Lipoic acid

Catalogue number C108648
Chemical nameLipoic acid
CAS Number62-46-4
Synonyms5-[(3R)-3-dithiolanyl]pentanoic acid
Molecular WeightC8H13O2S2
Formula205.32
Purity98%
Physical DescriptionYellow cryst.
SolventChloroform, Dichloromethane,DMSO
StorageStored at 2-8°C, Protected from air and light, refrigerate or freeze
ApplicationsPrevent organ dysfunction;
Reduce endothelial dysfunction and improve albuminuria;
Treat or prevent cardiovascular disease;
Accelerate chronic wound healing;
Reduce levels of ADMA in diabetic end-stage renal disease patients on hemodialysis;
Management of burning mouth syndrome;
Reduce iron overload;
Treat metabolic syndrome;
Improve or prevent age-related cognitive dysfunction;
Prevent or slow the progression of Alzheimer’s Disease;
Prevent erectile dysfunction (animal models);
Prevent migraines;
Treat multiple sclerosis;
Treat chronic diseases associated with oxidative stress;
Reduce inflammation;
Inhibit advanced glycation end products (AGE);
Treat peripheral artery disease.
1. Lipoic acid is an example of an existing drug whose therapeutic effect has been related to its antioxidant activity. 2. Antioxidant activity is a relative concept: it depends on the kind of oxidative stress and the kind of oxidizable substrate (e.g., DNA, lipid, protein). 3. In vitro, the final antioxidant activity of lipoic acid is determined by its concentration and by its antioxidant properties. Four antioxidant properties of lipoic acid have been studied: its metal chelating capacity, its ability to scavenge reactive oxygen species (ROS), its ability to regenerate endogenous antioxidants and its ability to repair oxidative damage. 4. Dihydrolipoic acid (DHLA), formed by reduction of lipoic acid, has more antioxidant properties than does lipoic acid. Both DHLA and lipoic acid have metal-chelating capacity and scavenge ROS, whereas only DHLA is able to regenerate endogenous antioxidants and to repair oxidative damage. 5. As a metal chelator, lipoic acid was shown to provide antioxidant activity by chelating Fe2+ and Cu2+; DHLA can do so by chelating Cd2+. 6. As scavengers of ROS, lipoic acid and DHLA display antioxidant activity in most experiments, whereas, in particular cases, pro-oxidant activity has been observed. However, lipoic acid can act as an antioxidant against the pro-oxidant activity produced by DHLA. 7. DHLA has the capacity to regenerate the endogenous antioxidants vitamin E, vitamin C and glutathione. 8. DHLA can provide peptide methionine sulfoxide reductase with reducing equivalents. This enhances the repair of oxidatively damaged proteins such as alpha-1 antiprotease. 9. Through the lipoamide dehydrogenase-dependent reduction of lipoic acid, the cell can draw on its NADH pool for antioxidant activity additionally to its NADPH pool, which is usually consumed during oxidative stress. 10. Within drug-related antioxidant pharmacology, lipoic acid is a model compound that enhances understanding of the mode of action of antioxidants in drug therapy.
References1. Tetrahedron Letters, 1985, 26(21), 2535-2538.
2. Free Radical Biology and Medicine, 1995, 19(2), 227-250.
3. J. Org. Chem., 1975, 40(1), 58-62.
4. Gen. Pharmacol., 1997, 29(3), 315-331.
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Lipoic acid
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