Preparation and Characterization of Water-Insoluble Gardenia Blue Pigment

Based on molecular simulations, the synthetic route of water-insoluble gardenia blue pigment was prepared by the reaction of genipin and L-Phenylalanine methyl ester hydrochloride. A highly purified pigment was obtained after extraction by chloroform and purification by silica gel column chromatogra...

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Autores principales: Yakun Gao, Jinchuan Xu, Guorong Liu, Rong Nie, Jiaojiao Duan, Duoxia Xu, Chengtao Wang
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Publicado: MDPI AG 2021
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spelling oai:doaj.org-article:1a6e94ba9da9421ea61e6b3dffdd43a52021-11-11T18:08:01ZPreparation and Characterization of Water-Insoluble Gardenia Blue Pigment10.3390/ma142165941996-1944https://doaj.org/article/1a6e94ba9da9421ea61e6b3dffdd43a52021-11-01T00:00:00Zhttps://www.mdpi.com/1996-1944/14/21/6594https://doaj.org/toc/1996-1944Based on molecular simulations, the synthetic route of water-insoluble gardenia blue pigment was prepared by the reaction of genipin and L-Phenylalanine methyl ester hydrochloride. A highly purified pigment was obtained after extraction by chloroform and purification by silica gel column chromatography, and the value of color is up to 288. A study on the structural characteristics of the pigment was implemented with a scanning electron microscope, ultraviolet-visible spectrophotometer, Fourier transform infrared spectrometer, X-ray photoelectron spectrometer, and quatropde-time of flight mass spectrometer. The results showed that the surface of the pigment was largely smooth and spherical; The <i>λ</i><sub>max</sub> was 607 nm, and the main functional groups include O-C=O, C=O, C-N, C=C, OH, and benzene ring; We detrained six different molecular weight and chemical structures of pigments and speculated the particular structures and formation mechanisms of three kinds of pigment, whose molecular weights are 690.1156, 720.1226, and 708.1246 Da, respectively. The pigment was only able to be dissolved in ethanol, methanol, acetone, ethyl acetate, and other strong polar organic solvents, but was not able to be dissolved in water, ethyl ether, petroleum ether, and other weak polar organic solvents. In terms of light and thermal stabilities, water-insoluble gardenia blue pigment is significantly better than water-soluble gardenia blue pigment (<i>p</i> < 0.05). When it is under direct light for 7 days or incubated at 80–120 °C for 24 h, the pigment residual rates were 74.90, 95.26, 88.27, and 87.72%, respectively.Yakun GaoJinchuan XuGuorong LiuRong NieJiaojiao DuanDuoxia XuChengtao WangMDPI AGarticlegardenia blue pigmentwater-insolublestructure studysolubility studystability studyTechnologyTElectrical engineering. Electronics. Nuclear engineeringTK1-9971Engineering (General). Civil engineering (General)TA1-2040MicroscopyQH201-278.5Descriptive and experimental mechanicsQC120-168.85ENMaterials, Vol 14, Iss 6594, p 6594 (2021)
institution DOAJ
collection DOAJ
language EN
topic gardenia blue pigment
water-insoluble
structure study
solubility study
stability study
Technology
T
Electrical engineering. Electronics. Nuclear engineering
TK1-9971
Engineering (General). Civil engineering (General)
TA1-2040
Microscopy
QH201-278.5
Descriptive and experimental mechanics
QC120-168.85
spellingShingle gardenia blue pigment
water-insoluble
structure study
solubility study
stability study
Technology
T
Electrical engineering. Electronics. Nuclear engineering
TK1-9971
Engineering (General). Civil engineering (General)
TA1-2040
Microscopy
QH201-278.5
Descriptive and experimental mechanics
QC120-168.85
Yakun Gao
Jinchuan Xu
Guorong Liu
Rong Nie
Jiaojiao Duan
Duoxia Xu
Chengtao Wang
Preparation and Characterization of Water-Insoluble Gardenia Blue Pigment
description Based on molecular simulations, the synthetic route of water-insoluble gardenia blue pigment was prepared by the reaction of genipin and L-Phenylalanine methyl ester hydrochloride. A highly purified pigment was obtained after extraction by chloroform and purification by silica gel column chromatography, and the value of color is up to 288. A study on the structural characteristics of the pigment was implemented with a scanning electron microscope, ultraviolet-visible spectrophotometer, Fourier transform infrared spectrometer, X-ray photoelectron spectrometer, and quatropde-time of flight mass spectrometer. The results showed that the surface of the pigment was largely smooth and spherical; The <i>λ</i><sub>max</sub> was 607 nm, and the main functional groups include O-C=O, C=O, C-N, C=C, OH, and benzene ring; We detrained six different molecular weight and chemical structures of pigments and speculated the particular structures and formation mechanisms of three kinds of pigment, whose molecular weights are 690.1156, 720.1226, and 708.1246 Da, respectively. The pigment was only able to be dissolved in ethanol, methanol, acetone, ethyl acetate, and other strong polar organic solvents, but was not able to be dissolved in water, ethyl ether, petroleum ether, and other weak polar organic solvents. In terms of light and thermal stabilities, water-insoluble gardenia blue pigment is significantly better than water-soluble gardenia blue pigment (<i>p</i> < 0.05). When it is under direct light for 7 days or incubated at 80–120 °C for 24 h, the pigment residual rates were 74.90, 95.26, 88.27, and 87.72%, respectively.
format article
author Yakun Gao
Jinchuan Xu
Guorong Liu
Rong Nie
Jiaojiao Duan
Duoxia Xu
Chengtao Wang
author_facet Yakun Gao
Jinchuan Xu
Guorong Liu
Rong Nie
Jiaojiao Duan
Duoxia Xu
Chengtao Wang
author_sort Yakun Gao
title Preparation and Characterization of Water-Insoluble Gardenia Blue Pigment
title_short Preparation and Characterization of Water-Insoluble Gardenia Blue Pigment
title_full Preparation and Characterization of Water-Insoluble Gardenia Blue Pigment
title_fullStr Preparation and Characterization of Water-Insoluble Gardenia Blue Pigment
title_full_unstemmed Preparation and Characterization of Water-Insoluble Gardenia Blue Pigment
title_sort preparation and characterization of water-insoluble gardenia blue pigment
publisher MDPI AG
publishDate 2021
url https://doaj.org/article/1a6e94ba9da9421ea61e6b3dffdd43a5
work_keys_str_mv AT yakungao preparationandcharacterizationofwaterinsolublegardeniabluepigment
AT jinchuanxu preparationandcharacterizationofwaterinsolublegardeniabluepigment
AT guorongliu preparationandcharacterizationofwaterinsolublegardeniabluepigment
AT rongnie preparationandcharacterizationofwaterinsolublegardeniabluepigment
AT jiaojiaoduan preparationandcharacterizationofwaterinsolublegardeniabluepigment
AT duoxiaxu preparationandcharacterizationofwaterinsolublegardeniabluepigment
AT chengtaowang preparationandcharacterizationofwaterinsolublegardeniabluepigment
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