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Determination of Energy Content of “Zero-Sugar” Artificial Sweeteners via Bomb Calorimetry and Theoretical Calculations 通过炸弹量热法和理论计算确定 "零糖 "人造甜味剂的能量含量
IF 3 3区 教育学 Q1 Social Sciences Pub Date : 2024-04-29 DOI: 10.1021/acs.jchemed.3c00691
Andrea D. Merry, John A. Means* and Tim E. Hall, 

In this laboratory activity, students were tasked with determining the heat of combustion for each of three common sugar substitutes: saccharin, aspartame, and sucralose. The heats of combustion were determined via three different methods: bomb calorimetry, heats of formation derived from semiempirical calculations, and tabulated average bond energies. Students were then tasked with writing a single laboratory report that combined and compared the results obtained from all three techniques. This gave them an experience more representative of writing a journal article than traditional laboratory reports that typically focused on outcomes from a single laboratory technique. The results from the two theoretical methods were compared via percent error and error analysis with the experimentally determined results. The comparison of the experimentally determined heats of combustion and the semiempirically derived heats of combustion all yielded errors of less than about 20%, while the comparisons of the experimentally determined heats of combustion and the bond-energy-derived heats of combustion yielded errors of 20–50%. In addition to the experience with writing the more complex laboratory report, students gained experience working with process hazards that involved elevated and changing gas pressure, performing computational calculations, and applying skills learned in previous chemistry courses. This laboratory activity is presented so that it will allow adoption by others, including student handouts for the bomb calorimetry and theoretical determination activities and notes for the instructor.

在这项实验活动中,学生们的任务是分别测定糖精、阿斯巴甜和蔗糖素(三氯蔗糖)这三种常见代糖的燃烧热。燃烧热是通过三种不同的方法测定的:炸弹量热法、半经验计算得出的形成热和制表平均键能。然后,学生们被要求撰写一份实验报告,综合并比较从所有三种技术中获得的结果。与通常只关注单一实验技术结果的传统实验报告相比,这给了学生更多撰写期刊论文的经验。通过误差百分比和误差分析,将两种理论方法得出的结果与实验测定的结果进行了比较。实验测定的燃烧热与半经验推导的燃烧热的比较结果误差均小于 20%,而实验测定的燃烧热与键能推导的燃烧热的比较结果误差为 20-50%。除了撰写更复杂的实验报告的经验外,学生们还获得了处理涉及升高和改变气体压强的危险过程、进行计算以及应用以前化学课程中学到的技能的经验。本实验活动的介绍便于其他人采用,包括炸弹量热和理论测定活动的学生讲义以及教师笔记。
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引用次数: 0
Visualization and Quantification of Sodium Chloride Formed during the Titration of Hydrochloric Acid with Sodium Hydroxide: An Extension to the Learning Outcomes During Acid–Base Titrations 盐酸与氢氧化钠滴定过程中形成的氯化钠的可视化和定量:扩展酸碱滴定过程中的学习成果
IF 3 3区 教育学 Q1 Social Sciences Pub Date : 2024-04-29 DOI: 10.1021/acs.jchemed.4c00177
Sobiya Khursheed, Zahid Hussain, Aasiya Gul, Muhammad Aabid Shah, Afzal Hussain, Mohamed F. Alajmi, Prince Firdoos Iqbal, Nusrat Rashid, Rayees Ahmad Shiekh, Jahangir Ahmad Rather, Akhtar Hussain Malik and Waseem A. Wani*, 

Titration is an important experimental skill that every chemistry educator and learner must master. Titration is often the method of choice in the science laboratory courses in secondary and postsecondary schools. During acid–base titration, chemistry learners are always told about salt formation. However, a practical visualization of the salt formed is not actually done. The evasion from the visualization of salt formed in acid–base titrations may prevent students from learning some key concepts of isolation, purification, quantification, and identification of salts. In view of the importance of titrations and salt formation therein, we demonstrate the titration of sodium hydroxide with hydrochloric acid with special focus on the visualization of the formation, isolation, purification, and identification of sodium chloride formed during the titration. The identification of sodium chloride was done by solubility studies and silver nitrate and flame tests. The approach serves as a unique and effective pedagogical method for understanding acid–base titrations and formation, isolation, purification, quantification, and identification of salts formed during acid–base neutralization reactions.

