1.0 2011-09-21 00:17:08 UTC 2025-11-19 02:42:09 UTC FDB022631 Lipoic acid A vitamin-like antioxidant that acts as a free-radical scavenger. Alpha-lipoic acid is also known as thioctic acid. It is a naturally occurring compound that is synthesized by both plants and animals. Lipoic acid contains two thiol groups which may be either oxidized or reduced. The reduced form is known as dihydrolipoic acid (DHLA). Lipoic acid (Delta E= -0.288) is therefore capable of thiol-disulfide exchange, giving it antioxidant activity. Lipoate is a critical cofactor for aerobic metabolism, participating in the transfer of acyl or methylamine groups via the 2-Oxoacid dehydrogenase (2-OADH) or alpha-ketoglutarate dehydrogenase complex. This enzyme catalyzes the conversion of alpha-ketoglutarate to succinyl CoA. This activity results in the catabolism of the branched chain amino acids (leucine, isoleucine and valine). Lipoic acid also participates in the glycine cleavage system(GCV). The glycine cleavage system is a multi-enzyme complex that catalyzes the oxidation of glycine to form 5,10 methylene tetrahydrofolate, an important cofactor in nucleic acid synthesis. Since Lipoic acid is an essential cofactor for many enzyme complexes, it is essential for aerobic life as we know it. This system is used by many organisms and plays a crucial role in the photosynthetic carbon cycle. Lipoic acid was first postulated to be an effective antioxidant when it was found it prevented vitamin C and vitamin E deficiency. It is able to scavenge reactive oxygen species and reduce other metabolites, such as glutathione or vitamins, maintaining a healthy cellular redox state. Lipoic acid has been shown in cell culture experiments to increase cellular uptake of glucose by recruiting the glucose transporter GLUT4 to the cell membrane, suggesting its use in diabetes. Studies of rat aging have suggested that the use of L-carnitine and lipoic acid results in improved memory performance and delayed structural mitochondrial decay. As a result, it may be helpful for people with Alzheimer's disease or Parkinson's disease. -- Wikipedia [HMDB] (+-)-1,2-Dithiolane-3-pentanoate (+-)-1,2-Dithiolane-3-pentanoic acid (+-)-1,2-Dithiolane-3-valerate (+-)-1,2-Dithiolane-3-valeric acid (+)-alpha-Lipoate (+)-alpha-Lipoic acid (R)-1,2-Dithiolane-3-pentanoate (R)-1,2-Dithiolane-3-pentanoic acid (RS)-alpha-Lipoate (RS)-alpha-Lipoic acid (RS)-Lipoate (RS)-Lipoic acid (S)-(−)-lipoic acid (S)-1,2-Dithiolane-3-pentanoic acid (S)-alpha-Lipoic acid 1,2-Dithiolane-3-pentanoate 1,2-Dithiolane-3-pentanoic acid 1,2-Dithiolane-3-valerate 1,2-Dithiolane-3-valeric acid 1,2-Dithiolane-3R-pentanoate 1,2-Dithiolane-3R-pentanoic acid 5-(1,2-Dithiolan-3-yl)pentanoate 5-(1,2-Dithiolan-3-yl)pentanoic acid 5-(1,2-Dithiolan-3-yl)valerate 5-(1,2-Dithiolan-3-yl)valeric acid 5-(Dithiolan-3-yl)valerate 5-(Dithiolan-3-yl)valeric acid 5-[3-(1,2-dithiolanyl)]pentanoate 5-[3-(1,2-dithiolanyl)]pentanoic acid 6-Thioctate 6-Thioctic acid 6-Thiotate 6-Thiotic acid 6,8-Dithiooctanoate 6,8-Dithiooctanoic acid 6,8-Thioctate 6,8-Thioctic acid 6,8-Thiotate 6,8-Thiotic acid acetate replacing factor Acetate-replacing factor alpha Lipoate alpha Lipoic acid alpha-Liponate alpha-Liponic acid alpha-Liponsaeure Biletan delta-[3-(1,2-dithiacyclopentyl)]pentanoate delta-[3-(1,2-dithiacyclopentyl)]pentanoic acid DL-1,2-Dithiolane 3-valerate DL-1,2-Dithiolane 3-valeric acid DL-6-Thioctate