Ergothioneine

Ergothioneine is a naturally occurring amino acid and is a thiourea derivative of histidine, containing a sulfur atom on the imidazole ring. This compound occurs in relatively few organisms, notably actinomycetota, cyanobacteria, and certain fungi. Ergothioneine was discovered by Charles Tanret in 1909 and named after the ergot fungus from which it was first purified, with its structure being determined in 1911.

Ergothioneine

Names
Preferred IUPAC name (2S)-3-(2-Sulfanylidene-2,3-dihydro-1H-imidazol-4-yl)-2-(trimethylazaniumyl)propanoate
Other names L-Ergothioneine; (+)-Ergothioneine; Thiasine; Sympectothion; Ergothionine; Erythrothioneine; Thiolhistidinebetaine
Identifiers
CAS Number	497-30-3 Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:4828 Y
ChemSpider	4508619 Y
ECHA InfoCard	100.007.131
KEGG	C05570 N
PubChem CID	5351619
UNII	BDZ3DQM98W Y
CompTox Dashboard (EPA)	DTXSID901020082
InChI InChI=1S/C9H15N3O2S/c1-12(2,3)7(8(13)14)4-6-5-10-9(15)11-6/h5,7H,4H2,1-3H3,(H2-,10,11,13,14,15)/t7-/m0/s1 Y Key: SSISHJJTAXXQAX-ZETCQYMHSA-N Y InChI=1/C9H15N3O2S/c1-12(2,3)7(8(13)14)4-6-5-10-9(15)11-6/h5,7H,4H2,1-3H3,(H2-,10,11,13,14,15)/t7-/m0/s1 Key: SSISHJJTAXXQAX-ZETCQYMHBA
SMILES C[N+](C)(C)C(CC1=CNC(=S)N1)C(=O)[O-] S=C1N\C(=C/N1)C[C@@H](C([O-])=O)[N+](C)(C)C
Properties
Chemical formula	C9H15N3O2S
Molar mass	229.30 g/mol
Appearance	white solid
Melting point	275 to 277 °C (527 to 531 °F; 548 to 550 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

In humans, ergothioneine is acquired exclusively through the diet and accumulates in erythrocytes, bone marrow, liver, kidney, seminal fluid, and eyes. Although the effect of ergothioneine in vivo is under preliminary research, its physiological role in humans is unknown. Ergothioneine is sold as a dietary supplement.