Washing crude epoxidized oil is an indispensable step for the removal of residual acetic acid and unreacted hydrogen peroxide after epoxidation. There are many studies on the epoxidation of vegetable oils but there are many discrepancies in the washing process which likely leads to water wastage, excess use of neutralizing agent, and additional processing time. Hence, this study aims to optimize the washing step by analyzing the quality of each washing step and developing a model that can predict the amount of acid removed. Soybean oil (1.5 kg) was epoxidized at 60°C for 5.5 h using Amberlite IR 120H as a heterogeneous catalyst. To determine the optimum water washing level, process parameters such as number of washing cycles (1–5), proportion of epoxidized oil to water volume (1:0.5, 1:1, 1:2, 1:3, 1:4, 1:5), and water temperature (20, 40, and 60°C) were examined. The main responses were the residual acid value and pH of the washed epoxidized oil. Results revealed that 64% of the acid was removed after 5 washing cycles irrespective of the washing water temperature and proportion. In contrast, approximately 57% of the acid was removed in the first two washing cycles. Increasing the temperature of the water affected acid removal; with approximately 54% of acid removed at 20°C compared to 60% at 60°C. Doubling or tripling the amount of water needed above a 1:0.5 ratio did not significantly affect the amount of acid removed. The model developed was significant with a predicted R2 of 96% and a root mean square error (RMSE) of 1.1 when the model was validated at different washing scenarios. Therefore, this study shows that it is possible to significantly reduce the amount of water used and processing time while maintaining resin qualities.
{"title":"Investigating the effect of refining parameters on acetic acid removal and the quality of crude epoxidized soybean oil","authors":"Tosin Oyewole, Niloy Chandra Sarker, Gurjot Dhaliwal, Emily Biggane, Ewumbua Monono","doi":"10.1002/aocs.12866","DOIUrl":"https://doi.org/10.1002/aocs.12866","url":null,"abstract":"Washing crude epoxidized oil is an indispensable step for the removal of residual acetic acid and unreacted hydrogen peroxide after epoxidation. There are many studies on the epoxidation of vegetable oils but there are many discrepancies in the washing process which likely leads to water wastage, excess use of neutralizing agent, and additional processing time. Hence, this study aims to optimize the washing step by analyzing the quality of each washing step and developing a model that can predict the amount of acid removed. Soybean oil (1.5 kg) was epoxidized at 60°C for 5.5 h using Amberlite IR 120H as a heterogeneous catalyst. To determine the optimum water washing level, process parameters such as number of washing cycles (1–5), proportion of epoxidized oil to water volume (1:0.5, 1:1, 1:2, 1:3, 1:4, 1:5), and water temperature (20, 40, and 60°C) were examined. The main responses were the residual acid value and pH of the washed epoxidized oil. Results revealed that 64% of the acid was removed after 5 washing cycles irrespective of the washing water temperature and proportion. In contrast, approximately 57% of the acid was removed in the first two washing cycles. Increasing the temperature of the water affected acid removal; with approximately 54% of acid removed at 20°C compared to 60% at 60°C. Doubling or tripling the amount of water needed above a 1:0.5 ratio did not significantly affect the amount of acid removed. The model developed was significant with a predicted <jats:italic>R</jats:italic><jats:sup>2</jats:sup> of 96% and a root mean square error (RMSE) of 1.1 when the model was validated at different washing scenarios. Therefore, this study shows that it is possible to significantly reduce the amount of water used and processing time while maintaining resin qualities.","PeriodicalId":501405,"journal":{"name":"The Journal of the American Oil Chemists’ Society","volume":"13 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141191611","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Ditte B. Hermund, Louise Kirstein Larsen, Sara Riegels Trangbæk, Quoc‐Khanh Rose‐Marie Therese Madsen, Ann‐Dorit Moltke Sørensen, Jacob Kaya, Charlotte Jacobsen
The content of phenolic compounds in chocolate depends on the processing of the cocoa from bean to bar. The aim of this study was to determine the fate of phenolic compounds and theobromine in cocoa beans during roasting at different temperatures. Based on a screening of 12 cocoa bean sorts, three beans (NM, NCC, and NB) with initial high total phenolic content (TPC) were selected for the roasting trial (100 and 150°C up to 20 min). The concentration of three major flavonoids ((−)‐catechin, (−)‐epicatechin and procyanidin B2) and one methylxanthine (theobromine) were evaluated in both raw and roasted beans. Results showed changes in the concentration of flavonoids and theobromine during roasting. Roasting at 150°C for 15 min was optimal for maintaining high flavonoid levels while reducing theobromine levels. However, sensory evaluation on final product is needed to confirm whether the suggested roasting condition would also result in a final product with pleasant sensory properties.
