Lipoic acid
Chemical compound / From Wikipedia, the free encyclopedia
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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).[3] ALA is made in animals normally, and is essential for aerobic metabolism. It is also manufactured and is available as a dietary supplement in some countries where it is marketed as an antioxidant, and is available as a pharmaceutical drug in other countries. Lipoate is the conjugate base of lipoic acid, and the most prevalent form of LA under physiological conditions.[3] Only the (R)-(+)-enantiomer (RLA) exists in nature and is essential for aerobic metabolism because RLA is an essential cofactor of many enzyme complexes.[3]
Names | |
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IUPAC name
(R)-5-(1,2-Dithiolan-3-yl)pentanoic acid | |
Other names
α-Lipoic acid; Alpha lipoic acid; Thioctic acid; 6,8-Dithiooctanoic acid | |
Identifiers | |
3D model (JSmol) |
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81851 | |
ChEBI | |
ChEMBL | |
ChemSpider |
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DrugBank |
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ECHA InfoCard | 100.012.793 |
EC Number |
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KEGG |
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MeSH | Lipoic+acid |
PubChem CID |
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UNII |
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CompTox Dashboard (EPA) |
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Properties | |
C8H14O2S2 | |
Molar mass | 206.32 g·mol−1 |
Appearance | Yellow needle-like crystals |
Melting point | 60–62 °C (140–144 °F; 333–335 K) |
Very Slightly Soluble(0.24 g/L)[1] | |
Solubility in ethanol 50 mg/mL | Soluble |
Pharmacology | |
A16AX01 (WHO) | |
Pharmacokinetics: | |
30% (oral)[2] | |
Related compounds | |
Related compounds |
Lipoamide Asparagusic acid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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