Synthesis, pyrolysis and its moisture retentivity of 2-L-alanine-2-deoxy-D-glucose

Authors

LU Changtong, Technology Center of China Tobacco Henan Industrial Co., Ltd., Zhengzhou, Henan 450000, China
ZHAO Yongzhen, Technology Center of China Tobacco Henan Industrial Co., Ltd., Zhengzhou, Henan 450000, China
WANG Hongwei, Technology Center of China Tobacco Henan Industrial Co., Ltd., Zhengzhou, Henan 450000, China
GU Liang, Technology Center of China Tobacco Henan Industrial Co., Ltd., Zhengzhou, Henan 450000, China
LI Yaoguang, Technology Center of China Tobacco Henan Industrial Co., Ltd., Zhengzhou, Henan 450000, China
WANG Pengfei, Technology Center of China Tobacco Henan Industrial Co., Ltd., Zhengzhou, Henan 450000, China
LI Hongtao, Technology Center of China Tobacco Henan Industrial Co., Ltd., Zhengzhou, Henan 450000, China
ZHAO Zhiwei, Technology Center of China Tobacco Henan Industrial Co., Ltd., Zhengzhou, Henan 450000, China
SUN Zhitao, Technology Center of China Tobacco Henan Industrial Co., Ltd., Zhengzhou, Henan 450000, China
DUAN Kun, Technology Center of China Tobacco Henan Industrial Co., Ltd., Zhengzhou, Henan 450000, China

Abstract

2-L-Alanine-2-deoxy-D-Glucose(Ala-Glu) was synthesized from L-Alanine(Ala) and D-fructose(Fru) through condensation dehydration and rearrangement reaction. The thermal weight loss and pyrolysis properties of Ala-Glu were investigated by thermogravimetry-derivative thermogravimetry(TG-DTG) and pyrolysis gas chromatography-mass spectroscopy(Py-GC/MS). Using the moisture content (d.b.) of tobacco shred as an indicator, the physical moisture retention properties of Ala-Glu were measured. The effect of these compounds on sensory comfort of cigarette was investigated. The results show that: ① The synthetic product was the target compound; ② The primary pyrolysis temperature of Ala-Glu was 178.9 ℃, and the thermal mass loss reached about 90% at 800 ℃. The number of pyrolytic products of the target compound increased with the rise of temperature, and the major pyrolytic products of Ala-Glu were including pyrazine, pyridine, pyrrole, furan, pyrone; ③ Moisture retention of Ala-Glu was better than that of propylene glycol and glycerin; ④ Ala-Glu can make mainstream cigarette smoke mellow and full, reduce irritation and miscellaneous odor, and have a role to enhance on cigarette sensory comfort.

Publication Date

4-28-2018

First Page

65

Last Page

70

DOI

10.13652/j.issn.1003-5788.2018.04.012

Recommended Citation

Changtong, LU; Yongzhen, ZHAO; Hongwei, WANG; Liang, GU; Yaoguang, LI; Pengfei, WANG; Hongtao, LI; Zhiwei, ZHAO; Zhitao, SUN; and Kun, DUAN (2018) "Synthesis, pyrolysis and its moisture retentivity of 2-L-alanine-2-deoxy-D-glucose," Food and Machinery: Vol. 34: Iss. 4, Article 12.
DOI: 10.13652/j.issn.1003-5788.2018.04.012
Available at: https://www.ifoodmm.cn/journal/vol34/iss4/12