{"title":"Fate of flavonoids and theobromine in cocoa beans during roasting: Effect of time and temperature","authors":"Ditte B. Hermund, Louise Kirstein Larsen, Sara Riegels Trangbæk, Quoc‐Khanh Rose‐Marie Therese Madsen, Ann‐Dorit Moltke Sørensen, Jacob Kaya, Charlotte Jacobsen","doi":"10.1002/aocs.12853","DOIUrl":"https://doi.org/10.1002/aocs.12853","url":null,"abstract":"The content of phenolic compounds in chocolate depends on the processing of the cocoa from bean to bar. The aim of this study was to determine the fate of phenolic compounds and theobromine in cocoa beans during roasting at different temperatures. Based on a screening of 12 cocoa bean sorts, three beans (NM, NCC, and NB) with initial high total phenolic content (TPC) were selected for the roasting trial (100 and 150°C up to 20 min). The concentration of three major flavonoids ((−)‐catechin, (−)‐epicatechin and procyanidin B2) and one methylxanthine (theobromine) were evaluated in both raw and roasted beans. Results showed changes in the concentration of flavonoids and theobromine during roasting. Roasting at 150°C for 15 min was optimal for maintaining high flavonoid levels while reducing theobromine levels. However, sensory evaluation on final product is needed to confirm whether the suggested roasting condition would also result in a final product with pleasant sensory properties.","PeriodicalId":501405,"journal":{"name":"The Journal of the American Oil Chemists’ Society","volume":"96 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141152748","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Biodiesel (fatty acid methyl esters [FAME]) is a renewable biomass‐based diesel (BBD) fuel made from plant oils, animal fats and waste greases. One of the main disadvantages of biodiesel is its poor oxidative stability, which is caused by the presence of high concentrations of unsaturated FAME. When stored in fuel terminals, vehicle tanks and fuel systems, biodiesel can react with oxygen in ambient air, causing it to degrade, which can adversely affect its viscosity and ignition quality. The shelf‐life (SL) of biodiesel is an important property that defines how long it can be stored at low temperatures. The objective of this work is to develop reliable mathematical models to estimate the SL of biodiesel at T = 25°C (298.15 K). This was done by measuring oxidation induction period with a Rancimat instrument (IPR) at variable temperatures. The data were analyzed by linear regression to determine ln(IPR) as a function of T (Model A) and T−1 (Model B) for canola, palm and soybean oil FAME (CaME, PME and SME), methyl oleate (MeC18:1) and methyl linoleate (MeC18:2). Statistical analysis of the Model A and Model B type equations showed that all inferred equations were good fits of the experimental data (adjusted coefficients of determination, R2 ≥ 0.985). The most dependable results were obtained from extrapolation of Model B type equations to predict the SLB values. For CaME, PME, SME and MeC18:1, SLB = 559.0, 1135, 378.3 and 4515 d were inferred. However, the reliability of SLA (extrapolated from its Model A type equation) and SLB values calculated for MeC18:2 (3.1 and 4.8 d) were questionable as estimates of its SL at 298.15 K.
生物柴油（脂肪酸甲酯 [FAME]）是一种可再生的生物质柴油（BBD）燃料，由植物油、动物脂肪和废油脂制成。生物柴油的主要缺点之一是氧化稳定性差，这是由高浓度的不饱和脂肪酸甲酯造成的。生物柴油储存在燃料终端、车辆油箱和燃料系统中时，会与环境空气中的氧气发生反应，导致生物柴油降解，从而对其粘度和点火质量产生不利影响。生物柴油的保质期（SL）是一项重要特性，它决定了生物柴油在低温条件下可以储存多长时间。这项工作的目的是建立可靠的数学模型，以估算生物柴油在 T = 25°C （298.15 K）时的保质期。具体方法是使用 Rancimat 仪器（IPR）测量不同温度下的氧化诱导期。通过线性回归分析，确定了油菜籽油、棕榈油和大豆油 FAME（CaME、PME 和 SME）、油酸甲酯（MeC18:1）和亚油酸甲酯（MeC18:2）的 ln（IPR）与 T（模型 A）和 T-1（模型 B）的函数关系。对模型 A 和模型 B 型方程的统计分析表明，所有推断方程都很好地拟合了实验数据（调整后的决定系数 R2 ≥ 0.985）。用模型 B 型方程外推预测 SLB 值的结果最为可靠。对于 CaME、PME、SME 和 MeC18:1，分别推断出 SLB = 559.0、1135、378.3 和 4515 d。然而，从 MeC18:2 的 SLA（根据其 A 型方程推断）和 SLB 值（3.1 和 4.8 d）来估计其在 298.15 K 下的 SL 值，其可靠性值得怀疑。
