A natural antioxidant
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L-(+)-Ergothioneine

Item No. 14905

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(αS)-α-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium, inner salt
CAS Number
497-30-3
Synonyms
  • 2-Mercaptohistidine Betaine
  • NSC 7175
Molecular Formula
C9H15N3O2S
Formula Weight
229.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 10 mg/ml
λmax
218, 265 nm
SMILES
C[N+](C)([C@@H](CC(N1)=CNC1=S)C([O-])=O)C
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $69

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    10 mg

    $127

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    25 mg

    $280

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    50 mg

    $493

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    Product Description

    L-(+)-Ergothioneine is a naturally-occurring amino acid derived from histidine via hercynine.1 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.2,3 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.2,4,5 Ergothioneine is transported by the organic cation/carnitine transporter 1, which has been linked with autoimmune diseases, including rheumatoid arthritis and Crohn’s disease.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Askari, A., and Melville, D.B. The reaction sequence in ergothioneine biosynthesis: Hercynine as an intermediate. The Journal of Biological Chemisty 237, 1615-1618 (1962).

    2. Rahman, I. Pharmacological antioxidant strategies as therapeutic interventions for COPD. Biochim. Biophys. Acta 1822(5), 714-728 (2012).

    3. Misiti, F., Castagnola, M., Zuppi, C., et al. Role of ergothioneine on S-nitrosoglutathione catabolism. Biochem. J. 356(3), 799-804 (2001).

    4. Cheah, I.K., and Halliwell, B. Ergothioneine; antioxidant potential, physiological function and role in disease. Biochim. Biophys. Acta 1822, 784-793 (2012).

    5. Aruoma, O.I., Spencer, J.P.E., and Mahmood, N. Protection against oxidative damage and cell death by the natural antioxidant ergothioneine. Food Chem. Toxicol. 37(11), 1043-1053 (1999).

    6. Nakamura, T., Yoshida, K., Yabuuchi, H., et al. Functional characterization of ergothioneine transport by rat organic cation/carnitine transporter Octn1 (slc22a4). Biol. Pharm. Bull. 31(8), 1580-1584 (2008).