Citation: ZHOU Yehong, MA Xuewen, LIANG Wenting, DONG Chuan, SHUANG Shaomin. Preparation and Physicochemical Properties of the Inclusion Complexes of β-Carotene with β-Cyclodextrin and Its Derivatives[J]. Chinese Journal of Applied Chemistry, ;2016, 33(7): 827-833. doi: 10.11944/j.issn.1000-0518.2016.07.150352 shu

Preparation and Physicochemical Properties of the Inclusion Complexes of β-Carotene with β-Cyclodextrin and Its Derivatives

a.
a. Institute of Environmental Science, Shanxi University, Taiyuan 030006, China;
b.
b. School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, China

Corresponding author: DONG Chuan, SHUANG Shaomin,
Received Date: 8 October 2015
Available Online: 6 January 2016
Fund Project:

The solid inclusion complexes of β-carotene with β-cyclodextrin, 2-hydroxypropyl-β-cyclodextrin and sulfobutylether-β-cyclodextrin were prepared in order to improve physicochemical properties of β-carotene, such as solubility and stability. The inclusion complexes of β-carotene with β-cyclodextrin and its derivatives were characterized by UV-Vis absorption spectroscopy, Fourier-transform infrared spectroscopy and ¹H NMR spectroscopy. The physicochemical properties of inclusion complexes indicate that the heat stability, light stability and antioxidant activity of β-carotene are evidently improved by the formation of inclusion complexes of β-carotene with β-cyclodextrin, 2-hydroxypropyl-β-cyclodextrin and sulfobutylether-β-cyclodextrin, respectively. The solubility of β-carotene increases 12 times and 18 times by the formation of inclusion complexes of β-carotene with 2-hydroxypropyl-β-cyclodextrin and sulfobutylether-β-cyclodextrin, respectively.
- β-carotene,
- cyclodextrins,
- inclusion complex,
1. [1]
  [1] Pfitzner I,Francz P I,Biesalski H K. Carotenoid:Methyl-β-cyclodextrin Formulations:An Improved Method for Supplementation of Cultured Cells[J]. Biochim Biophys Acta,2000,1474(2):163-168.
2. [2]
  [2] QIN Dezhi,SHAO Bin,YU Feng. The Form of Preparation of β-Carotene[J]. China Food Addit,2003,(6):66-69(in Chinese).秦德志,邵斌,喻峰. β-胡萝卜素的主要剂型[J]. 中国食品添加剂,2003,(6):66-69.
3. [3]
  [3] Mele A,Mendichi R,Selva A,et al. Non-covalent Associations of Cyclomaltooligosaccharides(cyclodextrins) with Carotenoids in Water. A Study on the α-and β-Cyclodextrin/carotene(lycopene) Systems by Light Scattering, Ionspray Ionization and Tandem Mass Spectrometry[J]. Carbohydr Res,2002,337(12):1129-1136.
4. [4]
  [4] FENG Guangzhu,LU Kui,LI Heping. Study on the Inclusion Complexation Interaction of β-cycloedxtrin and β-Carotene by UV-Vis Spectra[J]. Spectrosc Spectr Anal,2004,24(9):1009-1102(in Chinese).冯光炷,卢奎,李和平. 紫外-可见光谱研究β-环糊精与β-胡萝卜素的包结作用[J]. 光谱学与光谱分析,2004,24(9):1009-1102.
5. [5]
  [5] Hasebe K,Ando Y,Chikamatsu Y,et al. Preparation of Cyclodextrin Inclusion Compounds Containing β-Carotene as Material for Drug, Food and Cosmetics:JP,62267261[P],1987.
6. [6]
  [6] Murao T,Maruyama T,Yamamoto Y. Preparation of Cyclodextrin Inclusion Compounds Containing β-Carotene as Food Dyes and Antioxidants:JP 04244059[P],1992.
7. [7]
  [7] LIANG Tiantian,CHEN Zhiqun,HU Fuqiang,et al. Study on Inclusion Complex of β-Cyclodextrin and β-Carotene[J]. Chinese Pharm,1998,33(9):543-545(in Chinese).梁天天,陈志群,胡富强,等. β-胡萝卜素包合物的制备[J]. 中国药学杂志,1998,33(9):543-545.
8. [8]
  [8] Schwartz J L,Shklar G,Sikorski C. Decolorized Carotenoid-cyclodextrin Complexes:WO 9513047[P],1995.
9. [9]
  [9] WANG Hui,MEI Minghua. Photo-physical Behavior of Modified β-Cyclodextrin by Dimethylamino Chalcone in Different Solvents[J]. Acta Phys-Chim Sin,2002,18(6):495-499(in Chinese).王辉,梅明华. 二甲胺基查耳酮修饰的β-环糊精在不同溶剂中的光物理行为[J]. 物理化学学报,2002,18(6):495-499.
10. [10]
  [10] LU Ping,LIU Bin. Formation of the Inclusion Complex of β-Cyclodextrin with Methyl Orange and Its Photocatalytic Decolorization[J]. Chinese J Appl Chem,2003,20(2):108-113(in Chinese).路平,刘彬. β-环糊精与甲基橙包合物的形成及其光催化脱色[J]. 应用化学,2003,20(2):108-113.
11. [11]
  [11] Gong X,Hu Q,Paau M C,et al. Red-green-blue Fluorescent Hollow Carbon Nanoparticles Isolated From Chromatographic Fractions for Cellular Imaging[J]. Nanoscale,2014,6(14):8162-8170.
12. [12]
  [12] Gong X,Lu W,Liu Y,et al. Low Temperature Synthesis of Phosphorous and Nitrogen Co-doped Yellow Fluorescent Carbon Dots for Sensing and Bioimaging[J]. J Mater Chem B,2015,3:6813-6819.
13. [13]
  [13] Gong X,Lu W,Paau M C,et al. Facile Synthesis of Nitrogen-doped Carbon Dots for Fe³⁺ Sensing and Cellular Imaging[J]. Anal Chim Acta,2015,861:74-84.
14. [14]
  [14] Lu W,Gong X,Yang Z,et al. High-quality Water-soluble Luminescent Carbon Dots for Multicolor Patterning, Sensors, and Bioimaging[J]. RSC Adv,2015,5(22):16972-16979.
15. [15]
  [15] Li S,Purdy W C. Circular-Dichroism, Ultraviolet and Proton Nuclear Magnetic Resonance Spectroscopic Studies of the Chiral Recognition Mechanism of β-Cyclodextrin[J]. Anal Chem,1992,64(13):1405-1412.
16. [16]
  [16] Botsi A,Yannakopoulou K,Perly B,et al. Positive or Adverse Effects of Methylation on the Inclusion Behavior of Cyclodextrins. A Comparative NMR Study Using Pheromone Constituents of the Olive Fruit Fly[J]. J Org Chem,1995,60(13):4017-4023.
17. [17]
  [17] Ting S,Chi-Tang H. Antioxidant Activities of Buckwheat Extracts[J]. Food Chem,2005,90(4):743-749.
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