Enanthotoxin

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Structural formula
Structural formula of enanthotoxin
General
Surname Enanthotoxin
other names
  • (2 E , 8 E , 10 E , 14 R ) -Heptadeca-2,8,10-triene-4,6-diyne-1,14-diol
  • Oenanthotoxin
Molecular formula C 17 H 22 O 2
External identifiers / databases
CAS number 20311-78-8
PubChem 6436464
Wikidata Q3080860
properties
Molar mass 258.36 g mol −1
Melting point

87 ° C

solubility

soluble in ethanol , diethyl ether and chloroform

safety instructions
GHS hazard labeling
no classification available
Toxicological data

0.83 mg kg −1 ( LD 50mouseoral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Oenanthotoxin is a chemical compound from the group of alkynols and picrotoxins. It is structurally similar to Cicutoxin and was first isolated by Rudolf Boehm in 1876 ​​and analyzed by EFLJ Anet in 1953.

Occurrence

Oenanthotoxin occurs naturally in the saffron vine umbel ( Oenanthe crocata ). The compound is poisonous and causes poisoning in horses and cows.

Extraction and presentation

Ekkehard Winterfeldt was primarily concerned with the synthesis of enanthotoxin .

Individual evidence

  1. a b N. Barsel, AJ Birch, F. Bohlmann , H. Brockmann, H. Brown, JD Chanley, HJ Mannhardt, RA Morton, GAJ Pitt, H. Sobotka, C. Tamm: Progress in the chemistry of organic natural substances / Progress in the Chemistry of Organic Natural Products / Progrès Dans la Chimie des Substances Organiques Naturelles . Springer-Verlag, 2013, ISBN 978-3-7091-7164-6 , pp. 1 ( limited preview in Google Book search).
  2. ^ Annual report of the pharmacy . Deutscher Apotheker-Verlag, 1895, p. 211 ( limited preview in Google Book search).
  3. This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  4. Donald G. Barceloux: Medical Toxicology of Natural Substances Foods, Fungi, Medicinal Herbs, Plants, and Venomous Animals . John Wiley & Sons, 2008, ISBN 978-0-471-72761-3 , pp. 822 ( limited preview in Google Book search).
  5. Sven Sommerwerk, Lucie Heller, Bianka Siewert, René Csuk: Chemoenzymatic synthesis and cytotoxicity of oenanthotoxin and analogues. In: Bioorganic & Medicinal Chemistry. 23, 2015, p. 5595, doi: 10.1016 / j.bmc.2015.07.031 .
  6. Else Petri: Pathological anatomy and histology of poisonings . Springer-Verlag, 2013, ISBN 978-3-7091-6003-9 , pp. 446 ( limited preview in Google Book search).
  7. Mark Kalesse: Ekkehard Winterfeldt (1932-2014). In: Angewandte Chemie. 127, 2015, p. 35, doi: 10.1002 / anie.201410838 .