Gyrocyanin

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

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]

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

↑ Besl H, Bresinsky A, Steglish W, Zipfel K (1973). "Pilzpigmente, XVII. Über Gyrocyanin, das blauende Prinzip des Kornblumenröhrlings (Gyroporus cyanescens), und eine oxidative Ringverengung des Atromentins" [Fungus pigments .17. Gyrocyanin, blueing principle of Gyroporus cyanescens, and an oxidative ring contraction of atromentin]. Chemische Berichte/Recueil (in German). 106 (10): 3223–9. doi:10.1002/cber.19731061012.

[Besl_1973-1] Besl H, Bresinsky A, Steglish W, Zipfel K (1973). "Pilzpigmente, XVII. Über Gyrocyanin, das blauende Prinzip des Kornblumenröhrlings (Gyroporus cyanescens), und eine oxidative Ringverengung des Atromentins" [Fungus pigments .17. Gyrocyanin, blueing principle of Gyroporus cyanescens, and an oxidative ring contraction of atromentin]. Chemische Berichte/Recueil (in German). 106 (10): 3223–9. doi:10.1002/cber.19731061012.

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