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α-Lipoic Acid

CAS No.
1077-28-7
Chemical Name:
α-Lipoic Acid
Synonyms
ALA;THIOCTIC ACID;ALPHA-LIPOIC ACID;ALPHA-LIPOIC ACID;DL-THIOCTIC ACID;Thioctic acid CRS;A-LIPOIC ACID;alpha lipoic acid powder;DL-A-LIPOIC ACID;Alpha Acid Lipoic
CBNumber:
CB5180699
Molecular Formula:
C8H14O2S2
Molecular Weight:
206.33
MDL Number:
MFCD00005474
MOL File:
1077-28-7.mol
MSDS File:
SDS
Last updated:2024-03-13 22:06:18

α-Lipoic Acid Properties

Melting point 60-62 °C
Boiling point 160-165 °C(lit.)
Density 1.2888 (rough estimate)
refractive index 1.5200 (estimate)
Flash point 160-165°C
storage temp. 2-8°C
solubility ethanol: 50 mg/mL
form Crystals or Crystalline Powder
pka 4.75±0.10(Predicted)
color Yellow
Water Solubility 0.9 g/L (20 ºC)
Merck 14,9326
BRN 81853
Stability Stable. Incompatible with strong oxidizing agents.
InChIKey AGBQKNBQESQNJD-UHFFFAOYSA-N
LogP 2.530 (est)
CAS DataBase Reference 1077-28-7(CAS DataBase Reference)
FDA UNII 73Y7P0K73Y
NIST Chemistry Reference Dl-thioctic acid(1077-28-7)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS09
Signal word  Warning
Hazard statements  H302-H315-H317-H319-H411
Precautionary statements  P261-P273-P280-P301+P312-P302+P352-P305+P351+P338
Hazard Codes  Xn
Risk Statements  22-20/21/22
Safety Statements  37/39-26-24/25-36-36/37/39
WGK Germany  3
RTECS  JP1192000
HS Code  29349990
NFPA 704
1
2 0

α-Lipoic Acid price More Price(61)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 62320 (±)-α-Lipoic acid ≥98.0% 1077-28-7 5G $112 2024-03-01 Buy
Sigma-Aldrich PHR2561 Alpha Lipoic Acid 1077-28-7 1G $173 2024-03-01 Buy
Sigma-Aldrich 62320 (±)-α-Lipoic acid ≥98.0% 1077-28-7 25g $286 2024-03-01 Buy
Sigma-Aldrich 437692 α-Lipoic Acid - CAS 1077-28-7 - Calbiochem α-Lipoic Acid, CAS 1077-28-7 is an oxidized form with antioxidant properties. Reduces renal lipid peroxidation in rats with cisplatin n-induced nephrotoxicity. 1077-28-7 5G $111 2024-03-01 Buy
Sigma-Aldrich 1368201 Alpha Lipoic Acid United States Pharmacopeia (USP) Reference Standard 1077-28-7 500mg $394 2024-03-01 Buy
Product number Packaging Price Buy
62320 5G $112 Buy
PHR2561 1G $173 Buy
62320 25g $286 Buy
437692 5G $111 Buy
1368201 500mg $394 Buy

α-Lipoic Acid Chemical Properties,Uses,Production

Description

DL-α-Lipoic acid is a cyclic disulfide antioxidant that interconverts with its reduced dithiol form. It is an essential cofactor for decarboxylation reactions of the citric acid cycle, and acts as a general antioxidant. DL-α-lipoic acid can act as a direct radical scavenger, as a cofactor to regenerate reduced glutathione, and as a metal chelator.

Chemical Properties

Light-Yellow Solid

Originator

Neurium,Hexal

Uses

Lipoic acid [CAS: 1077-28-7] (6,8-dimercaptooctanoic acid), 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.

Uses

thioctic acid is also known as alpha lipoic acid. It is an anti-oxidant.

Uses

A fat-metabolism stimulator

Uses

(±)-α-Lipoic acid has been used in in vitro lipoylation studies and in the pyruvate dehydrogenase complex (PDC)-pyruvate dehydrogenase kinase (PDHK) functional assay. It has also been used to investigate its antioxidative effect on developing cerebellum of rats exposed to arsenic during postnatal period.

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 has a role as a fundamental metabolite and a geroprotector. It is a member of dithiolanes, a heterocyclic fatty acid and a thia fatty acid. It is functionally related to an octanoic acid. It is a conjugate acid of a lipoate.

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.

brand name

Liposan;Thioactacid.

Therapeutic Function

Growth factor, Lipotropic, Detoxicant

Synthesis Reference(s)

Journal of the American Chemical Society, 79, p. 6483, 1957 DOI: 10.1021/ja01581a033

General Description

Oxidized form. Has antioxidant properties. Growth factor for many bacteria and protozoa.

