1.Saturated long-chain esters of isopulegol as novel permeation enhancers for transdermal drug delivery.
Chen Y1, Cun D, Quan P, Liu X, Guo W, Peng L, Fang L. Pharm Res. 2014 Aug;31(8):1907-18. doi: 10.1007/s11095-013-1292-0. Epub 2014 Jan 22.
PURPOSE: Saturated long-chain esters of isopulegol were synthesized and their activities as permeation enhancers for transdermal delivery of amlodipine and flurbiprofen were investigated, in contrast to the saturated fatty acids and isopulegol, as well as their physical mixtures.
2.β-Cyclodextrin as the suitable molecular container for isopulegol enantiomers.
Ceborska M1, Szwed K, Suwinska K. Carbohydr Polym. 2013 Sep 12;97(2):546-50. doi: 10.1016/j.carbpol.2013.04.097. Epub 2013 May 17.
Isopulegol, an insoluble in water and highly volatile compound, due to its neuroactive properties is a potentially important agent for medical applications. Formation of "host-guest" molecular complexes with cyclodextrins would lead to the increase of its water solubility and bioavailability. Interactions between native cyclodextrins (α, β and γ) and isopulegol enantiomers were studied in solution proving the formation of inclusion complexes for β- and γ-cyclodextrins. For the more stable complexes with β-cyclodextrin crystal structures were obtained showing the formation of molecular capsules forming molecular container able to accommodate two guest molecules.
3.Intramolecular hydrogen transfer reaction: menthon from isopulegol.
Schaub T1, Rüdenauer S, Weis M. Org Lett. 2014 May 16;16(10):2575-7. doi: 10.1021/ol500811u. Epub 2014 Apr 29.
The flavor menthon (isomeric mixture of (-)-menthon and (+)-isomenthon) was obtained in good yields and selectivities by a solventless ruthenium catalyzed isomerization of the homoallylic alcohol (-)-isopulegol. In contrast to most previous assumptions on such "isomerization" reactions, this reaction follows an intermolecular pathway, with menthol and pulegon being the central intermediates in this transformation.
4.Enhancement of skin permeation of flurbiprofen via its transdermal patches using isopulegol decanoate (ISO-C10) as an absorption enhancer: pharmacokinetic and pharmacodynamic evaluation.
Chen Y1, Quan P1, Liu X1, Guo W1, Song W1, Cun D1, Wang Z1, Fang L1. J Pharm Pharmacol. 2015 Sep;67(9):1232-9. doi: 10.1111/jphp.12428. Epub 2015 May 21.
OBJECTIVES: The study aimed to prepare a transdermal patch for flurbiprofen using isopulegol decanoate (ISO-C10) as a permeation enhancer, and to evaluate the in-vitro and in-vivo percutaneous permeation of the drug, as well as the pharmacodynamic efficacy of the formulation.