滴定是每个化学教育者和学习者都必须掌握的重要实验技能。滴定法通常是中学和中学后科学实验课程的首选方法。在酸碱滴定过程中,化学学习者总是被告知盐的形成。然而,实际上并没有对形成的盐进行实际的直观观察。回避酸碱滴定中盐形成的可视化可能会妨碍学生学习盐的分离、纯化、定量和鉴定等一些关键概念。鉴于滴定和其中盐形成的重要性,我们演示了氢氧化钠与盐酸的滴定,特别强调了滴定过程中氯化钠形成、分离、纯化和鉴定的可视化。氯化钠的鉴定是通过溶解度研究、硝酸银和火焰试验完成的。该方法是了解酸碱滴定以及酸碱中和反应过程中形成的盐的形成、分离、纯化、定量和鉴定的一种独特而有效的教学方法。
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引用次数: 0
Aqueous and Solid Phase Synthesis of [Ni(Me3en)(acac)]BPh4 and its Solvatochromic Properties: A Laboratory Experiment for First-Year Undergraduates Ni(Me3en)(acac)]BPh4的水相和固相合成及其溶色性:面向一年级本科生的实验室实验
IF 3 3区 教育学 Q1 Social Sciences Pub Date : 2024-04-25 DOI: 10.1021/acs.jchemed.3c01273
Zhiqiang Dong, Bo Yi, Xin Chen, Yechao Chen, Ming-Qiang Qi and Yanping Ren, 

A laboratory experiment that involves the aqueous and solid phase synthesis, characterization, and solvatochromic properties exploration of red complex [Ni(Mei3en)(acac)]BPh4 has been developed for first-year undergraduates in the College of Chemistry and Chemical Engineering at Xiamen University. In contrast to previously reported synthesis methods (Fukuda, Y. Studies on mixed chelates─II Mixed nickel(II) chelates with N,N,N′,N′-tetramethylethylenediamine and β-diketones. J. Inorg. Nucl. Chem. 1972, 34, 2315–2328; Funasako, Y. Thermochromic and solvatochromic Nafion films incorporating cationic metal-chelate complexes. Chem. Comm 2013, 49, 4688–4690; Hosokawa, H. Colorimetric Humidity and Solvent Recognition Based on a Cation-Exchange Clay Mineral Incorporating Nickel(II)-Chelate Complexes. Langmuir 2015, 31, 13048–13053; Nguyen, T. N. Studies on Mixed Chelates. VII. Mixed Nickel(II) Chelates Containing N,N′- or N,N-Dialkylethylenediamines and Acetylacetone. Bull. Chem. Soc. Jpn. 1977, 50 (1), 154–157; Wei, X. J. Vis-Spectrum Investigation of Thermo-Solvatochromic Behaviors of a Mixed Diamine and β-Diketonate Ligand Ni(II) Complex in Different Alcoholic Solutions. Acta Phys.-Chim. Sin. 2009, 25 (7), 1449–1454; Inorganic and Analytical ChemistryExperiment Test of The 10th Chinese National Undergraduate ChemistryLaboratory Tournament https://chemlabs.nju.edu.cn/DFS/file/2019/08/26/20190826132901247mmvyr5.pdf?iid=2382 (accessed November 2023).), which using a large amount of organic solvents, the aqueous and solid phase synthesis methods described here are remarkably green, environmentally friendly, high efficiency and highly reproducible, and the complex [Ni(Me3en)(acac)]BPh4 showing a remarkable reversible solvatochromic phenomenon, so this experiment is very suitable as a classroom demonstration for first-year undergraduates in inorganic chemistry or general chemistry. By performing this experiment, students will gain experience in solid phase synthesis, purification, and UV–vis characterization of the complex. In addition, students will gain appreciation of how solvatochromism and thermochromism (in acetone) of the complex Ni(Me3en)(acac)]BPh4 and their mechanisms, and progress in the understanding of the effect of the configuration of a complex on crystal field splitting, and the effect of crystal field splitting on color.

