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Alpha Lipoic ACID (Granular) (ALA) is a cyclic disulfide antioxidant that interconverts with its reduced dithiol form.
Alpha Lipoic ACID (Granular) (ALA) is an essential cofactor for decarboxylation reactions of the citric acid cycle, and acts as a general antioxidant.
Alpha Lipoic ACID (Granular) (ALA) can act as a direct radical scavenger, as a cofactor to regenerate reduced glutathione, and as a metal chelator.
CAS: 1077-28-7
MF: C8H14O2S2
MW: 206.33
EINECS: 214-071-2
Synonyms
5 MG PNPP SUBSTRATE TABLETS REAGENT GR;DL-α-Lipoic acidUSP, 99.0-101.0% (Assay);5-(1,2)Dithiolan-3-yl-pentanoic acid for synthesis;TIMTEC-BB SBB003484;THIOOCTIC ACID;dl-1,2-Dithiolane3-valericacid;DL-6-Thioctic acid;dl-6-Thiocticacid
Alpha Lipoic ACID (Granular) (ALA) is a heterocyclic thia fatty acid comprising pentanoic acid with a 1,2-dithiolan-3-yl group at the 5-position.
Alpha Lipoic ACID (Granular) (ALA) has a role as a fundamental metabolite and a geroprotector.
Alpha Lipoic ACID (Granular) (ALA) is a member of dithiolanes, a heterocyclic fatty acid and a thia fatty acid.
Alpha Lipoic ACID (Granular) (ALA) is functionally related to an octanoic acid.
Alpha Lipoic ACID (Granular) (ALA) is a conjugate acid of a lipoate.
Alpha Lipoic ACID (Granular) (ALA), also known as α-lipoic acid, alpha-lipoic acid (ALA) and thioctic acid, is an organosulfur compound derived from caprylic acid (octanoic acid).
Alpha Lipoic ACID (Granular) (ALA), which is made in animals normally, is essential for aerobic metabolism.
Alpha Lipoic ACID (Granular) (ALA) is also available as a dietary supplement or pharmaceutical drug in some countries.
Alpha Lipoic ACID (Granular) (ALA) is the conjugate base of lipoic acid, and the most prevalent form of LA under physiological conditions.
Only the (R)-(+)-enantiomer (RLA) exists in nature.
RLA is an essential cofactor of many processes.
Alpha Lipoic ACID (Granular) (ALA) Chemical Properties
Melting point: 60-62 °C
Boiling point: 160-165 °C(lit.)
density: 1.2888 (rough estimate)
bulk density: 260kg/m3
refractive index: 1.5200 (estimate)
Fp: 160-165°C
storage temp.: 2-8°C
solubility ethanol: 50 mg/mL
pka: 4.75±0.10(Predicted)
form: Crystals or Crystalline Powder
color: Yellow
biological source: synthetic
Water Solubility: 0.9 g/L (20 ºC)
Merck: 14,9326
BRN: 81853
Stability: Stable. Incompatible with strong oxidizing agents.
Cosmetics Ingredients Functions: ANTIOXIDANT
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
LogP: 2.530 (est)
CAS DataBase Reference: 1077-28-7(CAS DataBase Reference)
NIST Chemistry Reference: Alpha Lipoic ACID (Granular) (ALA)(1077-28-7)
Physical and chemical properties
Alpha Lipoic ACID (Granular) (ALA) contains two sulfur atoms connected by a disulfide bond in the 1,2-dithiolane ring.
Alpha Lipoic ACID (Granular) (ALA) also carries a carboxylic acid group.
Alpha Lipoic ACID (Granular) (ALA) is considered to be oxidized relative to its acyclic relative dihydrolipoic acid, in which each sulfur exists as a thiol.
Alpha Lipoic ACID (Granular) (ALA) is a yellow solid.
Alpha Lipoic ACID (Granular) (ALA) occurs naturally, but (S)-(-)-lipoic acid (SLA) has been synthesized.
For use in dietary supplement materials and compounding pharmacies, the USP established an official monograph for R/S-LA.
Uses
Alpha Lipoic ACID (Granular) (ALA), a lipophilic endogenous disulfide that can be reduced to the dithiol dihydrolipoic acid, protects against free-radical-mediated injury both in vivo and in vitro.
Alpha Lipoic ACID (Granular) (ALA) has been used in in vitro lipoylation studies and in the pyruvate dehydrogenase complex (PDC)-pyruvate dehydrogenase kinase (PDHK) functional assay.
Alpha Lipoic ACID (Granular) (ALA) has also been used to investigate its antioxidative effect on developing cerebellum of rats exposed to arsenic during postnatal period.
Alpha Lipoic ACID (Granular) (ALA) is also known as alpha lipoic acid.
