L-(+)-Ergothioneine
SIGMA/E7521
Synonym: 2-mercaptohistidine trimethyl betaine; Ergothioneine; Sympectothion; Thiasine; Thiolhistidine-
CAS Number: 497-30-3
Empirical Formula (Hill Notation): C9H15N3O2S
Molecular Weight: 229.30
EC Number: 207-843-5
MDL Number: MFCD00167474
Linear Formula: C9H15N3O2S
Product Type: Chemical
| assay | ≥98.0% |
| biological source | fungus (Actinomycetales) |
| fungus (Ascomycota) | |
| fungus (Basidiomycota) | |
| form | powder |
| InChI | 1S/C9H15N3O2S/c1-12(2,3)7 |
| InChI key | SSISHJJTAXXQAX-ZETCQYMHSA |
| mol wt | 229.30 |
| Quality Level | 200  |
| SMILES string | C[N+](C)(C)[C@@H](Cc1c[nH |
| solubility | water: 50 mg/mL, clear, colorless |
| storage condition | (Keep container tightly closed in a dry and well-ventilated place) |
| storage temp. | −20°C |
| technique(s) | protein quantification: suitable |
| Application: | L-(+)-Ergothioneine is suitable for use in the study of its reactivity with 2,2′- and 4,4′-dipyridyl disulphide (2-Py-S-S-2-Py and 4-Py-S-S-4-Py). It may also be used for the incubation of experimental cells while performing in vitro kinase activity assays for ATM (Ataxia telangiectasia mutated) or ATR (ATM- and RAD3-related). L-(+)-Ergothioneine has been used: • as a component of the maturation medium for cumulus-oocyte complexes (COCs) to test protective function on lipid peroxide formation • as an antioxidant compound to test type 2 diabetes patients • as a positive control in solute carrier protein 22 A4 (SLC22A4) transport assay |
| 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. |
| 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. Research area: Apoptosis |
| Other Notes: | Natural amino acid found in the fungus Claviceps purpurea |
| Packaging: | Bottomless glass bottle. Contents are inside inserted fused cone. |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 3 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Purity | ≥98.0% |
| Storage Temp. | −20°C |
| UNSPSC | 12352209 |