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	{{chembox		{{chembox
			| verifiedrevid = 399423219
	| ImageFile = Protoanemonina.svg		| ImageFile = Protoanemonina.svg
			| ImageAlt = Skeletal formula of protoanemonin
⚫	| IUPACName = 5-Methylidenefuran-2-one
			| ImageFile1 = Protoanemonin 3D spacefill.png
			| ImageSize1 = 160
			| ImageAlt1 = Space-filling model of the protoanemonin molecule
		⚫	| PIN = 5-Methylidenefuran-2(5''H'')-one
	| OtherNames = 4-Methylenebut-2-en-4-olide		| OtherNames = 4-Methylenebut-2-en-4-olide
	| Reference = <ref name="druglead" /><ref name="Römpp" />		| Reference = <ref name="Römpp" />
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| CASNo = 108-28-1		| CASNo = 108-28-1
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = 66FQZ1A5SO
	| PubChem = 66948		| PubChem = 66948
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 60307		| ChemSpiderID = 60307
	| SMILES = C=C1C=CC(=O)O1		| SMILES = C=C1C=CC(=O)O1
	| InChI = 1/C5H4O2/c1-4-2-3-5(6)7-4/h2-3H,1H2		| InChI = 1/C5H4O2/c1-4-2-3-5(6)7-4/h2-3H,1H2
	| InChIKey = RNYZJZKPGHQTJR-UHFFFAOYAD		| InChIKey = RNYZJZKPGHQTJR-UHFFFAOYAD
			| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C5H4O2/c1-4-2-3-5(6)7-4/h2-3H,1H2		| StdInChI = 1S/C5H4O2/c1-4-2-3-5(6)7-4/h2-3H,1H2
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = RNYZJZKPGHQTJR-UHFFFAOYSA-N		| StdInChIKey = RNYZJZKPGHQTJR-UHFFFAOYSA-N
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| C=5 | H=4 | O=2		| C=5 | H=4 | O=2
	| MolarMass = 96.08 g/mol		| MolarMass = 96.08 g/mol
	| Appearance = Pale yellow oil		| Appearance = Pale yellow oil
	| Density =		| Density =
	| MeltingPt =		| MeltingPtC =
			| BoilingPtC = 73<ref>{{Cite book|chapter-url=https://books.google.com/books?id=bNDMBQAAQBAJ&pg=SA7-PA|title=CRC Handbook of Chemistry and Physics|last1=Haynes|first1=William M.|last2=Lide|first2=David R.|last3=Bruno|first3=Thomas J.|publisher=CRC Press|year=2014|isbn=9781482208689|edition=95th|location=Boca Raton, Florida|pages=370|chapter=3|oclc=908078665}}</ref>
	| BoilingPt = 45 ]
	| Boiling_notes = 2 ]
	| Solubility = }}		| Solubility = }}
	| Section3 = {{Chembox Hazards		|Section3={{Chembox Hazards
	| LD50 = 190 mg·kg<sup>−1</sup> (mouse)		| LD50 = 190 mg·kg<sup>−1</sup> (mouse)<ref>{{Cite journal
			| last1 = Martín
			| first1 = ML
			| last2 = San Román
			| first2 = L
			| last3 = Domínguez
			| first3 = A
			| title = In vitro activity of protoanemonin, an antifungal agent.
			| journal = Planta Medica
			| volume = 56
			| issue = 1
			| pages = 66–9
			| year = 1990
			| pmid = 2356244
			| doi = 10.1055/s-2006-960886
			| s2cid = 260283223
			|quote=The LD50 of protoanemonin in male Swiss albino mice was 190 mg/kg.
			}}
			</ref>
	| FlashPt =		| FlashPt =
	| Autoignition = }}		| AutoignitionPt = }}
	}}		}}
	'''Protoanemonin''' (sometimes called '''anemonol''' or '''ranunculol'''<ref name="Hager" />) is a ] found in all plants of the ] (Ranunculaceae). On maceration, for example when the plant is wounded, it is produced by an ] process from the ] ].<ref name="druglead" /> It is the ] of 4-hydroxy-2,4-pentadienoic acid.		'''Protoanemonin''' (sometimes called '''anemonol''' or '''ranunculol'''<ref name="Hager" />) is a ] found in all plants of the ] (Ranunculaceae). When the plant is wounded or ], the unstable ] found in the plant, ], is ] broken down into ] and the toxic protoanemonin.<ref name="Hunnius" /> It is the ] of 4-hydroxy-2,4-pentadienoic acid.
