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Details

Stereochemistry RACEMIC
Molecular Formula C8H14O2S2
Molecular Weight 206.326
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALPHA LIPOIC ACID

SMILES

OC(=O)CCCCC1CCSS1

InChI

InChIKey=AGBQKNBQESQNJD-UHFFFAOYSA-N
InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)

HIDE SMILES / InChI
Thioctic acid also known as alpha-lipoic acid is a dietary supplement, which is a common ingredient in OTC (over-the-counter) multivitamin formulas and anti-aging supplements. Thioctic acid exists in both R- and S-enantiomeric forms, however, only R-form is essential as a cofactor in biological systems (the acid is coupled via an amide linkage to a lysine of several multienzyme complexes, such as the pyruvate dehydrogenase complex, the alpha-ketoglutarate dehydrogenase complex, the glycine cleavage system and the branched-chain oxo acid dehydrogenase complex). Most commercially available thioctic acid supplements are a mixture of both R and S enantiomers or R-form alone. Several studies have shown that the acid has beneficial effect on diabetes complications, cancer, glaucome, liver disease, etc. The mechanisms of thioctic acid is related to its antioxidant properties, metal chelator properties, however, those mechanisms need futher confirmation.

Approval Year

Conditions
PubMed

PubMed

TitleDatePubMed
Crystalline alpha-lipoic acid; a catalytic agent associated with pyruvate dehydrogenase.
1951 Jul 27
Swinging arms and swinging domains in multifunctional enzymes: catalytic machines for multistep reactions.
2000
Lipoic acid in combination with a chelator ameliorates lead-induced peroxidative damages in rat kidney.
2002 Aug
Burning mouth syndrome (BMS): an open trial of comparative efficacy of alpha-lipoic acid (thioctic acid) with other therapies.
2002 Sep
Early oxidative stress in the diabetic kidney: effect of DL-alpha-lipoic acid.
2003 Jan 15
Effect of antioxidants and ACE inhibition on chemical modification of proteins and progression of nephropathy in the streptozotocin diabetic rat.
2004 Aug
Protective effect of DL-alpha-lipoic acid in cyclophosphamide induced oxidative injury in rat testis.
2004 Dec
Burning Mouth Syndrome: open trial of psychotherapy alone, medication with alpha-lipoic acid (thioctic acid), and combination therapy.
2004 Jan-Feb
Conformational stability and thermodynamic characterization of the lipoic acid bearing domain of human mitochondrial branched chain alpha-ketoacid dehydrogenase.
2004 Sep
The protective role of DL-alpha-lipoic acid in biogenic amines catabolism triggered by Abeta amyloid vaccination in mice.
2005 Apr 30
Combined efficacies of DL-alpha-lipoic acid and meso 2,3 dimercaptosuccinic acid against arsenic induced toxicity in antioxidant systems of rats.
2005 Dec 30
Beneficial effects of DL-alpha-lipoic acid on cyclophosphamide-induced oxidative stress in mitochondrial fractions of rat testis.
2005 Feb 28
Syntheses of novel indole lipoic acid derivatives and their antioxidant effects on lipid peroxidation.
2005 Mar
Oxidative stress on mitochondrial antioxidant defense system in the aging process: role of DL-alpha-lipoic acid and L-carnitine.
2005 May
dl-alpha-lipoic acid ameliorates cyclophosphamide induced cardiac mitochondrial injury.
2005 Nov 5
Carnitine and lipoic acid alleviates protein oxidation in heart mitochondria during aging process.
2006 Apr
[Oxaliplatin neurotoxicity].
2006 Feb 1
Antioxidants reduce cone cell death in a model of retinitis pigmentosa.
2006 Jul 25
Salubrious effects of lipoic acid against adriamycin-induced clastogenesis and apoptosis in Wistar rat bone marrow cells.
2006 May 15
Doxorubicin-induced reactive oxygen species generation and intracellular Ca2+ increase are reciprocally modulated in rat cardiomyocytes.
2006 Oct 31
Acrolein, a toxicant in cigarette smoke, causes oxidative damage and mitochondrial dysfunction in RPE cells: protection by (R)-alpha-lipoic acid.
2007 Jan
Zinc and the cytoskeleton in the neuronal modulation of transcription factor NFAT.
2007 Jan
Patents

