Quantum Chemical Calculation of the Formation Mechanism of the Sugar Smoking Pigment 5-(α-D-Glucopyranosyl-(1-6)-α-D-glucopyranosyloxymenthyl)-2-furancarboxaldehyde

被引：0

作者：

Ye G. ^{[1
]}

Niu Y. ^{[1
]}

Fan C. ^{[1
]}

Yang H. ^{[1
]}

Liu D. ^{[1
]}

机构：

[1] College of Food Science and Engineering, Bohai University, Jinzhou

来源：

Shipin Kexue/Food Science | 2024年 / 45卷 / 10期

关键词：

5-(α-D-glucopyranosyl-(1-6)-α-D-glucopyranosyloxymenthyl)-2-furancarboxaldehyde; density functional theory; quantum chemistry; sugar smoking pigment;

D O I：

10.7506/spkx1002-6630-20230515-128

中图分类号：

学科分类号：

摘要：

In order to explore the formation pathways of 5-(α-D-glucopyranosyl-(1-6)-α-D-glucopyranosyloxymenthyl)-2-furancarboxaldehyde (5-GGMF), a pigment formed during the process of sugar smoking, the thermal decomposition reaction site of sucrose, the dehydration reaction modes between glucose and 5-hydroxymethylfurfural (5-HMF) and between two molecules of glucose, and the formation pathways of 5-HMF and 5-GGMF were analyzed by quantum chemical calculation. The results showed that the initial position of thermal decomposition of sucrose was the cleavage of fructosyl-oxygen bond. van der Waals force played a leading role in the complexes formed by the interaction between glucose and 5-HMF and between two molecules of glucose, and the intermolecular dehydration reaction was promoted by strong hydrogen bonding. The formation of 5-HMF from the glucose moiety formed after the pyrolysis of sucrose needed more activation energy than from the fructose moiety formed with a lower reaction rate, indicating that the fructose moiety was more prone to form 5-HMF. Among the two formation pathways of 5-HMF from the fructose moiety, pathway 5 was more prone to occur than pathway 4, because pathway 5 showed obvious advantages in energy and reaction kinetics. In the formation pathways of 5-GGMF from sucrose, the energy barrier of the transglycosylation pathway was overall lower, which was more favorable than the disaccharide dehydration and trisaccharide dehydration pathways. Among them, pathway C2, including three steps: the pyrolysis of sucrose to produce fructose and glucose, the reaction of glucose with 5-HMF to form 5-glucosyloxymethylfurfural (5-GMF), and the reaction of 5-GMF with a molecule of free glucose to produce 5-GGMF, was most conducive to the generation of 5-GGMF from both an energy barrier and kinetic perspective. The results of this study can provide a theoretical basis and reference for controlling and intervening in the color of sugar smoked products in the future. © 2024 Chinese Chamber of Commerce. All rights reserved.

引用

页码：62 / 71

页数：9

共 24 条

[1]

HUMAID S, NAYYAR D, BOLTON J, Et al., Physicochemical properties and consumer acceptance of high-pressure processed, sous vide-cooked lobster tails, Journal of Food Science, 84, 12, pp. 3454-3462, (2019)

[2]

(2013)

[3]

WANG X, LIU D Y, DU C, Et al., Characteristics and formation mechanism of key volatile compounds in sugar-smoked chicken, Journal of Food Science and Technology, 59, 2, pp. 768-783, (2022)

[4]

CHANG H, WANG Y, XIA Q, Et al., Characterization of the physicochemical changes and volatile compound fingerprinting during the chicken sugar-smoking process, Poultry Science, 100, 1, pp. 377-387, (2021)

[5]

CHEN S, KAO T H, CHENC J, Et al., Reduction of carcinogenic polycyclic aromatic hydrocarbons in meat by sugar-smoking and dietary exposure assessment in Taiwan, Journal of Agricultural and Food Chemistry, 61, 31, pp. 7645-7653, (2013)

[6]

ZHANG L, WANG H, XIA X F, Et al., Comparative study on the formation of heterocyclic aromatic amines in different sugar smoking time, Food Control, 124, (2021)

[7]

(2020)

[8]

CHANG H, ZHOU C Y, HE J, Et al., Identifying and characterizing the components related to the brown color of Chinese sugar-smoked chicken during processing, Poultry Science, 100, 3, (2021)

[9]

(2019)

[10]

CEDILLO-FLORES O E, RODRIGUEZ-LAGUNA N, HIPOLITONAJERA A R, Et al., Effect of the pH on the thermodynamic stability of inclusion complexes of thymol and carvacrol in β-cyclodextrin in water, Food Hydrocolloids, 124, (2022)

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