Study on the Preparation of Geranyl Acetone and β-cyclodextrin Inclusion Complex and Its Application in Cigarette Flavoring

Overview

Journal Sci Rep

Specialty Science

Date 2020 Jul 25

PMID 32704066

Citations 7

Authors

Fu Du

Tingting Pan

Xiaoming Ji

Jingyan Hu

Tianbao Ren

Affiliations

Soon will be listed here.

Abstract

β-Cyclodextrin (β-CD) inclusion complex containing geranyl acetone as a guest was prepared by saturated water solution method. Furthermore, the structure and properties of the inclusion complex were studied. The formation of the inclusion complex was demonstrated by. Fourier transform infrared spectroscopy (FTIR), X-ray diffraction (X-RD), thermogravimetric analysis (TG) and differential scanning calorimetry (DSC). The thermodynamic analysis of the inclusion complex showed that the inclusion reaction is an endothermic spontaneous reaction. The average of △H, △S and △G is 11.66 kJ mol, 0.082 kJ mol and - 14.49 kJ mol, respectively. Moreover, the kinetic analysis of thermal decomposition of the inclusion compound showed that the thermal decomposition reaction is a first-order reaction (the inclusion ratio is 1:1), the average activation energy of the reaction is 180.90 kJ mol, and the binding force in the inclusion compound is mainly Van der Waals force. The flavor test of cigarettes showed that the inclusion compound improved the stability of geranyl acetone and the sensory quality of cigarettes. This study improves the solubility and thermal stability of geranyl acetone, and provides theoretical support and technical guidance for expanding the application of geranyl acetone.

Citing Articles

Host-Guest Complexation of Olmesartan Medoxomil by Heptakis(2,6-di-O-methyl)-β-cyclodextrin: Compatibility Study with Excipients.

Man D, Nitu E, Temereanca C, Sbarcea L, Ledeti A, Ivan D Pharmaceutics. 2025; 16(12.

PMID: 39771536 PMC: 11677897. DOI: 10.3390/pharmaceutics16121557.

Host-Guest Interaction Study of Olmesartan Medoxomil with β-Cyclodextrin Derivatives.

Andor M, Temereanca C, Sbarcea L, Ledeti A, Man D, Mornos C Molecules. 2024; 29(10).

PMID: 38792072 PMC: 11123892. DOI: 10.3390/molecules29102209.

Mushroom tyrosinase enzyme catalysis: synthesis of larvicidal active geranylacetone derivatives against and molecular docking studies.

Mullaivendhan J, Ahamed A, Arif I, Raman G, Akbar I Front Chem. 2024; 11:1303479.

PMID: 38268759 PMC: 10806150. DOI: 10.3389/fchem.2023.1303479.

Improving Bioaccessibility and Bioavailability of Isoflavone Aglycones from Chickpeas by Germination and Forming β-Cyclodextrin Inclusion Complexes.

He Y, Xiang J, Chen J, Fang S, Guo Z, Liang X Pharmaceutics. 2023; 15(12).

PMID: 38140025 PMC: 10747479. DOI: 10.3390/pharmaceutics15122684.

Heteroatom (B, N, P, and S)-Doped Cyclodextrin as a Hydroxyurea (HU) Drug Nanocarrier: A Computational Approach.

Afahanam L, Louis H, Benjamin I, Gber T, Ikot I, Manicum A ACS Omega. 2023; 8(11):9861-9872.

PMID: 36969463 PMC: 10035006. DOI: 10.1021/acsomega.2c06630.

References

Kawai T, Teshima S, Kusumoto K, Kawahara T, Kondo K, Kishi K . A non-toxic heat shock protein 70 inducer, geranyl-geranyl-acetone, restores the heat shock response in gastric mucosa of protein-malnourished rats. J Lab Clin Med. 2000; 136(2):138-48. DOI: 10.1067/mlc.2000.108157. View

Mabrouk S, Elaissi A, Ben Jannet H, Harzallah-Skhiri F . Chemical composition of essential oils from leaves, stems, flower heads and roots of Conyza bonariensis L. from Tunisia. Nat Prod Res. 2011; 25(1):77-84. DOI: 10.1080/14786419.2010.513685. View

Zingone G, Rubessa F . Preformulation study of the inclusion complex warfarin-beta-cyclodextrin. Int J Pharm. 2005; 291(1-2):3-10. DOI: 10.1016/j.ijpharm.2004.11.013. View

