62-46-4

Usage

Uses

Used in Pharmaceutical Industry:
Lipoic acid is used as a therapeutic agent for the treatment of acute and chronic hepatitis, cirrhosis, hepatic coma, fatty liver, and diabetes. It helps in neutralizing free radicals, promoting normal gene expression, and chelating or excreting toxic metals from the body.
Used in Antioxidant Applications:
Lipoic acid is used as an antioxidant due to its ability to neutralize free radicals, strengthen the role of other antioxidants, and be concentrated both inside and outside cells and cell membranes. It is an antioxidant that is naturally produced in the body and can also be found in certain foods.
Used in Alternative Medicine:
Lipoic acid is used as a possibly effective aid in weight loss, treating diabetic nerve pain, healing wounds, lowering blood sugar, improving skin discoloration caused by vitiligo, and decreasing complications of coronary artery bypass graft (CABG) surgery.
Used in Dietary Supplements:
Lipoic acid is available as a dietary supplement, such as Alpha Lipoic Acid 600 mg tablets, to support overall health and well-being.

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.

History

Alpha Lipoic Acid (ALA) was discovered in 1951. It is a sulfur-containing coenzyme, and when it was first isolated and studied, its main function was thought to be in the Krebs Cycle.In 1988, ALA was discovered to be a potent antioxidant, and is active in both fat- and watersoluble regions of the cell.

Pharmacology

The drug is a cofactor for the pyruvate dehydrogenase complex, ketoglutarate and amino acid hydrogenase complexes. This drug can inhibit lipid oxidation in nerve tissue, prevent glycosylation of proteins, inhibit aldose reductase, and prevent the conversion of glucose or galactose into sorbitol. Animal experiments show that this drug can prevent the development of diabetes, promote the utilization of glucose, and prevent neuropathy caused by hyperglycemia. Lipoic acid is easily reduced to dihydrolipoic acid after entering the human body, both of which can promote the regeneration of vitamin C and vitamin E, and play an antioxidant role. The drug can also increase intracellular glutathione and coenzyme Q10 and chelate certain metal ions.

InChI:InChI=1/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/p-1/t7-/m1/s1

Upstream product

• 114113-97-2 5-((7R,10S)-7-Isopropyl-10-methyl-1-oxo-1λ⁴,5-dithia-spiro[5.5]undec-2-yl)-pentanoic acid 
• 88818-23-9 (S)-methyl lipoate 
• 46236-19-5 1,2-dithiolane-3-pentanoic acid methyl ester 
• 98441-85-1 α-dihydrolipoic acid 
• 107554-84-7 (S)-6,8-dimethylsulfonyloxyoctane-1-carboxylic acid 
• 754188-59-5 (5R)-5-[(1R)-2-benzyloxy-1-hydroxyethyl]tetrahydrofuran-2-one 
• 629-11-8 1,6-hexanediol 
• 361534-46-5 Methanesulfonic acid (S)-1-(2-methanesulfonyloxy-ethyl)-6-(tetrahydro-pyran-2-yloxy)-hexyl ester 
• 88853-25-2 (6R)-(+)-methyl 6,8-dihydroxyoctanoate 
• 1634-04-4 tert-butyl methyl ether 
• 7732-18-5 water 
• 41324-23-6 methyl 6-oxooct-7-enoate 
• 101567-87-7 (+/-)-8-hydroxy-6-mercapto-octanoic acid 
• 17356-08-0 thiourea 

Downstream Products

• 119365-69-4 (R)-6,8-dimercaptooctanoic acid 
• 1365619-36-8 2-(2-(4-N-(4-(1,2-dithiolane)pentanecarboxy)aminophenyl))ethylamino-N⁽⁶⁾-(2,2-diphenylethyl)adenosine-5'-N-ethylcarboxamide 
• 1365619-29-9 2-(2-(4-N-(4-(1,2-dithiolane)pentanecarboxy)aminophenyl))ethylamino-2',3'-isopropylideneadenosine-5'-N-ethylcarboxamide 
• 462-20-4 dihydrolipoic acid 
• 16096-98-3 trans-1,2-dithiane-4,5-diol 
• 131760-68-4 1,2-dimethyl-3,8-dioxo-1,2,5,6-diazadithiocane 
• 138715-29-4 (4S,5R)-3-<5-(1,2-dithiolan-3-yl)-1-oxopentyl>-4-methyl-5-phenyloxazolidine-2-selone 
• 78010-69-2 5-[1,2]Dithiolan-3-yl-pentanoic acid 1-(4-chloro-benzoylamino)-2-(4-chloro-phenyl)-2-oxo-ethyl ester 
• 1892-29-1 bis(2-hydroxyethyl) disulfide 
• 62-46-4 α-lipoic acid radical cation 
• 184045-25-8 5-[1,2]Dithiolan-3-yl-pentanoic acid 2-{2-[2-(methoxy-phenyl-methyl)-4-methyl-thiazol-5-yl]-ethoxymethyl}-benzyl ester 
• 299189-12-1 N-{4-[(1,1-dimethylethoxy)carbonylamino]phenyl}-1,2-dithiolane-3-pentanamide 
• 457631-45-7 {4-[(5-[1,2]dithiolan-3-yl-pentanoylamino)-methyl]-phenyl}-carbamic acid tert-butyl ester 
• 457631-46-8 {4-[2-(5-[1,2]dithiolan-3-yl-pentanoylamino)-ethyl]-phenyl}-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

A lipoic acid injection and its preparation method (by machine translation)

