Ergothioneine

Синонимы: L-Ergothioneine, EGT, 2-Thio-L-histidine betaine, Thioneine, (S)-α-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium inner salt

Ergothioneine is a naturally occurring amino acid derivative of histidine, distinguished by a thione group at the 2-position of the imidazole ring and a trimethylammonium betaine moiety. This unique structure confers exceptional antioxidant stability, as the sulfur atom exists predominantly as a thione rather than a thiol, making it resistant to autoxidation and metal-catalyzed degradation. The compound acts as a potent scavenger of hydroxyl radicals, hypochlorous acid, and peroxynitrite, and its redox potential is such that it can be regenerated by glutathione, providing sustained cytoprotection.

First isolated from ergot fungus in 1909, ergothioneine is synthesized exclusively by certain bacteria and fungi, and it accumulates in higher organisms through dietary intake. It is found in high concentrations in mushrooms, particularly oyster mushrooms and shiitake, as well as in oat bran and some fermented foods. For commercial use, ergothioneine is produced via fermentation using engineered strains of Escherichia coli or Mycobacterium smegmatis, followed by purification to yield high-purity crystalline material. It is available in food-grade and pharmaceutical-grade qualities, with assay typically ≥98% by HPLC.

In the B2B arena, ergothioneine has gained traction as a functional ingredient in anti-aging and mitochondrial health formulations, as well as in topical skincare products targeting oxidative stress. Its stability and water solubility make it suitable for a range of dosage forms, including capsules, tablets, and serums. Research interest continues to grow around its role as a cytoprotectant and its potential to modulate cellular stress responses, driving demand from nutraceutical and cosmetic manufacturers seeking a differentiated antioxidant.

Chemical Structure & Properties

Ergothioneine exists as a zwitterion at physiological pH, with the carboxylic acid deprotonated and the trimethylammonium group bearing a positive charge. The thione tautomer predominates, giving the molecule a characteristic UV absorption maximum at 257 nm. It is highly stable in aqueous solution under acidic to neutral conditions, but degrades slowly under strongly alkaline conditions or in the presence of strong oxidizing agents. The compound is hygroscopic and should be stored in a cool, dry place away from light.

Механизм действия

• Direct antioxidant activity: Scavenges reactive oxygen and nitrogen species, including hydroxyl radicals and hypochlorous acid, through electron transfer and hydrogen atom donation.
• OCTN1-mediated uptake: Utilizes the carnitine/organic cation transporter OCTN1 (SLC22A4) to enter cells, where it accumulates in mitochondria and nuclei, providing localized protection.
• Metal chelation: Binds transition metal ions such as Fe2+ and Cu2+, inhibiting Fenton-type reactions that generate hydroxyl radicals.
• Regulation of cellular stress response: Modulates Nrf2/ARE pathway, upregulating antioxidant enzymes and supporting mitochondrial function.

Quality Specifications

Supply & Documentation

• Capacity: 5 metric tons per year
• Срок выполнения заказа: 3–5 рабочих дней (товары, имеющиеся в наличии)
• Documentation: COA, MSDS, TDS, nutritional analysis, allergen statement, BSE/TSE-free declaration
• Packaging: 1 kg, 5 kg, 25 kg fiber drums with double polyethylene liners; custom packaging available upon request

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