Study on Synthesis, Pyrolysis and Antioxidation of Ethyl Maltol Succinate Diester

doi:10.6023/cjoc202311011

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (5): 1526-1534.DOI: 10.6023/cjoc202311011 Previous Articles Next Articles

ARTICLES

乙基麦芽酚丁二酸双酯的合成、热解及抗氧化研究

于兆锦^a,†, 张展^b,†, 王海洋^a, 王波^c, 付光明^a, 张瑛^a, 杨晓朋^a^,^*(), 董爱君^c^,^*(), 姬小明^a^,^*()

a 河南农业大学烟草学院河南省香精香料与调香工程技术研究中心郑州 450046
b 河南中烟工业有限责任公司技术中心郑州 450000
c 湖北中烟工业有限责任公司技术中心武汉 430030

收稿日期:2023-11-09 修回日期:2024-01-18 发布日期:2024-02-07
作者简介:
†共同第一作者
基金资助:
湖北中烟工业有限责任公司(2021JSXL3JS2C032); 河南农业大学博士科研资金(30501420)

Study on Synthesis, Pyrolysis and Antioxidation of Ethyl Maltol Succinate Diester

Zhaojin Yu^a,†, Zhan Zhang^b,†, Haiyang Wang^a, Bo Wang^c, Guangming Fu^a, Ying Zhang^a, Xiaopeng Yang^a(), Aijun Dong^c(), Xiaoming Ji^a()

a Flavors and Fragrance Engineering & Technology Research Center of Henan Province, College of Tobacco Science, Henan Agricultural University, Zhengzhou 450046
b Technology Center, China Tobacco Henan Industrial Co., Ltd., Zhengzhou 450000
c Technology Center, China Tobacco Hubei Industrial Co., Ltd., Wuhan 430030

Received:2023-11-09 Revised:2024-01-18 Published:2024-02-07
Contact: *E-mail: xiaopengyang@henau.edu.cn; 19281034@qq.com; xiaomingji@henau.edu.cn
About author:
†These authors contributed equally to this work.
Supported by:
China Tobacco Hubei Industrial Co., Ltd.(2021JSXL3JS2C032); Doctoral Scientific Research Fund of Henan Agricultural University(30501420)

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Abstract

In order to develop burnt sweet fragrance compounds with stability. In this paper, nine ethyl maltol succinate diester compounds 2-ethyl-4-oxo-4H-pyran-3-yl phenethyl succinate (5a)~2-ethyl-4-oxo-4H-pyran-3-yl (2-methylallyl) succinate (5i) were obtained by a two-step method using succinic anhydride, flavor alcohols and ethyl maltol as raw materials, and were subjected to structural characterization, thermal stability and in vitro antioxidant studies. The results showed that compounds 5a~5i possessed a burnt sweet fragrance as well as other fragrances. Compounds 5a and cinnamyl (2-ethyl-4-oxo- 4H-pyran-3-yl) succinate (5b) had a highest weight loss at a temperature higher than that of raw materials, and a large amount of substances such as ethyl maltol and flavor alcohols were produced during pyrolysis. The 1,1-diphenyl-2-picrylhydrazyl (DPPH) and •OH scavenging abilities of compound 5a are higher than those of compounds 5b~5i and ethyl maltol. In summary, compound 5a has a burnt sweet fragrance, and exhibits high thermal stability and in vitro antioxidant capacity. This work may provide a new method to improve the stability of spices and expand their multifunctional application.

Key words: ethyl maltol, esterification, pyrolysis, antioxidant, flavors and fragrances

Cite this article

Zhaojin Yu, Zhan Zhang, Haiyang Wang, Bo Wang, Guangming Fu, Ying Zhang, Xiaopeng Yang, Aijun Dong, Xiaoming Ji. Study on Synthesis, Pyrolysis and Antioxidation of Ethyl Maltol Succinate Diester[J]. Chinese Journal of Organic Chemistry, 2024, 44(5): 1526-1534.

