Synthesis and pyrolysis of methyl cyclopentenolone succinate diester

IF 2.1 3区 农林科学 Q3 CHEMISTRY, APPLIED Flavour and Fragrance Journal Pub Date : 2023-04-21 DOI:10.1002/ffj.3746
Zhaojin Yu, Tingting Pan, Miao Lai, Yuhang Ji, Xiaopeng Yang, Aijun Dong, Xiaoming Ji
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引用次数: 1

Abstract

To develop a new class of enol diketone esters, succinic acid monoesters were synthesized using the reaction of succinic anhydride with various aromatic alcohols. Subsequently, six types of methyl cyclopentenolone succinate diesters were synthesized using dicyclohexylcarbodiimide (DCC) as the condensation agent and 4-dimethylaminopyridine (DMAP) as the catalyst for the condensation reaction with methyl cyclopentenolone. The target compounds were characterized by nuclear magnetic resonance (1H NMR, 13C NMR), infrared spectroscopy (IR) and high-resolution mass spectrometry (HRMS). The aromas characteristics of esters were evaluated using gas chromatography–mass spectrometry-olfactometer (GC–MS-O). Compounds 5a ~ 5c, which had a strong aroma, were conducted with thermogravimetry-derivative thermogravimetry (TG-DTG) to analyse their heating-stability. Additionally, these compounds were studied by pyrolysis-gas chromatography/mass spectrometry (Py-GC/MS) to analyse their pyrolysis behaviours at 300, 350 and 400°C. Results showed that methyl cyclopentenolone and a large number of small molecular flavouring substances were formed by 5a ~ 5c at the set temperature. The synthesis of methyl cyclopentenolone succinate diester can not only slow down the volatilization of methyl cyclopentenolone and aromatic alcohol, but also effectively enhance the aroma, improve the smoking taste of cigarettes, reduce the irritation and miscellaneous gas of smoking and provide more choices for cigarette flavouring.

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琥珀酸环戊诺酮二酯甲酯的合成与热解
为开发一类新的烯醇二酮酯,以丁二酸酐与多种芳香醇为原料合成了丁二酸单酯。随后,以双环己基碳二亚胺(DCC)为缩合剂,4-二甲氨基吡啶(DMAP)为催化剂,与甲基环戊诺酮进行缩合反应,合成了6种琥珀酸甲基环戊诺酮二酯。通过核磁共振(1H NMR, 13C NMR)、红外光谱(IR)和高分辨率质谱(HRMS)对目标化合物进行了表征。采用气相色谱-质谱-嗅觉法(GC-MS-O)评价了酯类化合物的香气特征。化合物5a ~ 5c具有较强的香气,用热重-导数热重法(TG-DTG)分析了其热稳定性。此外,通过热解-气相色谱/质谱(Py-GC/MS)分析了这些化合物在300、350和400°C下的热解行为。结果表明,在设定温度下,在5a ~ 5c的温度下,甲基环戊烯酮和大量小分子风味物质形成。合成琥珀酸环戊烯酮二酯不仅可以减缓甲基环戊烯酮和芳香醇的挥发,还可以有效增强香气,改善卷烟的吸味,减少吸烟的刺激性和杂气,为卷烟调味提供更多的选择。
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来源期刊
Flavour and Fragrance Journal
Flavour and Fragrance Journal 工程技术-食品科技
CiteScore
6.00
自引率
3.80%
发文量
40
审稿时长
1 months
期刊介绍: Flavour and Fragrance Journal publishes original research articles, reviews and special reports on all aspects of flavour and fragrance. Its high scientific standards and international character is ensured by a strict refereeing system and an editorial team representing the multidisciplinary expertise of our field of research. Because analysis is the matter of many submissions and supports the data used in many other domains, a special attention is placed on the quality of analytical techniques. All natural or synthetic products eliciting or influencing a sensory stimulus related to gustation or olfaction are eligible for publication in the Journal. Eligible as well are the techniques related to their preparation, characterization and safety. This notably involves analytical and sensory analysis, physical chemistry, modeling, microbiology – antimicrobial properties, biology, chemosensory perception and legislation. The overall aim is to produce a journal of the highest quality which provides a scientific forum for academia as well as for industry on all aspects of flavors, fragrances and related materials, and which is valued by readers and contributors alike.
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