Dihydrolipoic acid

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 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:18047 checkY
ChEMBL
  • ChEMBL225952 checkY
ChemSpider
  • 408 checkY
ECHA InfoCard 100.120.390 Edit this at Wikidata
IUPHAR/BPS
  • 6738
KEGG
  • C02147 checkY
MeSH Dihydrolipoic+acid
PubChem CID
  • 421
UNII
  • 7NV2KHU5JA checkY
CompTox Dashboard (EPA)
  • DTXSID50861946 DTXSID60963521, DTXSID50861946 Edit this at Wikidata
InChI
  • InChI=1S/C8H16O2S2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H,9,10) checkY
    Key: IZFHEQBZOYJLPK-UHFFFAOYSA-N checkY
  • 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
  • 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).
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Infobox references
Chemical compound

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.

See also

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.