α-Lipoic acid
thioctic acid
CAS: 62-46-4;57828-26-9
Molecular Formula: C8H14O2S2
α-Lipoic acid - Names and Identifiers
α-Lipoic acid - Physico-chemical Properties
| Molecular Formula | C8H14O2S2 |
| Molar Mass | 206.33 |
| Density | 1.2888 (rough estimate) |
| Melting Point | 48-52°C(lit.) |
| Boling Point | 315.2°C (rough estimate) |
| Flash Point | >230°F |
| Water Solubility | 0.9 g/L (20℃) |
| Solubility | Insoluble in water, soluble in ethanol, chloroform, ether |
| Vapor Presure | 3.07E-06mmHg at 25°C |
| Appearance | Pale yellow powder |
| Storage Condition | 2-8℃ |
| Refractive Index | 1.5200 (estimate) |
| Physical and Chemical Properties | Melting point 58-63°C boiling point 160-165°C water-soluble 0.9g/L (20°C) |
| Use | For the treatment of acute and chronic hepatitis, cirrhosis, hepatic Coma, fatty liver, diabetes |
α-Lipoic acid - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R22 - Harmful if swallowed |
| Safety Description | S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
α-Lipoic acid - Reference
| Reference Show more | 1. Shen Yao, Han Tao, Zhou Hui, et al. Protective effect of α-lipoic acid on chronic cadmium poisoning in rat liver [J]. Animal and Veterinary Science, 2016, 48(11):91-94. 2. Jiao Minya, Li Minmeng, Jiang Tongyu, etc. Optimization of lipofuscin-like model and in vitro scavenging effects of several natural antioxidants [J]. Food Science and Technology, 2019, v.44;No.338(12):290-296. 3. Deng Huilin, Yang Ke, Guo Li. Protective effect of α-lipoic acid on chondrocyte injury induced by interleukin-1β [J]. Anhui medical journal, 2021,25(01):57-63. 4. Xiaocui Chang. Protective effects of α-lipoic acid and chlorogenic acid on cadmium-induced liver injury in chickens [J]. Yangzhou University, 2020. 5. [IF = 11.878] Li Xinming et al."A fast and specific fluorecent probe for thioredoxin reductase that works via disulphide bond cleavage."Nat Commun. 2019 Jun;10(1):1-12 6. [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 |
α-Lipoic acid - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| Introduction | lipoic acid is an antioxidant that excels vitamins A, C, and E, and can eliminate the accelerated aging and pathogenic free radical substances. At the same time, lipoic acid has a variety of beneficial effects on the human body. Lipoic acid is a restrictive essential nutrient required by cells to use energy substances such as sugars to produce energy. It is also an effective antioxidant and heavy metal chelating agent. The body can synthesize an appropriate amount of lipoic acid, but when it is in a state of stress or disease, its synthesis cannot meet the required amount. Like many important substances in the body, the content of lipoic acid decreases with age. among many antioxidants, lipoic acid has its unique versatility. It is both water-soluble and fat-soluble, and can protect all tissues and tissue spaces in the body. It can resist oxidation anions, hydroxide ions, singlet oxygen and hydrogen peroxide and other free radicals, but also with metal ions (such as iron, copper, cadmium, lead, mercury and other metal ions) chelation (binding and neutralization) catalyzes the generation of free radicals. Another important role of lipoic acid is to lower blood sugar. Lipoic acid can prevent hyperglycemia and cross-linking formation (hyperglycemia and cross-linking are important causes of aging and are closely related to wrinkle formation) due to its anti-oxidation, metal chelation and blood sugar lowering properties. |
| B vitamins | lipoic acid belongs to a class of compounds in B vitamins, yeast and some microbial growth factors, which act as coenzymes in multiple enzyme systems, catalytic reaction of oxidative decarboxylation of pyruvate to acetic acid and oxidative decarboxylation of α-ketoglutarate to succinic acid. The chemical name is 5-[3-(1, 2-disulfide heterocycle)] pentanoic acid, the appearance is light yellow crystal, molecular weight 206.33. DL-body: Melting point 60-61 °c. L-body (natural product): Melting point 45-47.5 °c. Optical rotation [α]D23 113 °c. D-body (natural product): Melting point 46~48 °c. Optical rotation [α] D23 104 °c. Soluble in organic solvents. Insoluble in water. For the prevention and treatment of acute hepatitis, cirrhosis, hepatic coma, fatty liver and other diseases. Natural products are found in the liver, kidneys and heart. The final product is prepared by condensing ethylene and adipic acid monoester acyl chloride in the presence of aluminum trichloride to obtain chloropropionyl valeryl Ester, then condensing with sulfuric acid, reducing with sodium borohydride and hydrolyzing with caustic soda, and then reacting with thiourea and the like. 6, 8-dilipoic acid. Soluble in water, often exist with vitamin B1. There are two forms of oxidized and reduced (6, 8-dimercaptooctanoic acid). In living organisms, some hydrogen or acyl groups are accepted or transferred by the transformation of these two forms. Coenzymes that are α-keto acid-oxidizing decarboxylase and trans-hydroxyethylase act to transport acyl and hydrogen in metabolic reactions. The human body can synthesize, so there is no deficiency. But it is necessary for the growth and development of some microorganisms and protozoa. Liver and yeast are abundant. |
