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L-Ergothioneine
[CAS# 497-30-3]

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Identification
Classification Biochemical >> Inhibitor >> Metabolism
Name L-Ergothioneine
Synonyms NSC 7175; Phytothioneine; Sympectothion; Thiasine; Thioneine; Thiotane; thiotaine; (S)-; 2-Mercapto-N,N-dimethylhistidine methyl ester betaine; 2-Mercaptohistidine betaine; 2-Mercaptohistidine trimethylbetaine
Molecular Structure CAS # 497-30-3, L-Ergothioneine, NSC 7175, Phytothioneine, Sympectothion, Thiasine, Thioneine, Thiotane, thiotaine, (S)-, 2-Mercapto-N,N-dimethylhistidine methyl ester betaine, 2-Mercaptohistidine betaine, 2-Mercaptohistidine trimethylbetaine
Molecular Formula C9H15N3O2S
Molecular Weight 229.30
CAS Registry Number 497-30-3
EC Number 207-843-5
SMILES C[N+](C)(C)[C@@H](CC1=CNC(=S)N1)C(=O)[O-]
Properties
Solubility 1e+006 mg/L (25 ºC water)
Melting point 246.79 ºC
Boiling Point 573.21 ºC
Safety Data
Hazard Symbols symbol   GHS07 Warning    Details
Hazard Statements H315-H319-H335    Details
Precautionary Statements P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501    Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Specific target organ toxicity - single exposureSTOT SE3H335
Skin irritationSkin Irrit.2H315
Eye irritationEye Irrit.2H319
SDS Available
up Discovory and Applicatios
L-Ergothioneine (ET) is a naturally occurring amino acid derivative first discovered in 1909 by French chemist Joseph Louis Gautier. It was isolated from ergot fungus, a parasitic fungus that grows on rye and other grains. Gautier originally named it "ergothioneine" because it was related to ergot, but it was later discovered to be present in a variety of other organisms, including plants, animals, and bacteria. L-ergothioneine, whose chemical structure was elucidated in the 1930s, is a thiohistidine derivative with a sulfur atom in position 2 of the imidazole ring. L-Ergothioneine is known for its powerful antioxidant properties. It acts as a scavenger of reactive oxygen species (ROS) and reactive nitrogen species (RNS), protecting cells and tissues from oxidative damage caused by free radicals. The unique sulfur-histidine structure of L-ergothioneine enables it to effectively neutralize oxidative stress and mitigate the harmful effects of ROS on cellular components, including lipids, proteins, and DNA.

L-Ergothioneine also has anti-inflammatory properties. It modulates inflammatory pathways by inhibiting the production of proinflammatory cytokines and mediators, such as tumor necrosis factor-a (TNF-a), interleukin-6 (IL-6), and inducible nitric oxide synthase (iNOS). By reducing inflammation, ET helps reduce tissue damage, relieve pain, and promote tissue repair in a variety of inflammatory conditions. L-Ergothioneine plays an important role in skin health and protection against environmental stressors. It is actively transported into skin cells where it acts as a cellular antioxidant and UV protectant. ET helps counteract oxidative damage caused by UV rays, prevent DNA mutations, and maintain skin integrity, thereby reducing the risk of photoaging, sunburn, and skin cancer. Emerging research suggests that L-ergothioneine may exert neuroprotective effects and contribute to brain health. ET readily crosses the blood-brain barrier and accumulates in brain tissue, acting as a potent antioxidant and modulating neuroinflammatory pathways. L-Ergothioneine helps protect neuronal function, improve cognitive performance, and slow the progression of neurodegenerative diseases such as Alzheimer's disease, Parkinson's disease, and stroke. Research suggests that L-ergothioneine may be cardioprotective and beneficial to cardiovascular health. ET scavenges free radicals in the cardiovascular system, alleviates endothelial dysfunction caused by oxidative stress, and enhances nitric oxide bioavailability, thereby improving vascular function and reducing the risk of atherosclerosis, hypertension, and cardiovascular events.
Market Analysis Reports
List of Reports Available for L-Ergothioneine
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