The present invention to provide a high safety of the thioctic acid preparation, including lipoic acid, the solvent component, characterized in that the vinyl octoate in preparation, containing lipoic acid ethylenediamine double-substituent, wherein the lipoic acid ethylenediamine double-substituent content are not higher than 0.2%. The lipoic acid preparation high safety, low toxicity, can be better clinical efficacy of lipoic acid. (by machine translation)

Preparation method of R-(+)-lipoic acid

The invention discloses a preparation method of R-(+)-lipoic acid. The method comprises the following steps: performing salt formation on a raw material of racemic lipoic acid and a resolving agent ofR-phenylethylamine, so as to obtain diastereoisomeric R-phenylethylamine racemic lipoic acid salt; performing recrystallization separation on a raw material of the salt, so as to obtain a single enantiomer of R-phenylethylamine R-(+)-lipoic acid salt; finally, acidizing the single enantiomer of R-phenylethylamine R-(+)-lipoic acid salt, so as to obtain the target compound R-(+)-lipoic acid in a structure of the formula (I) at a yield of 40%. The method is simple in operation, lower in requirements on equipment, mild in conditions and higher in yield, so that the method is suitable for industrial production.

Oxidation-triggered aggregation of gold nanoparticles for naked-eye detection of hydrogen peroxide

Naked-eye detection of H2O2 was realized based on the color change of gold nanoparticles upon aggregation. The removal of polyethylene glycol chains from the nanoparticle surface under H2O2 treatment let to the exposure of inner hydrophobic ligands, causing the nanoparticle aggregation in aqueous medium. This detection system shows a wide dynamic range in the μM scale and a distinguishable limit of 10 μM.

Chirality induction and chiron approaches to enantioselective total synthesis of α-lipoic acid

Abstract An efficient, short and convenient asymmetric synthesis of (R)-(+)-lipoic acid in seven steps from chiral hydroxy aldehyde with 32.5% overall yield is described. Synthesis of S and R enantiomers of α-lipoic acid from cis-1,4-butene diol derived chiral lactone is reported with 34 % overall yield. The present synthesis involves use of simple reaction conditions making it a convenient synthesis.

Thiolates of arsenic(III), antimony(III), and bismuth(III) with dl-α-dihydrolipoic acid

Lipoic acid can be reduced to dihydrolipoic acid free of lipoic acid without using deoxygenated solvents. Dihydrolipoic acid reacted with phenylarsine oxide, As2O3, and AsCl3, SbCl 3 but not Sb2O3, and Bi2O 3, BiCl3, and Bi(NO3)3· 5H2O in various solvents giving thiolates. When the reactions were done in methanol, the HCl and HNO3 released caused esterification of the -COOH group. The reaction with As(III) compounds was sensitive to dioxygen, leading to production of lipoic acid derivatives as well, arsenite being particularly active for the autoxidation. Physical (1H NMR) and chemical [reactivity of >M-Cl and >Bi(NO3)] properties of the adducts are described. The six-membered dihydrolipoic acid complexes reacted with stoichiometric amounts of British Anti-Lewisite releasing the dihydrolipoic acid by forming the corresponding complexes of British Anti-Lewisite. Graphical Abstract: [Figure not available: see fulltext.]

Polyphenolic Bioprecursors

Cosmetic and therapeutic, in particular dermatological bioprecursors have the formula [A]n—PP—[B]m wherein PP is a polyphenol radical in which each hydroxyl function is protected by a group A or a group B, A is a saturated or unsaturated, substituted or unsubstituted alkyl radical having 1 to 20 carbon atoms which is bonded to the polyphenol, n is an integer not less than 1, and B is a precursor of a biologically active molecule, which is also bonded to the polyphenol, and m is an integer also not less than 1.

Process For Purifying Thioctic Acid in Water

Process for purifying thioctic acid in water comprising the following steps: a) dissolving the thioctic acid in an aqueous alkaline solution or alternatively dissolving a thioctic acid salt, if necessary adjusting the pH to alkaline values, b) acidifying the solution from step (a) with an acid chosen from the class consisting of sulfuric acid, phosphoric acid, methanesulfonic acid to a pH between 5.4 and 5.8. c) isolating the thioctic acid precipitated in step (b) by conventional methods.

NOVEL LIPOIC ACID CONJUGATED COMPOUNDS AND SKIN EXTERNAL APPLICATIONS CONTAINING THEREOF

The present invention relates to derivatives of lipoic acid and skin external applications containing thereof that represent whitening effect, soothing effect, anti-aging effect and acne- improving effect and preventing effects of bladness disorder and seborrheic skin disorder.

PROCESS FOR PURIFYING THIOCTIC ACID IN WATER

Process for purifying thioctic acid in water comprising the following steps: a) dissolving the thioctic acid in an aqueous alkaline solution or alternatively dissolving a thioctic acid salt, if necessary adjusting the pH to alkaline values, b) acidifying the solution from step (a) with an acid chosen from the class consisting of sulfuric acid, phosphoric acid, methanesulfonic acid to a pH between 5.4 and 5.8. c) isolating the thioctic acid precipitated in step (b) by conventional methods.

Simplistic expedient and practical synthesis of (±)-α-lipoic acid

Synthesis of α-lipoic acid has been achieved by a simple sequence of reactions. The synthesis highlights the use of α-chloroesters in a Reformatsky reaction. The intermediate keto acid is an intermediate from which both isomers of lipoic acid can be prepared. Georg Thieme Verlag Stuttgart.