Key Documents

L-(+)-Ergothioneine

Name: <SC>L</SC>-(+)-Ergothioneine
Brand: SIGMA

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

Select a Size

Change View

Size/SKU	Availability	Price

About This Item

Empirical Formula (Hill Notation):

C₉H₁₅N₃O₂S

CAS Number:

497-30-3

Molecular Weight:

229.30

NACRES:

NA.32

PubChem Substance ID:

24894650

UNSPSC Code:

12352209

EC Number:

207-843-5

MDL number:

MFCD00167474

Pricing and availability is not currently available.

Technical Service

Need help? Our team of experienced scientists is here for you.

Let Us Assist

Properties

Quality Segment

200

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

Description

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

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Natural amino acid found in the fungus Claviceps purpurea

Compare Similar Items

View Full Comparison

Show Differences

1 of 1

This Item	B0390	SMB00978	PHL25279
Sigma-Aldrich E7521 L-(+)-Ergothioneine	Sigma-Aldrich B0390 Bilirubin Oxidase from Myrothecium verrucaria	Sigma-Aldrich SMB00978 L-Hercynine	PHL25279 L-(+)-Ergothioneine
description -	description lyophilized powder, 15-65 units/mg protein	description ≥95% (HPLC)	description phyproof^® Reference Substance
biological source fungus (Ascomycota), fungus (Basidiomycota), fungus (Actinomycetales)	biological source fungus (Myrothecium verrucaria)	biological source -	biological source -
technique(s) protein quantification: suitable	technique(s) toxicology assay: suitable	technique(s) -	technique(s) gas chromatography (GC): suitable, HPLC: suitable
assay ≥98.0%	assay -	assay ≥95% (HPLC)	assay ≥90.0% (HPLC)
Quality Level 200	Quality Level 200	Quality Level 200	Quality Level -
form powder	form lyophilized powder	form solid	form -
storage temp. −20°C	storage temp. −20°C	storage temp. 2-8°C	storage temp. −20°C

Still not finding the right product?

Explore all of our products under L-(+)-Ergothioneine

Storage Class

11 - Combustible Solids

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

PPE (personal protective equipment)

Eyeshields, Gloves, type N95 (US)

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

It looks like we've run into a problem, but you can still download Certificates of Analysis from our Documents section.

If you need assistance, please contact Customer Support

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.