L-Ergothionine hydrochloride

Base Information

• Chemical Name: L-Ergothionine hydrochloride
• CAS No.: 497-30-3
• Molecular Formula: C9H15N3O2S
• Molecular Weight: 229.303
• Hs Code.: 2933299090
• NSC Number: 118378,7175
• Nikkaji Number: J238.781F,J3.400.909K
• ChEMBL ID: CHEMBL2004102
• Mol file: 497-30-3.mol

Synonyms:2 Thiol L histidine betaine;2-Thiol-L-histidine-betaine;Ergothioneine;Thioneine

Chemical Property of L-Ergothionine hydrochloride

Chemical Property:

• Appearance/Colour: White solid
• Melting Point: 275-277 °C (dec.)
• Refractive Index: 1.6740 (estimate)
• PSA: 100.97000
• Density: 1.2541 (rough estimate)
• LogP: 0.77420
• Storage Temp.: −20°C
• Solubility.: Soluble in Water (up to 10 mg/ml)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 230.09632294
• Heavy Atom Count: 15
• Complexity: 320

Purity/Quality:

99% ^*data from raw suppliers

L-(+)-Ergothioneine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[N+](C)(C)C(CC1=CNC(=S)N1)C(=O)O
• Description: L-(+)-Ergothioneine is a naturally-occurring amino acid derived from histidine via hercynine. Ergothioneine is a stable antioxidant that scavenges and detoxifies free radicals and oxidants, increases intracellular thiol levels, controls nuclear factor-κB activation, and inhibits inflammatory gene expression. In addition, it inhibits the peroxynitrite-dependent nitration of nitrotyrosine, blocks oxidative DNA damage and cell death, and prevents the formation of xanthine and hypoxanthine. Ergothioneine is transported by the organic cation/carnitine transporter 1, which has been linked with autoimmune diseases, including rheumatoid arthritis and Crohn’s disease.
• Uses: L-(+)-Ergothioneine is 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.

Technology Process of L-Ergothionine hydrochloride

There total 20 articles about L-Ergothionine hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

C20H30N3O2S(1+)*I(1-) → (2S)-3-(2-thioxo-1,3-dihydroimidazol-4-yl)-2-(trimethylammonio) propanoate (4756-85-8,497-30-3)

Guidance literature:

With hydrogenchloride; 5%-palladium/activated carbon; hydrogen; In methanol; water; for 20h; under 760.051 Torr;

Reference yield: 80.0%

(2S)-3-(2-{[(2R)-2-amino-2-carboxyethyl]thio}-1H-imidazol-5-yl)-2-(trimethylammonio)propanoate trihydrochloride hydrate → (2S)-3-(2-thioxo-1,3-dihydroimidazol-4-yl)-2-(trimethylammonio) propanoate (4756-85-8,497-30-3)

Guidance literature:

With 3-mercaptopropionic acid; In water; at 90 - 100 ℃; for 18h;

DOI:10.1039/c2gc35367a

Reference yield: 69.0%

2-{2-[(2-ammonio-2-carboxyethyl)thio]-1H-imidazol-4-yl}-1-carboxy-N,N,N-trimethylethanaminium dihydrochloride → (2S)-3-(2-thioxo-1,3-dihydroimidazol-4-yl)-2-(trimethylammonio) propanoate (4756-85-8,497-30-3)

Guidance literature:

2-{2-[(2-ammonio-2-carboxyethyl)thio]-1H-imidazol-4-yl}-1-carboxy-N,N,N-trimethylethanaminium dihydrochloride; With 3-mercaptopropionic acid; In water; at 85 ℃; for 72h;

With ammonia; In water; pH=6;

upstream raw materials:

methyl (S)-3-<1-(ethoxycarbonyl)-2-<(ethoxycarbonyl)thio>-1H-imidazol-4-yl>-2-(trimethylammonio)propionate iodide

methyl iodide

l-histidine methyl ester dihydrochloride

methyl (S)-3-(2-mercapto-1H-imidazol-4-yl)-2-(dimethylamino)propionate

Downstream raw materials:

Hercynine

carbon dioxide

hydrogen sulfide

ammonia

Refernces

• 1、 Irani, Seema,Naowarojna, Nathchar,Tang, Yang,Kathuria, Karan R.,Wang, Shu,Dhembi, Anxhela,Lee, Norman,Yan, Wupeng,Lyu, Huijue,Costello, Catherine E.,Liu, Pinghua,Zhang, Yan Jessie. "Snapshots of C-S Cleavage in Egt2 Reveals Substrate Specificity and Reaction Mechanism". . p. 519 - 4,529. Retrieved 2018/03/06.
• 2、 -. "Nα, Nα, Nα-trialkyl histidine derivatives useful for the preparation of ergothioneine compounds". Page/Page column 22. . Retrieved 2016/09/26.