DL-6-Thioctic acid DL-6,8-Dithiooctanoate DL-6,8-Dithiooctanoic acid DL-6,8-Thioctate DL-6,8-Thioctic acid DL-alpha-Lipoate DL-alpha-Lipoic acid dl-Lipoate dl-Lipoic acid dl-Thioctate dl-Thioctic acid DL-Thioctic acid > 98% Heparlipon L-1,2-Dithiolane 3-valeric acid L-6-Thioctic acid L-6,8-Thioctic acid Lip Lipoate Lipoic acid liponate liponic acid Liposan Lipothion Protogen A Pyruvate oxidation factor R-Lipoate R-Lipoic acid Rac-lipoate Rac-lipoic acid S-LA SLA Thioctacid Thioctan Thioctate Thioctic acid Thioctic acid d-form Thioctic acid dl-form Thioctic acid L-form Thioctidase Thioctsan Thioktsaeure Thiooctanoate Thiooctanoic acid Tioctacid Tioctan Tioctidasi Tioctidasi acetate replacing factor C8H14O2S2 206.326 206.043521072 5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid lipoic acid 1200-22-2 OC(=O)CCCC[C@@H]1CCSS1 InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/s1 AGBQKNBQESQNJD-SSDOTTSWSA-N belongs to the class of organic compounds known as lipoic acids and derivatives. Lipoic acids and derivatives are compounds containing a lipoic acid moiety (or a derivative thereof), which consists of a pentanoic acid (or derivative) attached to the C3 carbon atom of a 1,2-dithiolane ring. Lipoic acids and derivatives Organic compounds Organoheterocyclic compounds Dithiolanes Lipoic acids and derivatives Aliphatic heteromonocyclic compounds 1,2-dithiolanes Carbonyl compounds Carboxylic acids Heterocyclic fatty acids Hydrocarbon derivatives Medium-chain fatty acids Monocarboxylic acids and derivatives Organic disulfides Organic oxides Thia fatty acids 1,2-dithiolane Aliphatic heteromonocyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Fatty acyl Heterocyclic fatty acid Hydrocarbon derivative Lipoic_acid_derivative Medium-chain fatty acid Monocarboxylic acid or derivatives Organic disulfide Organic oxide Organic oxygen compound Organooxygen compound Thia fatty acid Thia fatty acids Thia fatty acids dithiolanes heterocyclic fatty acid lipoic acid thia fatty acid Solid logp 2.75 ALOGPS logs -2.96 ALOGPS solubility 2.24e-01 g/l ALOGPS logp 2.11 ChemAxon pka_strongest_acidic 4.52 ChemAxon iupac 5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid ChemAxon average_mass 206.326 ChemAxon mono_mass 206.043521072 ChemAxon smiles OC(=O)CCCC[C@@H]1CCSS1 ChemAxon formula C8H14O2S2 ChemAxon inchi InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/s1 ChemAxon inchikey AGBQKNBQESQNJD-SSDOTTSWSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 54.37 ChemAxon polarizability 21.74 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::MsIr 1283 Specdb::MsIr 1284 Specdb::MsIr 1285 Specdb::NmrOneD 1710 Specdb::MsMs 1580 Specdb::MsMs 1581 Specdb::MsMs 1582 Specdb::MsMs 179469 Specdb::MsMs 179470 Specdb::MsMs 179471 Specdb::MsMs 181797 Specdb::MsMs 181798 Specdb::MsMs 181799 Specdb::MsMs 2236189 Specdb::MsMs 2237205 Specdb::MsMs 2238327 Specdb::MsMs 2239242 Specdb::MsMs 2308539 Specdb::MsMs 2308540 Specdb::MsMs 2308541 Specdb::MsMs 2654048 Specdb::MsMs 2654049 Specdb::MsMs 2654050 Specdb::NmrTwoD 1651 Specdb::CMs 3089 Specdb::CMs 31800 Specdb::CMs 38079 Specdb::CMs 99686 Specdb::CMs 100076 Specdb::CMs 100077 Specdb::CMs 155727 HMDB14312 16494 #<Reference:0x000055ce33416070> #<Reference:0x000055ce33415eb8> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Milk (Cow) Type 2 specific Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Lipoyltransferase 1, mitochondrial Q9Y234 LIPT1