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Identification of Geometrical Isomers and Comparison of Different Isomeric Samples of Astaxanthin

Authors

  • Dan Qiu,

    1. Author Qiu is with College of Chemical Engineering, Ningbo Univ. of Technology, 89, Cuibai Road, Ningbo 315016, P.R. China; and Zhejiang NVB Co. Ltd., High-Tech Industry Zone (Second), XinChang 312500, P.R. China. Author Wu is with College of Chemical Engineering, Ningbo Univ. of Technology, 89, Cuibai Road, Ningbo 315016, P.R. China. Author Zhu is with Zhejiang NVB Co. Ltd., High-Tech Industry Zone (Second), XinChang 312500, P.R. China. Authors Yin and Yi are with Dept. of Chemical and Biological Engineering, Zhejiang Univ., 38, Zheda Road, Hangzhou 310027, P.R. China. Direct inquiries to author Qiu (E-mail: qiudan_zju@163.com) or author Yi (20928148@zju.edu.cn).
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  • Yue-Chan Wu,

    1. Author Qiu is with College of Chemical Engineering, Ningbo Univ. of Technology, 89, Cuibai Road, Ningbo 315016, P.R. China; and Zhejiang NVB Co. Ltd., High-Tech Industry Zone (Second), XinChang 312500, P.R. China. Author Wu is with College of Chemical Engineering, Ningbo Univ. of Technology, 89, Cuibai Road, Ningbo 315016, P.R. China. Author Zhu is with Zhejiang NVB Co. Ltd., High-Tech Industry Zone (Second), XinChang 312500, P.R. China. Authors Yin and Yi are with Dept. of Chemical and Biological Engineering, Zhejiang Univ., 38, Zheda Road, Hangzhou 310027, P.R. China. Direct inquiries to author Qiu (E-mail: qiudan_zju@163.com) or author Yi (20928148@zju.edu.cn).
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  • Wen-Li Zhu,

    1. Author Qiu is with College of Chemical Engineering, Ningbo Univ. of Technology, 89, Cuibai Road, Ningbo 315016, P.R. China; and Zhejiang NVB Co. Ltd., High-Tech Industry Zone (Second), XinChang 312500, P.R. China. Author Wu is with College of Chemical Engineering, Ningbo Univ. of Technology, 89, Cuibai Road, Ningbo 315016, P.R. China. Author Zhu is with Zhejiang NVB Co. Ltd., High-Tech Industry Zone (Second), XinChang 312500, P.R. China. Authors Yin and Yi are with Dept. of Chemical and Biological Engineering, Zhejiang Univ., 38, Zheda Road, Hangzhou 310027, P.R. China. Direct inquiries to author Qiu (E-mail: qiudan_zju@163.com) or author Yi (20928148@zju.edu.cn).
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  • Hong Yin,

    1. Author Qiu is with College of Chemical Engineering, Ningbo Univ. of Technology, 89, Cuibai Road, Ningbo 315016, P.R. China; and Zhejiang NVB Co. Ltd., High-Tech Industry Zone (Second), XinChang 312500, P.R. China. Author Wu is with College of Chemical Engineering, Ningbo Univ. of Technology, 89, Cuibai Road, Ningbo 315016, P.R. China. Author Zhu is with Zhejiang NVB Co. Ltd., High-Tech Industry Zone (Second), XinChang 312500, P.R. China. Authors Yin and Yi are with Dept. of Chemical and Biological Engineering, Zhejiang Univ., 38, Zheda Road, Hangzhou 310027, P.R. China. Direct inquiries to author Qiu (E-mail: qiudan_zju@163.com) or author Yi (20928148@zju.edu.cn).
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  • Long-Tao Yi

    1. Author Qiu is with College of Chemical Engineering, Ningbo Univ. of Technology, 89, Cuibai Road, Ningbo 315016, P.R. China; and Zhejiang NVB Co. Ltd., High-Tech Industry Zone (Second), XinChang 312500, P.R. China. Author Wu is with College of Chemical Engineering, Ningbo Univ. of Technology, 89, Cuibai Road, Ningbo 315016, P.R. China. Author Zhu is with Zhejiang NVB Co. Ltd., High-Tech Industry Zone (Second), XinChang 312500, P.R. China. Authors Yin and Yi are with Dept. of Chemical and Biological Engineering, Zhejiang Univ., 38, Zheda Road, Hangzhou 310027, P.R. China. Direct inquiries to author Qiu (E-mail: qiudan_zju@163.com) or author Yi (20928148@zju.edu.cn).
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Abstract

Abstract:  A high-performance liquid chromatographic (HPLC) analysis system for isomeric astaxanthin was developed. The separation system consisted of a C30 column and an elution system of methanol/MTBE/water/dichloromethane (77 : 13 : 8 : 2, v/v/v/v). Using the combination of HPLC diode array detector and HPLC atmospheric pressure chemical ionization mass spectrometry, 11 geometrical isomers and 4 epoxides of astaxanthin were successfully identified. Referred to crystal, only isomerization with different degrees was found for solvent dissolving and iodine catalysis, while melting of astaxanthin caused isomerization, slight oxidation, and more noticeable polymerization confirmed by gel permeation chromatography. Chemical changes in isomeric samples all caused a decrease in UV content. The vibrational spectra (infrared and Raman) showed that epoxide was the only new functional group generated for melting. Changes of several key bands and formations of new bands were found in iodine catalysis and melting samples because of isomerization.

Practical Application:  Eleven geometrical isomers and 4 epoxides, which were normally generated for solvent dissolving, iodine catalysis, and melting of astaxanthin, have been identified by C30-HPLC-MS technology. Furthermore, different samples were measured by gel permeation chromatography, UV, infrared, and Raman, based on the analysis of messages, the effect of each processing was well understood.

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