High Purity L-Ergothioneine Powder CAS 497-30-3 API for Cosmetics & Healthcare

L-Ergothioneine More Info

L-Ergothioneine, identified by the Chemical Abstracts Service Registry Number 497-30-3, is a naturally occurring sulfur-containing derivative of the amino acid histidine. Its molecular formula is C₉H₁₅N₃O₂S, with a molecular weight of approximately 229.30 grams per mole, and it exists as a white to off-white crystalline solid that is readily soluble in water. The IUPAC name for this compound is (2S)-3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)-2-(trimethylazaniumyl)propanoate, reflecting its distinctive structure which includes a trimethylated histidine backbone and a unique thione group on the imidazole ring where a sulfur atom replaces the typical hydrogen found in other histidine derivatives . This thione tautomer, which predominates at physiological pH, distinguishes ergothioneine from conventional thiol antioxidants like glutathione and confers remarkable stability against autoxidation, a property that underpins its biological functions .

The discovery of L-ergothioneine dates back to 1909 when it was first isolated from the ergot fungus, Claviceps purpurea, from which it derives its name, with its structure subsequently elucidated in 1911 . It is synthesized primarily by certain non-yeast fungi belonging to the divisions Basidiomycota and Ascomycota, as well as by Actinobacteria, and is not produced by the human body, making it a dietarily acquired compound . Humans obtain ergothioneine through dietary sources, with mushrooms being among the richest known sources, alongside other foods such as oats and certain beans. Once ingested, its cellular uptake is facilitated by a specific and high-affinity transporter known as the organic cation transporter novel type 1, encoded by the SLC22A4 gene, which allows for the selective accumulation of this molecule in tissues frequently exposed to oxidative stress or inflammation, including the liver, kidney, bone marrow, brain, and the lens of the eye .

The biological activity of L-ergothioneine is predominantly attributed to its potent antioxidant and cytoprotective properties. Unlike many other antioxidants that function by donating a hydrogen atom, ergothioneine acts through direct scavenging of a wide array of reactive oxygen and nitrogen species, including hydroxyl radicals, hypochlorous acid, and peroxynitrite . Additionally, it possesses the capacity to chelate divalent metal ions such as copper and iron, thereby preventing the generation of additional free radicals through Fenton-type reactions . This dual mechanism of direct scavenging and metal chelation contributes to its protective effects against oxidative damage to cellular components, and it has been shown to interact with and help regenerate other antioxidants within the cellular network, including glutathione and vitamin C. Its ability to cross the blood-brain barrier and accumulate in neural tissues has made it a subject of particular interest in research focused on neuroprotection, where it has demonstrated the capacity to protect neuronal cells from β-amyloid-induced apoptosis and mitigate neurotoxicity associated with various insults .

In regulatory and safety contexts, L-ergothioneine has been evaluated for its use in food and dietary supplements. The European Food Safety Authority has recognized it as a novel food ingredient, and in 2017, the European Commission authorized its placement on the market for use in food supplements at specified maximum levels, with a daily intake of up to thirty milligrams for the general population and twenty milligrams for children over the age of three . The United States Food and Drug Administration has also issued a Generally Recognized as Safe notice for its use as a nutrient supplement in various food categories, including baked goods, beverages, and confectionery, at levels intended to provide five milligrams of ergothioneine per serving . From a toxicological perspective, the compound is considered to have a favorable safety profile. Safety data sheets classify it as a mild irritant, with potential to cause skin, eye, and respiratory irritation upon direct exposure, but it is not classified as a hazardous substance or mixture under global harmonized system criteria, and it is not listed as a carcinogen by major regulatory agencies .

The research applications of L-ergothioneine span multiple fields, reflecting its diverse biological activities. In neuroscience, it is studied for its potential role in combating oxidative stress associated with age-related neurodegenerative conditions such as Alzheimer's and Parkinson's disease . In dermatology and cosmeceutical research, it has been shown to protect skin cells from ultraviolet-induced damage by suppressing the expression of matrix metalloproteinases and scavenging reactive oxygen species, supporting its investigation for anti-aging and skin health formulations . Furthermore, research has explored its potential benefits in metabolic health, vascular function, and inflammatory conditions such as rheumatoid arthritis, where its anti-inflammatory properties may contribute to protective effects . The compound is also being investigated in the context of reproductive health, where it has been used as a component in maturation media for cumulus-oocyte complexes to test its protective function against lipid peroxidation . The scientific literature consistently documents its role as a fundamental antioxidant and a subject of growing interest for its potential contributions to longevity and cellular health.

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