厦门大学化学化工学院为一年级本科生开设了红色络合物[Ni(Mei3en)(acac)]BPh4的水相和固相合成、表征和溶解变色性能探索实验。与之前报道的合成方法不同(Fukuda, Y. Studies on mixed chelates─II Mixed nickel(II) chelates with N,N,N′,N′-tetramethylethylenediamine and β-diketones. J. Inorg.Nucl.Chem.1972, 34, 2315-2328; Funasako, Y. Thermochromic and solvatochromic Nafion films incorporating cationic metal-chelate complexes. Chem.Hosokawa, H. Colorimetric Humidity and Solvent Recognition Based on a Cation-Exchange Clay Mineral Incorporating Nickel(II)-Chelate Complexes. Langmuir 2015, 31, 13048-13053; Nguyen, T. N. Studies on Mixed Chelates.VII.含有 N,N′- 或 N,N-二烷基乙二胺和乙酰丙酮的混合镍(II)螯合物。 Bull.Chem.Soc. Jpn.1977, 50 (1), 154-157; Wei, X. J. Vis-Spectrum Investigation of Thermo-Solvatochromic Behaviors of a Mixed Diamine and β-Diketonate Ligand Ni(II) Complex in Different Alcoholic Solutions. Acta Phys.-Chim.Sin.2009, 25 (7), 1449-1454; Inorganic and Analytical ChemistryExperiment Test of the 第十届全国大学生化学实验竞赛 https://chemlabs.nju.edu.cn/DFS/file/2019/08/26/20190826132901247mmvyr5.pdf?iid=2382 (accessed November 2023).本实验采用的水相和固相合成方法具有绿色、环保、高效、重现性强等特点,且配合物[Ni(Me3en)(acac)]BPh4显示出显著的可逆溶解变色现象,非常适合作为无机化学或普通化学专业一年级本科生的课堂演示实验。通过本实验,学生将获得复合物的固相合成、纯化和紫外-可见表征方面的经验。此外,学生还将了解络合物 Ni(Me3en)(acac)]BPh4 的溶解变色和热变色(在丙酮中)及其机理,并加深理解络合物构型对晶场分裂的影响以及晶场分裂对颜色的影响。
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引用次数: 0
ChatGPT Convincingly Explains Organic Chemistry Reaction Mechanisms Slightly Inaccurately with High Levels of Explanation Sophistication ChatGPT 令人信服地解释了有机化学反应机理,但解释略有不准确,解释复杂程度较高
IF 3 3区 教育学 Q1 Social Sciences Pub Date : 2024-04-25 DOI: 10.1021/acs.jchemed.4c00235
Brandon J. Yik*,  and , Amber J. Dood, 

The chemistry education research community values and emphasizes the role of constructing explanations and mechanistic reasoning to support students’ learning of organic chemistry. Emerging large language model (LLM) and generative artificial intelligence (GAI) technologies are uniquely equipped to advance the teaching and learning of chemistry. GAI-based chatbots, such as ChatGPT, have the potential to help students learn mechanistic reasoning through their generated responses. This study investigates the extent to which 255 ChatGPT-generated responses are accurate explanations of 85 different reaction mechanisms and exhibit mechanistic reasoning as categorized by the levels of explanation sophistication framework. The study also explores the effects of prompt engineering on mechanism accuracy and explanation sophistication through three types of prompt cueing. Study findings show that (1) a quarter of responses are fully accurate explanations of reaction mechanisms and the majority contain predominantly accurate explanations of chemical phenomena and identification of nucleophiles and electrophiles, (2) responses exhibit high levels of explanation sophistication, and (3) prompt engineering plays a significant role in eliciting high levels of explanation sophistication but not mechanism description accuracy. Results are situated in mechanistic reasoning and prompt engineering frameworks with a focus on how these new technologies can be integrated into the chemistry classroom.

