Thioctic 5-(dithiolan-3-yl)pentanoic acid (alpha-)lipoic acid
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Lipoic acid Basic information |
Product Name: | Lipoic acid |
Synonyms: | (R)-LIPOIC ACID;Thioctic;5-(dithiolan-3-yl)pentanoic acid;R-LIPOIC ACID POTASSIUM COMPOUND;6,8-Thioctic acid;6,8-Thiocticacid;6,8-Thiotic acid;6,8-Thioticacid |
CAS: | 62-46-4 |
MF: | C8H14O2S2 |
MW: | 206.33 |
EINECS: | 200-534-6 |
Product Categories: | Miscellaneous;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;PHARMACEUTICALS;FINE Chemical & INTERMEDIATES;chiral;API;Pharmaceutical intermediates;Inhibitors;bc0001;62-46-4 |
Mol File: | 62-46-4.mol |
Lipoic acid Chemical Properties |
Melting point | 48-52 °C(lit.) |
Boiling point | 315.2°C (rough estimate) |
density | 1.2888 (rough estimate) |
refractive index | 1.5200 (estimate) |
Fp | >230 °F |
storage temp. | 4°C, protect from light |
solubility | Very slightly soluble in water, very soluble in dimethylformamide, freely soluble in methanol. |
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 |
SMILES | S1CCC(CCCCC(O)=O)S1 |
CAS DataBase Reference | 62-46-4(CAS DataBase Reference) |
NIST Chemistry Reference | Lipoic acid(62-46-4) |
Safety Information |
WGK Germany | 3 |
MSDS Information |
Provider | Language |
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SigmaAldrich | English |
Lipoic acid Usage And Synthesis |
Description | Lipoic acid is a class of compounds belonging to the B class vitamins and is the growth factor of yeast and some kinds of microorganisms. It can play the role of coenzyme role in a multi-enzyme system that is responsible for catalyzing the acyl transfer effect in the reaction of oxidative decarboxylation of pyruvate into acetate and oxidative decarboxylation reaction of α-ketoglutarate into succinic acid. |
Chemical Properties | Its chemical name is 5-[3-(1,2-dithiol hetero-cycle)] pentanoic acid. The appearance is pale yellow crystals with the molecular weight being 206.33. DL-body: the melting point is 60~61 ℃. L-body (natural products): the melting point is 45~47.5 ℃. Optical rotation [α] D23 + 113 ℃. D-body (natural products): the melting point is 46~48 ℃. Optical rotation [α] D23 + 104 ℃. It is soluble in organic solvents but insoluble in water. It can be used for the prevention and treatment of acute hepatitis, liver cirrhosis, hepatic coma, fatty liver and other diseases. |
B vitamins | Synthetic products is obtained through condensation of ethylene and adipic acid mono-ester chloride in the presence of aluminum chloride into chloropropionyl pivaloyl ester, which further has condensation reaction with sulfuric acid, then go through reduction with sodium borohydride and sodium hydroxide hydrolysis, and finally have reaction with thiourea to obtain it. 6,8-lipoic acids can be dissolved in water and can often be presented together with vitamin B1. There are two forms including oxidized and reduced (6,8-dimercapto octanoic acid) types. Inside the body of organisms, some hydrogen group and acyl group can be accepted or transferred through the conversion of these two forms. It can be taken as the coenzyme of the α-keto acid oxidation decarboxylase and hydroxyethyl enzyme and play the role of acyl and hydrogen group transfer during metabolic pathways. Since the human body can synthesize it, no cases of deficiency have been reported before. However, it is indispensable factors for the growth and development of some microorganisms and protozoa. It is rich in liver and yeast. |
Uses | Alpha-lipoic acid is a kind of B vitamins and can be used for the treatment of acute and chronic hepatitis, cirrhosis, hepatic coma, fatty liver, diabetes, etc. other uses of lipoic acid are as follows: 1. Neutralize free radicals. 2. It is quickly absorbed and utilized by body cells. 3. Can strengthen the role of other antioxidants. 4. Can be concentrated on the inside and outside of cells and cell membranes. 5. Promote normal gene expression. 6. Chelate metal ions, or excrete toxic metals from the body. 7. Alpha-lipoic acid is an antioxidant that is made naturally in the body and also found in foods. |
Chemical Properties | Alpha lipoic acid (ALA) is synthesised enzymatically in the mitochondria from octanoic acid and plays a critical role in mitochondrial energy metabolism. ALA presents as two enantiomers: the R-(+) enantiomer, which is widely present in nature and is biologically active, and the S-(-) enantiomer, which is often included in synthetic-based ALA supplements but is believed to have limited biological activity. Formulations includes: R-alpha lipoic acid capsules, tablets, powders or drops Racemic mixture of R- and S- alpha lipoic acid enantiomers in capsules, tablets, powders or drops Intravenous administration of R-alpha lipoic acid |
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