Gyrocyanin

{{Use dmy dates|date=May 2026}} {{Chembox | ImageFile = Gyrocyanin.svg | ImageClass = skin-invert-image | IUPACName = 4-hydroxy-2,5-bis(4-hydroxyphenyl)-4-Cyclopentene-1,3-dione |Section1={{Chembox Identifiers | CASNo = 52591-12-5 | ChEBI = 174127 | ChemSpiderID = 35013702 | PubChem = 71438153 | StdInChI = InChI=1S/C17H12O5/c18-11-5-1-9(2-6-11)13-15(20)14(17(22)16(13)21)10-3-7-12(19)8-4-10/h1-8,13,18-19,22H | StdInChIKey = DIFAFZFNMSLGGN-UHFFFAOYSA-N | SMILES = O=C1C(O)=C(C(=O)C1C2=CC=C(O)C=C2)C=3C=CC(O)=CC3 }} |Section2={{Chembox Properties | C=17| H=12| O=5 }} |Section8={{Chembox Related }} }}

'''Gyrocyanin''' is a 2,5-diarylcyclopentane-1,3-dione natural product found in the sporophores (fruiting bodies) of several species of bolete fungus in the family Gyroporaceae, including ''Gyroporus cyanescens''.<ref name="Besl 1973">{{cite journal |vauthors=Besl H, Bresinsky A, Steglish W, Zipfel K |title=Pilzpigmente, XVII. Über Gyrocyanin, das blauende Prinzip des Kornblumenröhrlings (''Gyroporus cyanescens''), und eine oxidative Ringverengung des Atromentins |trans-title=Fungus pigments .17. Gyrocyanin, blueing principle of ''Gyroporus cyanescens'', and an oxidative ring contraction of atromentin |journal=Chemische Berichte/Recueil |year=1973 |volume=106 |issue=10 |pages=3223–9 |doi=10.1002/cber.19731061012 |language=German}}</ref>

It is likely that the blue staining of psychoactive bolete ''Lanmaoa asiatica'' is due to gyrocyanin or a related compound, since this species is not known to produce the psilocybin or psilocin that leads to blue staining of ''Psilocybe cubensis'' and related psychoactive fungi.

==Related compounds== * Involutin

==References== {{reflist}}

Category:4-Hydroxyphenyl compounds Category:Cyclopentenes Category:Cyclic ketones Category:Triols