化学教育研究界重视并强调建构解释和机理推理在支持学生学习有机化学方面的作用。新兴的大型语言模型(LLM)和生成人工智能(GAI)技术在推动化学教学方面具有独特的优势。基于 GAI 的聊天机器人,如 ChatGPT,有可能通过生成的回复帮助学生学习机械推理。本研究调查了 255 个 ChatGPT 生成的回复在多大程度上准确解释了 85 种不同的反应机理,并展示了按解释复杂程度框架分类的机理推理。研究还通过三种类型的提示线索,探讨了提示工程对机制准确性和解释复杂性的影响。研究结果表明:(1) 四分之一的答卷完全准确地解释了反应机理,大多数答卷主要准确地解释了化学现象以及亲核物和亲电物的识别;(2) 答卷表现出了高水平的解释复杂性;(3) 提示工程在激发高水平的解释复杂性而非机理描述准确性方面发挥了重要作用。研究结果以机理推理和提示工程框架为基础,重点关注如何将这些新技术融入化学课堂。
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引用次数: 0
The Bohr Radius Activity as a Touchpoint between Chemistry and Mathematics: An Interdisciplinary Collaboration 玻尔半径活动作为化学与数学的接触点:跨学科合作
IF 3 3区 教育学 Q1 Social Sciences Pub Date : 2024-04-24 DOI: 10.1021/acs.jchemed.3c01098
Bret R. Findley*, George L. Ashline, Barbara M. O’Donovan, Mitchell J. Andrea and Dylan R. Wawruck, 

This paper describes an interdisciplinary collaboration of faculty and students from chemistry and mathematics to develop and implement an activity showcasing the relevance of calculus in chemistry to first-semester calculus students. The activity focuses on using calculus optimization methods to maximize the ground-state radial probability distribution function for the hydrogen atom and verify that the Bohr radius gives the desired maximum. Broader goals include encouraging further mathematics study by chemistry students, enhancing awareness of calculus applications to the sciences, preparing students for physical chemistry, and cultivating scientists and mathematicians with broader and deeper backgrounds.

本文介绍了化学和数学系的师生通过跨学科合作,开发并实施了一项活动,向微积分第一学期的学生展示微积分与化学的相关性。活动的重点是使用微积分优化方法最大化氢原子的基态径向概率分布函数,并验证玻尔半径给出了所需的最大值。更广泛的目标包括鼓励化学学生进一步学习数学,提高微积分在科学中应用的意识,为学生学习物理化学做好准备,以及培养具有更广泛和更深厚背景的科学家和数学家。
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引用次数: 0
Advancing Chemical Education in Biotechnology Undergraduates: A Hands-On Laboratory Experiment to Teach the Lateral Flow Immunoassay for Biomarker Detection 推进生物技术本科生的化学教育:用于生物标记物检测的侧流免疫测定教学动手实验
IF 3 3区 教育学 Q1 Social Sciences Pub Date : 2024-04-24 DOI: 10.1021/acs.jchemed.3c01196
Yulieth D. Banguera-Ordoñez, Amadeo Sena-Torralba*, Sara Martorell-Tejedor, Ana Hernanz-Grimalt, Ángel Maquieira and Sergi Morais*, 

The lateral flow immunoassay (LFIA) is a simple and cost-effective rapid diagnostic test designed for the on-site detection of disease biomarkers. In the context of introducing this technique to undergraduate biotechnology students, we propose a comprehensive 5 h laboratory experiment. This experiment covers various aspects, including the bioconjugation of gold nanoparticles with antibodies, optimization of the bioconjugation procedure using the gold aggregation test, lab-scale manufacturing of the test strips, and the detection of the human protein biomarker lactate dehydrogenase as a proof of concept. Several strategies are employed to assess student learning in the context of this laboratory experiment. These strategies include pre-lab and post-lab discussions, a rubric for practical skills, observation and feedback, and a post-lab assessment requiring students to answer three in-depth questions on the material, procedure, and fundamentals covered, concluding with an end-of-lab report. The main goal of this experiment is to highlight the pedagogical potential inherent in utilizing cost-effective and accessible laboratory tools, specifically lateral flow immunoassays. The aim of integrating these methodologies is to provide students with a concrete and experiential understanding of analytical chemistry, biosensing, and nanotechnology, which are continually evolving fields.

