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| | L-(+)-Ergothioneine Basic information |
| Product Name: | L-(+)-Ergothioneine | | Synonyms: | L-(+)-ERGOTHIONEINE INNER SALT;ERGOLD;2-MERCAPTOHISTIDINE BETAINE;(S)-ALPHA-CARBOXY-2,3-DIHYDRO-N,N,N-TRIMETHYL-2-THIOXO-1H-IMIDAZOLE-4-ETHANAMINIUM INNER SALT;THIONEINE;(S)-[1-carboxy-2-(2-mercaptoimidazol-4-yl)ethyl]trimethylammonium hydroxide;1H-Imidazole-4-ethanaminium, .alpha.-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-, inner salt, (.alpha.S)-;3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoate | | CAS: | 497-30-3 | | MF: | C9H15N3O2S | | MW: | 229.3 | | EINECS: | 207-843-5 | | Product Categories: | Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds | | Mol File: | 497-30-3.mol |  |
| | L-(+)-Ergothioneine Chemical Properties |
| Melting point | 275-277°C (dec.) | | density | 1.2541 (rough estimate) | | refractive index | 1.6740 (estimate) | | storage temp. | -20°C | | solubility | Soluble in Water (up to 10 mg/ml) | | form | White solid. | | color | White or off-white | | PH | +47^o (c=1 in water) | | Stability: | Stable for 1 year from date of purchase as supplied. Solutions in water may be stored at -20°C for no more then 1 day. | | InChI | InChI=1/C9H15N3O2S/c1-12(2,3)7(8(13)14)4-6-5-10-9(15)11-6/h5,7H,4H2,1-3H3,(H2-,10,11,13,14,15)/t7-/s3 | | InChIKey | SSISHJJTAXXQAX-KPOCXSGKNA-N | | SMILES | [N+](C)(C)(C)[C@@H](CC1=CNC(S)=N1)C([O-])=O |&1:4,r| | | EPA Substance Registry System | 1H-Imidazole-4-ethanaminium, .alpha.-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-, inner salt, (.alpha.S)- (497-30-3) |
| WGK Germany | 3 | | HS Code | 2933299090 |
| | L-(+)-Ergothioneine Usage And Synthesis |
| 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. | | Chemical Properties | White Solid | | 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.
| | Definition | ChEBI: Ergothioneine is a L-histidine derivative that is N(alpha),N(alpha),N(alpha)-trimethyl-L-histidine in which the hydrogen at position 2 on the imdazole ring is replaced by a mercapto group. A naturally occurring metabolite of histidine synthesized by bacteria and fungi with antioxidant properties. It is found ubiquitously in plants and animals and is present in many human foodstuffs. It has a role as an antioxidant, a fungal metabolite, a plant metabolite, a xenobiotic metabolite and a chelator. It is an amino-acid betaine, a L-histidine derivative and a sulfur-containing amino acid. It is a conjugate base of an ergothioneine(1+). It is a tautomer of an ergothioneine thione form. | | benefits | L-(+)-Ergothioneine is a natural antioxidant, which has various physiological functions such as scavenging free radicals, detoxification, maintaining DNA biosynthesis, normal cell growth and cellular immunity. | | General Description | L-(+)-Ergothioneine (ET) is a sulfur-containing amino acid, which is only produced by Actinomycetales bacteria and non-yeast like fungi belonging to the division Basidiomycota and Ascomycota. It was originally isolated from Claviceps purpurea or rye ergot. It is obtained from L-histidine, which is converted into betaine form called hercynine. It is found in both animals and plants, and mammals usually obtain it from their diet, e.g. through mushrooms or oats. It is tautomeric in nature, and in neutral aqueous solution exists in thione form. | | Biochem/physiol Actions | L-(+)-Ergothioneine (ET) has the maximum concentrations in tissues subjected to oxidative stress, with the highest being in blood, eye lens, bone marrow, semen and liver. It acts as an anti-oxidant and prevents apoptosis, by scavenging reactive oxygen and nitrogen species. The anti-oxidant activity is attributable to sulfhydryl groups. It acts as a substrate for SLC22A4 (solute carrier family 22, member 4) transporter. In alveolar macrophages, it prevents the release of interleukin-8 (IL-8) by tumor necrosis factor (TNF)α. IL-8 is an inflammatory cytokine. It also regulates the oxidative damage in liver and kidneys, and has a protective action against lipid peroxidation. It is also responsible for the conservation of endogenous glutathione and α-tocopherol. ET being an antioxidant, protects against γ and UV radiation. In UV-irradiated human dermal fibroblasts, it scavenges reactive oxygen species (ROS), and suppresses matrix metalloproteinases 1 (MMP1) expression. It might also have anti-ageing effects on skin caused by UV-radiation. |
| | L-(+)-Ergothioneine Preparation Products And Raw materials |
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