Sample Use Guides

Recommended oral therapeutic dosages of alpha-lipoic acid range from 600-1800 mg daily.
Route of Administration: Oral
In Vitro Use Guide
Supplementation of Human Umbilical Vein Endothelial Cells with 100, 200, or 500 uM thioctic acid after inoculation with R. rickettsii restored the intracellular levels of thiols and glutathione peroxidase and reduced the intracellular peroxide levels in infected cells.
Name Type Language
.ALPHA.-LIPOIC ACID
Preferred Name English
ALPHA LIPOIC ACID
USP   USP-RS   VANDF  
USP  
Official Name English
THIOCTIC ACID
EP   HSDB   INCI   JAN   MART.   WHO-DD  
INCI  
Preferred Name English
THIOCTIC ACID [INCI]
Common Name English
DL-6,8-THIOCTIC ACID
Common Name English
ALPHA LIPOIC ACID [VANDF]
Common Name English
NSC-90788
Code English
BILETAN
Brand Name English
ALPHA-LIPOIC ACID
VANDF  
Common Name English
THIOCTIC ACID DL-FORM [MI]
Common Name English
THIOCTIC ACID, (±)-
Common Name English
NSC-628502
Code English
ACIDUM THIOCTICUM
Common Name English
6,8-THIOCTIC ACID
Common Name English
THIOCACID
Brand Name English
Thioctic acid [WHO-DD]
Common Name English
1,2-DITHIOLANE-3-PENTANOIC ACID
Systematic Name English
ALPHA-LIPOIC ACID [VANDF]
Common Name English
THIOCTIC ACID [MART.]
Common Name English
THIOCTIC ACID [JAN]
Common Name English
A-LIPOICUM ACIDUM
HPUS  
Common Name English
TIOCTIC ACID
Common Name English
LIPOIC ACID, DL-
Common Name English
THIOCTIC ACID [HSDB]
Common Name English
.DELTA.-(3-(1,2-DITHIACYCLOPENTYL))PENTANOIC ACID
Common Name English
ALPHA LIPOIC ACID [USP IMPURITY]
Common Name English
THIOCTIC ACID [MI]
Common Name English
THIOCTIC ACID [EP MONOGRAPH]
Common Name English
5-(3-(1,2-DITHIOLANYL))PENTANOIC ACID
Common Name English
A-LIPOICUM ACIDUM [HPUS]
Common Name English
ALPHA LIPOIC ACID [USP-RS]
Common Name English
.ALPHA.-LIPOIC ACID, (±)-
Common Name English
THIOCTATE
Common Name English
5-(1,2-DITHIOLAN-3-YL)VALERIC ACID
Systematic Name English
1,2-DITHIOLANE-3-VALERIC ACID
Systematic Name English
5-((3RS)-1,2-DITHIOLAN-3-YL)PENTANOIC ACID
Systematic Name English
THIOCTAN
Brand Name English
Classification Tree Code System Code
WHO-VATC QA16AX01
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
EU-Orphan Drug EU/3/16/1646
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
DSLD 8 (Number of products:2523)
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
WHO-ATC A16AX01
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
Code System Code Type Description
CAS
1077-28-7
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-534-6
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
ALTERNATIVE
CHEBI
30314
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
PRIMARY
FDA UNII
73Y7P0K73Y
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
PRIMARY
MESH
D008063
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
PRIMARY
RXCUI
6417
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
PRIMARY
PUBCHEM
864
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
PRIMARY
MERCK INDEX
m10749
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
PRIMARY Merck Index
SMS_ID
100000086014
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
PRIMARY
CHEBI
30313
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
PRIMARY
CHEBI
16494
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
PRIMARY
DRUG CENTRAL
4732
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
PRIMARY
ECHA (EC/EINECS)
214-071-2
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
PRIMARY
NSC
628502
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
PRIMARY
CAS
62-46-4
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
SUPERSEDED
EPA CompTox
DTXSID7025508
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
PRIMARY
DAILYMED
73Y7P0K73Y
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
PRIMARY
RS_ITEM_NUM
1368201
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
PRIMARY
ChEMBL
CHEMBL33864
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
PRIMARY
EVMPD
SUB15537MIG
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
PRIMARY
RXCUI
618060
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
ALTERNATIVE
NCI_THESAURUS
C61595
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
PRIMARY
NSC
90788
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
PRIMARY
HSDB
7818
Created by admin on Fri Dec 15 14:59:17 GMT 2023 , Edited by admin on Fri Dec 15 14:59:17 GMT 2023
PRIMARY