Ascorbigen - occurrence, synthesis, and analytics

Martina Opietnik, Sharifah Nabihah Syed Jaafar, Manuel Becker, Stefan Böhmdorfer, Andreas Hofinger, Thomas Rosenau

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Ascorbigen (2-C-(3-indolyl)-methyl-α-L-xylo-hex-3-ulofuranosono-1,4-lactone, 1) is a breakdown product of glucobrassicins found in cruciferous vegetables, such as cabbage, cauliflower, Brussel sprouts, or broccoli, formed by direct C-alkylation of ascorbic acid (vitamin C) by (3-indolyl)-methyl intermediates under physiological conditions. It is a labile compound, and direct synthesis approaches are hampered by the oxidative instability of the indol moiety and ring transformations of the ascorbyl part. The latter have also impeded ascorbigen analytics for decades, and only recently different ascorbigens have been shown to represent mixtures of compounds rather than individual ascorbigen-type compounds. Following a review of pertinent literature, timely aspects of ascorbigen chemistry, including the most recent synthesis approaches and in-depth characterization of the compound, are presented.

Original languageEnglish
Pages (from-to)411-417
Number of pages7
JournalMini-Reviews in Organic Chemistry
Volume9
Issue number4
DOIs
Publication statusPublished - 2012
Externally publishedYes

Fingerprint

Ascorbic Acid
Alkylation
Vegetables
Lactones
ascorbigen
glucobrassicin

Keywords

  • Ascorbic acid
  • Ascorbigen
  • Cruciferous vegetables
  • Glucobrassicin
  • Indol derivatives
  • Nuclear magnetic resonance pyrolysis-GC/MS

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Opietnik, M., Syed Jaafar, S. N., Becker, M., Böhmdorfer, S., Hofinger, A., & Rosenau, T. (2012). Ascorbigen - occurrence, synthesis, and analytics. Mini-Reviews in Organic Chemistry, 9(4), 411-417. https://doi.org/10.2174/157019312804699492

Ascorbigen - occurrence, synthesis, and analytics. / Opietnik, Martina; Syed Jaafar, Sharifah Nabihah; Becker, Manuel; Böhmdorfer, Stefan; Hofinger, Andreas; Rosenau, Thomas.

In: Mini-Reviews in Organic Chemistry, Vol. 9, No. 4, 2012, p. 411-417.

Research output: Contribution to journalArticle

Opietnik, M, Syed Jaafar, SN, Becker, M, Böhmdorfer, S, Hofinger, A & Rosenau, T 2012, 'Ascorbigen - occurrence, synthesis, and analytics', Mini-Reviews in Organic Chemistry, vol. 9, no. 4, pp. 411-417. https://doi.org/10.2174/157019312804699492
Opietnik, Martina ; Syed Jaafar, Sharifah Nabihah ; Becker, Manuel ; Böhmdorfer, Stefan ; Hofinger, Andreas ; Rosenau, Thomas. / Ascorbigen - occurrence, synthesis, and analytics. In: Mini-Reviews in Organic Chemistry. 2012 ; Vol. 9, No. 4. pp. 411-417.
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