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MedKoo Cat#: 597050 | Name: 319889
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ergothioneine is a naturally occurring thiol/thione derivative of histidine, synthesized by certain fungi and bacteria and acquired by humans through dietary sources like mushrooms. It functions as a potent antioxidant and cytoprotectant, accumulating in tissues exposed to oxidative stress via the highly specific transporter OCTN1 (SLC22A4). Ergothioneine has been implicated in cellular protection against oxidative damage, inflammation, and mitochondrial dysfunction, with growing interest in its potential roles in aging and chronic disease mitigation.

Chemical Structure

319889
319889
CAS#497-30-3

Theoretical Analysis

MedKoo Cat#: 597050

Name: 319889

CAS#: 497-30-3

Chemical Formula: C9H15N3O2S

Exact Mass: 229.0885

Molecular Weight: 229.29

Elemental Analysis: C, 47.14; H, 6.59; N, 18.33; O, 13.95; S, 13.98

Price and Availability

Size Price Availability Quantity
100mg USD 350.00 2 Weeks
250mg USD 650.00 2 Weeks
500mg USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
Ergothioneine; L-Ergothioneine; L-(+)-Ergothioneine; 2-Mercaotohistidine Betaine; Sympectothion; NSC 7175; NSC-7175; NSC7175;
IUPAC/Chemical Name
(S)-3-(2-thioxo-2,3-dihydro-1H-imidazol-4-yl)-2-(trimethylammonio)propanoate
InChi Key
SSISHJJTAXXQAX-ZETCQYMHSA-N
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
SMILES Code
S=C1NC(C[C@@H](C([O-])=O)[N+](C)(C)C)=CN1
Appearance
Solid powder
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Ergothioneine, an imidazole-2-thione derivative of histidine betaine, is synthesized by certain bacteria and fungi.
In vitro activity:
EGT (ergothioneine) pretreatment of keratinocytes significantly inhibited downregulation of the Nrf2/HO-1 pathway and HSP70, and protected keratinocytes by suppressing production of ROS and cleavage of proapoptotic proteins, including caspase-8 and PARP. Furthermore, EGT significantly reduced the paracrine cytokines, including IL-1β, IL-6, and TNF-α. In co-cultures of fibroblasts with EGT-treated keratinocytes, the expression levels of collagen degradation-related genes and fibroblast senescence were significantly decreased; however, synthesis of procollagen type I was significantly increased. These results confirm that EGT suppresses the modification of collagen homeostasis in fibroblasts by preventing downregulation of the Nrf2/HO-1 pathway and HSP70 in keratinocytes following UVB irradiation. Reference: Exp Cell Res. 2021 Mar 1;400(1):112516. https://pubmed.ncbi.nlm.nih.gov/33577831/
In vivo activity:
Ergothioneine significantly enhanced renal function in cisplatin-treated rats as manifested by increased GFR and decreased serum creatinine and blood urea nitrogen. Ergothioneine effectively reduced the cisplatin-induced oxidative stress and mitigated apoptosis and the histopathological changes. Reference: Life Sci. 2021 Aug 1;278:119572. https://pubmed.ncbi.nlm.nih.gov/33964294/
Solvent mg/mL mM
Solubility
PBS (pH 7.2) 10.0 43.61
Water 125.0 545.16
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 229.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Ko HJ, Kim J, Ahn M, Kim JH, Lee GS, Shin T. Ergothioneine alleviates senescence of fibroblasts induced by UVB damage of keratinocytes via activation of the Nrf2/HO-1 pathway and HSP70 in keratinocytes. Exp Cell Res. 2021 Mar 1;400(1):112516. doi: 10.1016/j.yexcr.2021.112516. Epub 2021 Feb 9. PMID: 33577831. 2. Samuel P, Tsapekos M, de Pedro N, Liu AG, Casey Lippmeier J, Chen S. Ergothioneine Mitigates Telomere Shortening under Oxidative Stress Conditions. J Diet Suppl. 