Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2021 Nov 2;14(21):6594.
doi: 10.3390/ma14216594.

Preparation and Characterization of Water-Insoluble Gardenia Blue Pigment

Yakun Gao  1   2 , Jinchuan Xu  3 , Guorong Liu  1 , Rong Nie  1 , Jiaojiao Duan  1 , Duoxia Xu  1 , Chengtao Wang  1
Affiliations

Preparation and Characterization of Water-Insoluble Gardenia Blue Pigment

Yakun Gao et al. Materials (Basel). .

Abstract

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 λmax 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 (p < 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.

Keywords: gardenia blue pigment; solubility study; stability study; structure study; water-insoluble.

PubMed Disclaimer

Conflict of interest statement

There is no conflict of interests regarding the publication of this paper.

Figures

Figure 1
Figure 1
Simulation of the chemical structural formula of the intermediate product 1 (a) and intermediate product 2 (b) of the water-insoluble gardenia blue pigment.
Figure 2
Figure 2
The SEM of water-insoluble gardenia blue pigment.
Figure 3
Figure 3
The UV-vis of water-insoluble gardenia blue pigment.
Figure 4
Figure 4
The FTIR of water-insoluble gardenia blue pigment.
Figure 5
Figure 5
The full-spectrum (a), C1s-spectrum (b), O1s-spectrum (c), and N1s-spectrum (d) XPS of water-insoluble gardenia blue pigment.
Figure 6
Figure 6
The fragmentation pathway of water-insoluble gardenia blue pigment Z-1 (a). The planar and 3D molecular structure simulation graphs of the pigment Z-1 (b) and (c) (C-gray, O-red, N-blue, H-white).
Figure 7
Figure 7
The fragmentation pathway of water-insoluble gardenia blue pigment Z-2 (a). The planar and 3D molecular structure simulation graphs of the pigment Z-2 (b) and (c) (C-ray, O-red, N-blue, H-white).
Figure 8
Figure 8
The fragmentation pathway of water-insoluble gardenia blue pigment Z-3 (a). The planar and 3D molecular structure simulation graphs of the pigment Z-3 (b) and (c) (C-gray, O-red, N-blue, H-white).
Figure 9
Figure 9
Light stability of water-soluble and water-insoluble gardenia blue pigments (residual rate).
Figure 10
Figure 10
Temperature stability of water-soluble and water-insoluble gardenia blue pigments (residual rate). Different latters mean there is a significant difference (p < 0.05).
See this image and copyright information in PMC

Similar articles

See all similar articles

References

    1. Jespersen L., Stromdahl L.D., Olsen K., Skibsted L.H. Heat and light stability of three natural blue colorants for use in confectionery and beverages. Eur. Food Res. Technol. 2005;220:261–266. doi: 10.1007/s00217-004-1062-7. - DOI
    1. Wu S., Wu Q., Xu L., Xu L.J. Progress in the development and application of natural edible pigment. Shandong Food Ferment. 2015;179:35–38.
    1. Li Z., Hu C., Jia J., Xia Y., Xie H., She M., Huang R., He L., Liu C., Wang S., et al. Establishment and evaluation of a simple size-selective method for exosome enrichment and purification. J. Biomed. Nanotechnol. 2019;15:1090–1096. doi: 10.1166/jbn.2019.2768. - DOI - PubMed
    1. Cho Y.J., Kim S.Y., Kim J., Choe E.K., Kim S.I., Shin H.J. One-step enzymatic synthesis of blue pigments from geniposide for fabric dyeing. Biotechnol. Bioprocess Eng. 2006;11:230–234. doi: 10.1007/BF02932035. - DOI
    1. Kim S.J., Jang H.G. Characterization and stability of Gardenia jasminoides biotransformed pigment produced in jar fermentor. J. Korean Soc. Food Sci. Nutr. 2005;34:880–884.

LinkOut - more resources