Ergothioneine

Title: Ergothioneine
CAS Registry Number: 497-30-3
CAS Name: (aS)-a-Carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium inner salt
Additional Names: [1-carboxy-2-[2-mercaptoimidazol-4-yl]ethyl]trimethylammonium hydroxide inner salt; L(+)-ergothioneine; thioneine; thiolhistidine-betaine; thiasine; sympectothion
Molecular Formula: C9H15N3O2S
Molecular Weight: 229.30
Percent Composition: C 47.14%, H 6.59%, N 18.33%, O 13.95%, S 13.98%
Literature 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).
Derivative Type: Dihydrate
Properties: Needles or leaflets from dil ethanol, dec 256-257°. [a]D20 +116.5°; [a]D27 +115° (H2O). uv max (water): 258 nm (e 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.
Optical Rotation: [a]D20 +116.5°; [a]D27 +115° (H2O)
Absorption maximum: uv max (water): 258 nm (e 16000)
Ergotinine Eriochrome?Black T Eriodictyol Eriodictyon Eritadenine

Ergothioneine
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Identifiers
CAS number 497-30-3 YesY
PubChem 5351619
ChemSpider 4508619 YesY
UNII BDZ3DQM98W YesY
ChEBI CHEBI:4828 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular 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
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Ergothioneine is a naturally occurring amino acid and is a thiourea derivative of histidine, containing a sulfur atom in the imidazole ring. This compound is made in rather few organisms, notably Actinobacteria and filamentous fungi.[1] Ergothioneine was discovered in 1909 and named after the ergot fungus from which it was first purified, with its structure being determined later, in 1911.[2] This amino acid has antioxidant properties, but its chemistry differs from conventional sulfur-containing antioxidants such as glutathione or lipoic acid.

Although ergothioneine cannot be made in human cells, it is present in some tissues at high levels as it is absorbed from the diet.[3] In humans ergothioneine is taken up from the gut and concentrated in some tissues by a specific transporter called ETT (gene symbol SLC22A4). However, even today, one hundred years after its discovery, precisely what ergothioneine does in the human body remains a mystery.[4][5]