References of 1H-Imidazole-4-ethanaminium,a-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-,inner salt, (aS)-
Title: Ergothioneine
CAS Registry Number: 497-30-3
CAS Name: (a
S)-a-Carboxy-2,3-dihydro-
N,N,N-trimethyl-2-thioxo-1
H-imidazole-4-ethanaminium inner salt
Synonyms: [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)