侧流免疫分析法(LFIA)是一种简单而经济有效的快速诊断检测方法,专为现场检测疾病生物标志物而设计。为了向生物技术专业的本科生介绍这项技术,我们提出了一个 5 小时的综合实验。该实验涉及多个方面,包括金纳米粒子与抗体的生物共轭、利用金聚集试验优化生物共轭过程、实验室规模的试纸生产,以及作为概念验证的人类蛋白质生物标志物乳酸脱氢酶的检测。本实验室实验采用了多种策略来评估学生的学习情况。这些策略包括实验前和实验后讨论、实践技能评分标准、观察和反馈,以及实验后评估,要求学生回答有关材料、程序和基础知识的三个深入问题,最后提交一份实验结束报告。本实验的主要目的是强调利用具有成本效益且易于获得的实验室工具(特别是侧向流动免疫分析法)所固有的教学潜力。整合这些方法的目的是让学生对分析化学、生物传感和纳米技术这些不断发展的领域有一个具体的体验式理解。
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引用次数: 0
Amino-structure: A Card Game for Amino Acids Learning in Biochemistry Classes 氨基酸结构:在生物化学课堂上学习氨基酸的纸牌游戏
IF 3 3区 教育学 Q1 Social Sciences Pub Date : 2024-04-24 DOI: 10.1021/acs.jchemed.3c01209
Paola Gómez Buitrago*, Hendrys Tobar-Muñoz and Danny Arteaga*, 

In response to the great challenge that the teaching of basic sciences currently entails in the new generations of young people and seeking to awaken the interest of our students in chemistry and its areas of influence, we developed an innovative card game named “Amino-structure” which served as a key tool to implement an active learning strategy in the study of the 20 amino acids in biochemistry classes. In this paper, we describe the results of this proposal, evaluated after the completion of three (3) phases: presentation of the game, implementation, and validation. 201 university students, from academic programs in science and engineering, participated in this fun activity, and through them, we evaluated the effectiveness of this pedagogical strategy which was carried out during their studies in the above-mentioned disciplines. The analysis of the results regarding parameters such as usability, playability, and satisfaction with the game showed a high degree of acceptance by most of the participants. In the final part of our study, through a quiz with two open-ended questions, we evaluated the learning objective. The analysis of the results, based on the responses of the participants, showed that 82.1% passed the knowledge test, which suggests that a high percentage of approval of the game as a pedagogical, guiding, and motivating tool was obtained.

为了应对目前基础科学教学对新一代年轻人提出的巨大挑战,并唤起学生对化学及其影响领域的兴趣,我们开发了一款名为 "氨基酸结构 "的创新纸牌游戏,作为在生物化学课堂上学习 20 种氨基酸时实施主动学习策略的重要工具。在本文中,我们介绍了这一建议的成果,并在完成游戏介绍、实施和验证三(3)个阶段后对其进行了评估。来自理工科专业的 201 名大学生参与了这一有趣的活动,通过他们,我们评估了这一教学策略在上述学科学习期间的有效性。对游戏的可用性、可玩性和满意度等参数的分析结果表明,大多数参与者对游戏的接受程度很高。在研究的最后一部分,我们通过两个开放式问题的测验对学习目标进行了评估。根据参与者的回答对结果进行的分析表明,82.1% 的人通过了知识测试,这表明该游戏作为一种教学、指导和激励工具得到了很高比例的认可。
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引用次数: 0
Survey of Instrumentation Use in Industry: What Does Industry Want New Chemists to Know? 工业仪器使用情况调查:工业界希望新化学家了解什么?
IF 3 3区 教育学 Q1 Social Sciences Pub Date : 2024-04-23 DOI: 10.1021/acs.jchemed.3c00990
David Hamilton, Alyssa Castillo and Molly B. Atkinson*, 

