Protoanemonin

Protoanemonin

Names
IUPAC name 5-Methylidenefuran-2-one
Other names 4-Methylenebut-2-en-4-olide
Identifiers
CAS Number	108-28-1
ChemSpider	60307 Y
Jmol 3D model	Interactive image
PubChem	66948
InChI InChI=1S/C5H4O2/c1-4-2-3-5(6)7-4/h2-3H,1H2 Y Key: RNYZJZKPGHQTJR-UHFFFAOYSA-N Y InChI=1/C5H4O2/c1-4-2-3-5(6)7-4/h2-3H,1H2 Key: RNYZJZKPGHQTJR-UHFFFAOYAD
SMILES C=C1C=CC(=O)O1
Properties
Chemical formula	C5H4O2
Molar mass	96.08 g/mol
Appearance	Pale yellow oil
Boiling point	45 °C (113 °F; 318 K) 2 hPa
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
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 carboxylic acid.

Biological pathway

	ranunculin
↓ – glucose	(maceration, enzymatically)
	protoanemonin
↓ dimerization	(air or water contact)
	anemonin
↓ hydrolyzation