Vincent J, Kirby D, Nguyen T, Vigh G . A Family of Single-Isomer Chiral Resolving Agents for Capillary Electrophoresis. 2. Hepta-6-sulfato-β-cyclodextrin. Anal Chem. 2011; 69(21):4419-28. DOI: 10.1021/ac970418o. View

Anselmi C, Centini M, Ricci M, Buonocore A, Granata P, Tsuno T . Analytical characterization of a ferulic acid/gamma-cyclodextrin inclusion complex. J Pharm Biomed Anal. 2005; 40(4):875-81. DOI: 10.1016/j.jpba.2005.08.019. View

Li N, Luo H, Liu S . Resonance Rayleigh scattering study of the inclusion complexation of chloramphenicol with beta-cyclodextrin. Talanta. 2008; 66(2):495-500. DOI: 10.1016/j.talanta.2004.11.022. View

Hedayati N, Montazer M, Mahmoudirad M, Toliyat T . Ketoconazole and Ketoconazole/β-cyclodextrin performance on cotton wound dressing as fungal skin treatment. Carbohydr Polym. 2020; 240:116267. DOI: 10.1016/j.carbpol.2020.116267. View

Ventura C, Giannone I, Paolino D, Pistara V, Corsaro A, Puglisi G . Preparation of celecoxib-dimethyl-beta-cyclodextrin inclusion complex: characterization and in vitro permeation study. Eur J Med Chem. 2005; 40(7):624-31. DOI: 10.1016/j.ejmech.2005.03.001. View

Wang H, Han J, Feng X . Spectroscopic study of orange G-beta-cyclodextrin complex and its analytical application. Spectrochim Acta A Mol Biomol Spectrosc. 2006; 66(3):578-85. DOI: 10.1016/j.saa.2006.03.035. View

10.

Nguyen T, Liu B, Zhao J, Thomas D, Hook J . An investigation into the supramolecular structure, solubility, stability and antioxidant activity of rutin/cyclodextrin inclusion complex. Food Chem. 2012; 136(1):186-92. DOI: 10.1016/j.foodchem.2012.07.104. View

11.

Dass C, Jessup W . Apolipoprotein A-I, cyclodextrins and liposomes as potential drugs for the reversal of atherosclerosis. A review. J Pharm Pharmacol. 2000; 52(7):731-61. DOI: 10.1211/0022357001774606. View

12.

Sambasevam K, Mohamad S, Muhamad Sarih N, Ismail N . Synthesis and Characterization of the Inclusion Complex of β-cyclodextrin and Azomethine. Int J Mol Sci. 2013; 14(2):3671-82. PMC: 3588064. DOI: 10.3390/ijms14023671. View

13.

Tang W, Zou C, Da C, Cao Y, Peng H . A review on the recent development of cyclodextrin-based materials used in oilfield applications. Carbohydr Polym. 2020; 240:116321. DOI: 10.1016/j.carbpol.2020.116321. View

14.

Archontaki H, Vertzoni M . Study on the inclusion complexes of bromazepam with beta- and beta-hydroxypropyl-cyclodextrins. J Pharm Biomed Anal. 2002; 28(3-4):761-9. DOI: 10.1016/s0731-7085(01)00679-3. View

15.

Kfoury M, Auezova L, Ruellan S, Greige-Gerges H, Fourmentin S . Complexation of estragole as pure compound and as main component of basil and tarragon essential oils with cyclodextrins. Carbohydr Polym. 2014; 118:156-64. DOI: 10.1016/j.carbpol.2014.10.073. View

16.

Tatman D, Mo H . Volatile isoprenoid constituents of fruits, vegetables and herbs cumulatively suppress the proliferation of murine B16 melanoma and human HL-60 leukemia cells. Cancer Lett. 2001; 175(2):129-39. DOI: 10.1016/s0304-3835(01)00723-6. View

17.

Jansook P, Ogawa N, Loftsson T . Cyclodextrins: structure, physicochemical properties and pharmaceutical applications. Int J Pharm. 2017; 535(1-2):272-284. DOI: 10.1016/j.ijpharm.2017.11.018. View

18.

Radulovic N, Stojanovic G, Palic R . Composition and antimicrobial activity of Equisetum arvense L. essential oil. Phytother Res. 2006; 20(1):85-8. DOI: 10.1002/ptr.1815. View

19.

Hedges A . Industrial Applications of Cyclodextrins. Chem Rev. 2002; 98(5):2035-2044. DOI: 10.1021/cr970014w. View