Instrumentation plays a vital role in almost every area of chemistry. As such, it is imperative that the undergraduate curriculum is designed to allow students to have opportunities to use a variety of instruments to best prepare them for careers in chemistry. Previous work has provided evidence of the types of instruments students use in undergraduate chemistry laboratories. However, little is known about employers’ expectations for specific instrument knowledge as chemistry students enter industry. With most chemistry undergraduate students entering careers in chemical industry upon graduation, the aim of this research was to determine the frequency of occurrence and value of specific instruments used in industry to help better align undergraduate chemistry laboratory curricula with the needs of industry. Additional data was also collected on the most important skills needed to succeed in industry, as well as the perceptions of the undergraduate courses where these skills are most effectively acquired. Results emphasize the need to improve how undergraduate students are taught instrumentation-specific skills and provide evidence on the best avenues in which to begin curricular improvement.

仪器在化学的几乎每个领域都起着至关重要的作用。因此,本科课程的设计必须让学生有机会使用各种仪器,为他们从事化学工作做好最充分的准备。以前的研究已经提供了学生在本科化学实验室中使用仪器类型的证据。然而,对于雇主在化学专业学生进入工业领域时对具体仪器知识的期望却知之甚少。由于大多数化学本科生毕业后都会进入化工行业工作,本研究旨在确定特定仪器在行业中的使用频率和价值,以帮助本科生化学实验室课程更好地适应行业需求。此外,还收集了有关在行业中取得成功所需的最重要技能的其他数据,以及对最有效地掌握这些技能的本科课程的看法。研究结果表明,有必要改进对本科生传授仪器特定技能的方式,并为开始改进课程提供了最佳途径。
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引用次数: 0
The Recycling of Lithium-Ion Batteries LiCoO2 Cathode: Balancing Sustainability and Efficiency 钴酸锂阴极锂离子电池的回收:兼顾可持续性和效率
IF 3 3区 教育学 Q1 Social Sciences Pub Date : 2024-04-23 DOI: 10.1021/acs.jchemed.4c00204
Eleonora Carena, Riccardo Morina, Gabriele Brugnetti, Nicolò Pianta, Simona Olga Binetti and Chiara Ferrara*, 

We are all users of lithium-ion batteries (LIBs), the electrochemical energy storage devices that revolutionized our life, making the diffusion of portable and wearable devices possible and now driving the switch from a combustion engine to electric vehicles in the transportation sector. These positive trends are however leading to two whiplash effects: the issue related to management of LIBs when they reach the end of their life (EoL-LIBs) and the supply of the critical raw materials (CRMs) needed to produce the essential LIBs’ components. Recycling of EoL-LIBs is the answer to these two problems, addressing the aspects of waste management while providing a secondary source of CRMs needed to produce new LIBs, in a closed-loop circular economy scheme. The proposed laboratory activity is specifically focused on the recycling of LiCoO2, the most diffused cathode material and also the one containing the highest amount of CRMs. The students will be called to analyze the degradation procedure through acidic leaching, comparing the method today mostly exploited at industrial level (using inorganic acid) and the method recently proposed in the scientific literature (exploiting organic acids). Students will be called to consider not only quantitative chemical indicators (yields of degradation and recovery of CRMs) but also the cost, safety, and disposal of the procedure. The aim of this experience is to drive the students to critically consider all aspects related to sustainability, to present them the tools to quantitatively assess it, and to create awareness regarding a technology involved in our everyday life.

