62320

(±)-α-Lipoic acid

≥98.0%

• Synonym(s): (±)-1,2-Dithiolane-3-pentanoic acid, 6,8-Dithiooctanoic acid, DL-α-Lipoic acid, DL-6,8-Thioctic acid, Lip(S₂)
• Empirical Formula (Hill Notation): C₈H₁₄O₂S₂
• CAS Number: 1077-28-7
• Molecular Weight: 206.33
• Beilstein: 81853
• EC Number: 214-071-2
• MDL number: MFCD00005474
• UNSPSC Code: 12352100
• PubChem Substance ID: 57651855
• NACRES: NA.21

Properties

• Quality Level: 200
• Assay: ≥98.0% (HPLC); ≥98.0%
• form: solid
• ign. residue: ≤0.1%
• loss: ≤0.2% loss on drying
• bp: >286 °C/1.013 hPa
• mp: 60-62 °C
• solubility: water: 0.87 g/L at 22 °C
• density: 1.4 g/cm³ at 23 °C
• functional group: carboxylic acid; disulfide
• storage temp.: 2-8°C
• SMILES string: [OC(=O)CCCCC1CCSS1]; OC(=O)CCCCC1CCSS1
• InChI: [1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)]; 1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)
• InChI key: [AGBQKNBQESQNJD-UHFFFAOYSA-N]; AGBQKNBQESQNJD-UHFFFAOYSA-N
• Gene Information: human ... ACHE(43) , BCHE(590) ; rat ... Adra1a(29412) , Adra1b(24173) , Adra1d(29413)

Description

General description

α-lipoic acid (ALA, thioctic acid) is a natural organosulfur compound produced in plants, animals and humans. It is a powerful antioxidant and plays a role in the forming nucleic acids, building blocks of DNA.[1]

This product is a racemic mixture.

Application

(±)-α-Lipoic acid has been used:

• In in vitro lipoylation studies and in the pyruvate dehydrogenase complex (PDC)-pyruvate dehydrogenase kinase (PDHK) functional assay.[2]
• To investigate its antioxidative effect on developing cerebellum of rats exposed to arsenic during postnatal period.[3]

Biochem/physiol Actions

(±)-α-Lipoic acid exhibits direct free radical scavenging property[4] and reduces the increased oxidative stress.[5] In addition, it might also exhibit prooxidant activity.[4] α-Lipoic acid functions as an important prosthetic group in α-keto acid dehydrogenase complexes of the mitochondria.[6] It acts as a potential therapeutic for diabetic patients with distal symmetric polyneuropathy (DSP).[5] α-Lipoic acid is also used in the treatment of energy-impaired and redox unbalanced diseases.[6]

Antioxidant and coenzyme needed for the activity of enzyme complexes such as pyruvate dehydrogenase and glycine decarboxylase.

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.

Safety Information

• 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 Classifications: Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 2
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves