Ichthyothereol

Ichthyothereol
Names
Preferred IUPAC name
(2S,3R)-2-[(1E)-Non-1-ene-3,5,7-triyn-1-yl]oxan-3-ol
Other names
(−)-Ichthyothereol, Cunaniol
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C14H14O2/c1-2-3-4-5-6-7-8-11-14-13(15)10-9-12-16-14/h8,11,13-15H,9-10,12H2,1H3/b11-8+/t13-,14+/m1/s1
  • CC#CC#CC#C/C=C/[C@H]1[C@@H](CCCO1)O
Properties
C14H14O2
Molar mass 214.264 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Ichthyothereol is a toxic polyyne compound found in the leaves and flowers of several plants in South and Central America. These plant sources and their extracts are known for their toxic effects on fish, and have long been used by various native tribes in the lower Amazon basin for fishing.[1][2] The name of the genus Ichthyothere, the members of which contain noticeable amounts of the natural product in their leaves, literally translates as fish poison. It is so toxic, fish will jump out of the water if Ichthyothere terminalis leaves are used as bait.[citation needed] This chemical is also found in the leaves and flowers of Dahlia coccinea. The actual chemical was isolated by several different groups and its full chemical structure determined in 1965.[1] The first total synthesis was published in 2001.[1]

It is also toxic to mice and dogs, producing convulsant effects that are similar to those of picrotoxin.[3]

  1. ^ a b c Mukai, Chisato; Miyakoshi, Naoki; Hanaoka, Miyoji (2001). "First Total Synthesis of (−)-Ichthyothereol and Its Acetate". J. Org. Chem. 66 (17): 5875–5880. doi:10.1021/jo0104532. PMID 11511265.
  2. ^ Mukai, Chisato (2005). "7. Total Synthesis Based on Alkyne–Co2(CO)6 Complexes. III. First Total Synthesis of (–)-Ichthyothereol". In Harmata, Michael (ed.). Strategies And Tactics in Organic Synthesis. Vol. 6. Elsevier. pp. 223–229.
  3. ^ Cascon, Seiva C.; Mors, Walter B.; Tursch, Bernard M.; Aplin, Robin T.; Durham, Lois J. (1965). "Ichthyothereol and Its Acetate, the Active Polyacetylene Constituents of Ichthyothere terminalis (Spreng.) Malme, a Fish Poison from the Lower Amazon". Journal of the American Chemical Society. 87 (22): 5237–5241. doi:10.1021/ja00950a044. ISSN 0002-7863.