Flammability and Explosibility

Not classified

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. It contains a disulfide group, which can be transformed in the body to a dithiol group.
ALA has been on the market since the 1950s as a dietary supplement. It is a natural antioxidant usually made by the body. The advantage of 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 ALA can chelate mercury once it is transformed into the dithiol-containing compound. 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. ALA has not received FDA approval as a chelating agent, but it is still sold as a food supplement.

Biochem/physiol Actions

Antioxidant and coenzyme needed for the activity of enzyme complexes such as those of pyruvate dehydrogenase and glycine decarboxylase. Exogenous thioctic acid is reduced intracellularly by two or more enzymes. The reduced form then influences a number of cell processes by direct radical scavenging, recycling of other antioxidants, increasing glutathione synthesis, and modulating transcription factor activity particularly that of NF-κB. Decreases the phagocytosis of myelin by macrophages.

storage

Store at +4°C

Purification Methods

It forms yellow needles from cyclohexane or hexane and has been distilled at high vacuum; and sublimes at ~90o and very high vacuum. It is insoluble in H2O but dissolves in alkaline solution. [Lewis & Raphael J Chem Soc 4263 1962, Soper et al. J Am Chem Soc 76 4109, Reed & Niu J Am Chem Soc 77 416 1955, Tsuji et al. J Org Chem 43 3606 1978, Calvin Fed Proc USA 13 703 1954.] The S-benzylisothiuronium salt has m 153-154o (evacuated capillary, from MeOH), 132-134o, 135-137o (from EtOH). The dand lforms have m 45-47.5o and [] D 23 ±113o (c 1.88, *C6H6) and have UV in MeOH with max at 330nm ( 140). [Beilstein 19/7 V 237.] The reduced form, (±)-6,8-dimercaptooctanoic acid, [7516-48-5] M 208.3, is a light yellow liquid which is sold in sealed ampoules.

α-Lipoic Acid Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from α-Lipoic Acid manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Alpha lipoic acid -API pictures 2024-03-19 Alpha lipoic acid -API
1077-28-7
US $0.00 / KG 1KG 99.9% 6000KG Shandong Luning Pharmaceutical Co., Ltd.
thioctic acid-API pictures 2024-03-19 thioctic acid-API
1077-28-7
US $0.00 / KG 1KG 99% 6000KG Shandong Luning Pharmaceutical Co., Ltd.
Alpha lipoic acid pictures 2024-03-19 Alpha lipoic acid
1077-28-7
US $60.00 / KG 1KG 99.9% 6000KG Shandong Luning Pharmaceutical Co., Ltd.
  • Alpha lipoic acid pictures
  • Alpha lipoic acid
    1077-28-7
  • US $60.00 / KG
  • 99.9%
  • Shandong Luning Pharmaceutical Co., Ltd.
5 MG PNPP SUBSTRATE TABLETS REAGENT GR (1)-ALPHA-LIPOIC ACID 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 Thioctic acid, dl-form DL-PROTOGEN A DL-1,2-DITHIOLANE-3-PENTANOIC ACID DITHIOOCTANIC ACID DL-6,8-DITHIOOCTANOIC ACID DL-6,8-THIOCTIC ACID OXIDIZED FORM DL-6,8-THIOOCTIC ACID LIP(S2) LIPOIC ACID, DL-ALPHA- 5-(1,2)DITHIOLAN-3-YL-PENTANOIC ACID 6,8-DITHIOOCTANOIC ACID (+/-)-ALPHA-LIPOIC ACID ALPHA-LIPONIC ACID (+/-)-1,2-DITHIOLANE-3-VALERIC ACID 1,2-DITHIOLANE-3-VALERIC ACID DL-α-Lipoic acid (-ALPHA-LIPOIC ACID (-ALPHA-LIPOIC ACID Dl-ThiocticAcid,Oxidized R(+)-Alpha-LipoicAcid99% DL-Thioctic acid, 98+% 5GR LIPOIC ACID, DL-ALPHA-(AS) DL-a-Lipoic acid USP DL-ThioCLic Acid alpha-lipoic acid (CAS ) DL-α-Lipoic acid (+/-)-alpha-Lipoic acid >=98.0% (+-)-2-dithiolane-3-pentanoicacid (+-)-2-dithiolane-3-valericacid (+/-)-2-dithiolane-3-pentanoicacid 1,2-Dithiolane-3-pentanoicacid,(+-)-(9CI) DL-Thioctic acid, 98+% (RS)-a-Lipoic Acid NSC 628502 NSC 90788 rac a-Lipoic Acid Alpha-Thioctic LIPOICACID,REAGENT A-THIOCTIC ACID (Low Solvent Residue) α-Lipic acid (RS)-Lipoic acid 1,2-Dithiolane-3-valeric acid, (+-)- (8CI) a-Liponic acid α-Lipic acid(Low Solvent Residue) 2-Dithiolane-3-valericacid,(+-)-1 DL-1,2-Dithiolan-3-valeriansaeure DL-1,2-Dithiolane 3-valeric acid DL-ALPHA-LIPOIC ACID (DL THIOCTIC ACID) Alpha Lipoic Acid ( or DL-Thioctic Acid )