Size | Price | Stock | Qty |
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500mg |
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2g |
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5g |
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10g |
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Purity: ≥98%
α-Lipoic Acid (Thioctic acid; (±)-α-Lipoic acid; DL-α-Lipoic acid) is a novel organosulfur compound which acts as an antioxidant, and is an essential cofactor of mitochondrial enzyme complexes. α-Lipoic Acid prevents NF-κB-dependent HIV-1 LTR activation.
Targets |
Human Endogenous Metabolite; NF-κB; Mitochondrial bioenergetics; HIV-1
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ln Vitro |
The long terminal repeat (LTR) of HIV-1 is the target of cellular transcription factors such as NF-κB, and serves as the promoter-enhancer for the viral genome when integrated in host DNA[1]. The dithiol compound α-Lipoic Acid (Alpha-Lipoic acid, ALA), which is a naturally occurring substance, is crucial to mitochondrial bioenergetics. By controlling the transcriptional factors SREBP-1, FoxO1, and Nrf2 and their downstream lipogenic targets through the activation of the SIRT1/LKB1/AMPK pathway, α-Lipoic Acid reduces lipid accumulation in the liver. The NAD+/NADH ratio in HepG2 cells is markedly elevated following treatment with -lipoic acid (250, 500, and 1000 μM) (P<0.05 or P<0.01). In HepG2 cells, treatment with -lipoic acid (50, 125, 250, and 500 μM) increases SIRT1 activity. In HepG2 cells, α-Lipoic Acid (50, 125, 250, 500, and 1000 μM) increases AMPK and acetyl-CoA carboxylase (ACC) phosphorylation in a dose-dependent manner[1].
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ln Vivo |
In order to cause nonalcoholic fatty liver disease (NAFLD), C57BL/6J mice are divided into four groups and fed a high-fat diet (HFD) for 24 weeks. Each group is then given daily administration of α-Lipoic Acid. The effects of α-Lipoic Acid are then examined in long-term HFD-fed mice with regard to hepatic lipid accumulation. Mice with visceral fat mass are significantly lessened after receiving 100 mg/kg or 200 mg/kg of -lipoic acid. Additionally, α-Lipoic Acid (100 mg/kg or 200 mg/kg) treatment reduces appetite and results in significant weight loss (all P0.05)[1].
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Cell Assay |
The human hepatocellular carcinoma (HepG2) cell line is grown in Dulbecco's modified Eagle's medium at 37°C and 5% CO2 with 10% fetal bovine serum. The following substances are applied to HepG2 cells: AMPK inhibitor (CC, 20 μM, 0.5 h), SIRT1 inhibitor (NA, 10 mM, 12 or 24 h), AMPK activator (AICAR, 2 mM, 1 h), palmitate (PA, 125 μM, 12 h), and -Lipoic Acid (250 μM, 6 or 12 h)[1].
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Animal Protocol |
Mice: Male C57BL/6J mice (6 weeks old; body weight: 22-24 g) are divided into four groups (n=8) and given access to a normal diet and water ad libitum for two weeks. These groups are: normal diet (ND) (10% energy from fat), high-fat diet (HFD) (60% energy from fat), and HFD plus α-Lipoic Acid (100 mg/kg or 200 mg/kg). After the mice's eyes are removed for the preparation of the serum, blood samples are taken 24 weeks after the start of treatment. Centrifugation at 2000×g for 10 min. at 4 °C is used to separate the serum. Harvested in liquid nitrogen and kept at -80°C are the liver tissues.
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References |
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Additional Infomation |
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.