			Contact with a wounded plant causes itch, rashes or blistering on contact with the skin or ]. Ingesting the toxin can cause ], vomiting, ], ]s, acute ], ], or ].<ref>{{Cite journal|title = Lesser celandine (pilewort) induced acute toxic liver injury: The first case report worldwide|journal = World Journal of Hepatology|date = 2015-02-27|issn = 1948-5182|pmc = 4342611|pmid = 25729484|pages = 285–288|volume = 7|issue = 2|doi = 10.4254/wjh.v7.i2.285|first1 = Bulent|last1 = Yilmaz|first2 = Barış|last2 = Yilmaz|first3 = Bora|last3 = Aktaş|first4 = Ozan|last4 = Unlu|first5 = Emir Charles|last5 = Roach | doi-access=free }}</ref><ref>{{Cite book|title = List of Substances of the Competent Federal Government and Federal State Authorities: Category "Plants and plant parts"|url = https://books.google.com/books?id=RdKEBAAAQBAJ|publisher = Springer|date = 2014-09-12|isbn = 9783319107325|language = en|first = Bundesamt für|last = Verbraucherschutz}}</ref><ref>{{Cite book|title = Lewis' Dictionary of Toxicology|url = https://books.google.com/books?id=caTqdbD7j4AC|publisher = CRC Press|date = 1998-03-23|isbn = 9781566702232|language = en|first = Robert Alan|last = Lewis}}</ref>
	A wounded plant releases the substance, causing itch, rashes or blistering on contact with the skin or ]. Ingesting fresh Ranunculaceae can lead to ], vomiting, ], ]s, or ].
	When drying the plant, protoanemonin comes into contact with air and ]s to ], which is further ]d to a non-toxic ].<ref name="Hunnius" /><ref name="Gmelin" />		When drying the plant, protoanemonin comes into contact with air and ]s to ], which is further ]d to a non-toxic ].<ref name="Hunnius" /><ref name="Gmelin" />
	==Biological pathway==		==Biological pathway==
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	| ] || ]		| ] || ]
	|-		|-
	| ↓ – ] || (], ]ally)		| ↓ – ] || (], ]ally)
	|-		|-
	| ]|| protoanemonin		| ]|| protoanemonin
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	| ↓ ]		| ↓ ]
	|-		|-
	| ]		| ] || 4,7-dioxo-2-decenedioic acid
	|}		|}
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	<ref name="Hager">{{cite book|editor1-first=PH|editor1-last=List|editor2-first=L|editor2-last=Hörhammer|title=Hagers Handbuch der pharmazeutischen Praxis|edition=4|publisher=Springer Verlag|year=1979|language=German|isbn=3-540-07738-3}}</ref>		<ref name="Hager">{{cite book|editor1-first=PH|editor1-last=List|editor2-first=L|editor2-last=Hörhammer|title=Hagers Handbuch der pharmazeutischen Praxis|edition=4|publisher=Springer Verlag|year=1979|language=German|isbn=3-540-07738-3}}</ref>
	<ref name="Hunnius">{{cite book|editor1-first=Artur|editor1-last=Berger|editor2-first=Helmut|editor2-last=Wachter|title=Hunnius Pharmazeutisches Wörterbuch|edition=8|publisher=Walter de Gruyter Verlag|year=1998|language=German|isbn=3-11-015793-4}}</ref>		<ref name="Hunnius">{{cite book|editor1-first=Artur|editor1-last=Berger|editor2-first=Helmut|editor2-last=Wachter|title=Hunnius Pharmazeutisches Wörterbuch|edition=8|publisher=Walter de Gruyter Verlag|year=1998|language=German|isbn=3-11-015793-4}}</ref>
	<ref name="druglead">{{cite web|url=http://www.druglead.com/chemical/Protoanemonin.html|publisher=DrugLead|title=Protoanemonin|accessdate=27 November 2010}}</ref>
	<ref name="Römpp">{{cite book|first1=Hermann|last1=Römpp|first2=Jürgen|last2=Falbe|first3=Manfred|last3=Regitz|title=Römpp Lexikon Chemie|edition=9|publisher=Georg Thieme Verlag|location=Stuttgart|year=1992|language=German}}</ref>		<ref name="Römpp">{{cite book|first1=Hermann|last1=Römpp|first2=Jürgen|last2=Falbe|first3=Manfred|last3=Regitz|title=Römpp Lexikon Chemie|edition=9|publisher=Georg Thieme Verlag|location=Stuttgart|year=1992|language=German}}</ref>
	<ref name="Gmelin">, Leopold Gmelin {{de icon}}</ref>		<ref name="Gmelin">, Leopold Gmelin {{in lang|de}}</ref>
	}}		}}
	]		]
	]		]
			]
			]
	{{heterocyclic-stub}}
	]
	]
	]
	]