{"title":"Shelf‐life of biodiesel by isothermal oxidation induction period at variable temperatures","authors":"Robert O. Dunn","doi":"10.1002/aocs.12848","DOIUrl":"https://doi.org/10.1002/aocs.12848","url":null,"abstract":"Biodiesel (fatty acid methyl esters [FAME]) is a renewable biomass‐based diesel (BBD) fuel made from plant oils, animal fats and waste greases. One of the main disadvantages of biodiesel is its poor oxidative stability, which is caused by the presence of high concentrations of unsaturated FAME. When stored in fuel terminals, vehicle tanks and fuel systems, biodiesel can react with oxygen in ambient air, causing it to degrade, which can adversely affect its viscosity and ignition quality. The shelf‐life (SL) of biodiesel is an important property that defines how long it can be stored at low temperatures. The objective of this work is to develop reliable mathematical models to estimate the SL of biodiesel at T = 25°C (298.15 K). This was done by measuring oxidation induction period with a Rancimat instrument (IP<jats:sub>R</jats:sub>) at variable temperatures. The data were analyzed by linear regression to determine ln(IP<jats:sub>R</jats:sub>) as a function of T (Model A) and T<jats:sup>−1</jats:sup> (Model B) for canola, palm and soybean oil FAME (CaME, PME and SME), methyl oleate (MeC18:1) and methyl linoleate (MeC18:2). Statistical analysis of the Model A and Model B type equations showed that all inferred equations were good fits of the experimental data (adjusted coefficients of determination, <jats:italic>R</jats:italic><jats:sup>2</jats:sup> ≥ 0.985). The most dependable results were obtained from extrapolation of Model B type equations to predict the SL<jats:sup>B</jats:sup> values. For CaME, PME, SME and MeC18:1, SL<jats:sup>B</jats:sup> = 559.0, 1135, 378.3 and 4515 d were inferred. However, the reliability of SL<jats:sup>A</jats:sup> (extrapolated from its Model A type equation) and SL<jats:sup>B</jats:sup> values calculated for MeC18:2 (3.1 and 4.8 d) were questionable as estimates of its SL at 298.15 K.","PeriodicalId":501405,"journal":{"name":"The Journal of the American Oil Chemists’ Society","volume":"30 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141061709","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The increasing global population, coupled with the effects of climate change on agricultural activities has spurred a demand for sustainable food production to meet human needs. In response to this, there has been a growing interest in sustainable food production initiatives. One of such initiatives is harnessing microbial and insect lipids as valuable ingredients to address increase in demand for lipids across various sectors, including functional food, nutritional supplements, and biodiesel production. Over the last decades, there has been increasing scientific investigations exploring lipid from algae, microbes, and insects as alternatives to traditional agro‐ and marine‐based sources. This review, therefore, presents progress made in microbial and insect oils production, with emphasis on sustainability. Emerging extraction techniques, regulatory and safety requirements, and challenges that exist in the production and utilization of these new lipids are also discussed. The review shows that lipids from a wide range of oleaginous microorganisms and insect species have the potential to serve as a valuable ingredient for healthful food preparation. However, challenges such as cultural acceptance, lack of standardized regulations, high cost, and low yield associated with most emerging environmentally friendly extraction technologies continue to hinder widespread use or adoption of microbial and insect lipids on a global scale. These challenges call for innovations to reduce cost of production and improve lipids yield. So far, a substantial progress has been made in the utilization of readily available feedstocks such as industrial food wastes and sugar‐rich industrial wastewater to grow insects and microorganisms which will significantly reduce the processing costs.
