Dihydrolipoic acid

Dihydrolipoic acid
Names
	Preferred IUPAC name 6,8-Bis(sulfanyl)octanoic acid
	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).

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.

References

^ 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.

[iupac2013-1] 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.

[1]

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).

Dihydrolipoic acid

See also

References