ChemicalBook > CAS DataBase List > α-Lipoic Acid

α-Lipoic Acid

Product Name
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
Formula Weight
206.33
MOL File
1077-28-7.mol
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α-Lipoic Acid Property

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
pka
4.75±0.10(Predicted)
form 
Crystals or Crystalline Powder
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)
NIST Chemistry Reference
Dl-thioctic acid(1077-28-7)
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Safety

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
Hazardous Substances Data
1077-28-7(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
62320
Product name
(±)-α-Lipoic acid
Purity
≥98.0%
Packaging
5G
Price
$112
Updated
2024/03/01
Sigma-Aldrich
Product number
PHR2561
Product name
Alpha Lipoic Acid
Packaging
1G
Price
$173
Updated
2024/03/01
Sigma-Aldrich
Product number
62320
Product name
(±)-α-Lipoic acid
Purity
≥98.0%
Packaging
25g
Price
$286
Updated
2024/03/01
Sigma-Aldrich
Product number
437692
Product name
α-Lipoic Acid - CAS 1077-28-7 - Calbiochem
Purity
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.
Packaging
5G
Price
$111
Updated
2024/03/01
Sigma-Aldrich
Product number
1368201
Product name
Alpha Lipoic Acid
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
500mg
Price
$394
Updated
2024/03/01
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α-Lipoic Acid Chemical Properties,Usage,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

(±)-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.

Uses

A fat-metabolism stimulator

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

Sinoway Industrial co., ltd.
Product
Nanoactive Alpha Lipoic Acid (ALA) 1077-28-7
Price
US $0.00/Kg/Bag
Min. Order
2Kg/Bag
Purity
99% up, High Density
Supply Ability
10 tons
Release date
2022-05-20
CONTIDE BIOTECH CO.,LTD
Product
α-Lipoic Acid 1077-28-7
Price
US $0.00/G
Min. Order
1G
Purity
99%
Supply Ability
20
Release date
2024-04-15
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Alpha Lipoic Acid 1077-28-7
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
99%-101%; USP
Supply Ability
1 ton
Release date
2021-05-27

1077-28-7, α-Lipoic AcidRelated Search:

THIOCITIC ACID/DL-THIOCTIC ACID Folic acid Isovaleric acid Citric acid DIHYDROLIPOIC ACID DL-Malic acid Ethyl 2-(Chlorosulfonyl)acetate alpha-lipoic acid-NHS Ascoric Acid R-alpha-Lipoic acid tromethamine salt Sodium thioctate 5-[(3S)-Dithiolan-3-yl]pentanoic acid Valeric acid D,L-ALPHA-LIPOIC ACID-NHS 3-(5-[1,2]DITHIOLAN-3YL-PENTANOYLAMINO)-PROPYL-AMIDE α-Lipoic Acid LIPOIC ACID, DL-ALPHA-(P) {DL-THIOCTIC ACID (A-LIPOIC Alpha-Lipoic Acid

  • 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
  • D-[3-(1,2-DITHIACYCLOPENTYL)]PENTANOIC ACID
  • DL-THIOCTIC ACID
  • DL-PROTOGEN A
  • DL-1,2-DITHIOLANE-3-PENTANOIC ACID
  • DITHIOOCTANIC ACID
  • DL-6,8-DITHIOOCTANOIC ACID
  • DL-6,8-THIOCTIC ACID
  • DL-6,8-THIOCTIC ACID OXIDIZED FORM
  • DL-6,8-THIOOCTIC ACID
  • DL-A-LIPOIC ACID
  • DL-ALPHA-LIPOIC ACID
  • LIP(S2)
  • LIPOIC ACID, DL-ALPHA-
  • 5-(1,2)DITHIOLAN-3-YL-PENTANOIC ACID
  • 6,8-DITHIOOCTANOIC ACID
  • 5-(dithiolan-3-yl)valeric acid
  • (+/-)-ALPHA-LIPOIC ACID
  • ALPHA-LIPOIC ACID
  • ALPHA-LIPONIC ACID
  • A-LIPOIC ACID
  • (+/-)-1,2-DITHIOLANE-3-VALERIC ACID
  • 1,2-DITHIOLANE-3-VALERIC ACID
  • DL-6,8-Thioctic acid Lip(S2)
  • 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-<i>α</i>-Lipoic acid
  • (+/-)-alpha-Lipoic acid >=98.0%
  • Alpha-lipoic acid,free flowing agent
  • Alpha sulfur acid
  • ALA
  • α-Lipoic Acid ((±)-α-Lipoic acid
  • THIOCTIC ACID
  • (+-)-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