2020 Dec 7:1-14. doi: 10.1080/19390211.2020.1854919. Epub ahead of print. PMID: 33287595. 3. Salama SA, Abd-Allah GM, Mohamadin AM, Elshafey MM, Gad HS. Ergothioneine mitigates cisplatin-evoked nephrotoxicity via targeting Nrf2, NF-κB, and apoptotic signaling and inhibiting γ-glutamyl transpeptidase. Life Sci. 2021 Aug 1;278:119572. doi: 10.1016/j.lfs.2021.119572. Epub 2021 May 6. PMID: 33964294. 4. Matsuda Y, Ozawa N, Shinozaki T, Wakabayashi KI, Suzuki K, Kawano Y, Ohtsu I, Tatebayashi Y. Ergothioneine, a metabolite of the gut bacterium Lactobacillus reuteri, protects against stress-induced sleep disturbances. Transl Psychiatry. 2020 May 28;10(1):170. doi: 10.1038/s41398-020-0855-1. PMID: 32467627; PMCID: PMC7256047.
In vitro protocol:
1. Ko HJ, Kim J, Ahn M, Kim JH, Lee GS, Shin T. Ergothioneine alleviates senescence of fibroblasts induced by UVB damage of keratinocytes via activation of the Nrf2/HO-1 pathway and HSP70 in keratinocytes. Exp Cell Res. 2021 Mar 1;400(1):112516. doi: 10.1016/j.yexcr.2021.112516. Epub 2021 Feb 9. PMID: 33577831. 2. Samuel P, Tsapekos M, de Pedro N, Liu AG, Casey Lippmeier J, Chen S. Ergothioneine Mitigates Telomere Shortening under Oxidative Stress Conditions. J Diet Suppl. 2020 Dec 7:1-14. doi: 10.1080/19390211.2020.1854919. Epub ahead of print. PMID: 33287595.
In vivo protocol:
1. Salama SA, Abd-Allah GM, Mohamadin AM, Elshafey MM, Gad HS. Ergothioneine mitigates cisplatin-evoked nephrotoxicity via targeting Nrf2, NF-κB, and apoptotic signaling and inhibiting γ-glutamyl transpeptidase. Life Sci. 2021 Aug 1;278:119572. doi: 10.1016/j.lfs.2021.119572. Epub 2021 May 6. PMID: 33964294. 2. Matsuda Y, Ozawa N, Shinozaki T, Wakabayashi KI, Suzuki K, Kawano Y, Ohtsu I, Tatebayashi Y. Ergothioneine, a metabolite of the gut bacterium Lactobacillus reuteri, protects against stress-induced sleep disturbances. Transl Psychiatry. 2020 May 28;10(1):170. doi: 10.1038/s41398-020-0855-1. PMID: 32467627; PMCID: PMC7256047.
1: Gamage AM, Liao C, Cheah IK, Chen Y, Lim DRX, Ku JWK, Chee RSL, Gengenbacher M, Seebeck FP, Halliwell B, Gan YH. The proteobacterial species Burkholderia pseudomallei produces ergothioneine, which enhances virulence in mammalian infection. FASEB J. 2018 Jun 11:fj201800716. doi: 10.1096/fj.201800716. [Epub ahead of print] PubMed PMID: 29890088. 2: de Visser SP. Mechanistic Insight on the Activity and Substrate Selectivity of Nonheme Iron Dioxygenases. Chem Rec. 2018 Jun 7. doi: 10.1002/tcr.201800033. [Epub ahead of print] Review. PubMed PMID: 29878456. 3: Halliwell B, Cheah IK, Tang RMY. Ergothioneine - a diet-derived antioxidant with therapeutic potential. FEBS Lett. 2018 May 31. doi: 10.1002/1873-3468.13123. [Epub ahead of print] Review. PubMed PMID: 29851075. 4: Gökçe G, Arun MZ, Ertuna E. Ergothioneine prevents endothelial dysfunction induced by mercury chloride. Exp Ther Med. 2018 Jun;15(6):4697-4702. doi: 10.3892/etm.2018.6079. Epub 2018 Apr 18. PubMed PMID: 29805489; PubMed Central PMCID: PMC5958736. 5: Zhang D, Tang Z, Liu W. Biosynthesis of Lincosamide Antibiotics: Reactions Associated with Degradation and Detoxification Pathways Play a Constructive Role. Acc Chem Res. 2018 May 24. doi: 10.1021/acs.accounts.8b00135. [Epub ahead of print] PubMed PMID: 29792672. 6: Zhao H, Zhang M, Liu Q, Wang X, Zhao R, Geng Y, Wong T, Li S, Wang X. A comprehensive screening shows that ergothioneine is the most abundant antioxidant in the wild macrofungus Phylloporia ribis Ryvarden. J Environ Sci Health C Environ Carcinog Ecotoxicol Rev. 2018 Apr 3;36(2):98-111. doi: 10.1080/10590501.2018.1450201. PubMed PMID: 29667505. 