L-(+)-ERGOTHIONEINE

Basic Information7

• Chemical Name: L-(+)-ERGOTHIONEINE, also known as 2 - mercaptohistidine betaine, (S)-3-(2 - thio - 2,3 - dihydro - 1H - imidazol - 4 - yl)-2 - (trimethylammonium) propionate.
• CAS Number: 497 - 30 - 3.
• Molecular Formula: C9H15N3O2S.
• Molecular Weight: 229.30. It is a sulfur - containing derivative of the amino acid histidine and belongs to the class of imidazole alkaloids.

Description

• Physical Properties: Appears as a white crystal, soluble in water with a solubility of 0.9 mol/L at room temperature7. It exists in a tautomeric form between the thione and thiol structures in solution7. It does not self - oxidize under physiological pH conditions and in strongly alkaline solutions7.
• Source: Produced by actinomycetes and non - yeast - like fungi, and widely present in animals and plants2. It is particularly abundant in mushrooms, red and black beans, oat bran, and the meat of animals that have consumed ergothioneine - rich plants4.

Data

• Purity: Can be as high as 99.5%, with an optical rotation (α)d ≥ (+) 122°. It has a unique high - purity crystal structure, which is rod - shaped.

Functions

• Antioxidant: It can scavenge reactive oxygen species (ROS) and reactive nitrogen species (RNS), protect cellular components such as DNA, proteins, and lipids from oxidative damage, and regenerate other antioxidants such as vitamin C and glutathione4.
• Cell Defense: It activates antioxidant response elements (AREs) in genes, leading to the production of various protective enzymes4. It also modulates inflammatory responses, reduces the risk of chronic inflammation - related conditions, and acts as a cytoprotectant, safeguarding cells against environmental toxins and stressors4.
• Disease Prevention and Management4: It may help protect neurons from oxidative stress, which is implicated in neurodegenerative diseases such as Alzheimer's and Parkinson's diseases. Its antioxidant properties may support heart health by preventing the oxidation of LDL cholesterol. It might also improve insulin sensitivity and protect against diabetic complications. Additionally, it could play a role in reducing the risk of certain types of cancer through its antioxidant and anti - inflammatory effects.

Applications

• Cosmetics: It is used in anti - aging products and sunscreens, which can protect the skin from oxidative stress, prevent wrinkles and fine lines, enhance the skin barrier, and improve skin texture. It is also suitable for reactive or sensitive skin types due to its anti - inflammatory properties.
• Medicine: It can be used to treat inflammation and is made into tablets, capsules, oral preparations, etc7. It may also have applications in organ transplantation for protecting transplanted organs and in ophthalmology for developing eye - care products7.
• Health Supplements: It can be made into functional foods and drinks to help prevent diseases such as cancer and is included in the EU's list of novel food resources