DL-6,8-Dithiooctanoic acid
DL-Lipoic acid
CAS: 1077-28-7
Molecular Formula: C8H14O2S2
DL-6,8-Dithiooctanoic acid - Names and Identifiers
DL-6,8-Dithiooctanoic acid - Physico-chemical Properties
| Molecular Formula | C8H14O2S2 |
| Molar Mass | 206.33 |
| Density | 1.2888 (rough estimate) |
| Melting Point | 60-62°C |
| Boling Point | 160-165°C(lit.) |
| Flash Point | 160-165°C |
| Water Solubility | 0.9 g/L (20 ºC) |
| Solubility | Soluble in benzene, methanol, ethanol, slightly soluble in petroleum ether, almost insoluble in water |
| Appearance | Yellow crystalline powder |
| Color | Yellow |
| Merck | 14,9326 |
| BRN | 81853 |
| pKa | 4.75±0.10(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| Sensitive | Sensitive to light |
| Refractive Index | 1.5200 (estimate) |
| MDL | MFCD00005474 |
| Physical and Chemical Properties | The appearance of alpha-lipoic acid is pale yellow powder crystals, almost tasteless, the chemical structure is 6,8 one or two DL-lipoic acid, in 6,8 between carbon disulfide bonds to form internal disulfide compounds. When reduced, the disulfide bond breaks to form dihydrodl-lipoic acid. Alpha-lipoic acid is insoluble in water but soluble in lipid solvents, which is listed as a fat-soluble vitamin; It is soluble in methanol, ethanol, chloroform, ether. |
| Use | This product is for scientific research only and shall not be used for other purposes. |
| In vitro study | 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 study | 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). |
DL-6,8-Dithiooctanoic acid - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R22 - Harmful if swallowed R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S37/39 - Wear suitable gloves and eye/face protection S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. |
| WGK Germany | 3 |
| RTECS | JP1192000 |
| HS Code | 29349990 |
DL-6,8-Dithiooctanoic acid - Reference
| Reference Show more | 1. Niu Huan Cong Xiao Lin Cong Chen Yang. Protective Effect of α-lipoic Acid on Human Lens Epithelial Cells Cultured under High Glucose Conditions [J]. New Progress in Ophthalmology 2018 38(003):230-234. 2. Wang Huxuan, Zhang Shuqing, Liao Chuan, et al. Evaluation of Antimicrobial Activity and Antimicrobial Mechanism of Plant-derived Active Substances on Luchicz-zygomycosis [J]. Journal of Shaanxi University of Science and Technology, 2020, 038(001):P.64-70. 3. Wu, T., Li, L., Song, G. et al. An ultrasensitive electrochemical sensor based on cotton carbon composites for the determination of superoxide anion release from cells. Microchim Acta 186,198 (2019). https://doi.org/10.1007/s00604-019-3304-1 4. Lyu, Man, et al. "Inhibition effect of thiol-type antioxidants on protein oxidative aggregation used by free radicals." Biophysical chemistry 260 (2020): 106367.https://doi.org/10.1016/j.bpc. 2020.106367 5. Wu, Tiaodi, et al. "Construction of silver-cotton carbon fiber sensing interface and study on the protective effect of antioxidants on hypoxia-induced cell damage." Microchemical Journal 159 (2020): 105345.https://doi.org/10.1016/j.microc. 2020.105345 6. [IF=5.833] Wu Tiaodi et al."An ultrasensitive electrochemical sensor based on cotton carbon fiber composites for the determination of superoxide anion release from cells."Microchim Acta. 2019 Mar;186(3):1-9 7. [IF=17.881] Chao Dang et al."Cellulose melt processing assisted by small biomass molecule to fabricate recyclable ionogels for versatile stretchable triboelectric nanogenerators."Nano Energy. 2021 Dec;90:106619 8. [IF=4.821] Tiaodi Wu et al."Construction of silver-cotton carbon fiber sensing interface and study on the protective effect of antioxidants on hypoxia-induced cell damage."Microchem J. 2020 Dec;159:105345 9. [IF=4.242] Yunfeng Xiong et al."Dietary α-lipoic acid requirement and its effects on antioxidant status, carbohydrate metabolism, and intestinal microflora in oriental river prawn Macrobrachium nipponense (De Haan)."Aquaculture. 2022 Jan;547:737531 10. [IF=2.752] Jiabin Shi et al."Protective Effects of α-Lipoic Acid and Chlorogenic Acid on Cadmium-Induced Liver Injury in Three-Yellow Chickens."Animals-Basel. 2021 Jun;11(6):1606 11. [IF=2.352] Man Lyu et al."Inhibition effect of thiol-type antioxidants on protein oxidative aggregation caused by free radicals."Biophys Chem. 2020 May;260:106367 |
DL-6,8-Dithiooctanoic acid - Introduction
Hydrogen transfer auxiliary factors. Substrate for thiooctam dehydrogenase. As coenzymes such as pyruvate dehydrogenase (pyruvate dehydrogenase) and glycine decarboxylase (glycine decarboxylase), exogenous lipoic acid is reduced by two or more enzymes in the cell. This reduced form affects the process of cell scavenging free radicals. Increase glutathione (glutathione) synthesis and regulate transcription factor activity. Decreased phagocytosis of macrophage myelin.
