Selective Synthesis of Unsaturated N-Acylethanolamines by Lipase-Catalyzed N-Acylation of Ethanolamine with Unsaturated Fatty Acids

P. Plastina, J.P. Vincken, H. Gruppen, R.F. Witkamp, B. Gabriele

Research output: Contribution to journalArticleAcademicpeer-review

22 Citations (Scopus)

Abstract

The selective synthesis of unsaturated N-acylethanolamines 1b-6b by lipase-catalyzed direct condensation between unsaturated fatty acids 1a-6a and ethanolamine is reported. Reactions were carried out in hexane at 40 °C, in the presence of Candida antarctica Lipase B as the catalyst, to give the corresponding amides 1b-6b with yields ranging from 80 to 88%.
Original languageEnglish
Pages (from-to)444-447
JournalLetters in Organic Chemistry
Volume6
Issue number6
DOIs
Publication statusPublished - 2009

Fingerprint

Acylation
Ethanolamine
Hexanes
Lipase
Unsaturated Fatty Acids
Amides
Condensation
Catalysts
N-acylethanolamines
Candida antarctica lipase B

Keywords

  • enzymatic-synthesis
  • amide surfactants
  • carboxylic-acids
  • ionic liquids
  • solvent
  • anandamide
  • endocannabinoids
  • amidation
  • pressure
  • amines

Cite this

@article{ea9dff2496484650a786e17080d36b14,
title = "Selective Synthesis of Unsaturated N-Acylethanolamines by Lipase-Catalyzed N-Acylation of Ethanolamine with Unsaturated Fatty Acids",
abstract = "The selective synthesis of unsaturated N-acylethanolamines 1b-6b by lipase-catalyzed direct condensation between unsaturated fatty acids 1a-6a and ethanolamine is reported. Reactions were carried out in hexane at 40 °C, in the presence of Candida antarctica Lipase B as the catalyst, to give the corresponding amides 1b-6b with yields ranging from 80 to 88{\%}.",
keywords = "enzymatic-synthesis, amide surfactants, carboxylic-acids, ionic liquids, solvent, anandamide, endocannabinoids, amidation, pressure, amines",
author = "P. Plastina and J.P. Vincken and H. Gruppen and R.F. Witkamp and B. Gabriele",
year = "2009",
doi = "10.2174/157017809789124885",
language = "English",
volume = "6",
pages = "444--447",
journal = "Letters in Organic Chemistry",
issn = "1570-1786",
publisher = "Bentham Science Publishers",
number = "6",

}

Selective Synthesis of Unsaturated N-Acylethanolamines by Lipase-Catalyzed N-Acylation of Ethanolamine with Unsaturated Fatty Acids. / Plastina, P.; Vincken, J.P.; Gruppen, H.; Witkamp, R.F.; Gabriele, B.

In: Letters in Organic Chemistry, Vol. 6, No. 6, 2009, p. 444-447.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Selective Synthesis of Unsaturated N-Acylethanolamines by Lipase-Catalyzed N-Acylation of Ethanolamine with Unsaturated Fatty Acids

AU - Plastina, P.

AU - Vincken, J.P.

AU - Gruppen, H.

AU - Witkamp, R.F.

AU - Gabriele, B.

PY - 2009

Y1 - 2009

N2 - The selective synthesis of unsaturated N-acylethanolamines 1b-6b by lipase-catalyzed direct condensation between unsaturated fatty acids 1a-6a and ethanolamine is reported. Reactions were carried out in hexane at 40 °C, in the presence of Candida antarctica Lipase B as the catalyst, to give the corresponding amides 1b-6b with yields ranging from 80 to 88%.

AB - The selective synthesis of unsaturated N-acylethanolamines 1b-6b by lipase-catalyzed direct condensation between unsaturated fatty acids 1a-6a and ethanolamine is reported. Reactions were carried out in hexane at 40 °C, in the presence of Candida antarctica Lipase B as the catalyst, to give the corresponding amides 1b-6b with yields ranging from 80 to 88%.

KW - enzymatic-synthesis

KW - amide surfactants

KW - carboxylic-acids

KW - ionic liquids

KW - solvent

KW - anandamide

KW - endocannabinoids

KW - amidation

KW - pressure

KW - amines

U2 - 10.2174/157017809789124885

DO - 10.2174/157017809789124885

M3 - Article

VL - 6

SP - 444

EP - 447

JO - Letters in Organic Chemistry

JF - Letters in Organic Chemistry

SN - 1570-1786

IS - 6

ER -