Polyacetylenes from water hemlock, Cicuta virosa
Related Experiment Video
Updated: Jul 17, 2026

Towards Biomimicking Wood: Fabricated Free-standing Films of Nanocellulose, Lignin, and a Synthetic Polycation
Published on: June 17, 2014
U Wittstock1, F Hadacek, G Wurz
1Institut für Pharmazeutische Biologie der Ernst-Moritz-Arndt Universität Greifswald, Jahnstrasse 15a, D-17489 Greifswald, Germany.
Abstract:
Isolation of polyacetylenes from aerial and subterranean parts of water hemlock, Cicuta virosa L. (Apiaceae. Apioideae), yielded eleven C (17)-polyacetylenes: cicutoxin, cicutol, (8 E,10 E)-heptadecadiene-4,6-diyne-1,12-diol (cicudiol, 7), 2,3-dihydrooenanthetol and (8 E)-heptadecene-4,6-diyne-1,10-diol already known to occur in water hemlock, the configurational isomers of cicutoxin (isocicutoxin) and of cicutol (isocicutol, and two incompletely characterised isomers with two cis-double bonds), all of them not described in previous investigations, falcarindiol, (1,8 E,10 E)-heptadecatriene-4,6-diyn-3-ol, already known from other Apiaceae, and the novel polyacetylene (1,8 E/ Z,10 E,12 E)-heptadecatetraene-4,6-diyn-3-ol. Keto compounds, postulated to occur in water hemlock, could not be detected. HPLC profiles of the lipophilic extracts of different organs, individuals, and provenances of water helmock harvested at different seasons revealed quantitative but not qualitative variations of the polyacetylene composition.
More Related Videos
Related Concept Videos
Aldehydes and Ketones with Alcohols: Hemiacetal Formation
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
Acid-Catalyzed Hydration of Alkenes
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