| efficacy and function | lipoic acid, also known as α-lipoic acid, refers specifically to the naturally occurring form in nature, it was first isolated from porcine liver by Reed in 1951. Lipoic acid is a disulfide compound of a class of vitamins that are commonly considered as B vitamins. Lipoic acid is an important coenzyme in the living body, is an important cofactor of pyruvate dehydrogenase, ketoglutarate dehydrogenase and aminocaproate dehydrogenase, is one of the indispensable substances in the process of the tricarboxylic acid cycle. The human body is able to synthesize sufficient amounts of lipoic acid itself, which has not yet appeared in patients with lipoic acid deficiency. However, it was found that lipoic acid supplementation in vitro can inhibit lipid oxidation of nerve tissue, prevent protein glycosylation, inhibit aldose reductase, and prevent the conversion of glucose or galactose into sorbitol, it is used in Europe as a drug for the treatment of diabetic neuropathy or neurological complications. In addition to playing the role of coenzyme, lipoic acid also has a powerful antioxidant function, can eliminate lead to accelerated aging and pathogenic free radicals, antioxidant, anti-aging, improve immunity, prevention of cardiovascular disease, alleviate the symptoms of diabetes and other effects. At the moment of the rise of antioxidant food, lipoic acid is from the traditional medicinal to edible transition, in view of its powerful health care function, in June 2004, the thick Labor province changed its classification from medicine to food, in addition, the United States, Canada and other regions have listed lipoic acid as a dietary supplement. |
| Antioxidant mechanism of lipoic acid | lipoic acid has a strong antioxidant capacity, its ability to resist free radicals than VC, VE is 400 times better, it can remove the active oxygen components that cause skin aging, and it is smaller than the molecule of VE. In addition, it is both water soluble and fat soluble, so skin absorption is quite easy. Lipoic acid not only has a strong resistance to long-term oxidative damage, but also can effectively repair the serious oxidative damage of VC and VE, which can not be repaired. studies have shown that lipoic acid can be converted into dihydrolipoic acid in vivo, both of which have strong antioxidant properties and act synergistically in vivo. At the same time, the molecular weight of lipoic acid is between ascorbic acid and tocopherol, and has the amphiphilic property of water and fat. It can play a comprehensive antioxidant effect in the body, which is called "universal antioxidant". The antioxidant effect of lipoic acid is mainly reflected in three aspects: 1. Direct scavenging of free radicals, lipoic acid can directly affect hydroxyl free radicals, singlet oxygen and other free radicals play a scavenging role; 2, inhibition of metal induced oxidation, lipoic acid has the role of chelating metal ions, thereby reducing the peroxidation of lipids and other macromolecules caused by metal ions; 3. To promote the recovery of other antioxidant components, lipoic acid can restore the ability of vitamin E, glutathione and other endogenous antioxidants in the body, so as to enhance the overall antioxidant capacity of the body. |
| boost "anti-glycation" | Anti-glycation is a popular new concept of health, its purpose is to reduce the damage to the cells of the reaction end products produced by reducing sugars and proteins in the body under non-enzymatic conditions, the most typical of which is to reduce the destruction of skin collagen. collagen has a slower turnover rate than other proteins, and is also more susceptible to glycation reactions, resulting in a dull skin and reduced elasticity. In the anti-glycation market, antioxidants are the absolute main force, which can effectively resist the effect of glycation reaction on the skin, and lipoic acid in anti-glycation with blood sugar stability and prevent the combination of sugar and collagen double protection, is one of the key development direction of anti-sugar beauty products. At the same time, the activation of vitamin C by lipoic acid can make up for the reduced level of resistance to ultraviolet rays and enhance the skin's ability to resist external stimuli. |
| liver protection | lipoic acid is a chelator of many metals, which synergistically with dihydrolipoic acid can chelate cadmium, nickel, copper, lead, ferric iron and other metal ions, reduce the toxicity of metals to the liver, so early also used as a food poisoning or metal poisoning antidote. At the same time, the synergistic effect of lipoic acid and other antioxidants in the body can reduce the damage of free radicals to liver cells, reduce inflammatory response and maintain liver function. Some studies have pointed out that lipoic acid has a clear effect on the accumulation of fat caused by non-alcoholic fatty liver and reduces the burden on the liver. |
| Use | B vitamins for the treatment of acute and chronic hepatitis, cirrhosis, hepatic Coma, fatty liver, for acute and chronic hepatitis, liver cirrhosis, hepatic Coma, etc. Antioxidant A coenzyme present in the mitochondria, catalytic reaction of oxidative decarboxylation of pyruvate to acetic acid and oxidative decarboxylation of α-ketoglutarate to succinic acid. |
Last Update：2024-04-10 22:29:15
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