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).^[3] 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.^[3] Only the (R)-(+)-enantiomer (RLA) exists in nature. RLA is an essential cofactor of many processes.^[3]

^ "Lipoic Acid". Pubmed. NCBI. Retrieved October 18, 2018.
^ Teichert, J; Hermann, R; Ruus, P; Preiss, R (November 2003). "Plasma kinetics, metabolism, and urinary excretion of alpha-lipoic acid following oral administration in healthy volunteers". The Journal of Clinical Pharmacology. 43 (11): 1257–67. doi:10.1177/0091270003258654. PMID 14551180. S2CID 30589232.
^ ^a ^b ^c "Lipoic acid". Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis. 1 January 2019. Retrieved 5 November 2019.

[pubmed-1] "Lipoic Acid". Pubmed. NCBI. Retrieved October 18, 2018.

[2] Teichert, J; Hermann, R; Ruus, P; Preiss, R (November 2003). "Plasma kinetics, metabolism, and urinary excretion of alpha-lipoic acid following oral administration in healthy volunteers". The Journal of Clinical Pharmacology. 43 (11): 1257–67. doi:10.1177/0091270003258654. PMID 14551180. S2CID 30589232.

[lpi-3] "Lipoic acid". Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis. 1 January 2019. Retrieved 5 November 2019.

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