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(±)-thioctic acid
DL-lipoic acid

Sponsors

Name:5-(dithiolan-3-yl)pentanoic acid
CAS Number: 1077-28-7Picture of molecule3D/inchi
Other:62-46-4
ECHA EINECS - REACH Pre-Reg:214-071-2
FDA UNII:73Y7P0K73Y
Nikkaji Web:J38.321J
Beilstein Number:0081853
MDL:MFCD00005474
XlogP3-AA:1.70 (est)
Molecular Weight:206.32798000
Formula:C8 H14 O2 S2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome or firefox)
Category:antioxidants
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 47.50 °C. @ 760.00 mm Hg (est)
Boiling Point: 362.46 °C. @ 760.00 mm Hg (est)
Vapor Pressure:9.490000 mm/Hg @ 25.00 °C. (est)
Flash Point: 343.00 °F. TCC ( 173.00 °C. ) (est)
logP (o/w): 2.530 (est)
Soluble in:
 water, 126.6 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: antioxidants
 
Suppliers:
Aceto
alpha-Lipoic Acid
AIDP
Alpha Lipoic Acid ALA 99% min
Balchem
Alpha-Lipoic Acid
VitaShure®
Flavor: characteristic
Vitashure is an extensive line of microencapsulated vitamins, minerals, amino acids, and bioactive substances, specifically designed for the supplementation and fortification industries.
BOC Sciences
For experimental / research use only.
DL-ThioCtic acid 98%
Odor: characteristic
Use: DL-a-Lipoic acid is an non-specific free radical scavenger and has anti-oxidant properties. It could be used as a fat-metabolism stimulator. DL--Lipoic acid is an non-specific free radical scavenger and has anti-oxidant properties.
Changsha Organic Herb
Alpha-Lipoic Acid
Charkit Chemical
ALPHA LIPOIC ACID
Jiangyin Healthway
Alpha-Lipoic Acid
New functional food ingredients
Penta International
alpha-LIPOIC ACID USP, Kosher
Penta International
alpha-LIPOIC ACID
Qingdao Dacon Trading
alpha-Lipoic Acid
Sabinsa Corporation
Alpha-Lipoic Acid
Sigma-Aldrich
For experimental / research use only.
Thioctic Acid European Pharmacopoeia (EP) Reference Standard
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD50 235 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 284, 1971.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category: antioxidants
Recommendation for (±)-thioctic acid usage levels up to:
 not for fragrance use.
 
Recommendation for (±)-thioctic acid flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
Daily Med:search
NLM Hazardous Substances Data Bank:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
Env. Mutagen Info. Center:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :864
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
5-(dithiolan-3-yl)pentanoic acid
Chemidplus:0001077287
RTECS:JP1192000 for cas# 1077-28-7
 
References:
 5-(dithiolan-3-yl)pentanoic acid
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:1077-28-7
Pubchem (cid):864
Pubchem (sid):134980444
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
Metabolomics Database:Search
KEGG (GenomeNet):C00725
HMDB (The Human Metabolome Database):HMDB01451
FooDB:FDB022631
YMDB (Yeast Metabolome Database):YMDB00334
Export Tariff Code:2934.90.5000
MedlinePlusSupp:View
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
RSC Learn Chemistry:View
Formulations/Preparations:
•oral: capsules 30 mg coenzyme q10, 12-5 mg alpha-lipoic acid, coquinone 30 (usana health sciences inc). coquinone 30 •juvenon: acetyl-l-carnitine and alpha lipoic acid
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 broccoli asparagus broccoli plant
Search Trop Picture
 spinach plant
Search Trop Picture
 
Synonyms:
 acid, a-lipoic
 alphaflam
 alphalipogamma
 alphalipoic acid
 alphaLippon AL
 alphavibolex
 azulipont
 biletan
 biomo lipon
 biomo-lipon
 biomolipon
6,8-dihydrothioctic acid
5-(dithiolan-3-yl) valeric acid
5-(dithiolan-3-yl)pentanoic acid
5-(1,2-dithiolan-3-yl)pentanoic acid
5-(dithiolan-3-yl)valeric acid
5-(1,2-dithiolan-3-yl)valeric acid
(±)-1,2-dithiolane-3-pentanoic acid
