08561
(S)-(−)-α -Lipoic acid
≥97% (HPLC)
Synonym(s):
(S)-1,2-Dithiolane-3-pentanoic acid, (S)-6,8-Thioctic acid
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About This Item
Empirical Formula (Hill Notation):
C8H14O2S2
CAS Number:
Molecular Weight:
206.33
Beilstein:
81852
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.25
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Quality Level
Assay
≥97% (HPLC)
optical purity
enantiomeric excess: ≥98.0% (HPLC)
storage temp.
−20°C
SMILES string
OC(=O)CCCC[C@H]1CCSS1
InChI
1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m0/s1
InChI key
AGBQKNBQESQNJD-ZETCQYMHSA-N
Biochem/physiol Actions
Biological antioxidant with prooxidant activities . Method for enantioseparation of lipoic acid in dietary supplements by capillary electrophoresis.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Certificates of Analysis (COA)
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Ronald Bentley
Chemical Society reviews, 34(7), 609-624 (2005-06-21)
Chiral structures profoundly influence chemical and biological processes. While chiral carbon biomolecules have received much attention, chirality is also possible in certain sulfur compounds; just as with carbon, there can be differences in the physiological behavior of chiral sulfur compounds.
Shuji Kodama et al.
Electrophoresis, 33(15), 2441-2445 (2012-08-14)
Lipoic acid, an antioxidant, naturally occurs as the (R)-enantiomer, while synthetic lipoic acid is racemic. It is thus of interest to know the (R)-enantiomer content of lipoic acid supplements. Here, we used capillary electrophoresis to directly enantioseparate lipoic acid in
Hadi Moini et al.
Toxicology and applied pharmacology, 182(1), 84-90 (2002-07-20)
Reactive oxygen (ROS) and nitrogen oxide (RNOS) species are produced as by-products of oxidative metabolism. A major function for ROS and RNOS is immunological host defense. Recent evidence indicate that ROS and RNOS may also function as signaling molecules. However
L Packer et al.
Free radical biology & medicine, 19(2), 227-250 (1995-08-01)
alpha-Lipoic acid, which plays an essential role in mitochondrial dehydrogenase reactions, has recently gained considerable attention as an antioxidant. Lipoate, or its reduced form, dihydrolipoate, reacts with reactive oxygen species such as superoxide radicals, hydroxyl radicals, hypochlorous acid, peroxyl radicals
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