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Lipoic acid information


Lipoic acid
Names
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
CAS Number
  • 1077-28-7 (racemate) checkY
  • 1200-22-2 (R) checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
81851
ChEBI
  • CHEBI:30314 checkY
ChEMBL
  • ChEMBL134342 checkY
ChemSpider
  • 5886 checkY
DrugBank
  • DB00166 checkY
ECHA InfoCard 100.012.793 Edit this at Wikidata
EC Number
  • 214-071-2
IUPHAR/BPS
  • 4822
KEGG
  • C16241 checkY
MeSH Lipoic+acid
PubChem CID
  • 6112
UNII
  • 73Y7P0K73Y (racemate) checkY
  • VLL71EBS9Z (R) checkY
CompTox Dashboard (EPA)
  • DTXSID7025508 Edit this at Wikidata
InChI
  • InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/s1 checkY
    Key: AGBQKNBQESQNJD-SSDOTTSWSA-N checkY
  • InChI=1/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/s1
    Key: AGBQKNBQESQNJD-SSDOTTSWBZ
SMILES
  • O=C(O)CCCC[C@H]1SSCC1
Properties
Chemical formula
C8H14O2S2
Molar mass 206.32 g·mol−1
Appearance Yellow needle-like crystals
Melting point 60–62 °C (140–144 °F; 333–335 K)
Solubility in water
Very Slightly Soluble(0.24 g/L)[1]
Solubility in ethanol 50 mg/mL Soluble
Pharmacology
ATC code
A16AX01 (WHO)
Pharmacokinetics:
Bioavailability
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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Infobox references

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]

  1. ^ "Lipoic Acid". Pubmed. NCBI. Retrieved October 18, 2018.
  2. ^ Teichert, J; Hermann, R; Ruus, P; Preiss, R (November 2003). "Plasma kinetics, metabolism, and urinary excretion of alpha-lipoic acid following oral administration in healthy volunteers". The Journal of Clinical Pharmacology. 43 (11): 1257–67. doi:10.1177/0091270003258654. PMID 14551180. S2CID 30589232.
  3. ^ a b c "Lipoic acid". Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis. 1 January 2019. Retrieved 5 November 2019.

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Lipoic acid

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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...

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Asparagusic acid

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asparagusic acid can substitute for lipoic acid in α-keto-acid oxidation systems such as the citric acid cycle. The (R)-(+)-enantiomer of α-lipoic acid is a...

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Fatty acid synthesis

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malonyl-CoA from acetyl-CoA. The fatty acids, such as octanoyl-ACP (C8), which forms the starting substrate of lipoic acid biosynthesis, are formed via further...

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Dysgeusia

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pilocarpine, zinc supplementation, alterations in drug therapy, and alpha lipoic acid. The alterations in the sense of taste, usually a metallic taste, and...

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Dihydrolipoic acid

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Dihydrolipoic acid is an organic compound that is the reduced form of lipoic acid. This carboxylic acid features a pair of thiol groups, and therefore...

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Citric acid cycle

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The citric acid cycle—also known as the Krebs cycle, Szent–Györgyi–Krebs cycle or the TCA cycle (tricarboxylic acid cycle)—is a series of biochemical reactions...

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Prosthetic group

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Lodge JK, Marcocci L, Tritschler HJ, Packer L, Rihn BH (1998). "Alpha-lipoic acid in liver metabolism and disease". Free Radic. Biol. Med. 24 (6): 1023–39...

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Bile acid

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acids are steroid acids found predominantly in the bile of mammals and other vertebrates. Diverse bile acids are synthesized in the liver. Bile acids...

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Caloric restriction mimetic

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therefore comparable in effect to calorie restriction (CR). Lipoic Acid (α-Lipoic Acid, Alpha Lipoic Acid, or ALA) has failed to extend lifespan in normal mice...

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Lipoamide

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trivial name for 6,8-dithiooctanoic amide. It is the functional form of lipoic acid, i.e the carboxyl group is attached to protein via an amine with an amide...

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Mitochondrion

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mtFASII, which also forms the starting substrate of lipoic acid biosynthesis. Since lipoic acid is the cofactor of important mitochondrial enzyme complexes...

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Organosulfur chemistry

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Dibenzothiophene, a component of crude oil Perfluorooctanesulfonic acid, a controversial surfactant Lipoic acid, an essential cofactor of four mitochondrial enzyme complexes...

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Copper toxicity

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There is some evidence that alpha-lipoic acid (ALA) may work as a milder chelator of tissue-bound copper. Alpha lipoic acid is also being researched for chelating...

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Oxoglutarate dehydrogenase complex

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peroxide consumption via glutaredoxin. Glutathionylation “protects” the lipoic acid of the E2 domain from undergoing oxidative damage, which helps spare...

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Pyruvate dehydrogenase complex

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PMID 24798336. Billgren ES, Cicchillo RM, Nesbitt NM, Booker SJ (2010). "Lipoic Acid Biosynthesis and Enzymology". Comprehensive Natural Products. 2 (7):...

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Alkylbenzene sulfonate

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are then sulfonated with sulfur trioxide to give the sulfonic acid. The sulfonic acid is subsequently neutralized with sodium hydroxide. The term "linear"...

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Omeprazole

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use in pregnancy is unclear. It works by blocking the release of stomach acid. Omeprazole was patented in 1978, and approved for medical use in 1988. It...

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Ellagic acid

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Ellagic acid is a polyphenol found in numerous fruits and vegetables. It is the dilactone of hexahydroxydiphenic acid. The name comes from the French...

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Neuropathic pain

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of studies found that injected (parenteral) administration of alpha lipoic acid (ALA) was found to reduce the various symptoms of peripheral diabetic...

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Antioxidant

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Teichert J, Preiss R (November 1992). "HPLC-methods for determination of lipoic acid and its reduced form in human plasma". International Journal of Clinical...

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Chelation therapy

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Other chelating agents, such as 2,3-dimercaptopropanesulfonic acid (DMPS) and alpha lipoic acid (ALA), are used in conventional and alternative medicine....

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N2a cell

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It also increases the activity of MEF2, mainly MEF2C, in N2a cells. α-lipoic acid (LA) mainly causes N2a differentiation through phosphorylation of the...

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Permethrin

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is a coupling of a DV-acid ester and an alcohol. In the case of permethrin synthesis, the DV-acid cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2...

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Peripheral neuropathy

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identify any study comparing acupuncture with treatment as usual." Alpha lipoic acid (ALA) with benfotiamine is a proposed pathogenic treatment for painful...

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Valproate

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Valproate (valproic acid, VPA, sodium valproate, and valproate semisodium forms) are medications primarily used to treat epilepsy and bipolar disorder...

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Cystinuria

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February 2017, an article was published in Nature Medicine entitled "Alpha lipoic acid treatment prevents cystine urolithiasis in a mouse model of cystinuria"...

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