Hercynine Chemical Properties

Melting point:

237-238° (dec)

alpha 

D22 +44.5° (5N HCl)

storage temp. 

2-8°C

solubility 

Methanol (Slightly), Water (Slightly)

form 

Solid

color 

Off-White to Pale Yellow

Stability:

Hygroscopic

InChI

InChI=1/C9H15N3O2/c1-12(2,3)8(9(13)14)4-7-5-10-6-11-7/h5-6,8H,4H2,1-3H3,(H-,10,11,13,14)/t8-/s3

InChIKey

GPPYTCRVKHULJH-SBYBRXNCNA-N

SMILES

[C@H](C(=O)[O-])([N+](C)(C)C)CC1NC=NC=1 |&1:0,r|

Hercynine Usage And Synthesis

Uses

L-Hercynine is a precursor of L-(+)-Ergothioneine (E600000); a natural molecule isolated from the rye ergot fungus and later identified in rat erythrocytes and liver and in numerous other animal tissues. Its antioxidizing properties may afford the compound therapeutic potential or it may be used as a food additive or in cosmetics.

Definition

ChEBI: N(alpha),N(alpha),N(alpha)-trimethyl-L-histidine is an amino-acid betaine and a member of N(alpha)-methyl-L-histidines. It is a conjugate base of a N(alpha),N(alpha),N(alpha)-trimethyl-L-histidinium(1+).

Definition

Hercynine is an intermediate (precursor) in ERGO biosynthesis; thus, fungi and mycobacteria can synthesize hercynine, but animals cannot. A human study showed that hercynine was detected in whole blood, plasma, urine, and saliva, and another clinical study showed that the levels of hercynine correlated with those of ERGO in whole blood, which suggested that hercynine is a metabolite of ERGO. However, the levels of hercynine were lower than those of ERGO, which presented the possibility that hercynine was further oxidized.