N G, Simovic S, Prestidge C A. Chemical stability and phase distribution of all-trans-retinol in nanoparticle-coated emulsions. Int J Pharm, 2009, 376: 186–194
Loveday S M, Singh H. Recent advances in technologies for Vitamin A protection in foods. Trends Food Sci Technol, 2008, 19: 657–668
Manabu H, Tomoya O, Akito O, et al. Vitamin A-containing ophthalmic compositions method for Vitamin A stabilization using polyoxyethylene-polyoxypropylene glycols. Japanese Patent, 2009173638
Semenzato A, Bau A, Dallaglio C, et al. Stability of Vitamin A palmitate in cosmetic emulsions: Influence of physical parameters. J Cosmet Sci, 2007, 16: 139–147
Young A M, Gregoriadis G. Photolysis of retinol in liposomes and its protection with tocopherol and oxybenzone. Photochem Photobiol, 1996, 63: 344–352
Carlotti M E, Sapino S, Trotta M, et al. Photostability and stability over time of retinyl palmitate in an O/W emulsion and in SLN introduced in the mulsion. J Dispersion Sci Technol, 2005, 26: 125–138
Carlotti M E, Rossatto V, Gallatate M, et al. Vitamin A palmitate potostability and stability over time. J Cosmet Sci, 2004, 55: 233–252
Sapino S, Carlotti M E, Cavalli R, et al. Effect of akyl-γ-cyclo-dextrins on the stability of retinol. J Incl Phenom Macrocycl Chem, 2007, 57: 451–455
Terech P, Weiss R G. Low molecular mass gelators of organic liquids and the properties of their gels. Chem Rev, 1997, 97: 3133–3159
George M, Weiss R G. Molecular organogels. Soft matter comprised of low-molecular-mass organic gelators and organic liquids. Acc Chem Res, 2006, 39: 489–497
Banerjee S, Das R K, Maitra U. Supramolecular gels “in action”. J Mater Chem, 2009, 19: 6649–6687
Miyata T, Uragami T, Nakamae K. Biomolecule-sensitive hydrogels. Adv Drug Deliv Rev, 2002, 54: 79–98
Mohmeyer N, Wang P, Schmidt H, et al. Quasi-solid-state dye sensitized solar cells with 1,3:2,4-di-O-benzylidene-D-sorbitol derivatives as low molecular weight organic gelators. J Mater Chem, 2004, 14: 1905–1909
Watase M, Itagaki H. Thermal and rheological properties of physical gels formed from benzyllidene-D-sorbitol derivatives. Bull Chem Soc Jpn, 1998, 71: 1457–1466
Watase M, Nakatani Y, Itagaki H. On the origin of the formation and stability of physical gels of di-O-benzylidene-D-sorbitol. J Phys Chem B, 1999, 103: 2366–2373
Wang H, Zhang W, Dong X, et al. Thermo-reversibility of the fluorescence enhancement of acridine orange induced by supramolecular self-assembly. Talanta, 2009, 77: 1864–1868
Wang H, Zhang J, Zhang W, et al. Host-guest interactions of 5-fluorouracil in supramolecular organogels. Eur J Pharm Biopharm, 2009, 73: 357–360
Friggeri A, Feringa B L, van Esch J. Entrapment and release of quinoline derivatives using a hydrogel of a low molecular weight gelator. J Control Release, 2004, 97: 241–248
Bastiat G, Leroux J. Pharmaceutical organogels prepared from aromatic amino acid derivatives. J Mater Chem, 2009, 19: 867–877
Sutton S, Campbell N, Cooper A I, et al. Controlled release from modified amino acid hydrogels governed by molecular size or network dynamics. Langmuir, 2009, 25: 10285–10291
Wilder E A, Hall C K, Khan S A, et al. Effects of composition and matrix polarity on network development in organogels of poly (ethylene glycol) and dibenzylidene sorbitol. Langmuir, 2003, 19: 6004–6013
Zhu G, Dordick J S. Solvent effect on organogel formation by low molecular weight molecules. Chem Mater, 2006, 18: 5988–5995
Inamura I, Isshiki M, Aroki T. Solubilization of hemin in neutral and acidic aqueous solutions by forming complexes with water-soluble macromolecules. Bull Chem Soc Jpn, 1989, 62: 2413–2415
Author information
Authors and Affiliations
Corresponding author
Additional information
This article is published with open access at Springerlink.com
Rights and permissions
This article is published under an open access license. Please check the 'Copyright Information' section either on this page or in the PDF for details of this license and what re-use is permitted. If your intended use exceeds what is permitted by the license or if you are unable to locate the licence and re-use information, please contact the Rights and Permissions team.
About this article
Cite this article
Wang, H., Fang, F., Li, X. et al. Improved photostability of Vitamin A palmitate originating from self-assembled supramolecular gels. Chin. Sci. Bull. 57, 4257–4263 (2012). https://doi.org/10.1007/s11434-012-5451-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11434-012-5451-1