(R)-lipoic acid (CED0016424)

(R)-lipoic acid belongs to the lipoic acids and derivatives, a subclass of dithiolanes within the organic compounds. This endogenous compound has the formula C8H14O2S2, an average molecular weight of 206.33 g/mol, and exists as a solid at room temperature. It is classified as an organoheterocyclic compound. Biologically, (R)-lipoic acid serves as a cofactor (PMC7765667), prosthetic group, and antioxidant (PMC5832356, PMC7932781). It has been shown to have a therapeutic effect on inflammation (PMC5832356) and is used as a nutraceutical. The compound is detected in various tissues, including the liver, kidney, placenta, muscle, skeletal muscle, and nerve cells. Its recorded protein targets include the mitochondrial lipoyl synthase (LIAS), mitochondrial lipoyl amidotransferase LIPT1, the sodium-dependent multivitamin transporter (SLC5A6), prostaglandin G/H synthase 2 (PTGS2), and acetylcholinesterase (ACHE), for which it acts as an inhibitor. (R)-lipoic acid is one of two enantiomers; while the R-enantiomer is generally the biologically active form, the S-enantiomer can assist in the reduction of the R-enantiomer when a racemic mixture is provided, though some studies suggest the S-enantiomer may have an inhibiting effect on the R-enantiomer. The compound is found in several recorded sources, including alimentary tract and metabolism products, household cleaning and consumer products such as soap detergents and perfumes within detergents and soaps, and food processing activities including the preparation of vinegar, wine, sparkling wine, and fermentation processes for beer. It is also associated with electrical and electronic equipment, including electrodes, amplifiers, and electric hearing aids. Recorded exposure routes include topical and oral administration.