References

[1] 李亚丽, 刘晓徐, 郑培华, 等. 美拉德反应研究进展[J]. 食品科技, 2012, 37(9): 82-87.
[2] 肖怀秋, 李玉珍, 林亲录. 美拉德反应及其在食品风味中的应用研究[J]. 中国食品添加剂, 2005(2): 27-30.
[3] 付莉, 李铁刚. 简述美拉德反应[J]. 食品科技, 2006, 31(12): 9-11.
[4] TANJA M W, CHRISTIANE K. The Amadori rearrangement as key reaction for the synthesis of neoglycoconjugates[J]. Carbohydrate Research, 2008, 30(343): 2 057-2 066.
[5] STEFANOWICH P, KAPCZYNSKA K, KLUCZYK K, et al. A new procedure for the synthesis of peptide-derived Amadori products on a solid support[J]. Tetrahedron Letters, 2007, 48(6): 967-969.
[6] SANZ M L, CASTILLO M D, CORZO N, et al. Formation of Amadori compounds in dehydrated fruits[J]. Journal of Agricultural and Food Chemistry, 2001, 49(11): 5 228-5 231.
[7] DAVIDEK T, KRAEHENHUBEL K, DEVAUD S, et al. Analysis of Amadori compounds by high-performance cation exchange chromatography coupled to tandem mass spectrometry[J]. Analytical Chemistry, 2005, 77(1): 140-147.
[8] YUAN Heng, SUN Lin-juan, WANG Jun. The simultaneous analysis of amadori and heyns compounds in dried fruits by high performance liquid chromatography tandem mass spectrometry[J]. Food Analytical Methods, 2017, 10(4): 1 097-1 105.
[9] HUYGHUS-DESPOINTES A, YAYLAYAN V A, KEYHANI A. Pyrolysis/GC/MS Analysis of 1-[(2′-carboxyl) pyrrolidinyl]-1-deoxy-D-fructose (ProlineAmadori Compound)[J]. Journal of Agricultural and Food Chemistry, 1994, 42(11): 2 519-2 524.
[10] YAYLAYAN V A, HUYGHUES-DESPINTES A. Identifica-tion of per-O-(trimethylsilyl) derivatives of aldoses generated from thermal decomposition of N-(1-deoxy-D-fructopyranos-1-yl) proline: Reversibility of the Amadorirearrangement[J]. Carbohydrate Research, 1996, 286: 179-187.
[11] KOCH J C. Analysis of FruHis, a potential bioactive Amadori compound in processed tomatoes[D]. Columbus: The Ohio State University, 2014: 38-55.
[12] HA K S, JO S H, KANG B H, et al. In vitro and in vivo antihyperglycemic effect of 2 amadori rearrangement compounds, arginyl-fructose and arginyl-fructosyl-glucose[J]. Journal of Food Science, 2011, 76(8): H188-H193.
[13] UMEMURA K, KAWAI S. Modification of chitosan by the Maillard reaction using cellulose model compounds[J]. Carboltydrate Polymers, 2007, 68: 242-248.
[14] 何保江, 刘强, 赵明月, 等. 烟草保润性能测试方法[J]. 烟草科技, 2009(2): 25-28.
[15] 济南市轻工研究所. 合成食用香料手册[M]. 北京: 中国轻工业出版社, 1985: 302-765.
[16] 李明, 王培义, 田怀香. 香精香料应用基础[M]. 北京: 中国纺织出版社, 2010: 75-270.
[17] BAN J O, HWANG I G, KIM T M, et al. Anti-proliferate and pro-apoptotic effects of 2, 3-dihydro-3,5-dihydroxy-6-methyl-4H-pyranone through inactivation of NF-B in human colon cancer cells[J]. Archives of Pharmacal Research, 2007, 30(11): 1 455-1 463.
[18] YOSHIKI Y, OKUBO K. Active oxygen scavenging activity of DDMP(2, 3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one) saponin in soybean seed[J]. Bioscience Biotechnology and Biochemistry, 1995, 58(8): 1 556-1 557.
[19] 毛多斌, 鞠华波, 牟定荣, 等. 1-L-亮氨酸-1-脱氧-D-果糖和1-L-异亮氨酸-1-脱氧-D-果糖的热裂解分析[J]. 中国烟草学报, 2010, 16(6): 1-9.
[20] YAYLAYAN V A, MANDEVILLE S. Stereochemical control of maltol formation in Maillard reaction[J]. Journal of Agricultural and Food Chemistry, 1994, 42(3): 771-775.
[21] AMEUR L A, REGA B. The fate of furfurals and other volatile markers during the baking process of a model cookie[J]. Food Chemistry, 2008, 111(3): 758-763.
[22] KIM M O, BALTES W. On the role of 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4 (H)-pyran-4-one in the Maillard reaction[J]. Journal of Agricultural and Food Chemistry, 1996, 44(1): 282-289.
[23] ALEXIS H D, VAROUJAN A Y, KEYHANI A. Pyrolysis/GC/MS analysis of proline Amadori compounds[J]. Journal of Agricultural and Food Chemistry, 1994, 42(2): 2 519-2 524.
[24] PAINE J B, PITJAWALLA Y B, NAWORAL J D. Carbohydrate pyrolysis mechanisms from isotopic labeling: Part 4. The pyrolysis of D-glucose: The formation of furans[J]. Journal of Analytical and Applied Pyrolysis, 2008, 83(1): 37-63.
[25] 毛多斌, 马宇平, 梅业安. 卷烟配方和香精香料[M]. 北京: 化学工业出版社, 2001: 100-120.
[26] PAIN J B, PITHAWALLA Y B, NAWORAL J D. Carbohydrate pyrolysis mechanisms from isotopic labeling Part 3: The pyrolysis of D-glucose: Formation of C3 and C4 carbonyl compounds and a cyclopentendion isomer by eletrocyclic fragmentation mechanisms[J]. Journal of Agricultural and Applied Pyrolysis, 2008, 82(1): 42-69.