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A facile synthesis of 4-hydroxy-2(E)-nonenal

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Lipids

Abstract

A facile, efficient synthesis of 4-hydroxy-2(E)-nonenal is presented as an alternative to the approaches published previously, which either employed four to six separate steps or furnished low yields. The commercially available 3(Z)-nonenol was sequentially oxidized into 3,4-epoxynonanol by 3-chloroperoxybenzoic acid followed by oxidation of the alcohol by periodinane to afford 4-hydroxy-2(E)-nonenal by this two-step procedure in 48±7% yield.

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Abbreviations

COSY:

correlative spectroscopy

DEPT:

distortionless enhancement by polarization transfer

EI-MS:

electron impact-mass spectrometry

FT-IR:

Fourier transform-infrared

GC/MS:

gas chromatography/mass spectrometry

GLC:

gas-liquid chromatography

4HNE:

4-hydroxy-2(E)-nonenal

HPLC:

high-performance liquid chromatography

IR:

infrared

NMR:

nuclear magnetic resonance

TLC:

thin-layer chromatography

TMS:

tetramethylsilane

UV:

ultraviolet

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Authors and Affiliations

  1. National Center for Agricultural Utilization Research, Agricultural Research Service, USDA, 1815 N. University Street, 61604, Peoria, Illinois

    H. W. Gardner, R. J. Bartelt & D. Weisleder

Authors
  1. H. W. Gardner
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  2. R. J. Bartelt
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  3. D. Weisleder
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Gardner, H.W., Bartelt, R.J. & Weisleder, D. A facile synthesis of 4-hydroxy-2(E)-nonenal. Lipids 27, 686–689 (1992). https://doi.org/10.1007/BF02536025

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  • DOI: https://doi.org/10.1007/BF02536025

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