{"title":"Microbial and insect oils: A sustainable approach to functional lipid","authors":"Ityotagher P. Aondoakaa, Casimir C. Akoh","doi":"10.1002/aocs.12851","DOIUrl":"https://doi.org/10.1002/aocs.12851","url":null,"abstract":"The increasing global population, coupled with the effects of climate change on agricultural activities has spurred a demand for sustainable food production to meet human needs. In response to this, there has been a growing interest in sustainable food production initiatives. One of such initiatives is harnessing microbial and insect lipids as valuable ingredients to address increase in demand for lipids across various sectors, including functional food, nutritional supplements, and biodiesel production. Over the last decades, there has been increasing scientific investigations exploring lipid from algae, microbes, and insects as alternatives to traditional agro‐ and marine‐based sources. This review, therefore, presents progress made in microbial and insect oils production, with emphasis on sustainability. Emerging extraction techniques, regulatory and safety requirements, and challenges that exist in the production and utilization of these new lipids are also discussed. The review shows that lipids from a wide range of oleaginous microorganisms and insect species have the potential to serve as a valuable ingredient for healthful food preparation. However, challenges such as cultural acceptance, lack of standardized regulations, high cost, and low yield associated with most emerging environmentally friendly extraction technologies continue to hinder widespread use or adoption of microbial and insect lipids on a global scale. These challenges call for innovations to reduce cost of production and improve lipids yield. So far, a substantial progress has been made in the utilization of readily available feedstocks such as industrial food wastes and sugar‐rich industrial wastewater to grow insects and microorganisms which will significantly reduce the processing costs.","PeriodicalId":501405,"journal":{"name":"The Journal of the American Oil Chemists’ Society","volume":"95 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-05-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140942559","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The aim of this study was to use oleogels in compound chocolates. A control sample with cocoa butter (CNT) and two compound chocolates with hazelnut oil‐sunflower wax oleogel (SWO‐CC), and polyglycerol stearate oleogel (PGSO‐CC) were prepared with the same recipe. The main properties and compositions of the samples were quite similar. While CNT sample included only 37.97% of total unsaturated fatty acids, it was 74.19 and 63.08% in the SWO‐CC and PGSO‐CC, respectively. The melting peak temperatures were 32.1, 25.4, and 23.8°C for CNT, SWO‐CC and PGSO‐CC. The samples had 11.75%, 74.25%, and 74.25% shape retention index values at 60°C. Clearly compound chocolates melted at lower temperatures, but retained their shape at higher temperatures. After 15‐day temperature fluctuation storage, no fat bloom was developed. Rheological data showed that the PGSO‐CC sample was stiffer among all, and the compound chocolates melted slowly up to 40°C, but CNT melted sharply at 38°C. Further, the PGSO‐CC sample showed a lubricating behavior. Although CNT sample included 7 volatile aromatics, SWO‐CC and PGSO‐CC samples had 17 and 14 compounds, respectively. Trained panel described the samples with 13 attributes, and most profoundly the compound chocolates had lower shape, surface gloss, coffee, bitter, cooling, hardness scores, and higher coating scores. Consumer test revealed that compound chocolates had lower appearance scores, and equal aroma scores. The flavor score and acceptability were highest for the PGSO‐CC sample. Overall, this study proved that heat stable and sensorially acceptable compound chocolates could be prepared from the oleogels.
{"title":"Utilization of hazelnut oil oleogels for the preparation of milk couverture type compound chocolates: Composition, properties, and sensory evaluations","authors":"Emin Yılmaz, Ceren Öz","doi":"10.1002/aocs.12850","DOIUrl":"https://doi.org/10.1002/aocs.12850","url":null,"abstract":"The aim of this study was to use oleogels in compound chocolates. A control sample with cocoa butter (CNT) and two compound chocolates with hazelnut oil‐sunflower wax oleogel (SWO‐CC), and polyglycerol stearate oleogel (PGSO‐CC) were prepared with the same recipe. The main properties and compositions of the samples were quite similar. While CNT sample included only 37.97% of total unsaturated fatty acids, it was 74.19 and 63.08% in the SWO‐CC and PGSO‐CC, respectively. The melting peak temperatures were 32.1, 25.4, and 23.8°C for CNT, SWO‐CC and PGSO‐CC. The samples had 11.75%, 74.25%, and 74.25% shape retention index values at 60°C. Clearly compound chocolates melted at lower temperatures, but retained their shape at higher temperatures. After 15‐day temperature fluctuation storage, no fat bloom was developed. Rheological data showed that the PGSO‐CC sample was stiffer among all, and the compound chocolates melted slowly up to 40°C, but CNT melted sharply at 38°C. Further, the PGSO‐CC sample showed a lubricating behavior. Although CNT sample included 7 volatile aromatics, SWO‐CC and PGSO‐CC samples had 17 and 14 compounds, respectively. Trained panel described the samples with 13 attributes, and most profoundly the compound chocolates had lower shape, surface gloss, coffee, bitter, cooling, hardness scores, and higher coating scores. Consumer test revealed that compound chocolates had lower appearance scores, and equal aroma scores. The flavor score and acceptability were highest for the PGSO‐CC sample. Overall, this study proved that heat stable and sensorially acceptable compound chocolates could be prepared from the oleogels.","PeriodicalId":501405,"journal":{"name":"The Journal of the American Oil Chemists’ Society","volume":"24 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140829267","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Microscopic image analysis is a crucial tool in fat crystallization research, enabling the analysis of crystal size, network structure, fractal dimension and other parameters through binarization. It is essential to seek an appropriate thresholding algorithm to binarize fat crystal images, which plays a vital role in image segmentation. In this article, the effectiveness of 17 thresholding algorithms such as Default, Mean, IsoData, Otsu, Li and Triangle were analyzed in processing fat crystal images with different shapes, background colors and image intensities. This was expected to discover a stable and objective thresholding algorithm for the binarization of fat crystal images. The performance evaluation was conducted according to the peak signal noise ratio (PSNR), structural similarity index (SSIM) and region non‐uniformity (RNU) parameter. Moreover, the comparative analysis of crystal size error, crystal area fraction and intraclass correlation coefficients (ICC) for fractal dimension values would provide a foundation for the selection of thresholding techniques for fat crystal network images. The results indicated that the Default algorithm exhibited remarkable robustness and applicability with high‐quality and stable outputs in fat crystal image processing.
