Lipoic acid

Lipoic acid
Names
	IUPAC name (R)-5-(1,2-Dithiolan-3-yl)pentanoic acid
	Other names α-Lipoic acid; Alpha lipoic acid; Thioctic acid; 6,8-Dithiooctanoic acid
Identifiers
CAS Number	1077-28-7 (racemate) ; 1200-22-2 (R) ;
3D model (JSmol)	Interactive image;
Beilstein Reference	81851
ChEBI	CHEBI:30314 ;
ChEMBL	ChEMBL134342 ;
ChemSpider	5886 ;
DrugBank	DB00166 ;
ECHA InfoCard	100.012.793
EC Number	214-071-2;
IUPHAR/BPS	4822;
KEGG	C16241 ;
MeSH	Lipoic+acid
PubChem CID	6112;
UNII	73Y7P0K73Y (racemate) ; VLL71EBS9Z (R) ;
CompTox Dashboard (EPA)	DTXSID7025508 ;
	InChI InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/s1 Key: AGBQKNBQESQNJD-SSDOTTSWSA-N ; InChI=1/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/s1 Key: AGBQKNBQESQNJD-SSDOTTSWBZ;
	SMILES O=C(O)CCCC[C@H]1SSCC1;
Properties
Chemical formula	C8H14O2S2
Molar mass	206.32 g·mol−1
Appearance	Yellow needle-like crystals
Melting point	60–62 °C (140–144 °F; 333–335 K)
Solubility in water	Very Slightly Soluble(0.24 g/L)
Solubility in ethanol 50 mg/mL	Soluble
Pharmacology
ATC code	A16AX01 (WHO)
	Pharmacokinetics:
Bioavailability	30% (oral)
Related compounds
Related compounds	Lipoamide; Asparagusic acid
	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

Lipoic acid (LA), also known as α-lipoic acid, alpha-lipoic acid (ALA) and thioctic acid, is an organosulfur compound derived from caprylic acid (octanoic acid). ALA, which is made in animals normally, is essential for aerobic metabolism. It is also available as a dietary supplement or pharmaceutical drug in some countries. Lipoate is the conjugate base of lipoic acid, and the most prevalent form of LA under physiological conditions. Only the (R)-(+)-enantiomer (RLA) exists in nature. RLA is an essential cofactor of many processes.