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62320

Sigma-Aldrich

(±)-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)

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About This Item

Empirical Formula (Hill Notation):
C8H14O2S2
CAS Number:
Molecular Weight:
206.33
Beilstein:
81853
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.21

Assay

≥98.0% (HPLC)
≥98.0%

form

solid

ign. residue

≤0.1%

loss

≤0.2% loss on drying

mp

60-62 °C

storage temp.

2-8°C

SMILES string

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)

InChI key

AGBQKNBQESQNJD-UHFFFAOYSA-N

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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.

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.
  • To investigate its antioxidative effect on developing cerebellum of rats exposed to arsenic during postnatal period.

Biochem/physiol Actions

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

Pictograms

Exclamation markEnvironment

Signal Word

Warning

Hazard Statements

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ameliorative role of antioxidant supplementation on sodium-arsenite induced adverse effects on the developing rat cerebellum
Kaushal P, et al.
Journal of Ayurveda and integrative medicine (2019)
Insights on the Use of ?-Lipoic Acid for Therapeutic Purposes
Salehi B., et. al.
Biomolecules, 9(8), 356-356 (2019)
M. Koike et al.
Antibiotics, Vitamins and Hormones, 112-112 (1977)
Component co-expression and purification of recombinant human pyruvate dehydrogenase complex from baculovirus infected SF9 cells
Jiang Y, et al.
Protein Expression and Purification, 97, 9-16 (2014)
Oral treatment with alpha-lipoic acid improves symptomatic diabetic polyneuropathy: the SYDNEY 2 trial
Ziegler D, et al.
Diabetes Care, 29(11), 2365-2370 (2006)

Articles

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.

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