| Anthocyanin, the molecular formula is C15H11O6. The common types are Cyanidin, malvidin, peonidin and so on. Anthocyanin is a type of the water soluble natural pigment distributed very extensively in plants, which has good physiological function and prospects for development and utilization. Due to its lack of stabilities, lower lipid-soluble and poor bioavailability, the further developments and utilizations of anthocyanin suffer certain impacts. Therefore, in order to make the anthocyanin better used in the future of food industry field, the study was in the premise of maintaining anthocyanin’s good physiological active functions, using the Cyanidin-3-O-glucoside, the most plentiful elements in the Anthocyanin, as the basic material, with the method of acylation to proceed chemical modification, to provide possibilities to realize widely integrated utilizations of the anthocyanin.The experiments used Cyanidin-3-O-glucoside as acylated material, lauric acid was used as the acyl donor, compared with effects between enzymic method and chemical methods contained lauric acid and lauryl chloride, chemical method of lauric acid was chosen to proceed the acylated experiments. Lauric acid, long chain fat acid, was used as acyl donor, DMF and HOBT were used as the condensation agents to catalyze the reaction. DMF was used as the solvent. Prep-LC was used to separate and purify the acylated cyanidin-3-glucoside. FTIR and LC-MS were used to confirm the basic structure of cyanidin-3-O-glucoside. The acylated Cyanidin-3-O-glucoside was compared with unacylated Cyanidin-3-O-glucoside in the instability in the following aspects:temperature, illumination, addictive, metal ion and reductant-oxidant. Meanwhile, the experiments make the lipotropism comparison between the unacylated and acylated Cyanidin-3-glucoside. The analysis results are as followings:1) The experiments used the reacting compounds of HOBT, EDC and Lauric acid in the environment of DMF as the esterifying agent of the acylating action, Cyanidin-3-O-glucoside, as the material, in the opaque background and airtight environments to react about 48h, using mass spectrometer to monitor the experimental process during the experiments, then spin dry to weight as the acylated rate is around 31% . In the experiments of Laurie acid was combined with cyanidin-3-glucoside. Combined with the analysis of FTIR and LC-MS, Laurie acid reacted with the glucoside"s primary hydroxyl group and removed a molecule of water, thereby resulting in the obtained structure.2) The compositions of the unacylated cyanidin-3-O-glucoside and acylated cyanidin-3-glucoside were compared under different temperature, different time of illumination and different concentration of Oxidation-reductants. The effects of different concentrations of additive compounds and metal cations on the stabilities of acylated cyanidin-3-O-glucoside were compared. Stability of acylated cyanidin-3-O-glucoside is obviously higher than that of unacylated cyanidin-3-O-glucoside because the stability of the ester group was higher than the hydroxyl group. The primary hydroxyl esterification of glucoside improved cyanidin-3-glucoside’s stability. It was showed that addictive can increase the stability of acylated cyanidin-3-glucoside, and K+, Na+Cu2+ and Fe2+ under 0.05mol/L have no obviously impact on acylated cyanidin-3-glucoside. Ca2+/Fe" and Mg2+, Fe2+ of O.1mol/L can destroy its stability, Mg2+ below 0.05mol/L can increase acylated cyanidin-3-O-glucoside’s stability. The experiments also showed the lipotropy comparison between unacylated and acylated Cyanidin-3-O-glucoside, oil-water partition coefficients of acylated product was 7.98, obviously higher than unacylated Cyanidin-3-O-glucoside’s 0.24, so the lipotropy was obviously increased after acylated. |
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