Loading AI tools
Chemical compound From Wikipedia, the free encyclopedia
Protoanemonin (sometimes called anemonol or ranunculol[4]) 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.[5] It is the lactone of 4-hydroxy-2,4-pentadienoic acid.
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 |
PubChem CID |
|
UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
Properties | |
C5H4O2 | |
Molar mass | 96.08 g/mol |
Appearance | Pale yellow oil |
Boiling point | 73[2] °C (163 °F; 346 K) |
Hazards | |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
190 mg·kg−1 (mouse)[3] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
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.[6][7][8]
When drying the plant, protoanemonin comes into contact with air and dimerizes to anemonin, which is further hydrolyzed to a non-toxic dicarboxylic acid.[5][9]
ranunculin | |
↓ – glucose | (maceration, enzymatically) |
protoanemonin | |
↓ dimerization | (air or water contact) |
anemonin | |
↓ hydrolyzation | |
4,7-dioxo-2-decenedioic acid |
Seamless Wikipedia browsing. On steroids.
Every time you click a link to Wikipedia, Wiktionary or Wikiquote in your browser's search results, it will show the modern Wikiwand interface.
Wikiwand extension is a five stars, simple, with minimum permission required to keep your browsing private, safe and transparent.