3663. Ergothioneine

Nomenclature

CAS number: 497-30-3
(αS)-α-Carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium inner salt; [1-carboxy-2-[2-mercaptoimidazol-4-yl]ethyl]trimethylammonium hydroxide inner salt; l(+)-ergothioneine; thioneine; thiolhistidine-betaine; thiasine; sympectothion.
C9H15N3O2S; mol wt 229.30.
C 47.14%, H 6.59%, N 18.33%, O 13.95%, S 13.98%.

Description and references

First discovered in the sclerotia of the ergot fungus, Claviceps purpurea, by Tanret, J. Pharm. Chim. 30, 145 (1909). Has since been found to occur in blood, semen and various mammalian tissues, principally liver and kidneys. Biosynthesis from histidine by Claviceps purpurea cultures: Heath, Wildy, Nature 179, 196 (1957); also produced by Neurospora crassa: Melville et al., Fed. Proc. 15, 314 (1956). Chemical synthesis: Heath et al., J. Chem. Soc. 1951, 2215. Occurrence in the Linulus polyphemus L. (king crab): Ackermann, List, Z. Physiol. Chem. 313, 30 (1958). Review: Melville, Vitam. Horm. 17, 155 (1959).

Chemical structure

Derivative

Dihydrate.

Properties

Needles or leaflets from dil ethanol, dec 256-257°. [α]D20 +116.5°; [α]D27 +115° (H2O). uv max (water): 258 nm (ε 16000). One gram dissolves in 5 ml at 25°, much more sol in hot water. Slightly sol in hot methanol, hot ethanol, acetone. Practically insol in ether, chloroform, benzene.