Lipase-catalyzed production of novel hydroxylated fatty amides in organic solvent

Levinson, William E.; Kuo, Tsung Min; Kurtzman, Cletus P.

doi:10.1016/j.enzmictec.2005.02.001

Cited by 44 publications

(24 citation statements)

References 23 publications

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“…23 Hence, the synthesis of oleoylethanolamide included purification of oleic acid from a commercial product and amidation reaction between oleic acid and ethanolamine with a lipase. This method is economical because of the low cost of oleic acid and efficient because of the high selectivity of lipase for the amidation reaction, and the method was improved and proved suitable for large-scale synthesis in a quantity needed for biological function evaluation in animal or human systems.…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis of Oleoylethanolamide Using Lipase

Wang

2011

J. Agric. Food Chem.

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An effective process for the enzymatic synthesis of oleoylethanolamide is described in this study. The process included purification of a commercial oleic acid product and then optimization of the reaction between the purified oleic acid and ethanolamine in the presence of hexane and a lipase. Under the optimal amidation reaction conditions identified, oleoylethanolamide was obtained with 96.6% purity. The synthesis was also conducted on a large scale (50 mmol of each of the reactants), and oleoylethanolamide purity and yield after crystallization purification were 96.1 and 73.5%, respectively. Compared to the previous studies, the current method of preparing high-purity oleoylethanolamide is more effective and economically feasible. The scalability and ease for such synthesis make it possible to study the biological and nutritional functions of the cannabinoid-like oleoylethanolamide in animal or human subjects. ABSTRACT: An effective process for the enzymatic synthesis of oleoylethanolamide is described in this study. The process included purification of a commercial oleic acid product and then optimization of the reaction between the purified oleic acid and ethanolamine in the presence of hexane and a lipase. Under the optimal amidation reaction conditions identified, oleoylethanolamide was obtained with 96.6% purity. The synthesis was also conducted on a large scale (50 mmol of each of the reactants), and oleoylethanolamide purity and yield after crystallization purification were 96.1 and 73.5%, respectively. Compared to the previous studies, the current method of preparing high-purity oleoylethanolamide is more effective and economically feasible. The scalability and ease for such synthesis make it possible to study the biological and nutritional functions of the cannabinoid-like oleoylethanolamide in animal or human subjects.

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Section: ■ Introductionmentioning

confidence: 99%

Synthesis of Oleoylethanolamide Using Lipase

Wang

2011

J. Agric. Food Chem.

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“…Fatty amides can be synthesized from fatty acids or their esters through treatments with amine compounds 6,7) . Enzymatic synthesis of these compounds from the same starting material has also been reported [8][9][10] . Triglycerides can be converted into their fatty amides via amidation using ammonia or amine compounds 11,12) .…”

Section: Introductionmentioning

confidence: 94%

Enzymatic Synthesis of Fatty Amides fromPalm Olein

et al. 2010

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“…Candida antrarctica-B lipasehas a strong preference towards elaidic acid (trans fat found in hydrogenated oils), whereasCandida rugosa prefers oleic acid (fatty acid that occurs naturally in oils) [23].…”

Section: A Screening Of Lipases For the Transesterification Reactionmentioning

confidence: 99%

Lipase Catalyzed Preparation of Biodiesel from a Lollipop Effluent Stream

2016

International Conference on Advances in Science, Engineering, Technology and Natural Resources (ICASETNR-16) Nov. 24-25, 2016 P

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Abstract-Biodiesel fuel is produced from waste oil in order to make the production process more economically feasible. In this paper, the production of biodiesel from a lollipop effluent stream, using enzymatic transesterification methods, was investigated. The production of biodiesel through enzymatic methods offers several advantages over chemical catalyzed methods that is currently applied. By the screening of lipases, it was found that immobilized Candida antarctica-B lipase gave the highest conversion of oil to FAME. A 96 % biodiesel conversion was obtained at a temperature of 40°C and a molar ratio of 1:4 oil to methanol. In order to prevent the deactivation of the lipase a two-step addition of methanol was conducted over a time period of 12 hours.

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Lipase-catalyzed production of novel hydroxylated fatty amides in organic solvent

Cited by 44 publications

References 23 publications

Synthesis of Oleoylethanolamide Using Lipase

Synthesis of Oleoylethanolamide Using Lipase

Enzymatic Synthesis of Fatty Amides fromPalm Olein

Lipase Catalyzed Preparation of Biodiesel from a Lollipop Effluent Stream

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