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
3D model (JSmol)
81851
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.012.793 Edit this at Wikidata
EC Number
  • 214-071-2
KEGG
MeSH Lipoic+acid
UNII
  • 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 checkY
    Key: AGBQKNBQESQNJD-SSDOTTSWSA-N checkY
  • 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
  • O=C(O)CCCC[C@H]1SSCC1
Properties
C8H14O2S2
Molar mass 206.32 g·mol−1
Appearance Yellow needle-like crystals
Melting point 60–62 °C (140–144 °F; 333–335 K)
Very Slightly Soluble(0.24 g/L)[1]
Solubility in ethanol 50 mg/mL Soluble
Pharmacology
A16AX01 (WHO)
Pharmacokinetics:
30% (oral)[2]
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).
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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]

  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.
  3. ^ a b c "Lipoic acid". Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis. 1 January 2019. Retrieved 5 November 2019.