Protoanemonin

Protoanemonin
Names
	Preferred IUPAC name 5-Methylidenefuran-2(5H)-one
	Other names 4-Methylenebut-2-en-4-olide
Identifiers
CAS Number	108-28-1;
3D model (JSmol)	Interactive image;
ChemSpider	60307 ;
ECHA InfoCard	100.003.244
PubChem CID	66948;
UNII	66FQZ1A5SO ;
CompTox Dashboard (EPA)	DTXSID10148346 ;
	InChI InChI=1S/C5H4O2/c1-4-2-3-5(6)7-4/h2-3H,1H2 Key: RNYZJZKPGHQTJR-UHFFFAOYSA-N ; 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	73 °C (163 °F; 346 K)
Hazards
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	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). verify (what is ?) Infobox references

Protoanemonin (sometimes called anemonol or ranunculol) is a toxin whose glyosidic precursor ranunculin is found in many plants of the buttercup family (Ranunculaceae). When the plant is wounded or macerated, ranunculin is enzymatically broken down into glucose and protoanemonin. This toxin's ability to inhibit both gram positive and gram negative bacteria is linked to the presence of a 5-membered lactone ring with a highly reactive double bond system.