{"title":"Comparison of threshold algorithms for automatic processing of fat crystal microscopic images based on ImageJ","authors":"Miao Xiong, Ang Qi, Lu Zhang","doi":"10.1002/aocs.12846","DOIUrl":"https://doi.org/10.1002/aocs.12846","url":null,"abstract":"Microscopic image analysis is a crucial tool in fat crystallization research, enabling the analysis of crystal size, network structure, fractal dimension and other parameters through binarization. It is essential to seek an appropriate thresholding algorithm to binarize fat crystal images, which plays a vital role in image segmentation. In this article, the effectiveness of 17 thresholding algorithms such as Default, Mean, IsoData, Otsu, Li and Triangle were analyzed in processing fat crystal images with different shapes, background colors and image intensities. This was expected to discover a stable and objective thresholding algorithm for the binarization of fat crystal images. The performance evaluation was conducted according to the peak signal noise ratio (PSNR), structural similarity index (SSIM) and region non‐uniformity (RNU) parameter. Moreover, the comparative analysis of crystal size error, crystal area fraction and intraclass correlation coefficients (ICC) for fractal dimension values would provide a foundation for the selection of thresholding techniques for fat crystal network images. The results indicated that the Default algorithm exhibited remarkable robustness and applicability with high‐quality and stable outputs in fat crystal image processing.","PeriodicalId":501405,"journal":{"name":"The Journal of the American Oil Chemists’ Society","volume":"17 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140803979","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Vitamin E succinate has gained substantial attention as a potential therapeutic agent for cancer treatment due to its biomedical activities. One of the prominent methods of synthesizing vitamin E succinate is through enzymatic processes, which, although advantageous, presents inherent challenges related to optimization, scalability, and particularly, the poor stability of lipases in organic solvents. Our study addresses these challenges by conducting a comprehensive comparative analysis between Lipase UM1 and three other immobilized commercial lipases, demonstrating Lipase UM1's enhanced resistance to organic solvents and its superior efficiency in vitamin E succinate production. Further optimization experiments with Lipase UM1 led to an unprecedented conversion of 99%. Additionally, we scaled the reaction to a proof‐of‐concept industrial level. The synthesized product was verified using Fourier transform infrared spectroscopy and nuclear magnetic resonance analysis, ensuring its quality and consistency. This study validates Lipase UM1 as an efficient catalyst for vitamin E succinate synthesis, offering a promising avenue for industrial production with potential applications in cancer therapy and beyond.
维生素 E 琥珀酸酯因其生物医学活性而成为治疗癌症的潜在药物，受到广泛关注。合成维生素 E 琥珀酸酯的主要方法之一是酶法工艺，这种方法虽然具有优势，但在优化、可扩展性方面存在固有的挑战，特别是脂肪酶在有机溶剂中的稳定性较差。为了应对这些挑战，我们的研究对脂肪酶 UM1 和其他三种固定化商用脂肪酶进行了全面的比较分析，结果表明脂肪酶 UM1 对有机溶剂的耐受性更强，在维生素 E 琥珀酸酯的生产中效率更高。利用脂肪酶 UM1 进行的进一步优化实验使转化率达到了前所未有的 99%。此外，我们还将该反应放大到了概念验证的工业水平。合成产品通过傅立叶变换红外光谱和核磁共振分析进行了验证，确保了其质量和一致性。这项研究验证了脂肪酶 UM1 是合成维生素 E 琥珀酸酯的高效催化剂，为工业化生产提供了一条前景广阔的途径，在癌症治疗等领域具有潜在的应用价值。
{"title":"Efficient enzymatic synthesis of vitamin E succinate using an organic solvent‐stable immobilized lipase","authors":"Wenlin Li, Sen Lin, Dongming Lan, Yonghua Wang","doi":"10.1002/aocs.12847","DOIUrl":"https://doi.org/10.1002/aocs.12847","url":null,"abstract":"Vitamin E succinate has gained substantial attention as a potential therapeutic agent for cancer treatment due to its biomedical activities. One of the prominent methods of synthesizing vitamin E succinate is through enzymatic processes, which, although advantageous, presents inherent challenges related to optimization, scalability, and particularly, the poor stability of lipases in organic solvents. Our study addresses these challenges by conducting a comprehensive comparative analysis between Lipase UM1 and three other immobilized commercial lipases, demonstrating Lipase UM1's enhanced resistance to organic solvents and its superior efficiency in