(RS)-thioctic acid

Also known as 1,2-dithiolane-3-pentanoic acid, 1,2-dithiolane-3-valeric acid, 5-(1,2-dithiolan-3-yl)valeric acid, 5-(dithiolan-3-yl)valeric acid, 5-[3-(1,2-dithiolanyl)]pentanoic acid, 6-thioctic acid, 6-thiotic acid, 6,8-thioctic acid

pair of enantiomers

In the Vinony graph

Within Vinony's link graph, (RS)-thioctic acid is referenced by 658 other articles, and connects out to disulfide, enzyme and antioxidant.

It is catalogued under topics including 1,2-Dithiolanes, Anti-aging substances and Antioxidants.

Its subject is documented across 33 Wikipedia language editions.

Chemical data

Formula: C8H14O2S2
Molecular weight: 206.3 g/mol
IUPAC name: 5-(dithiolan-3-yl)pentanoic acid
SMILES: C1CSSC1CCCCC(=O)O
InChIKey: AGBQKNBQESQNJD-UHFFFAOYSA-N
XLogP: 1.7
Polar surface area: 87.9 Å²
H-bond donors: 1
H-bond acceptors: 4
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Phase 3
Molecule type: Small molecule
Indications: carpal tunnel syndrome, peripheral neuropathy, optic neuritis, age-related macular degeneration

via ChEMBL · EBI

Research

88 papers

Poly(thioctic acid): From Bottom-Up Self-Assembly to 3D-Fused Deposition Modeling Printing.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2022
(+)-Lipoic acid reduces mitochondrial unfolded protein response and attenuates oxidative stress and aging in an in vitro model of non-alcoholic fatty liver disease.Journal of translational medicine · 2024
Neuroprotective effects of α-lipoic acid on ischemia/reperfusion injury in global cerebral ischemia mouse model.Scientific reports · 2025
Efficacy of Alpha Lipoic Acid Supplementation in Sperm Parameters: A Systematic Review and Meta-Analysis of Randomized Trials.International braz j urol : official journal of the Brazilian Society of Urology · 2025
Potential Glioprotective Strategies Against Diabetes-Induced Brain Toxicity.Neurotoxicity research · 2021

via PubMed

Wikidata facts

Has part: sulfur
Mass: 206.043522
Has use: medication

Show 5 more facts

Commons category: Lipoic acid
chemical formula: C₈H₁₄O₂S₂
subject has role: antioxidant
canonical SMILES: C1CSSC1CCCCC(=O)O
found in taxon: Homo sapiens

Sources (4)

via Wikidata · CC0

~15 min read

Encyclopedic overview

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.

Physical and chemical properties

Excerpted from Wikipedia’s “(RS)-thioctic acid” article, available under the CC BY-SA 4.0 licence.