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References 22

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Yield/% of 3	Yield/% of 5	Odor description of 5
83	46	Burnt sweet fragrance, rose fragrance, herb fragrance
80	55	Burnt sweet fragrance, alco- hol fragrance, bean aroma, herb fragrance
85	56	Burnt sweet fragrance, frui- ty flavour, nut fragrance
81	44	Burnt sweet fragrance, frui- ty flavour, nut fragrance
87	57	Burnt sweet fragrance, alco- hol fragrance, fruity flavour
87	62	Sour flavor, burnt sweet fragrance, spicy fragrance
86	46	Burnt sweet fragrance, sour flavor, fat wax fragrance
82	50	Burnt sweet fragrance, ba- ked fragrance, spicy frag- rance, fat wax fragrance
85	49	Burnt sweet fragrance, gra- ss fragrance, fruity flavour, sour flavor

Yield/% of 3	Yield/% of 5	Odor description of 5
83	46	Burnt sweet fragrance, rose fragrance, herb fragrance
80	55	Burnt sweet fragrance, alco- hol fragrance, bean aroma, herb fragrance
85	56	Burnt sweet fragrance, frui- ty flavour, nut fragrance
81	44	Burnt sweet fragrance, frui- ty flavour, nut fragrance
87	57	Burnt sweet fragrance, alco- hol fragrance, fruity flavour
87	62	Sour flavor, burnt sweet fragrance, spicy fragrance
86	46	Burnt sweet fragrance, sour flavor, fat wax fragrance
82	50	Burnt sweet fragrance, ba- ked fragrance, spicy frag- rance, fat wax fragrance
85	49	Burnt sweet fragrance, gra- ss fragrance, fruity flavour, sour flavor

Peak	Retention time/min	Pyrolysis product	Structure	Match	Relative content/%
Peak	Retention time/min	Pyrolysis product	Structure	Match	300 ℃	350 ℃	400 ℃
Compound 5a
1	9.12	Succinic anhydride		91	0.10	0.56	2.15
2	11.78	Phenethyl alcohol		94	6.64	10.42	12.40
3	15.23	Ethyl maltol		94	79.88	82.98	83.47
4	31.58	4-((2-Ethyl-4-oxo-4H-pyran-3-yl)oxy)- 4-oxobutanoic acid		90	1.53	0.32	—
Compound 5b
1	16.36	Ethyl maltol		94	77.81	79.98	81.41
2	19.39	Cinnamyl alcohol		96	11.10	12.30	15.11
3	31.51	4-((2-Ethyl-4-oxo-4H-pyran-3-yl)oxy)- 4-oxobutanoic acid		91	1.17	0.92	0.09
4	36.15	4-(Cinnamyloxy)-4-oxobutanoic acid		98	2.97	0.09	—

Peak	Retention time/min	Pyrolysis product	Structure	Match	Relative content/%
Peak	Retention time/min	Pyrolysis product	Structure	Match	300 ℃	350 ℃	400 ℃
Compound 5a
1	9.12	Succinic anhydride		91	0.10	0.56	2.15
2	11.78	Phenethyl alcohol		94	6.64	10.42	12.40
3	15.23	Ethyl maltol		94	79.88	82.98	83.47
4	31.58	4-((2-Ethyl-4-oxo-4H-pyran-3-yl)oxy)- 4-oxobutanoic acid		90	1.53	0.32	—
Compound 5b
1	16.36	Ethyl maltol		94	77.81	79.98	81.41
2	19.39	Cinnamyl alcohol		96	11.10	12.30	15.11
3	31.51	4-((2-Ethyl-4-oxo-4H-pyran-3-yl)oxy)- 4-oxobutanoic acid		91	1.17	0.92	0.09
4	36.15	4-(Cinnamyloxy)-4-oxobutanoic acid		98	2.97	0.09	—

乙基麦芽酚丁二酸双酯的合成、热解及抗氧化研究

Study on Synthesis, Pyrolysis and Antioxidation of Ethyl Maltol Succinate Diester

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