1,2-dithiolane-3-pentanoic acid
(±)-1,2-dithiolane-3-valeric acid
1,2-dithiolane-3-valeric acid
DL-1,2-dithiolane-3-valeric acid
5-[3-(1,2-dithiolanyl)]pentanoic acid
6,8-dithiooctanoic acid
DL-6,8-dithiooctanoic acid
 duralipon
 espa lipon
 espa-lipon
 espalipon
 fenint
a-lipogamma
 lipoic acid
(±)-lipoic acid
(±)-a-lipoic acid
(RS)-lipoic acid
(RS)-a-lipoic acid
a-lipoic acid
alpha-lipoic acid
DL-lipoic acid
DL-a-lipoic acid
 lipoicacid
a-lipon stada
a-liponaure heumann
 liponic acid
a-liponic acid
a-liponsaeure
a-liponsaure sofotec
 liponsaure-ratiopharm
 liposan
 lipothion
a-lippon AL
 neurium
 pleomix A
 pleomix-A
 pleomixalpha
 rac-lipoate
 thioctacid
6-thioctic acid
6,8-thioctic acid
DL-thioctic acid
DL-6-thioctic acid
DL-6,8-thioctic acid
 thioctic acid DL-form
DL-thiocticacid
 thiogamma oral
 thiooctic acid
6-thiotic acid
6,8-thiotic acid
 thiotomin
 tromlipon
 verla lipon
 verla-lipon
 verlalipon
a-vibolex
 

Articles:

PubMed:α-Lipoic acid reduces fatty acid esterification and lipogenesis in adipocytes from overweight/obese subjects.
PubMed:The effect of dietary α-lipoic acid, betaine, l-carnitine, and swimming on the obesity of mice induced by a high-fat diet.
PubMed:α-Tocopherol supplementation reduces biomarkers of oxidative stress in children with Down syndrome: a randomized controlled trial.
PubMed:Effect of dietary α-lipoic acid on the mRNA expression of genes involved in drug metabolism and antioxidation system in rat liver.
PubMed:Phosphorylation of hypothalamic AMPK on serine(485/491) related to sustained weight loss by alpha-lipoic acid in mice treated with olanzapine.
PubMed:Wheat germ oil enrichment in broiler feed with α-lipoic acid to enhance the antioxidant potential and lipid stability of meat.
PubMed:Effects of combined lipoic acid and pyridoxine on albuminuria, advanced glycation end-products, and blood pressure in diabetic nephropathy.
PubMed:Efficacy of food supplement to improve metabolic syndrome parameters in patients affected by moderate to severe psoriasis during anti-TNFα treatment.
PubMed:R-α lipoic acid γ-cyclodextrin complex increases energy expenditure: a 4-month feeding study in mice.
PubMed:Protective effect of alpha-lipoic acid on cypermethrin-induced oxidative stress in Wistar rats.
PubMed:Rapid Method for Glutathione Quantitation Using High-Performance Liquid Chromatography with Coulometric Electrochemical Detection.
PubMed:The effects of α-lipoic acid on liver oxidative stress and free fatty acid composition in methionine-choline deficient diet-induced NAFLD.
PubMed:Wheat germ oil and α-lipoic acid predominantly improve the lipid profile of broiler meat.
PubMed:Acetyl-L-carnitine and lipoic acid improve mitochondrial abnormalities and serum levels of liver enzymes in a mouse model of nonalcoholic fatty liver disease.
PubMed:Characterization of genome-wide transcriptional changes in liver and adipose tissues of ZDF (fa/fa) rats fed R-α-lipoic acid by next-generation sequencing.
PubMed:Asparagusic acid.
PubMed:Calorie restriction and dietary restriction mimetics: a strategy for improving healthy aging and longevity.
PubMed:Comprehensive rehabilitation in chronic heart failure.
PubMed:Attenuation of uremia by orally feeding alpha-lipoic acid on acetaminophen induced uremic rats.
PubMed:Reduction of aggregation of β-lactoglobulin during heating by dihydrolipoic acid.
PubMed:Role of α-lipoic acid in dextran sulfate sodium-induced ulcerative colitis in mice: studies on inflammation, oxidative stress, DNA damage and fibrosis.
PubMed:The endocrine control of energy homeostasis in chickens.
PubMed:The protective effect of alpha-lipoic Acid in lipopolysaccharide-induced acute lung injury is mediated by heme oxygenase-1.
PubMed:The effect of alpha-lipoic acid on mitochondrial superoxide and glucocorticoid-induced hypertension.