vitamin E succinate production. Further optimization experiments with Lipase UM1 led to an unprecedented conversion of 99%. Additionally, we scaled the reaction to a proof‐of‐concept industrial level. The synthesized product was verified using Fourier transform infrared spectroscopy and nuclear magnetic resonance analysis, ensuring its quality and consistency. This study validates Lipase UM1 as an efficient catalyst for vitamin E succinate synthesis, offering a promising avenue for industrial production with potential applications in cancer therapy and beyond.","PeriodicalId":501405,"journal":{"name":"The Journal of the American Oil Chemists’ Society","volume":"20 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140806574","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Oilcane is an engineered sugarcane with the ability to hyper‐accumulate vegetative lipids. It is processed to obtain juice and bagasse as a potential substrate for the production of biofuels and biochemicals. The juice comprises solid particles that are separated as waste mud before the fermentation of the juice. In this study, the oilcane waste mud (OWM) generated from 1000 liters of oilcane juice was quantified and evaluated as a potential resource for recovering biobased waxes. Hexane and ethyl acetate were evaluated as two different solvents for extracting waxes from OWM followed by its purification using acetone. The extracted biobased wax samples were characterized for their chemical and thermal profiles which were then compared with commercial natural waxes. Detailed mass balance shows that 53.6 ± 2.6 kg (dry basis) of solid OWM gets generated upon processing 1000 L (~1068 kg) of oilcane juice. Hexane and ethyl acetate led to a crude wax yield of 25.6 ± 0.2% and 16.6 ± 0.4% (wt/wt, dry basis) respectively from OWM at the end of 8 h. The relative purification of the wax samples was reported in the range of 58%–65% (wt/wt). The purified OWM wax has a melting point of 74.7°C. The waste mud was valorized as a source of biobased waxes with characteristic chemical and thermal profiles comparable to commercial natural waxes (carnauba and beeswax). Considering the decline in the supply of petroleum wax in the future coupled with the switch to “greener” alternative products by consumers, OWM could be a valuable source of natural wax in the industrial sector reducing the dependence on petroleum waxes. Eventually, recovering biobased wax as a co‐product from OWM would bring in an additional stream of revenue leading to the development of a zero‐waste biorefinery based on bioenergy crops.
{"title":"Harnessing the potential of oilcane waste mud for recovering biobased waxes","authors":"Shivali Banerjee, Kristen K. Eilts, Vijay Singh","doi":"10.1002/aocs.12844","DOIUrl":"https://doi.org/10.1002/aocs.12844","url":null,"abstract":"Oilcane is an engineered sugarcane with the ability to hyper‐accumulate vegetative lipids. It is processed to obtain juice and bagasse as a potential substrate for the production of biofuels and biochemicals. The juice comprises solid particles that are separated as waste mud before the fermentation of the juice. In this study, the oilcane waste mud (OWM) generated from 1000 liters of oilcane juice was quantified and evaluated as a potential resource for recovering biobased waxes. Hexane and ethyl acetate were evaluated as two different solvents for extracting waxes from OWM followed by its purification using acetone. The extracted biobased wax samples were characterized for their chemical and thermal profiles which were then compared with commercial natural waxes. Detailed mass balance shows that 53.6 ± 2.6 kg (dry basis) of solid OWM gets generated upon processing 1000 L (~1068 kg) of oilcane juice. Hexane and ethyl acetate led to a crude wax yield of 25.6 ± 0.2% and 16.6 ± 0.4% (wt/wt, dry basis) respectively from OWM at the end of 8 h. The relative purification of the wax samples was reported in the range of 58%–65% (wt/wt). The purified OWM wax has a melting point of 74.7°C. The waste mud was valorized as a source of biobased waxes with characteristic chemical and thermal profiles comparable to commercial natural waxes (carnauba and beeswax). Considering the decline in the supply of petroleum wax in the future