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2-L-苏氨酸-2-脱氧-D-葡萄糖的合成、热裂解及抗氧化性能

Synthesis, pyrolysis and antioxidant activity of 2-L-threonine-2-deoxy-D-glucose

  • 摘要: 为开发一种基于美拉德反应中间体Heyns化合物的烟用香原料,以D-果糖(Fru)和L-苏氨酸(Thr)为原料合成了2-L-苏氨酸-2-脱氧-D-葡萄糖(Thr-Glu),利用红外光谱(IR)、核磁共振波谱(1H NMR、13C NMR)和高分辨质谱(HRMS)等技术对其进行了表征,采用热重-差热分析(TG-DTA)和在线裂解气相色谱/质谱联用法(Py-GC/MS)进行热裂解分析,并采用1,1-二苯基-2-三硝基苯肼(DPPH)自由基清除法和还原能力法检测了体外抗氧化活性。结果表明:①Thr-Glu的纯度(质量分数)达到99%,产率为69.7%。②Thr-Glu的初始裂解温度为118.65℃,500℃时总失重达到80%;裂解产物的数量随温度的升高而增加,裂解产物主要为杂环类、醛类、羧酸类和酮类化合物,具有焦甜香、烘焙香、坚果香、甜香、花香和奶香等香韵。③Thr-Glu具有较强的DPPH自由基清除能力和还原能力,是一种潜在的抗氧化剂。

     

    Abstract: In order to develop new cigarette flavors based on Heyns compounds, a Maillard reaction intermediate, 2-L-threonine-2-deoxy-D-glucose (Thr-Glu), was synthesized from D-fructose (Fru) and L-threonine (Thr). The structure of the target product was characterized by IR, 1H NMR, 13C NMR and HRMS spectra. The thermal stability of the product was investigated by thermogravimetry-differential thermal analysis (TG-DTA) and online pyrolysis gas chromatography-mass spectroscopy (Py-GC/MS). The antioxidant activity of the product was tested with DPPH free radical scavenging assay and reducing capacity assay. The results showed that:1)The synthesized product was the target compound (Thr-Glu) with 99% purity, and the yield of 69.7%. 2)The initial pyrolysis temperature of Thr-Glu was 118.65℃, its total thermal mass loss reached about 80% up to 500℃. The number of pyrolytic products of Thr-Glu increased with the rise of temperature, and the major pyrolytic products were heterocyclic hydrocarbons, aldehydes, carboxylic acids, and ketones. Thr-Glu featured burnt-sweet, toasted, nutty, sweet, floral and creamy aroma. 3) Thr-Glu had a strong DPPH scavenging activity and reducing capacity, and was a potential antioxidant.

     

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