Dihydrolipoic acid

Dihydrolipoic acid is an organic compound that is the reduced form of lipoic acid. This carboxylic acid features a pair of thiol groups, and therefore is a dithiol. 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.

Dihydrolipoic acid

Names
Preferred IUPAC name 6,8-Bis(sulfanyl)octanoic acid[1]
Other names 6,8-Dimercaptooctanoic acid Reduced lipoic acid
Identifiers
CAS Number	462-20-4
3D model (JSmol)	Interactive image
ChEBI	CHEBI:18047
ChEMBL	ChEMBL225952
ChemSpider	408
ECHA InfoCard	100.120.390
IUPHAR/BPS	6738
KEGG	C02147
MeSH	Dihydrolipoic+acid
PubChem CID	421
UNII	7NV2KHU5JA
CompTox Dashboard (EPA)	DTXSID60963521
InChI InChI=1S/C8H16O2S2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H,9,10) Key: IZFHEQBZOYJLPK-UHFFFAOYSA-N InChI=1/C8H16O2S2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H,9,10) Key: IZFHEQBZOYJLPK-UHFFFAOYAP
SMILES C(CCC(=O)O)CC(CCS)S
Properties
Chemical formula	C8H16O2S2
Molar mass	208.33 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
verify (what is  ?)
Infobox references

See also

• Dihydrolipoamide
• Lipoamide

References

1. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 697. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. The prefixes ‘mercapto’ (–SH), and ‘hydroseleno’ or selenyl (–SeH), etc. are no longer recommended.