coupled with the switch to “greener” alternative products by consumers, OWM could be a valuable source of natural wax in the industrial sector reducing the dependence on petroleum waxes. Eventually, recovering biobased wax as a co‐product from OWM would bring in an additional stream of revenue leading to the development of a zero‐waste biorefinery based on bioenergy crops.","PeriodicalId":501405,"journal":{"name":"The Journal of the American Oil Chemists’ Society","volume":"50 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140631060","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Jill K. Winkler‐Moser, Richard D. Ashby, Hailemichael O. Yosief, Joseph Msanne, Steven C. Peterson, Grigor B. Bantchev, Steven C. Cermak, Frederick C. Felker
Sophorolipids (SL) are glycolipids composed of a sophorose head‐group linked to a hydroxy‐fatty acid tail which makes them a potential source of structurally unique biobased hydroxy fatty acids. Furthermore, Lesquerella is a native southwestern plant that has been commercially cultivated as a replacement for castor seed oil due to high seed oil concentrations of 14‐hydroxy‐eicosenoic acid (14‐OH‐C20:1c11). In this study, SL‐derived hydroxy fatty acids and methyl esters containing 15‐hydroxy‐palmitic acid (15‐OH‐C16), 17‐hydroxy‐stearic acid (17‐OH‐C18), 15‐hydroxy‐palmitic acid methyl ester (15‐OH‐C16ME), 17‐hydroxy‐stearic acid methyl ester (17‐OH‐C18ME), and 13‐hydroxy‐behenic acid methyl ester (13OH‐C22ME) were obtained from the SL produced by two yeast strains. In addition, hydrogenated Lesquerella oil (HLO) was made with ~62% 14‐OH‐eicosanoic (C20) acid (14‐OH‐C20). These materials, along with 12‐hydroxy‐stearic acid (12‐OH‐C18) as a standard for comparison were used to make soybean oil oleogels, and their properties determined. The minimum gelation concentration (MGC) of 12‐OH‐C18 was 1% (wt/wt), while the MGC of 15‐OH‐C16 and 17‐OH‐C18 were 5% and 10%, respectively. The MGC for 15‐OH‐C16ME was 5%, but 17‐OH‐C18ME was unable to form a stable gel at concentrations up to 10%. HLO formed a viscous solution rather than an oleogel, but its crystal morphology underwent a large transformation during storage over a 2.5‐month period, after which it was able to form a stable gel. SL‐based hydroxy fatty acids were able to form oleogels in soybean oil and have the potential to be considered as a new source of low‐molecular weight oleogelators as well as biobased hydroxy fatty acids.
槐糖脂（SL）是由槐糖头基与羟基脂肪酸尾相连的糖脂，这使其成为结构独特的生物基羟基脂肪酸的潜在来源。此外，莱斯奎拉是一种原产于美国西南部的植物，由于其种子油中含有高浓度的 14-羟基二十烯酸（14-OH-C20:1c11），已被商业化栽培作为蓖麻籽油的替代品。在这项研究中，SL 衍生的羟基脂肪酸和甲酯含有 15-羟基棕榈酸（15-OH-C16）、17-羟基硬脂酸（17-OH-C18）、15-羟基棕榈酸甲酯（15-OH-C16ME）、17-hydroxy-stearic acid methyl ester (17-OH-C18ME), and 13-hydroxy-behenic acid methyl ester (13OH-C22ME) were obtained from the SL produced by two yeast strains.此外，氢化莱斯奎拉油（HLO）是用约 62% 的 14-OH-二十烷酸（C20）（14-OH-C20）制成的。这些材料与作为比较标准的 12-羟基硬脂酸（12-OH-C18）一起被用来制造大豆油油凝胶，并测定其性质。12-OH-C18 的最小凝胶浓度（MGC）为 1%（重量比），而 15-OH-C16 和 17-OH-C18 的最小凝胶浓度分别为 5%和 10%。15-OH-C16ME 的 MGC 为 5%，但 17-OH-C18ME 在浓度达到 10% 时也无法形成稳定的凝胶。HLO 形成的是粘稠溶液而非油凝胶，但其晶体形态在 2.5 个月的储存过程中发生了巨大变化，之后便能形成稳定的凝胶。基于 SL 的羟基脂肪酸能够在大豆油中形成油凝胶，有望被视为低分子量油凝胶剂和生物基羟基脂肪酸的新来源。
{"title":"Properties of soybean oil oleogels produced from sophorolipid‐derived hydroxy fatty acids, methyl esters and hydrogenated Lesquerella seed oil","authors":"Jill K. Winkler‐Moser, Richard D. Ashby, Hailemichael O. Yosief, Joseph Msanne, Steven C. Peterson, Grigor B. Bantchev, Steven C. Cermak, Frederick C. Felker","doi":"10.1002/aocs.12843","DOIUrl":"https://doi.org/10.1002/aocs.12843","url":null,"abstract":"Sophorolipids (SL) are glycolipids composed of a sophorose head‐group linked to a hydroxy‐fatty acid tail which makes them a potential source of structurally unique biobased hydroxy fatty acids. Furthermore, Lesquerella is a native southwestern plant that has been commercially cultivated as a replacement for castor seed oil due to high seed oil concentrations of 14‐hydroxy‐eicosenoic acid (14‐OH‐C20:1<jats:italic>c</jats:italic>11). In this study, SL‐derived hydroxy fatty acids and methyl esters containing 15‐hydroxy‐palmitic acid (15‐OH‐C16), 17‐hydroxy‐stearic acid (17‐OH‐C18), 15‐hydroxy‐palmitic acid methyl ester (15‐OH‐C16ME), 17‐hydroxy‐stearic acid methyl ester (17‐OH‐C18ME), and 13‐hydroxy‐behenic acid methyl ester (13OH‐C22ME) were obtained from the SL produced by two yeast strains. In addition, hydrogenated Lesquerella oil (HLO) was made with ~62% 14‐OH‐eicosanoic (C20) acid (14‐OH‐C20). These materials, along with 12‐hydroxy‐stearic acid (12‐OH‐C18) as a standard for comparison were used to make soybean oil oleogels, and their properties determined. The minimum gelation concentration (MGC) of 12‐OH‐C18 was 1% (wt/wt), while the MGC of 15‐OH‐C16 and 17‐OH‐C18 were 5% and 10%, respectively. The MGC for 15‐OH‐C16ME was 5%, but 17‐OH‐C18ME was unable to form a stable gel at concentrations up to 10%. HLO formed a viscous solution rather than an oleogel, but its crystal morphology underwent a large transformation during storage over a 2.5‐month period, after which it was able to form a stable gel. SL‐based hydroxy fatty acids were able to form oleogels in soybean oil and have the potential to be considered as a new source of low‐molecular weight oleogelators as well as biobased hydroxy fatty acids.","PeriodicalId":501405,"journal":{"name":"The Journal of the American Oil Chemists’ Society","volume":"34 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140564968","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Olive leaves currently represent a waste from olive oil industry that can be reused as source of polyphenols and other compounds. The objective of this study was to test whether incorporation of olive leaf powder directly in olive oils can enhance and modify its chemical‐sensory quality. Thus, leaves from cultivar “Koroneiki” were washed, sanitized, dried (37–40°C for 48 h) and milled until obtaining a powder that was added to “Arbequina” and “Koroneiki” extra virgin olive oils, at 1% and 3%. The oils were stored in dark conditions at room temperature and samples were checked after 0, 3, 6 and 12 months. The quality parameters, sensory properties, and nutrition quality (total phenolics, antioxidant, oleuropein and alpha‐tocopherol) were evaluated. The olive leaves affected quality and chemical composition, mainly increasing resistance to oxidation, which was not verified in samples without leaves addition. The incorporation of leaves powder significantly increased the contents of C6‐C5 alcohols/aldehydes, intensity of the green fruity and bitter, also artichoke, herbs, tomato leaf, olive leaves and banana peels sensations.
{"title":"Impact of olive leaves powder addition on extra virgin olive oil: Sensory, quality, nutritional and volatile compounds implications","authors":"Andressa Anelo Álvares, Lucas Tolio Silva, Luana Souza Cavalcante, Dafne Marcelle Alves Pires, Isabel Cristina Kasper Machado, Ana Lúcia Aboy, Wendell Mello, Camila Scheid, Josias Merib, Juliano Garavaglia","doi":"10.1002/aocs.12841","DOIUrl":"https://doi.org/10.1002/aocs.12841","url":null,"abstract":"Olive leaves currently represent a waste from olive oil industry that can be reused as source of polyphenols and other compounds. The objective of this study was to test whether incorporation of olive leaf powder directly in olive oils can enhance and modify its chemical‐sensory quality. Thus, leaves from cultivar “Koroneiki” were washed, sanitized, dried (37–40°C for 48 h) and milled until obtaining a powder that was added to “Arbequina” and “Koroneiki” extra virgin olive oils, at 1% and 3%. The oils were stored in dark conditions at room temperature and samples were checked after 0, 3, 6 and 12 months. The quality parameters, sensory properties, and nutrition quality (total phenolics, antioxidant, oleuropein and alpha‐tocopherol) were evaluated. The olive leaves affected quality and chemical composition, mainly increasing resistance to oxidation, which was not verified in samples without leaves addition. The incorporation of leaves powder significantly increased the contents of C6‐C5 alcohols/aldehydes, intensity of the green fruity and bitter, also artichoke, herbs, tomato leaf, olive leaves and banana peels sensations.","PeriodicalId":501405,"journal":{"name":"The Journal of the American Oil Chemists’ Society","volume":"41 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140564996","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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