7: Misson L, Burn R, Vit A, Hildesheim J, Beliaeva MA, Blankenfeldt W, Seebeck FP. Inhibition and Regulation of the Ergothioneine Biosynthetic Methyltransferase EgtD. ACS Chem Biol. 2018 May 18;13(5):1333-1342. doi: 10.1021/acschembio.8b00127. Epub 2018 Apr 16. PubMed PMID: 29658702. 8: Mishra A, Reddy IJ, Dhali A, Javvaji PK. l-Ergothioneine improves the developmental potential of in vitro sheep embryos without influencing OCTN1-mediated cross-membrane transcript expression. Zygote. 2018 Apr 2:1-13. doi: 10.1017/S0967199418000047. [Epub ahead of print] PubMed PMID: 29607799. 9: Naowarojna N, Cheng R, Chen L, Quill M, Xu M, Zhao C, Liu P. Mini-Review: Ergothioneine and Ovothiol Biosyntheses, an Unprecedented Trans-Sulfur Strategy in Natural Product Biosynthesis. Biochemistry. 2018 Apr 6. doi: 10.1021/acs.biochem.8b00239. [Epub ahead of print] PubMed PMID: 29589901. 10: Tschirka J, Kreisor M, Betz J, Gründemann D. Substrate Selectivity Check of the Ergothioneine Transporter. Drug Metab Dispos. 2018 Jun;46(6):779-785. doi: 10.1124/dmd.118.080440. Epub 2018 Mar 12. PubMed PMID: 29530864. 11: Janata J, Kamenik Z, Gazak R, Kadlcik S, Najmanova L. Biosynthesis and incorporation of an alkylproline-derivative (APD) precursor into complex natural products. Nat Prod Rep. 2018 Mar 1;35(3):257-289. doi: 10.1039/c7np00047b. Epub 2018 Mar 8. PubMed PMID: 29517100. 12: Irani S, Naowarojna N, Tang Y, Kathuria KR, Wang S, Dhembi A, Lee N, Yan W, Lyu H, Costello CE, Liu P, Zhang YJ. Snapshots of C-S Cleavage in Egt2 Reveals Substrate Specificity and Reaction Mechanism. Cell Chem Biol. 2018 May 17;25(5):519-529.e4. doi: 10.1016/j.chembiol.2018.02.002. Epub 2018 Mar 1. PubMed PMID: 29503207; PubMed Central PMCID: PMC5959753. 13: Tang RMY, Cheah IK, Yew TSK, Halliwell B. Distribution and accumulation of dietary ergothioneine and its metabolites in mouse tissues. Sci Rep. 2018 Jan 25;8(1):1601. doi: 10.1038/s41598-018-20021-z. PubMed PMID: 29371632; PubMed Central PMCID: PMC5785509. 14: Nigam SK. The SLC22 Transporter Family: A Paradigm for the Impact of Drug Transporters on Metabolic Pathways, Signaling, and Disease. Annu Rev Pharmacol Toxicol. 2018 Jan 6;58:663-687. doi: 10.1146/annurev-pharmtox-010617-052713. PubMed PMID: 29309257. 15: Kerley RN, McCarthy C, Kell DB, Kenny LC. The potential therapeutic effects of ergothioneine in pre-eclampsia. Free Radic Biol Med. 2018 Mar;117:145-157. doi: 10.1016/j.freeradbiomed.2017.12.030. Epub 2017 Dec 25. Review. PubMed PMID: 29284116. 16: Osawa R, Kamide T, Satoh Y, Kawano Y, Ohtsu I, Dairi T. Heterologous and High Production of Ergothioneine in Escherichia coli. J Agric Food Chem. 2018 Feb 7;66(5):1191-1196. doi: 10.1021/acs.jafc.7b04924. Epub 2018 Jan 15. PubMed PMID: 29276826. 17: Mollica A, Macedonio G, Stefanucci A, Carradori S, Akdemir A, Angeli A, Supuran CT. Five- and Six-Membered Nitrogen-Containing Compounds as Selective Carbonic Anhydrase Activators. Molecules. 2017 Dec 9;22(12). pii: E2178. doi: 10.3390/molecules22122178. PubMed PMID: 29232847. 18: Salinas G, Comini MA. Alternative Thiol-Based Redox Systems. Antioxid Redox Signal. 2018 Feb 20;28(6):407-409. doi: 10.1089/ars.2017.7464. Epub 2018 Jan 5. PubMed PMID: 29207877. 19: Chien RC, Lin YC, Mau JL. Apoptotic Effect of Taiwanofungus salmoneus (Agaricomycetes) Mycelia and Solid-State Fermented Products on Cancer Cells. Int J Med Mushrooms. 2017;19(9):777-495. doi: 10.1615/IntJMedMushrooms.2017024264. PubMed PMID: 29199553. 20: Song TY, Yang NC, Chen CL, Thi TLV. Protective Effects and Possible Mechanisms of Ergothioneine and Hispidin against Methylglyoxal-Induced Injuries in Rat Pheochromocytoma Cells. Oxid Med Cell Longev. 2017;2017:4824371. doi: 10.1155/2017/4824371. Epub 2017 Oct 17. PubMed PMID: 29181125; PubMed Central PMCID: PMC5664345.

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