PubMed:Α-lipoic acid supplementation up-regulates antioxidant capacity in adults with G6PD deficiency.
PubMed:Lipoic acid inhibits adiponectin production in 3T3-L1 adipocytes.
PubMed:Direct and indirect antioxidant properties of α-lipoic acid and therapeutic potential.
PubMed:Formation of stable nanocarriers by in situ ion pairing during block-copolymer-directed rapid precipitation.
PubMed:Synthesis and bioactivity profile of 5-s-lipoylhydroxytyrosol-based multidefense antioxidants with a sizeable (poly)sulfide chain.
PubMed:Molecular characterization of a thermostable aldehyde dehydrogenase (ALDH) from the hyperthermophilic archaeon Sulfolobus tokodaii strain 7.
PubMed:The effects of alpha lipoic acid on liver cells damages and apoptosis induced by polyunsaturated fatty acids.
PubMed:Kinetic modeling and scale up of lipoic acid (LA) production from Saccharomyces cerevisiae in a stirred tank bioreactor.
PubMed:Alpha-lipoic acid protects against indomethacin-induced gastric oxidative toxicity by modulating antioxidant system.
PubMed:Effects of lipoic acid on lipolysis in 3T3-L1 adipocytes.
PubMed:A combination cocktail improves spatial attention in a canine model of human aging and Alzheimer's disease.
PubMed:Effects of heat treatment on structural modification and in vivo antioxidant capacity of soy protein.
PubMed:Determination of lipoic acid by flow-injection and high-performance liquid chromatography with chemiluminescence detection.
PubMed:α-Lipoic acid reduced weight gain and improved the lipid profile in rats fed with high fat diet.
PubMed:High-fat diets impair spatial learning of mice in the Y-maze paradigm: ameliorative potential of α-lipoic acid.
PubMed:Combined effect of sesamin and α-lipoic acid on hepatic fatty acid metabolism in rats.
PubMed:Effects of lipoic acid on AMPK and adiponectin in adipose tissue of low- and high-fat-fed rats.
PubMed:A combination of lipoic acid plus coenzyme Q10 induces PGC1α, a master switch of energy metabolism, improves stress response, and increases cellular glutathione levels in cultured C2C12 skeletal muscle cells.
PubMed:Enhancement of lipid stability of broiler breast meat and meat products fed on alpha lipoic acid and alpha tocopherol acetate supplemented feed.
PubMed:Lipoic acid mitigates bisphenol A-induced testicular mitochondrial toxicity in rats.
PubMed:Development of a simple and high-throughput method for detecting aflatoxins production in culture media.
PubMed:Lipoic acid administration prevents nonalcoholic steatosis linked to long-term high-fat feeding by modulating mitochondrial function.
PubMed:Lipoic acid improves mitochondrial function in nonalcoholic steatosis through the stimulation of sirtuin 1 and sirtuin 3.
PubMed:Lipoic acid attenuates high-fat-diet-induced oxidative stress and B-cell-related immune depression.
PubMed:Bioactive compounds with effects on inflammation markers in humans.
PubMed:Effects of α-lipoic acid and L-carnosine supplementation on antioxidant activities and lipid profiles in rats.
PubMed:Fatty acids and gene expression responses to bioactive compounds in Atlantic salmon (Salmo salar L.) hepatocytes.
PubMed:Direct analysis of carbohydrates in animal plasma by ion chromatography coupled with mass spectrometry and pulsed amperometric detection for use as a non-invasive diagnostic tool.
PubMed:Novel Conjugates of 1,3-Diacylglycerol and Lipoic Acid: Synthesis, DPPH Assay, and RP-LC-MS-APCI Analysis.
PubMed:Impact of α-lipoic acid on liver peroxisome proliferator-activated receptor-α, vascular remodeling, and oxidative stress in insulin-resistant rats.
PubMed:Alpha-lipoic acid protects against myocardial ischemia/reperfusion injury via multiple target effects.
PubMed:Lipid stability and antioxidant profile of microsomal fraction of broiler meat enriched with α-lipoic acid and α-tocopherol acetate.
PubMed:Effects of α-lipoic acid, vitamins E and C upon the heat stress in Japanese quails.
PubMed:Reciprocal effects of α-lipoic acid on adenosine monophosphate-activated protein kinase activity in obesity induced by ovariectomy in rats.
PubMed:Effects of lipoic acid on apelin in 3T3-L1 adipocytes and in high-fat fed rats.
