Lipase‐catalyzed transesterification of virgin and refined hemp seed oil with ferulic acid ethyl ester

David L. Compton, Bryant A. Pero, Garris H. C. Radloff, Roque L. Evangelista, Jill K. Winkler‐Moser, James A. Kenar, Steven C. Cermak, Michael Appell, Kervin O. Evans, Evan C. Wegener, Hanah T. Rheay, Christopher D. Skory
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Abstract

The transesterification of ethyl ferulate (EF) and unrefined, virgin, cold pressed hemp seed oil (HOV) and refined, bleached, deodorized cold pressed hemp seed oil (HOR) using a commercial lipase, Novozym 435 (Candida antarctica B lipase immobilized on an acrylic resin), was examined in 150‐mL, shaken, batch reactions at 60°C for 2 weeks. The reactions produced feruloylated hemp seed oils, FHOV and FHOR, respectively, and the reactions were monitored to determine the difference between virgin and refined hemp seed oil on the transesterifications. The FHOV and FHOR reactions both reached EF conversion equilibrium of 58% after ca. 168 h. Ultraviolet (UV) absorbing and antioxidant capacity of the FHOV and FHOR were determined. Both FHOV and FHOR (50 μM in ethanol) were excellent UVA II absorbers, λmax 322 nm, and exhibited absorption into the UVB. The DDPH* radical (200 μM) scavenging of the FHOV and FHOR (0.25–2.5 mM) were both shown to be rapid antioxidants (50% DDPH* radical scavenged in <5 min) at 1.0 and 2.5 mM suggesting that inherent components contained in the HOV did not adversely affect enzyme activity relative to transesterification using HOR. Overall, using less expensive, unrefined, virgin hemp seed oil versus more expensive, refined hemp seed oil did not appreciably affect the enzyme kinetics of the transesterification reactions nor the UV absorbing and antioxidant efficacy of the resultant feruloylated hemp seed oils, making FHOV a less expensively produced feruloylated hemp seed oil for cosmetic and personal care applications.
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脂肪酶催化初榨和精炼大麻籽油与阿魏酸乙酯的酯交换反应
使用商用脂肪酶 Novozym 435(固定在丙烯酸树脂上的 Candida antarctica B 脂肪酶),在 150 毫升、摇动、批量反应中,在 60°C 下持续 2 周,考察了阿魏酸乙酯(EF)与未精炼、初榨、冷榨大麻籽油(HOV)和精炼、漂白、脱臭冷榨大麻籽油(HOR)的酯交换反应。反应分别产生阿魏酰化大麻籽油 FHOV 和 FHOR,并对反应进行监测,以确定初榨大麻籽油和精炼大麻籽油在酯交换反应上的差异。FHOV 和 FHOR 反应均在约 168 小时后达到 58% 的 EF 转化平衡。测定了 FHOV 和 FHOR 的紫外线(UV)吸收能力和抗氧化能力。FHOV 和 FHOR(在乙醇中的浓度为 50 μM)都具有极佳的紫外线吸收能力,λmax 为 322 nm,并具有紫外线吸收能力。FHOV 和 FHOR(0.25-2.5 毫摩尔)的 DDPH* 自由基清除率(200 μM)在 1.0 和 2.5 毫摩尔时均显示为快速抗氧化剂(50% 的 DDPH* 自由基在 <5 分钟内被清除),这表明相对于使用 HOR 进行酯交换,HOV 所含的固有成分不会对酶活性产生不利影响。总之,使用价格较低、未经精炼的初榨大麻籽油与价格较高的精炼大麻籽油相比,并不会明显影响酯交换反应的酶动力学,也不会影响所得阿魏酰化大麻籽油的紫外线吸收和抗氧化功效,因此 FHOV 是一种用于化妆品和个人护理产品的价格较低的阿魏酰化大麻籽油。
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