Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-23 23:19:33 UTC
Update Date2024-04-30 20:34:02 UTC
Metabolite IDMMDBc0047967
Metabolite Identification
Common NameDihydrolipoate
DescriptionDihydrolipoic acid is an organic compound that is the reduced form of lipoic acid. This carboxylic acid features a pair of thiol groups. It is optically active but only the R-enantiomer is biochemically significant. The lipoic acid/dihydrolipoic acid pair participate in a variety of biochemical transformations.( from Wiki). Inside the cell, alpha lipoic acid is readily reduced or broken down to dihydrolipoic acid. Dihydrolipoic acid is even more potent than alpha lipoic acid, neutralizing free radicals, preventing them from causing harm. It directly destroys damaging superoxide radicals, hydroperoxy radicals and hydroxyl radicals. It has been shown in vitro that dihydrolipoate (DL-6,8-dithioloctanoic acid) has antioxidant activity against microsomal lipid peroxidation.Dihydrolipoate is tested for its neuroprotective activity using models of hypoxic and excitotoxic neuronal damage in vitro and rodent models of cerebral ischemia in vivo. Dihydrolipoate, similarly to dimethylthiourea, is able to protect neurons against ischemic damage by diminishing the accumulation of reactive oxygen species within the cerebral tissue.(PMID: 1345759 ).
Structure
Synonyms
ValueSource
6,8-Bis-sulfanyloctanoic acidChEBI
6,8-Dihydrothioctic acidChEBI
6,8-Dimercapto-octanoic acidChEBI
6,8-Dimercaptooctanoic acidChEBI
DHLAChEBI
Dihydro-alpha-lipoic acidChEBI
Dihydro-lipoic acidChEBI
Dihydrothioctic acidChEBI
Dihydrolipoic acidKegg
6,8-Bis-sulfanyloctanoateGenerator
6,8-Bis-sulphanyloctanoateGenerator
6,8-Bis-sulphanyloctanoic acidGenerator
6,8-DihydrothioctateGenerator
6,8-Dimercapto-octanoateGenerator
6,8-DimercaptooctanoateGenerator
Dihydro-a-lipoateGenerator
Dihydro-a-lipoic acidGenerator
Dihydro-alpha-lipoateGenerator
Dihydro-α-lipoateGenerator
Dihydro-α-lipoic acidGenerator
Dihydro-lipoateGenerator
DihydrothioctateGenerator
6,8-DisulfanyloctanoateHMDB
6,8-Disulfanyloctanoic acidHMDB
D,L-DihydrolipoateHMDB
D,L-Dihydrolipoic acidHMDB
dihydro-DL-alpha-LipoateHMDB
dihydro-DL-alpha-Lipoic acidHMDB
dihydro-Thioctic acidHMDB
dihydro-Thiocytic acidHMDB
DL-dihydro-a-6-Thioctic acidHMDB
DL-dihydro-alpha-6-Thioctic acidHMDB
Reduced DL-6,8-thioctic acidHMDB
Reduced lipoateHMDB
Reduced lipoic acidHMDB
Reduced thioctic acidHMDB
Dihydrolipoic acid, (+-)-isomerMeSH, HMDB
Dihydrolipoic acid, sodium saltMeSH, HMDB
Molecular FormulaC8H16O2S2
Average Mass208.341
Monoisotopic Mass208.059171136
IUPAC Name6,8-disulfanyloctanoic acid
Traditional Namedihydrolipoic acid
CAS Registry Number462-20-4
SMILES
OC(=O)CCCCC(S)CCS
InChI Identifier
InChI=1S/C8H16O2S2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H,9,10)
InChI KeyIZFHEQBZOYJLPK-UHFFFAOYSA-N