PubMed:A Regenerative Antioxidant Protocol of Vitamin E and α-Lipoic Acid Ameliorates Cardiovascular and Metabolic Changes in Fructose-Fed Rats.
PubMed:Inhibitory effect of α-lipoic acid on platelet aggregation is mediated by PPARs.
PubMed:Lipoic acid inhibits leptin secretion and Sp1 activity in adipocytes.
PubMed:Effects of lipoic acid on proliferation and apoptosis of liver cells in rats with metabolic stress.
PubMed:Formulation of a medical food cocktail for Alzheimer's disease: beneficial effects on cognition and neuropathology in a mouse model of the disease.
PubMed:Vitamin C, resveratrol and lipoic acid actions on isolated rat liver mitochondria: all antioxidants but different.
PubMed:Pharmacokinetics of orally administered DL-α-lipoic acid in dogs.
PubMed:The proglycation effect of caffeic acid leads to the elevation of oxidative stress and inflammation in monocytes, macrophages and vascular endothelial cells.
PubMed:Lipoic acid nanoparticles: effect of polymeric stabilizer on appetite suppression.
PubMed:Antiplatelet activity of alpha-lipoic acid.
PubMed:Comparative proteome analysis of splenic lymphocytes in long-term high-fat diet and dietary supplement with lipoic acid mice.
PubMed:Cytoprotective effects of DL-alpha-lipoic acid or squalene on cyclophosphamide-induced oxidative injury: an experimental study on rat myocardium, testicles and urinary bladder.
PubMed:Protective effect of lipoic acid against methotrexate-induced oxidative stress in liver mitochondria.
PubMed:Effects of duodenal redox status on calcium absorption and related genes expression in high-fat diet-fed mice.
PubMed:Role of oxidative stress and nitric oxide in the protective effects of alpha-lipoic acid and aminoguanidine against isoniazid-rifampicin-induced hepatotoxicity in rats.
PubMed:Effect of POLY-MVA, a palladium alpha-lipoic acid complex formulation against declined mitochondrial antioxidant status in the myocardium of aged rats.
PubMed:Dyslipidemic high-fat diet affects adversely bone metabolism in mice associated with impaired antioxidant capacity.
PubMed:Reactive oxygen species serve as signals mediating glucose-stimulated somatostatin secretion from cultured rat gastric primary D-cells.
PubMed:Vitamin E as a novel enhancer of macroautophagy in rat hepatocytes and H4-II-E cells.
PubMed:Lipoic acid: an immunomodulator that attenuates glycinin-induced anaphylactic reactions in a rat model.
PubMed:A new method for the detection and characterization of alpha-lipoic acid mixed disulphides.
PubMed:Effects of alpha-lipoic acid on cell proliferation and apoptosis in MDA-MB-231 human breast cells.
PubMed:Improved efficacy of appetite suppression by lipoic acid particles prepared by nanocomminution.
PubMed:Lipoic acid attenuates high fat diet-induced chronic oxidative stress and immunosuppression in mice jejunum: a microarray analysis.
PubMed:Mechanism of alpha-lipoic acid-induced apoptosis of lung cancer cells.
PubMed:Prevention of high-fat diet-induced muscular lipid accumulation in rats by alpha lipoic acid is not mediated by AMPK activation.
PubMed:Alpha-lipoic acid as a dietary supplement: molecular mechanisms and therapeutic potential.
PubMed:Lipoic acid prevents body weight gain induced by a high fat diet in rats: effects on intestinal sugar transport.
PubMed:Effects of antioxidant supplements intervention on the level of plasma inflammatory molecules and disease severity of rheumatoid arthritis patients.
PubMed:Electrochemical immunosensor for detection of celiac disease toxic gliadin in foodstuff.
PubMed:The effect of lipoic acid on macro and trace metal levels in living tissues exposed to oxidative stress.
PubMed:Palladium alpha-lipoic acid complex formulation enhances activities of Krebs cycle dehydrogenases and respiratory complexes I-IV in the heart of aged rats.
PubMed:Foods and supplements in the management of migraine headaches.
PubMed:Protective effect of lipoic acid against acrolein-induced cytotoxicity in IMR-90 human fibroblasts.
PubMed:A piezoelectric immunosensor for the determination of pesticide residues and metabolites in fruit juices.
PubMed:Carotenoid extraction from plants using a novel, environmentally friendly solvent.