我们都是锂离子电池(LIB)的用户,这种电化学储能设备彻底改变了我们的生活,使便携式和可穿戴设备的普及成为可能,现在又推动了交通领域从内燃机向电动汽车的转变。然而,这些积极的趋势也带来了两方面的影响:一是锂电池寿命到期后的管理问题,二是生产锂电池重要组件所需的关键原材料(CRM)的供应问题。EoL-LIBs 的回收利用可以解决这两个问题,在闭环循环经济计划中,既解决了废物管理问题,又提供了生产新 LIBs 所需的二次 CRMs 来源。拟议的实验活动特别关注钴酸锂的回收利用,钴酸锂是扩散性最强的阴极材料,也是含有最多有证材料的材料。将要求学生分析通过酸性浸出的降解过程,比较目前在工业层面主要使用的方法(使用无机酸)和最近在科学文献中提出的方法(使用有机酸)。学生们不仅要考虑定量化学指标(降解率和有证可循物质回收率),还要考虑该过程的成本、安全性和处置问题。这次体验的目的是促使学生批判性地考虑与可持续发展有关的各个方面,向他们提供定量评估的工具,并培养他们对日常生活中所涉及的技术的认识。
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引用次数: 0
Efficient and Simple Extraction Protocol for Triterpenic Acids from Apples 从苹果中提取三萜酸的高效简便提取方案
IF 3 3区 教育学 Q1 Social Sciences Pub Date : 2024-04-22 DOI: 10.1021/acs.jchemed.3c01328
Michelle Wiebel, Kathrin Bensberg, Luca Wende, Rebecca Grandrath, Kathrin Plitzko, Claudia Bohrmann-Linde, Stefan F. Kirsch and Nils Helge Schebb*, 

Triterpenic acids (TA), a class of triterpenoids, are widely distributed as secondary metabolites in plants. They have a pentacyclic structure and show high structural diversity. In this work, a simple but efficient method for extraction and detection of TA derivatives from apple peels is described. The method is technically straightforward and robust and can be implemented in both undergraduate laboratories and science classes or projects in school: Apple peels are (i) extracted with ethyl acetate, (ii) degreased with cyclohexane, and (iii) reconstituted in ethanol. Yields of about 2.1 g of extract/100 g of dry weight apple peel were obtained, which consisted of >70% TA (56% ursolic acid (UA), 10% oleanolic acid (OA)). The TA pattern can be evaluated by thin layer chromatography (TLC) using simple detection with a KMnO4 solution. The separation of the different TA derivatives on normal phase TLC plates enables learning how the chemical structure affects the chromatographic separation. The whole procedure requires 3–4 h without the drying steps. The TA extraction represents suitable content for student education since they learn and discuss natural products and secondary plant metabolites. The performance of an extraction, purification of natural products, and observation of chromatographic separation and detection are also learned in this method. Using this simple procedure, up to 1 g/100 g of dry weight UA can be generated from apple peels. While only apple peel is used for the experiment, the rest of the apple fruit was eaten by the students. Thus, the experiment itself is a demonstration of how side streams of food production can be used as a source for chemical compounds.

三萜酸(TA)是一类三萜类化合物,广泛分布于植物中的次级代谢产物。它们具有五环结构,并显示出高度的结构多样性。本研究介绍了一种从苹果皮中提取和检测 TA 衍生物的简单而高效的方法。该方法技术简单、稳健,可在本科生实验室、科学课或学校项目中实施:苹果皮(i)用乙酸乙酯提取,(ii)用环己烷脱脂,(iii)在乙醇中重组。提取物的产量约为 2.1 克/100 克苹果皮干重,其中 TA 占 70%(熊果酸(UA)56%,齐墩果酸(OA)10%)。用 KMnO4 溶液进行简单检测,即可通过薄层色谱法(TLC)对 TA 模式进行评估。通过在正相 TLC 板上分离不同的 TA 衍生物,可以了解化学结构对色谱分离的影响。整个过程需要 3-4 小时,不包括干燥步骤。TA 萃取是学生学习和讨论天然产品和植物次生代谢物的合适内容。通过这种方法还可以学习萃取的性能、天然产品的纯化以及色谱分离和检测的观察。使用这种简单的方法,可以从苹果皮中提取出高达 1 克/100 克干重的 UA。虽然实验中只使用了苹果皮,但其余的苹果果实都被学生们吃掉了。因此,该实验本身就展示了如何利用食品生产的副产品作为化合物的来源。
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引用次数: 0
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