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Dihydrolipoic acid

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Dihydrolipoic acid
Names
Preferred IUPAC name 6,8-Bis(sulfanyl)octanoic acid
Other names 6,8-Dimercaptooctanoic acid
Reduced lipoic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.120.390 Edit this at Wikidata
IUPHAR/BPS
KEGG
MeSH Dihydrolipoic+acid
PubChem CID
UNII
CompTox Dashboard (EPA)
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) 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.
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