1.0 2010-04-08 22:06:12 UTC 2025-11-18 22:55:58 UTC FDB004339 alpha-Lipoic acid Lipoate, also known as lipoic acid or 6,8-thioctate, belongs to lipoic acids and derivatives class of compounds. Those 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. Lipoate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Lipoate can be synthesized from octanoic acid. Lipoate can also be synthesized into lipoamide and lipoyl-AMP. Lipoate can be found in broccoli and spinach, which makes lipoate a potential biomarker for the consumption of these food products. Lipoate may be a unique E.coli metabolite. Lipoate is a non-carcinogenic (not listed by IARC) potentially toxic compound. C8H14O2S2 206.326 206.043521072 5-(1,2-dithiolan-3-yl)pentanoic acid 6,8-thioctic acid 62-46-4 OC(=O)CCCCC1CCSS1 InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10) AGBQKNBQESQNJD-UHFFFAOYSA-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 Prosthetic group [Fig] dithiolanes heterocyclic fatty acid thia fatty acid 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-(1,2-dithiolan-3-yl)pentanoic acid ChemAxon average_mass 206.326 ChemAxon mono_mass 206.043521072 ChemAxon smiles OC(=O)CCCCC1CCSS1 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) ChemAxon inchikey AGBQKNBQESQNJD-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 54.37 ChemAxon polarizability 22 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 112144 Specdb::CMs 125546 Specdb::CMs 875443 Specdb::CMs 875444 Specdb::MsMs 24557 Specdb::MsMs 24558 Specdb::MsMs 24559 Specdb::MsMs 31115 Specdb::MsMs 31116 Specdb::MsMs 31117 Specdb::MsMs 2245284 Specdb::MsMs 2251448 Specdb::MsMs 2252848 Specdb::MsMs 2253635 Specdb::MsMs 2254865 Specdb::MsMs 2255698 Specdb::MsMs 2258825 Specdb::MsMs 2259740 Specdb::MsMs 3430437 Specdb::MsMs 3430438 Specdb::MsMs 3430439 Specdb::MsMs 3430440 Specdb::MsMs 3430441 Specdb::MsMs 3430442 Specdb::NmrOneD 4668 Specdb::NmrOneD 4690 Broccoli Type 1 specific Brassica oleracea var. italica 36774 Spinach Type 1 specific Spinacia oleracea 3562 Anti-oxidant 502 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.