Gyrocyanin

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.^[1]

Quick facts Names, Identifiers ...

Gyrocyanin

Names
IUPAC name 4-hydroxy-2,5-bis(4-hydroxyphenyl)-4-Cyclopentene-1,3-dione
Identifiers
CAS Number	52591-12-5
3D model (JSmol)	Interactive image
ChEBI	CHEBI:174127
ChemSpider	35013702
PubChem CID	71438153
CompTox Dashboard (EPA)	DTXSID201180617
InChI 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 Key: DIFAFZFNMSLGGN-UHFFFAOYSA-N
SMILES O=C1C(O)=C(C(=O)C1C2=CC=C(O)C=C2)C=3C=CC(O)=CC3
Properties
Chemical formula	C17H12O5
Molar mass	296.278 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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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.