Experimental and theoretical study of the influence of water on hydrolyzed product formation during the feruloylation of vegetable oil

Compton, David L.; Evans, Kervin O.; Appell, Michael

doi:10.1002/jsfa.8145

Cited by 4 publications

(2 citation statements)

References 32 publications

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“…Residual water >250 μg g −1 in the vegetable oil, enzyme support, and the ferulate ester, combined, thermodynamically favored triacylglycerol hydrolysis and ethyl ferulate hydrolysis, resulting in a complex mixture of unwanted side products (Compton et al, ; Laszlo et al, ). Common drying reagents and techniques and careful monitoring of the reaction's water activity limited the unwanted side reactions (Compton et al, ; Laszlo et al, ).…”

Section: Introductionmentioning

confidence: 99%

Protection of Antioxidants, Vitamins E and C, from Ultraviolet Degradation using Feruloylated Vegetable Oil

Compton

Evans

Appell

et al. 2019

J Americ Oil Chem Soc

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Natural antioxidants are often used in topical personal care formulations to protect the skin from oxidative stresses but are susceptible to degradation due to ultraviolet (UV) radiation. Feruloyl soy glycerols (FSG) are UV absorbers synthesized from the biocatalytic conversion of soybean oil and ferulic acid ethyl ester that have a total UV absorbance and photostability comparable to the commercial UV absorber, 2-ethylhexyl-4-methoxycinnamate (octinoxate, ONX). We examined the ability of FSG and ONX to photoprotect the antioxidant capacity of Vitamin E (VE), Vitamin C (VC), Vitamin E, and their derivatives, 6-hydroxy-2,-5,7,8-tetramethylchroman-2-carboxylic acid (Trolox, TLX) and L-ascorbic acid 6-palmitate (Vitamin C palmitate, VCP), from UV degradation. VE, VC, TLX, and VCP (100 μM solutions) acted as rapid antioxidants, scavenging >50% of the spontaneously formed free radical, 2,2-diphenyl-1-picrylhydrazyl (DPPH*, 200 μM), within 5 min in acetonitrile solutions. The vitamins and TLX were rendered slow antioxidants in the DDPH* assays, scavenging <50% of DPPH* within 30 min, after exposure of the acetonitrile solutions to UV radiation for 4 hours. VCP solutions were rendered moderate antioxidants, scavenging >50% of DPPH* within 30 min, after 4 hours exposure to UV radiation. FSG (100-1000 μM) was added to acetonitrile solutions of the vitamins and their derivatives to determine if FSG could photoprotect VE, TLX, VC, and VCP, allowing them to retain their antioxidant activities after 4 hours of UV irradiation. The addition of FSG, 500 and 1000 μM, allowed TLX and VE to retain rapid antioxidant activity after 4-hour UV exposure. VC retained rapid antioxidant capacity with 100 μM FSG after 4 hours of UV exposure. FSG performed comparably to slightly better than the commercial UV absorber, ONX, in protecting the antioxidant activities of vitamins and their derivatives from UV degradation. FSG also possessed intrinsic antioxidant capacity that ONX did not, which may have contributed to its better performance when mixed with the vitamins and their derivatives in the DPPH* assays. Keywords Antioxidant Á Feruloyl soy glycerols Á Vitamin C Á Vitamin E Á Ultraviolet degradation J Am Oil Chem Soc (2019) 96: 999-1009.Abbreviations AAPH 2,2 0 -azobis(2-amindinoprpoahe) dihydrochloride AVO avobenzone, 4-tert-butyl-4 0 -methoxydibenzoyl methane Supporting information Additional supporting information may be found online in the Supporting Information section at the end of the article.

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Section: Introductionmentioning

confidence: 99%

Protection of Antioxidants, Vitamins E and C, from Ultraviolet Degradation using Feruloylated Vegetable Oil

Compton

Evans

Appell

et al. 2019

J Americ Oil Chem Soc

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“…FG and F 2 G are known byproducts (<1%) of the bioreactor transesterification process but have been considered undesirable due to the lack of a fatty acid moiety on the glycerol. Increased water content in the bioreactor has been shown to increase the amount of hydrolysis biproducts, FG, F 2 G, and ferulic acid [24,25]. In addition, conducting the bioreactor transesterification of ethyl ferulate with a mixture of vegetable oil mono-and diacylglycerols (MAG and DAG, respectively) instead of vegetable oil TAG resulted in higher quantities (~4%) FG and F 2 G. Herein, we report methods for harvesting FG and F 2 G and purifying them in >10 g quantities by flash chromatography, an improvement over the milligram to low gram quantities obtained by preparative HPLC and column chromatography methods reported to date [5,14,26].…”

Section: Introductionmentioning

confidence: 99%

Enzymatic Synthesis and Flash Chromatography Separation of 1,3-Diferuloyl-sn-Glycerol and 1-Feruloyl-sn-Glycerol

Compton

Appell

Kenar

et al. 2020

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Ethyl ferulate was transesterified with Enova Oil (a soy-based vegetable oil containing 80–85% diacylglycerol) using Novozym 435 at 60 °C. The resultant feruloylated vegetable oil reaction product produced a precipitate (96.4 g, 4.02 wt%) after 7 d of standing at room temperature. Preliminary characterization of the precipitate identified the natural phenylpropenoids 1,3-diferuloyl-sn-glycerol (F2G) and 1-feruloyl-sn-glycerol (FG) as the major components. A flash chromatography method was developed and optimized (e.g., mass of sample load, flow rate, binary solvent gradient slope, and separation run length) using a binary gradient of hexane and acetone mobile phase and silica gel stationary phase to separate and isolate F2G and FG. The optimized parameters afforded F2G (1.188 ± 0.052 g, 39.6 ± 1.7%) and FG (0.313 ± 0.038 g, 10.4 ± 1.3%) from 3.0 g of the transesterification precipitate, n = 10 trials. Overall, all flash chromatography separations combined, F2G (39.1 g, 40.6%) and FG (9.4 g, 9.8%) were isolated in a combined yield of 48.5 g (51.4%), relative to the 96.4 g of transesterification precipitate collected. The optimized flash chromatography method was a necessary improvement over previously reported preparative HPLC and column chromatography methods used to purify milligram to low gram quantities of F2G and FG to be able to process ~100 g of material in a timely, efficient manner.

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

Compton,

Pero,

Radloff

et al. 2024

J Americ Oil Chem Soc

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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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Experimental and theoretical study of the influence of water on hydrolyzed product formation during the feruloylation of vegetable oil

Cited by 4 publications

References 32 publications

Protection of Antioxidants, Vitamins E and C, from Ultraviolet Degradation using Feruloylated Vegetable Oil

Protection of Antioxidants, Vitamins E and C, from Ultraviolet Degradation using Feruloylated Vegetable Oil

Enzymatic Synthesis and Flash Chromatography Separation of 1,3-Diferuloyl-sn-Glycerol and 1-Feruloyl-sn-Glycerol

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

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