Lipoic acid
- Thioctic acid
- 1,2- dithiolane -3- pentanoic acid
- (R ) - ( ) -5 - ( - dithiolan -3-yl ) - pentanoic acid
- A16AX01
- N07XB52
Yellowish needles [( RS)- lipoic acid ]
Neuropathy means
Fixed
- 60-61 ° C [( RS)- lipoic acid ]
- 46-48 ° C, [(R) -lipoic acid ]
160-165 ° C, [(R) -lipoic acid ]
5.4
Almost insoluble in water ( 127 mg · l-1 at 25 ° C), poor in ethanol (50 g · l -1)
Attention
502 mg · kg -1 ( LD50, mouse, oral)
Template: Infobox chemical / molecular formula search available
α -lipoic acid, fine ( R) - lipoic acid ( LA for the English lipoic acid) is a natural substance that occurs as a coenzyme and a component of the pyruvate dehydrogenase complex in mitochondria in almost all eukaryotes. The salts of lipoic acid hot lipoates.
Function
α -lipoic acid acts in many enzymatic reactions, primarily in oxidative decarboxylation, as a coenzyme. Your task is to hydrogen and acyl group transfer. Plays an important role in the pyruvate dehydrogenase complex of the mitochondria, the link between glycolysis and citric acid cycle, and the α -ketoglutarate dehydrogenase complex in the citric acid cycle. With its reduced form, dihydrolipoic acid α -lipoic acid is a biochemical redox system. α -lipoic acid is a free radical scavenger and powerful antioxidant that can regenerate in the body consumed antioxidants such as vitamin C, vitamin E, coenzyme Q10 or glutathione.
Structure
The natural α -lipoic acid is the (only) the stereogenic center (R) -configuration; - configured enantiomer is (S). In nature, only the ( R) -lipoic acid (synonym L- lipoic acid ) and its reduced form, dihydrolipoic acid ( 6,8- Dithiooctansäure ), biologically active. Structural analogs with six or more membered rings are biologically inactive.
As a drug is out of the (R) -lipoic acid and the racemic ( RS)- lipoic acid [ Synonyms: DL- lipoic acid, ( ±)- lipoic acid ] was used.
Use
α -lipoic acid has been used for 1966 is used in Germany as a drug for the treatment of liver diseases and peripheral neuropathies.
In chelation therapy can α -lipoic acid are used in poisoning with inorganic mercury compounds. Unlike other chelators such as DMSA or DMPS lipoic acid is able to penetrate into all areas of the central and peripheral nervous system, can, in particular the blood- brain barrier. Their effectiveness for this purpose is mainly due to its reduced form, dihydrolipoic acid, a dithiol, which has strong antioxidant properties and can form chelate bonds. The excretion of these complexes takes place almost exclusively via the bile ducts.
In the alternative medicine lipoic acid is part of sg Cutler protocol for detoxification of mercury use.
Trade names
Alpha Lipogamma (D ), alpha - lipoic STADA (D ), alpha - Vibolex (D), biomolecules lipoic (D), espa - lipoic (D), lipoic acid -ratiopharm (D), Neurium (D), Pleomix - Alpha ( D), Sana Alpha -lipoic acid (D), Thioctacid (D, A), Thiogamma (D), Tromlipon (D), Vita Trans ( D).