# Gyrocyanin

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> Markdown URL: https://mediated.wiki/source/Gyrocyanin.md
> Source: https://en.wikipedia.org/wiki/Gyrocyanin
> Source revision: 1354237836
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{{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](/source/bolete) fungus in the family [Gyroporaceae](/source/Gyroporaceae), including ''[Gyroporus cyanescens](/source/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](/source/Lanmaoa_asiatica)'' is due to gyrocyanin or a related compound, since this species is not known to produce the [psilocybin](/source/psilocybin) or [psilocin](/source/psilocin) that leads to blue staining of ''[Psilocybe cubensis](/source/Psilocybe_cubensis)'' and related psychoactive fungi.

==Related compounds==
* [Involutin](/source/Involutin)

==References==
{{reflist}}

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

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Adapted from the Wikipedia article [Gyrocyanin](https://en.wikipedia.org/wiki/Gyrocyanin) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Gyrocyanin?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.