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T1395 Sigma-Aldrich

(±)-α-Lipoic acid

BioReagent, cell culture tested, ≥99%

Synonym: (±)-1,2-Dithiolane-3-pentanoic acid, 6,8-Dithiooctanoic acid, DL-α-Lipoic acid, DL-6,8-Thioctic acid, Lip(S2), Thioctic acid

  • CAS Number 1077-28-7

  • Empirical Formula (Hill Notation) C8H14O2S2

  • Molecular Weight 206.33

  •  Beilstein/REAXYS Number 81853

  •  EC Number 214-071-2

  •  MDL number MFCD00005474

  •  PubChem Substance ID 24899963

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Properties

Related Categories Antioxidant, Antioxidants and Cytoprotectants, Cell Biology, Cell Signaling and Neuroscience, Cell Stress,
InChI Key   AGBQKNBQESQNJD-UHFFFAOYSA-N
product line   BioReagent
assay   ≥99%
solubility   ethanol: 50 mg/mL
suitability   cell culture tested
Gene Information   human ... ACHE(43), BCHE(590)
rat ... Adra1a(29412), Adra1b(24173), Adra1d(29413)

Description

General description

α-Lipoic acid (LA), a nutritional component found in vegetables and meat, has both antioxidant and oxidant properties. LA exerts therapeutic potential to many diseases like liver cirrhosis, heavy metal poisoning, and diabetic polyneuropathy. LA exerts apoptotic potential in cancer cells either by oxidative stress related pathway or by activation of caspases. LA improves mitochondrial function and plays a key role in mitochondrial energy metabolism.

Application

Lipoic acid has been used:
• for induction of eryptosis in erythrocytes
• as a constituent in NS21 media for neuronal cultures
• to evaluate its effect on liver energy metabolism by high performance liquid chromatography (HPLC) and assessing mitochondrial function by mitochondrial gene expression studies in lipopolysaccharide (LPS) pre-treated mice
• to elucidate its effect on paraquat poisoning in lungs

Packaging

1, 5 g in poly bottle

Biochem/physiol Actions

Antioxidant and coenzyme needed for the activity of enzyme complexes such as those of pyruvate dehydrogenase and glycine decarboxylase. Exogenous thioctic acid is reduced intracellularly by two or more enzymes. The reduced form then influences a number of cell processes by direct radical scavenging, recycling of other antioxidants, increasing glutathione synthesis, and modulating transcription factor activity particularly that of NF-κB. Decreases the phagocytosis of myelin by macrophages.

Other Notes

Oxidized form

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
RTECS 
JP1192000

Documents

Certificate of Analysis

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Certificate of Origin

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Milli-Q® Water Purification Solutions
Protocols & Articles

Articles

Dietary Antioxidants

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.1 During the oxi...
Biofiles Volume 2 Article 2
Keywords: Adhesion, Anti-inflammatory agents, Applications, Cancer, Cardiovascular, Catalysis, Diabetes, Diseases, Gene expression, Metabolism, Neurodegenerative Diseases, Peroxidations, Phosphorylations, Prebiotics, Probiotics, Reductions, Transcription, Transduction, Vitamins

Mitochondrial Stress and ROS

Oxidative stress is implicated in the pathogenesis of lipotoxicity in both animal and human studies. Chronic oxidative stress is linked to insulin resistance in multiple tissues. Oxidative stress is ...
BioFiles 2011, 6.4, 22.
Keywords: Anti-inflammatory agents, Apoptosis, Cancer, Cell signaling, Cellular processes, Gene expression, Indicators, Metabolism, Oxidations, Respiratory

Related Content

Lipoic (thioctic) acid, in Cell Culture

Importance and uses of lipoic acid in serum-free eukaryotic, including hybridoma and Chinese Hamster Ovary (CHO) cell, cultures
Keywords: Apoptosis, Asymmetric synthesis, Cell culture, Citric Acid Cycle, Culture media, Lipid peroxidation, Metabolism, Oxidations, Peroxidations, Redox Reactions, Reductions, Vitamins

Peer-Reviewed Papers
15

References

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