Alpha Lipoic ACID (Granular) (ALA) is an anti-oxidant.
Pharmaceutical Applications
Lipoic acid(ALA), also known as α-lipoic acid (alpha-lipoic acid) or thioctic acid, has the formula C8H14S2O2 and systematic name 5-(1,2-dithiolan-3-yl)pentanoic acid.
Alpha Lipoic ACID (Granular) (ALA) contains a disulfide group, which can be transformed in the body to a dithiol group.
Alpha Lipoic ACID (Granular) (ALA) has been on the market since the 1950s as a dietary supplement.
Alpha Lipoic ACID (Granular) (ALA) is a natural antioxidant usually made by the body.
The advantage of Alpha Lipoic ACID (Granular) (ALA) over other antioxidants such as vitamin C and E is that it is soluble both in water and in fat.
Researchers in the former Soviet Union found that Alpha Lipoic ACID (Granular) (ALA) can chelate mercury once it is transformed into the dithiol-containing compound.
Alpha Lipoic ACID (Granular) (ALA) can penetrate both the blood–brain barrier and the cell membrane and therefore would be a very interesting chelating agent.
Nevertheless, there is much debate about its mode of action, side effects and effectiveness.
Other antidotes, such as BAL and DMSA, are more efficient in the removal of heavy metals.
Alpha Lipoic ACID (Granular) (ALA) has not received FDA approval as a chelating agent, but it is still sold as a food supplement.
Manufacturing Process
To a suspension of 106 g of anhydrous aluminum chloride in 450 ml of carbontetrachloride is added dropwise, with vigorous stirring, 70 g of ethyl 8- chloroformylvalerate (H. Bergs, C. Wittfeld and H. Frank, Ber., 67B, 1622 (1947)).
The temperature is maintained at 25°C.
The cooling bath is removed and ethylene is passed in for a period of 2 hours.
The reaction mixture is poured onto cracked ice, the organic layer separated, and the aqueous layer extracted with 200 ml of chloroform.
The combined organic extracts are dried over anhydrous sodium sulfate and the solvent removed in vacuo.
The dark colored oil remaining, crude ethyl 8-chloro-6-oxooctanoate is distilled in vacuo through a 6 in. Vigreaux column.
After small forerun, the main fraction, 48-54 g (72-80%), B.P. 112-114°C (2 mm.); n25 D1-4485, is collected.
Redistilled thiolacetic acid (14.7 g) is cooled in an ice-bath and neutralized to the phenolphthalein end-point with a 10% solution of potassium hydroxide in ethanol (approximately 135 ml required).
To this solution is added 29 g of ethyl-6,8-dibromooctanoate and the mixture is stirred and heated under reflux in an atmosphere of nitrogen for 5 hours.
The reaction mixture, which contains ethyl 6,8-diacetyl-mercaptooctanoate, is cooled and 35 g of potassium hydroxide (85%) is added.
The reaction mixture is stirred at room temperature in an atmosphere of nitrogen for 17 hours, then acidified (pH less than 1) with 6 N hydrochloric acid.
Ethanol is removed in vacuo, sufficient water is added to dissolve the inorganic solids and the mixture is extracted with two 150 ml portions of chloroform.
To the combined organic extracts, which contain 6,8-dimercaptooctanoic acid, is added 575 ml of chloroform and 210 ml of water.
This mixture is stirred vigorously in an atmosphere of nitrogen While sufficient iodoform reagent (R. L. Shriner and R. C. Fuson, "Identification of Organic Compounds," 2nd. Ed., John Wiley and Sons, New York, N.Y., 1940, p. 53) is added dropwise during a 6 hour period to give a permanent brown color.
Approximately 185 ml of iodoform reagent is required. The organic layer is separated, washed with 500 ml of 1% sodium thiosulfate solution, and then extracted with two 250 ml portions of 5% sodium bicarbonate solution.
The aqueous extracts are acidified (pH less than 1) with 6 N hydrochloric acid and extarcted with two 125 ml portions of chloroform.
The combined chloroform extracts are dried over anhydrous sodium sulfate and the solvent is then removed in vacuo.
The yellow viscous oil remaining solidifies when cooled and scratched.
This solid material is extracted with three 300 ml portions of boiling Skelly B solvent (essentially nhexane).
The combined extracts are seeded with crystalline DL-α-lipoic acid and allowed to stand at room temperature overnight and then in a refrigerator for several hours.
Large yellow crystals separate, M.P. 60.5-61.5°C.
The yield of product is 10.8-12.3 g (60-68%).
1,2-Dithiolane-3-pentanoic acid was recrystallized from Skelly B solvent, M.P. 61-62°C.
