E7521
L-(+)-Ergothioneine
Synonym(s):
2-mercaptohistidine trimethyl betaine, Ergothioneine, Sympectothion, Thiasine, Thiolhistidine-betaine, Thioneine, (S)-α-Carboxy-N,N,N-trimethyl-2-mercapto-1H-imidazole-4-ethanaminium inner salt
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About This Item
Empirical Formula (Hill Notation):
C9H15N3O2S
CAS Number:
Molecular Weight:
229.30
EC Number:
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.32
Recommended Products
biological source
fungus (Actinomycetales)
fungus (Ascomycota)
fungus (Basidiomycota)
Assay
≥98.0%
form
powder
mol wt
229.30
storage condition
(Keep container tightly closed in a dry and well-ventilated place)
technique(s)
protein quantification: suitable
solubility
water: 50 mg/mL, clear, colorless
storage temp.
−20°C
SMILES string
C[N+](C)(C)[C@@H](Cc1c[nH]c(S)n1)C([O-])=O
InChI
1S/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-/m0/s1
InChI key
SSISHJJTAXXQAX-ZETCQYMHSA-N
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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
Research area: Apoptosis
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:
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.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Other Notes
Natural amino acid found in the fungus Claviceps purpurea
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.
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Customers Also Viewed
Monica Deiana et al.
Clinical nutrition (Edinburgh, Scotland), 23(2), 183-193 (2004-03-20)
L-ergothioneine is a fungal metabolite exhibiting antioxidant functions in cells. The aim of this study was to assess the effect of oral administration of L-ergothioneine on the oxidative damage in vivo caused by the Fenton reagent ferric-nitrilotriacetate. Rats were supplemented
Irwin K Cheah et al.
Biochimica et biophysica acta, 1822(5), 784-793 (2011-10-18)
Since its discovery, the unique properties of the naturally occurring amino acid, L-ergothioneine (EGT; 2-mercaptohistidine trimethylbetaine), have intrigued researchers for more than a century. This widely distributed thione is only known to be synthesized by non-yeast fungi, mycobacteria and cyanobacteria
J Carlsson et al.
The Biochemical journal, 139(1), 221-235 (1974-04-01)
1. The reactions of 2,2'- and 4,4'-dipyridyl disulphide (2-Py-S-S-2-Py and 4-Py-S-S-4-Py) with l-ergothioneine (2-mercapto-l-histidine betaine), 2-mercaptoimidazole, 1-methyl-2-mercaptoimidazole, thiourea, thioacetamide, 2-thiopyridone (Py-2-SH) and 4-thiopyridone (Py-4-SH) were investigated spectrophotometrically in the pH range approx. 1-9. 2. These reactions involve two sequential reversible
Substantial fibrin amyloidogenesis in type 2 diabetes assessed using amyloid-selective fluorescent stains
Pretorius E, et al.
Cardiovascular Diabetology, 16(1), 141-141 (2017)
Irina Borodina et al.
Nutrition research reviews, 33(2), 190-217 (2020-02-14)
Ergothioneine (ERG) is an unusual thio-histidine betaine amino acid that has potent antioxidant activities. It is synthesised by a variety of microbes, especially fungi (including in mushroom fruiting bodies) and actinobacteria, but is not synthesised by plants and animals who
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