Lipoic acid is a heterocyclic thia fatty acid comprising pentanoic acid with a 1,2-dithiolan-3-yl group at the 5-position. It has a role as a fundamental metabolite and a geroprotector. It is 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 lipoate. A vitamin-like antioxidant. Lipoic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). lipoate is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Thioctic acid is a natural product found in Arabidopsis thaliana, Homo sapiens, and other organisms with data available. Alpha-Lipoic Acid is a naturally occurring micronutrient, synthesized in small amounts by plants and animals (including humans), with antioxidant and potential chemopreventive activities. Alpha-lipoic acid acts as a free radical scavenger and assists in repairing oxidative damage and regenerates endogenous antioxidants, including vitamins C and E and glutathione. This agent also promotes glutathione synthesis. In addition, alpha-lipoic acid exerts metal chelating capacities and functions as a cofactor in various mitochondrial enzyme complexes involved in the decarboxylation of alpha-keto acids. 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. |
Molecular Formula |
C₈H₁₄O₂S₂
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Molecular Weight |
206.3256
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Exact Mass |
206.04352203
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CAS # |
1077-28-7
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Related CAS # |
α-Lipoic Acid;1077-28-7
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PubChem CID |
864
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Appearance |
Light yellow to yellow solid powder
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Density |
1.2±0.1 g/cm3
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Boiling Point |
362.5±11.0 °C at 760 mmHg
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Melting Point |
60-62ºC
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Flash Point |
173.0±19.3 °C
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Vapour Pressure |
0.0±1.7 mmHg at 25°C
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Index of Refraction |
1.562
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LogP |
2.16
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tPSA |
87.90
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SMILES |
C1CSSC1CCCCC(=O)O
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InChi Key |
AGBQKNBQESQNJD-UHFFFAOYSA-N
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InChi Code |
InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)
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Chemical Name |
5-(dithiolan-3-yl)pentanoic acid
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Synonyms |
Lipoic Acid; (R)-5-(1,2-Dithiolan-3-yl)pentanoic acid; R-(+)-alpha-Lipoic acid; (+)-alpha-Lipoic acid; Verla-Lipon; Lipoate; Verla Lipon; VerlaLipon; Thioctic Acid; Thioctacide T; Thiogamma Injekt; Thiogamma oral; thioctic acid; dl-Thioctic acid; 1077-28-7; alpha-Lipoic acid; lipoic acid; 5-(1,2-Dithiolan-3-yl)pentanoic acid; DL-alpha-Lipoic acid; 1,2-dithiolane-3-pentanoic acid;
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HS Tariff Code |
2934.99.9001
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Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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Solubility (In Vitro) |
DMSO: ~100 mg/mL (~484.7 mM)
H2O: < 0.1 mg/mL |
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Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 :Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400  (Please use freshly prepared in vivo formulations for optimal results.) |
Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
1 mM | 4.8466 mL | 24.2330 mL | 48.4660 mL | |
5 mM | 0.9693 mL | 4.8466 mL | 9.6932 mL | |
10 mM | 0.4847 mL | 2.4233 mL | 4.8466 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration: mg/mL;
Method for preparing DMSO stock solution: mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation::Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
NCT03161028 | Active Recruiting |
Drug: Lipoic acid Drug: Placebo |
Multiple Sclerosis | VA Office of Research and Development |
July 1, 2018 | Phase 2 |
NCT00765310 | Active Recruiting |
Dietary Supplement: R-alpha lipoic acid Dietary Supplement: Placebo |
Atherosclerosis | Oregon State University | April 2009 | Phase 2 Phase 3 |
NCT00764270 | Active Recruiting |
Dietary Supplement: R-alpha lipoic acid |
Atherosclerosis | Oregon State University | August 2011 | Phase 2 Phase 3 |
NCT02910531 | Active Recruiting |
Dietary Supplement: Alpha lipoic acid Drug: Placebo |
Cystinuria | Thomas Chi, MD | June 19, 2017 | Phase 2 |
NCT02168140 | Active Recruiting |
Drug: bendamustine hydrochloride Drug: 6,8-bis(benzylthio)octanoic acid |
Peripheral T-cell Lymphoma Hepatosplenic T-cell Lymphoma |
Wake Forest University Health Sciences |
September 2014 | Phase 1 |