Protoanemonin

Protoanemonin
Skeletal formula of protoanemonin
Space-filling model of the protoanemonin molecule
Names
Preferred IUPAC name
5-Methylidenefuran-2(5H)-one
Other names
4-Methylenebut-2-en-4-olide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.244 Edit this at Wikidata
UNII
  • InChI=1S/C5H4O2/c1-4-2-3-5(6)7-4/h2-3H,1H2 checkY
    Key: RNYZJZKPGHQTJR-UHFFFAOYSA-N checkY
  • InChI=1/C5H4O2/c1-4-2-3-5(6)7-4/h2-3H,1H2
    Key: RNYZJZKPGHQTJR-UHFFFAOYAD
  • C=C1C=CC(=O)O1
Properties
C5H4O2
Molar mass 96.08 g/mol
Appearance Pale yellow oil
Boiling point 73 °C (163 °F; 346 K)
Hazards
Lethal dose or concentration (LD, LC):
190 mg·kg−1 (mouse)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Protoanemonin (sometimes called anemonol or ranunculol) is a toxin found in all plants of the buttercup family (Ranunculaceae). When the plant is wounded or macerated, the unstable glucoside found in the plant, ranunculin, is enzymatically broken down into glucose and the toxic protoanemonin. It is the lactone of 4-hydroxy-2,4-pentadienoic acid.

Contact with a wounded plant causes itch, rashes or blistering on contact with the skin or mucosa. Ingesting the toxin can cause nausea, vomiting, dizziness, spasms, acute hepatitis, jaundice, or paralysis.

When drying the plant, protoanemonin comes into contact with air and dimerizes to anemonin, which is further hydrolyzed to a non-toxic dicarboxylic acid.

Biological pathway

ranunculin
↓ – glucose (maceration, enzymatically)
protoanemonin
dimerization (air or water contact)
anemonin
hydrolyzation
4,7-dioxo-2-decenedioic acid

This page was last updated at 2024-01-27 19:50 UTC. Update now. View original page.

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