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62320 Sigma-Aldrich

(±)-α-Lipoic acid

≥98.0%

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

  • 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 57651855

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Properties

Related Categories Acids, Acids & Bases, Antioxidant, Cell Biology, Chemical Synthesis,
InChI Key   AGBQKNBQESQNJD-UHFFFAOYSA-N
assay   ≥98.0% (HPLC)
  ≥98.0%
ign. residue   ≤0.1%
loss   ≤0.2% loss on drying
mp   60-62 °C
storage temp.   2-8°C
Gene Information   human ... ACHE(43), BCHE(590)
rat ... Adra1a(29412), Adra1b(24173), Adra1d(29413)

Description

Application

(±)-α-Lipoic acid has been used in in vitro lipoylation studies and in the pyruvate dehydrogenase complex (PDC)-pyruvate dehydrogenase kinase (PDHK) functional assay. It has also been used to investigate its antioxidative effect on developing cerebellum of rats exposed to arsenic during postnatal period.

Packaging

5, 25 g in glass bottle

Biochem/physiol Actions

(±)-α-Lipoic acid exhibits direct free radical scavenging property and reduces the increased oxidative stress. In addition, it might also exhibit prooxidant activity. α-Lipoic acid functions as an important prosthetic group in α-keto acid dehydrogenase complexes of the mitochondria. It acts as a potential therapeutic for diabetic patients with distal symmetric polyneuropathy (DSP). α-Lipoic acid is also used in the treatment of energy-impaired and redox unbalanced diseases.

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

Review

Safety & Documentation

Safety Information

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

Documents

Certificate of Analysis

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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...
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Keywords: Adhesion, Anti-inflammatory agents, Applications, Cancer, Cardiovascular, Catalysis, Diabetes, Diseases, Gene expression, Metabolism, Neurodegenerative Diseases, Peroxidations, Phosphorylations, Prebiotics, Probiotics, Reductions, Transcription, Transduction, Vitamins

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Peer-Reviewed Papers
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References

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