PubMed:Chronic lipoic acid treatment worsens energy imbalances in streptozotocin-induced diabetic rats.
PubMed:[Effect of lipoic acid on gene expression related to oxidative stress, lipid and glucose metabolism of mice fed with high fat diet].
PubMed:Dihydrolipoic acid inhibits tetrachlorohydroquinone-induced tumor promotion through prevention of oxidative damage.
PubMed:Dietary lipoic acid supplementation can mimic or block the effect of dietary restriction on life span.
PubMed:Chitosan microspheres for encapsulation of alpha-lipoic acid.
PubMed:Lipoic acid prevents high-fat diet-induced dyslipidemia and oxidative stress: a microarray analysis.
PubMed:Dietary lipoic acid-dependent changes in the activity and mRNA levels of hepatic lipogenic enzymes in rats.
PubMed:Nonvitamin, nonmineral dietary supplementation in HIV-positive people.
PubMed:[Safety and structural analysis of polymers produced in manufacturing process of alpha-lipoic acid].
PubMed:alpha-Lipoic acid in dietary supplements: development and comparison of HPLC-CEAD and HPLC-ESI-MS methods.
PubMed:Comparison of the total oxyradical scavenging capacity and oxygen radical absorbance capacity antioxidant assays.
PubMed:S-allylcysteine scavenges singlet oxygen and hypochlorous acid and protects LLC-PK(1) cells of potassium dichromate-induced toxicity.
PubMed:Transepithelial transport of alpha-lipoic acid across human intestinal Caco-2 cell monolayers.
PubMed:Protection against arsenic trioxide-induced autophagic cell death in U118 human glioma cells by use of lipoic acid.
PubMed:Effect of antioxidant capacity on blood lipid metabolism and lipoprotein lipase activity of rats fed a high-fat diet.
PubMed:Paraquat-induced oxidative stress in drosophila melanogaster: effects of melatonin, glutathione, serotonin, minocycline, lipoic acid and ascorbic acid.
PubMed:Safety evaluation of alpha-lipoic acid (ALA).
PubMed:Long-term safety of alpha-lipoic acid (ALA) consumption: A 2-year study.
PubMed:Dietary antioxidants and behavioral enrichment enhance neutrophil phagocytosis in geriatric Beagles.
PubMed:[The role of antioxidants in prevention].
PubMed:Alpha-lipoic acid prevents lipotoxic cardiomyopathy in acyl CoA-synthase transgenic mice.
PubMed:Diabetes--a man made disease.
PubMed:Obesity: the role of hypothalamic AMP-activated protein kinase in body weight regulation.
PubMed:alpha-Lipoic acid induces apoptosis in human colon cancer cells by increasing mitochondrial respiration with a concomitant O2-*-generation.
PubMed:Role of hypothalamic 5'-AMP-activated protein kinase in the regulation of food intake and energy homeostasis.
PubMed:The role of antioxidant micronutrients in the prevention of diabetic complications.
PubMed:Increasing trends in elderly persons' use of nonvitamin, nonmineral dietary supplements and concurrent use of medications.
PubMed:alpha-Lipoic acid prevents diabetes mellitus in diabetes-prone obese rats.
PubMed:Alpha-lipoic acid, an anti-obesity agent?
PubMed:Determination of lipoic acid in dietary supplement preparations by capillary electrophoresis.
PubMed:The effects of the antioxidant lipoic acid on beef longissimus bloom time.
PubMed:Effects of alpha-lipoic acid supplementation on maternal diabetes-induced growth retardation and congenital anomalies in rat fetuses.
PubMed:Natural antioxidants and neurodegenerative diseases.
PubMed:[Effects of DL-alpha-lipoic acid on the experimentally induced diabetic cataract in rats].
PubMed:Effects of a medium chain triglyceride oil mixture and alpha-lipoic acid diet on body composition, antioxidant status, and plasma lipid levels in the Golden Syrian hamster.
PubMed:Anti-obesity effects of alpha-lipoic acid mediated by suppression of hypothalamic AMP-activated protein kinase.
PubMed:Prior experience, antioxidants, and mitochondrial cofactors improve cognitive function in aged beagles.
PubMed:Long-term treatment with antioxidants and a program of behavioral enrichment reduces age-dependent impairment in discrimination and reversal learning in beagle dogs.
PubMed:Redox regulation of mitochondrial permeability transition: effects of uncoupler, lipoic acid and its positively charged analog LA-plus and selenium.
