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)

Flash point:

>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

• Language:English Provider:SigmaAldrich

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

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.

Uses

α-lipoic acid (ALA, thioctic acid) is an organosulfur component produced from plants, animals, and humans. It has various properties, among them great antioxidant potential and is widely used as a racemic drug for diabetic polyneuropathy-associated pain and paresthesia. It has been used in alternative medicine 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.

Alpha Lipoic Acid 600 mg | 45 Tablets

Definition

ChEBI: Lipoic acid is a heterocyclic thia fatty acid comprising pentanoic acid with a 1,2-dithiolan-3-yl group at the 5-position. It belongs to a vitamin of the vitaminB complex. Lipoic acid is one of thecoenzymes involved in the decarboxylationof pyruvate by the enzymepyruvate dehydrogenase. Goodsources of lipoic acid include liverand yeast.

Biological Functions

Lipoic acid is a cofactor for five enzymes or classes of enzymes: pyruvate dehydrogenase, a-ketoglutarate dehydrogenase, the glycine cleavage system, branched chain keto acid dehydrogenase, and the alpha-oxo(keto)adipate dehydrogenase. The first two are critical to the citric acid cycle. The GCS regulates glycine concentrations.

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.

Side effects

Alpha-lipoic acid is generally considered safe with little to no side effects. In some cases, people may experience mild symptoms like nausea, rashes, or itching.

Structure and conformation

Lipoic acid contains two sulfur atoms (at C6 and C8) connected by a disulfide bond and is thus considered to be oxidized although either sulfur atom can exist in higher oxidation states.The carbon atom at C6 is chiral and the molecule exists as two enantiomers (R)-(+)-lipoic acid (RLA) and (S)-(-)-lipoic acid (SLA) and as a racemic mixture (R/S)-lipoic acid (R/S-LA).

Lipoic acid (62-46-4)Related Product Information

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• A-LIPOIC ACID,(+/-)-ALPHA-LIPOIC ACID,ALPHA-LIPOIC ACID,DL-A-LIPOIC ACID,LIPOIC ACID, DL-ALPHA-
• 1,2-Dithiolane-3-valeramide~DL-6,8-Dithiooctanoic acid amide~alpha-Lipoic acid amide,A-LIPOIC ACID AMIDE
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• A-LIPOIC ACID AMIDE
• (R)-Lipoic Acid Tromethamine Salt,R(A)ALPHA LIPOIC ACID TROMETHAMINE SALT,r-alpha-lipoic acid tromethamine salt
• (R)-LIPOIC ACID,R-(+)-ALPHA-LIPOIC ACID,R-ALPHA-LIPOIC ACID,R-(+)-Alpha-Lipoic Acid 1200-22-2,R (+) Alpha lipoic Acid ( D-Form)
• OCTOTIAMINE
• DIHYDROLIPOIC ACID