EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

R-lipoate
1,2-dithiolane-3-pentanoic acid, (R)-

Supplier Sponsors

Name:5-[(3R)-dithiolan-3-yl]pentanoic acid
CAS Number: 1200-22-2Picture of molecule3D/inchi
Other(deleted CASRN):57828-26-9
FDA UNII: VLL71EBS9Z
Nikkaji Web:J9.331I
MDL:MFCD01631142
XlogP3-AA:1.70 (est)
Molecular Weight:206.32798000
Formula:C8 H14 O2 S2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:special dietary and nutritional additives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"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: 362.50 °C. @ 760.00 mm Hg (est)
Vapor Pressure:9.490000 mmHg @ 25.00 °C. (est)
Flash Point: 343.00 °F. TCC ( 173.00 °C. ) (est)
logP (o/w): 2.160 (est)
Soluble in:
 water, 126.6 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
(R)-(+)-Lipoic acid 98%
Odor: characteristic
Use: Lipoic Acid, an organosulfur compound, is widely used as dietary supplements and antioxidant. It has been also found to influence the activity of nuclear factor kappa-B. Lipoic Acid is widely used as dietary supplements and antioxidant.
Glentham Life Sciences
(R)-(+)-alpha-Lipoic acid
Santa Cruz Biotechnology
For experimental / research use only.
(+)-a-Lipoic Acid
Sigma-Aldrich: Sigma
For experimental / research use only.
(R)-(+)-a-Lipoic acid ≥98.0% (HPLC)
sds
TCI AMERICA
For experimental / research use only.
(R)-a-Lipoic Acid >98.0%(HPLC)(T)
sds
 
Safety Information:
Preferred SDS: View
 
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:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
special dietary and nutritional additives
Recommendation for R-lipoate usage levels up to:
 not for fragrance use.
 
Recommendation for R-lipoate flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
Daily Med:search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :6112
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
5-[(3R)-dithiolan-3-yl]pentanoic acid
Chemidplus:0001200222
 
References:
 5-[(3R)-dithiolan-3-yl]pentanoic acid
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:1200-22-2
Pubchem (cid):6112
Pubchem (sid):135115683
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (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
KEGG (GenomeNet):C16241
HMDB (The Human Metabolome Database):HMDB01451
FDA Listing of Food Additive Status:View
ChemSpider: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
 not found in nature
 
Synonyms:
 berlition
 byodinoral 300
5-[(3R)-dithiolan-3-yl]pentanoic acid
(R)-1,2-dithiolane-3-pentanoic acid
1,2-dithiolane-3-pentanoic acid, (R)-
(+)-alpha-lipoic acid
(R)-lipoic acid
(R)-(+)-alpha-lipoic acid
(R)-alpha-lipoic acid
D-thioctic acid
R-(+)-thioctic acid
 thioctic acid dextro-form
 thioctic acid, D form
 thioderm
 thiogamma
 tiobec retard
 

Articles:

PubMed:Antidiabetic effect of the α-lipoic acid γ-cyclodextrin complex.
PubMed:α-Lipoic acid protects kidney from oxidative stress and mitochondrial dysfunction associated to inflammatory conditions.
PubMed:α-Lipoic acid inhibits Helicobacter pylori-induced oncogene expression and hyperproliferation by suppressing the activation of NADPH oxidase in gastric epithelial cells.
PubMed:Effects of alpha-lipoic acid supplementation in different stages on growth performance, antioxidant capacity and meat quality in broiler chickens.
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: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: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: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: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: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:Alpha-lipoic acid protects against indomethacin-induced gastric oxidative toxicity by modulating antioxidant system.
PubMed:A combination cocktail improves spatial attention in a canine model of human aging and Alzheimer's disease.
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: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: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: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: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:Formulation of a medical food cocktail for Alzheimer's disease: beneficial effects on cognition and neuropathology in a mouse model of the disease.
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: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: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: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: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: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:Effects of antioxidant supplements intervention on the level of plasma inflammatory molecules and disease severity of rheumatoid arthritis patients.
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:Carotenoid extraction from plants using a novel, environmentally friendly solvent.
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: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:Transepithelial transport of alpha-lipoic acid across human intestinal Caco-2 cell monolayers.
PubMed:Safety evaluation of alpha-lipoic acid (ALA).
PubMed:Long-term safety of alpha-lipoic acid (ALA) consumption: A 2-year study.
PubMed:Alpha-lipoic acid prevents lipotoxic cardiomyopathy in acyl CoA-synthase transgenic mice.
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: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:Effects of alpha-lipoic acid supplementation on maternal diabetes-induced growth retardation and congenital anomalies in rat fetuses.
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:Copper toxicity, oxidative stress, and antioxidant nutrients.
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:Age-associated decline in ascorbic acid concentration, recycling, and biosynthesis in rat hepatocytes--reversal with (R)-alpha-lipoic acid supplementation.
 
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.
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