| Synonyms |
Thioctic acid; alpha-Lipoic acid; (+-)-2-dithiolane-3-pentanoic acid; (+-)-2-dithiolane-3-valeric acid; (+/-)-2-dithiolane-3-pentanoic acid; 1,2-Dithiolane-3-pentanoic acid; 1,2-Dithiolane-3-pentanoic acid, (±)-; 1,2-Dithiolane-3-valeric acid, (±)-; (RS)-Lipoic acid; (RS)-α-Lipoic acid; (±)-Lipoic acid; (±)-Thioctic acid; (±)-α-Lipoic acid; 5-(1,2-Dithiolan-3-yl)pentanoic acid; 5-(1,2-Dithiolan-3-yl)valeric acid; 6,8-Thioctic acid; 6-Thioctic acid; DL-6,8-Thioctic acid; DL-6-Thioctic acid; DL-Lipoic acid; DL-α-Lipoic acid; Alipure; Biletan; Byodinoral-R; dl-α-Lipoic acid; Espa-lipon; Liposan; Lipothion; NSC 628502; NSC 90788; Octolipen; Oktolipen; Protogen A; Pyruvate oxidation factor; Thioctic acid; Thioctsan; Tioctidasi; Tioctidasi acetate replacing factor; α-(±)-Lipoic acid; α-lipon 300; α-Liponic acid |
| IUPAC Name |
5-(dithiolan-3-yl)pentanoic acid |
| Molecular Weight |
206.32 |
| Molecular Formula |
C8H14O2S2 |
| Canonical SMILES |
C1CSSC1CCCCC(=O)O |
| InChI |
InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10) |
| InChIKey |
AGBQKNBQESQNJD-UHFFFAOYSA-N |
| Boiling Point |
160-165°C |
| Melting Point |
60-61°C |
| Flash Point |
173°C |
| Purity |
98% |
| Density |
1.218±0.06 g/cm3 |
| Solubility |
Soluble in Chloroform (Sparingly), DMSO (Slightly), Ethanol (50 mg/mL), Methanol (Slightly) |
| Appearance |
Light-Yellow Solid |
| Shelf Life |
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly |
| Storage |
Store at -20°C |
| Animal Admin |
Male C57BL/6J mice (6-week-old; body weight: 22-24 g) are allowed ad libitum access to normal diet and water for 2 weeks before dividing into four groups (n=8): 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 24 weeks of treatment, blood samples are collected after the eyeballs of the mice are extracted for serum preparation by centrifugation at 2000×g for 10 min at 4°C. The liver tissues are harvested in liquid nitrogen and stored at -80°C. |
| Index Of Refraction |
1.562 |
| In 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. α-Lipoic Acid (Alpha-Lipoic acid, ALA), a naturally occurring dithiol compound, plays an essential role in mitochondrial bioenergetics. α-Lipoic Acid reduces lipid accumulation in the liver by regulating the transcriptional factors SREBP-1, FoxO1, and Nrf2, and their downstream lipogenic targets via the activation of the SIRT1/LKB1/AMPK pathway. Treatment of cells with α-Lipoic Acid (250, 500 and 1000 μM) significantly increases the NAD+/NADH ratio in HepG2 cells (P<0.05 or P<0.01). Treatment with α-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 phosphorylation of AMPK and acetyl-CoA carboxylase (ACC) in HepG2 cells in a dose-dependent fashion. |
| In Vivo |
C57BL/6J mice, divided into four groups, are fed an high-fat diet (HFD) for 24 weeks to induce nonalcoholic fatty liver disease (NAFLD) followed by daily administration of α-Lipoic Acid. Then, the effects of α-Lipoic Acid on hepatic lipid accumulation in long-term HFD-fed mice are assessed. Administration of α-Lipoic Acid (100 mg/kg or 200 mg/kg) markedly reduces visceral fat mass in mice. In addition, α-Lipoic Acid (100 mg/kg or 200 mg/kg) treatment inhibits the appetite and causes a dramatic weight loss (all P<0.05). |
| PSA |
87.9 |
| Target |
NF-κB; HIV; Mitochondrial Metabolism; Endogenous Metabolite; Apoptosis |
| Vapor Pressure |
0.0±1.7 mmHg at 25°C |
![{PARAM:[Name]}()](https://resource.bocsci.com/structure/1077-28-7.gif)
