Lipoic acid

HCID 6112

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Basic information

CAS
1200-22-2
Standard SMILES
O=C(O)CCCC[C@@H]1CCSS1
InChIKey
AGBQKNBQESQNJD-SSDOTTSWSA-N
Molecular formula
C8H14O2S2
Average molar mass
206.3 g/mol
Monoisotopic mass
206.04352169

Overview

(R)-lipoic acid is the (R)-enantiomer of lipoic acid. A vitamin-like, C8 thia fatty acid with anti-oxidant properties. It has a role as a cofactor, a prosthetic group and a nutraceutical. It is a lipoic acid, a member of dithiolanes, a heterocyclic fatty acid and a thia fatty acid. It is functionally related to an octanoic acid. It is a conjugate acid of a (R)-lipoate. It is an enantiomer of a (S)-lipoic acid.

Names & identifiers

Preferred name
Lipoic acid
IUPAC
5-[(3R)-dithiolan-3-yl]pentanoic acid

Names & synonyms

lipoic acid(R)-lipoic acid(R)-5-(1,2-Dithiolan-3-yl)pentanoic acid(R)-alpha-Lipoic acidD-Thioctic acid(R)-(+)-1,2-Dithiolane-3-pentanoic acidR-(+)-Thioctic acid(+)-alpha-Lipoic acid1,2-Dithiolane-3-pentanoic acid, (3R)-R-alpha-Lipoic acidThioctic acid d-form5-[(3R)-dithiolan-3-yl]pentanoic acid
Show more names
BerlitionThiogammaLipoecTiobec5-[(3R)-1,2-dithiolan-3-yl]pentanoic acidR-Lipoic acid(R)-(+)-lipoic acid(R)-1,2-Dithiolane-3-pentanoic acid

Database identifiers

CAS
1200-22-2、62-46-4
PubChem CID
6112
DTXSID
DTXSID20152651
ChEBI
CHEBI:30314
UNII
VLL71EBS9Z
Nikkaji
J9.331I

Properties

Computed structural propertiesFilling in

XLogP
1.7
Topological polar surface area
87.9 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
5
Heavy atoms
12

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Thia fatty acids [FA0113]
SpringerMaterials PropertiesCrystal structure
SolubilityInsoluble
Melting Point60.5 °C
Physical DescriptionSolid

Chemistry & industry

Pharmacology

Pharmacodynamics · 1 item

Lipoic acid (or α-lipoic acid) is able to pass the blood-brain barrier and is putatively used for detoxification of mercury attached to the brain cells. It can mobilise bound mercury into the blood stream as it is a mercaptan (sulfur compound which readily binds to the mercury). In the blood stream, another chelator such as dimercaptosuccinic acid (DMSA) or methylsulfonylmethane (MSM) is used to transfer mercury safely into the urine for excretion. Since DMSA cannot cross the blood-brain barrier, both lipoic acid and DMSA tend to be used together. It is hypothesized that this treatment-along with carnitine, dimethylglycine (DMG), Vitamin B6, folic acid, and magnesium—could be used to treat autism and amalgam poisoning. In this hypothesis, the reason why autism is difficult to treat is that mercury is attached to the brain cells and most medicines and vitamin supplements do not penetrate the blood-brain barrier. However, α-lipoic acid and perhaps vitamin B12 could making it possible for other chelators to remove mercury safely out of the body and could perhaps one day be used as a treatment for autism. Because lipoic acid is related to cellular uptake of glucose and it is both soluble in water and fat, it is being used for treatment in diabetes. It may be helpful for people with Alzheimer's disease or Parkinson's disease.

Mechanism of Action · 1 item

Lipoic Acid is generally involved in oxidative decarboxylations of keto acids and is presented as a growth factor for some organisms. Lipoic acid exists as two enantiomers, the R-enantiomer and the S-enantiomer. Normally only the R-enantiomer of an amino acid is biologically active, but for lipoic acid the S-enantiomer assists in the reduction of the R-enantiomer when a racemic mixture is given. Some recent studies have suggested that the S-enantiomer in fact has an inhibiting effect on the R-enantiomer, reducing its biological activity substantially and actually adding to oxidative stress rather than reducing it. Furthermore, the S-enantiomer has been found to reduce the expression of GLUT-4s in cells, responsible for glucose uptake, and hence reduce insulin sensitivity.

Tissue LocationsKidney
Cellular LocationsCytoplasm
Metabolite Pathways3-Phosphoglycerate dehydrogenase deficiency

Suppliers100 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
北京安司莫森技术有限公司010-82954736 13391601435 · [email protected]
南京凯天化工有限公司+86 (25) 5860-8846 · [email protected]

Related reactions

49 records

Compound notes

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