PubMed:Copper toxicity, oxidative stress, and antioxidant nutrients.
PubMed:Demonstration of labeless detection of food pathogens using electrochemical redox probe and screen printed gold electrodes.
PubMed:Mercury toxicity and antioxidants: Part 1: role of glutathione and alpha-lipoic acid in the treatment of mercury toxicity.
PubMed:Alpha-lipoic acid inhibits glycogen synthesis in rat soleus muscle via its oxidative activity and the uncoupling of mitochondria.
PubMed:Safety of long-term feeding of dl-alpha-lipoic acid and its effect on reduced glutathione:oxidized glutathione ratios in beagles.
PubMed:Alpha-lipoic acid modulates NF-kappaB activity in human monocytic cells by direct interaction with DNA.
PubMed:Lipoic acid improves survival in transgenic mouse models of Huntington's disease.
PubMed:Chronic fatigue syndrome: oxidative stress and dietary modifications.
PubMed:Cataract development in diabetic sand rats treated with alpha-lipoic acid and its gamma-linolenic acid conjugate.
PubMed:Ability of amino acids, dipeptides, polyamines, and sulfhydryls to quench hexanal, a saturated aldehydic lipid oxidation product.
PubMed:Ability of carnosine and other skeletal muscle components to quench unsaturated aldehydic lipid oxidation products.
PubMed:Chromatographic analysis of lipoic acid and related compounds.
PubMed:Age-associated decline in ascorbic acid concentration, recycling, and biosynthesis in rat hepatocytes--reversal with (R)-alpha-lipoic acid supplementation.
PubMed:Influence of food intake on the bioavailability of thioctic acid enantiomers.
PubMed:Inhibition of lecithin: cholesterol acyltransferase activity in human blood plasma by cigarette smoke extract and reactive aldehydes.
PubMed:Amanita poisoning during the second trimester of pregnancy. A case report and a review of the literature.
PubMed:Cardiac recovery during post-ischemic reperfusion is improved by combination of vitamin E with dihydrolipoic acid.
PubMed:Determination of lipoic acid in meat of commercial quality.
PubMed:Development of an improved chemically defined minimal medium for Listeria monocytogenes.
 
Notes:
an octanoic acid bridged with two sulfurs so that it is sometimes also called a pentanoic acid in some naming schemes. it is biosynthesized by cleavage of linoleic acid and is a coenzyme of oxoglutarate dehydrogenase ( ketoglutarate dehydrogenase complex). it is used in dietary supplements. A vitamin-like antioxidant that acts as a free-radical scavenger. Alpha-lipoic acid is also known as thioctic acid. It is a naturally occurring compound that is synthesized by both plants and animals. Lipoic acid contains two thiol groups which may be either oxidized or reduced. The reduced form is known as dihydrolipoic acid (DHLA). Lipoic acid (Delta E= -0.288) is therefore capable of thiol-disulfide exchange, giving it antioxidant activity. Lipoate is a critical cofactor for aerobic metabolism, participating in the transfer of acyl or methylamine groups via the 2-Oxoacid dehydrogenase (2-OADH) or alpha-ketoglutarate dehydrogenase complex. This enzyme catalyzes the conversion of alpha-ketoglutarate to succinyl CoA. This activity results in the catabolism of the branched chain amino acids (leucine, isoleucine and valine). Lipoic acid also participates in the glycine cleavage system(GCV). The glycine cleavage system is a multi-enzyme complex that catalyzes the oxidation of glycine to form 5,10 methylene tetrahydrofolate, an important cofactor in nucleic acid synthesis. Since Lipoic acid is an essential cofactor for many enzyme complexes, it is essential for aerobic life as we know it. This system is used by many organisms and plays a crucial role in the photosynthetic carbon cycle. Lipoic acid was first postulated to be an effective antioxidant when it was found it prevented vitamin C and vitamin E deficiency. It is able to scavenge reactive oxygen species and reduce other metabolites, such as glutathione or vitamins, maintaining a healthy cellular redox state. Lipoic acid has been shown in cell culture experiments to increase cellular uptake of glucose by recruiting the glucose transporter GLUT4 to the cell membrane, suggesting its use in diabetes. Studies of rat aging have suggested that the use of L-carnitine and lipoic acid results in improved memory performance and delayed structural mitochondrial decay. As a result, it may be helpful for people with Alzheimer's disease or Parkinson's disease. -- Wikipedia [HMDB]
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