Last Update：2022-10-16 17:11:54
DL-6,8-Dithiooctanoic acid - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| introduction | DL-lipoic acid is a unique anti-free radical substance, usually called a wide range of antioxidants. It is a vitamin-like substance produced in the body. Unlike other antioxidants with special effects produced in the body, DL-lipoic acid is neither strictly fat-soluble nor water-soluble, which allows it to promote the activity of other antioxidants in the body, and it is also widely available when antioxidants are insufficient. Substitute. For example, if the vitamin C and vitamin E stored in the body are very low, DL-lipoic acid can be temporarily supplemented. Because DL-lipoic acid can pass through the blood-brain barrier, it can help reverse the adverse reactions caused by stroke. DL-lipoic acid also helps maintain normal blood sugar levels and prevent serious complications of diabetes. With age, the human body will not be able to make sufficient DL-lipoic acid to maintain health. If it's over forties. Then don't miss the opportunity to supplement DL-lipoic acid. Commercially available DL-lipoic acid is a tablet or an antioxidant formulation product containing DL-lipoic acid. It is recommended to take 1~2 tablets of 50mg DL-lipoic acid every day. |
| use | α-lipoic acid is also a highly effective antioxidant and plays an important role in the prevention and treatment of many diseases. Vitamin drugs can stimulate fat metabolism. For the treatment and curative effect of acute and chronic hepatitis, liver cirrhosis, hepatic coma, fatty liver, diabetes and other diseases antioxidants and as pyruvate dehydrogenase (pyruvate dehydrogenase) and glycine decarboxylase (glycine decarboxylase) coenzyme, exogenous lipoic acid is reduced by two or more enzymes in the cell. This reduced form affects the process of cell scavenging free radicals. Increase glutathione (glutathione) synthesis and regulate transcription factor activity. Decreased phagocytosis of macrophage myelin. |
| Biochemical function | DL-lipoic acid can transfer hydrogen and become an antioxidant through mutual transformation between oxidized and reduced types. The human body can synthesize the required DL-lipoic acid. At present, no deficiency of DL-lipoic acid has been found. DL-lipoic acid (1ipoic acid) is a sulfur-containing octa-carbon fatty acid, which exists in two forms: oxidized and reduced. In nature, DL-lipoic acid is bound to protein, and its carboxyl group is the lysine in the protein molecule-NH. Connect. DL-lipoic acid is an acyl carrier, which exists in pyruvate dehydrogenase and a ketoglutarate dehydrogenase and is closely related to sugar metabolism. The oxidized and reduced DL-lipoic acid interconversion acids have the function of coupling acyl transfer and electron transfer during the oxidation and decarboxylation of a keto acid. DL-lipoic acid is widely distributed in nature, especially abundant in liver and yeast. It often exists in food at the same time as vitamin B. |
| application | in the field of medicine, α-lipoic acid is widely used in the prevention and adjuvant treatment of diabetes and its related complications. It can enhance glucose metabolism, reduce oxidative stress, relieve diabetic neuropathy symptoms, prevent diabetic cataract, and prevent diabetic cardiovascular damage. |
| Biological activity | Thioctic acid (DL-α-Lipoic acid) is a cyclic disulfide antioxidant that can be converted to its reducing disulfide phenol form. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:01:54
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