The Preservation and Enantiomeric Selection of Linalool by Nanoencapsulation Using Cyclodextrins

Tanaporn Poonphatanapricha,Luckhana Lawtrakul,Sasimas Katanyutanon,Kulpavee Jitapunkul,Pisanu Toochinda

doi:10.3390/scipharm89030042

The Preservation and Enantiomeric Selection of Linalool by Nanoencapsulation Using Cyclodextrins

Tanaporn Poonphatanapricha, Luckhana Lawtrakul + Show 3 more

Open Access

https://doi.org/10.3390/scipharm89030042

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Journal: Scientia Pharmaceutica	Publication Date: Sep 3, 2021
Citations: 3	License type: CC BY 4.0

Affiliation: Thammasat University

Abstract

Linalool, a volatile terpene alcohol, is responsible for a characteristic aroma in food, beverages, and cosmetics. However, linalool’s low aqueous solubility and high volatility limit the applications and shelf life of linalool-containing products. Nanoencapsulation using beta-cyclodextrin (BCD), methyl-beta-cyclodextrin (MBCD) and hydroxypropyl-beta-cyclodextrin (HPBCD) was studied to improve the aqueous solubility and stability of linalool. Linalool has two enantiomers with distinct flavors and odors which affect product quality. The enantiomeric selectivity of the cyclodextrins (CDs) toward racemic linalool standard was evaluated. A computational simulation was performed to predict the conformations and interactions of the inclusion complexes. The 1:1 host-guest ratio from the computer simulation was implemented in the experimental study. Phase solubility study shows an improvement in linalool aqueous solubility after being encapsulated by CDs. The encapsulation efficiencies of linalool/BCD, linalool/MBCD, and linalool/HPBCD inclusion complexes are 66.30%, 51.38% and 32.31%, respectively. Nanoencapsulation by CDs can preserve linalool in the form of inclusion complexes compared to its free form. The amount of remaining linalool in linalool/BCD, linalool/MBCD, and linalool/HPBCD inclusion complexes are 89.57%, 87.07%, and 74.86%, respectively which are considerably larger than that of pure linalool (42.30%). CDs also show the enantiomeric selectivity toward (R)-linalool as evident from (R)-linalool percentage of 54.53% in the inclusion complex.

Highlights

Linalool, an unsaturated terpene alcohol from plants, provides a remarkable aroma which is used in several industries such as food, beverage, and cosmetic
Since there are no experimental studies confirming linalool enantiomeric selection together with the aqueous solubility and stability improvement by an encapsulation technique, this study focused on linalool encapsulation using BCD, MBCD, and HPBCD based on the computational simulation results
The minimized energy of the representative docked conformation from each cluster is presented in Table 2, and their conformations are represented in Figures 3 and 4 for (R)- and (S)-linalool inclusion complexes with BCD, respectively

Summary

Introduction

An unsaturated terpene alcohol from plants, provides a remarkable aroma which is used in several industries such as food, beverage, and cosmetic. Commercial products containing linalool may suffer from limited shelf life due to linalool’s low aqueous solubility and high volatility [2]. To increase the shelf life of the products and prevent linalool degradation, a nanoencapsulation technique can be utilized to preserve and stabilize linalool. Linalool has two enantiomers which are (R)-linalool and (S)-linalool. The two enantiomers have considerably different perception thresholds for humans. (R)-linalool has the odor perception of 0.008 ppm in air which is around 10 times lower than that of (S)-linalool [4,5]. The difference in linalool enantiomer ratio leads to different taste and odor of linalool-containing products. With a higher ratio of (S)-linalool, the flowery note will become intense and overpower the other two notes [6]

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