(±)-α-Lipoic acid
SIGMA/62320 - ≥98.0%
Synonym: (±)
CAS Number: 1077-28-7
Empirical Formula (Hill Notation): C8H14O2S2
Molecular Weight: 206.33
EC Number: 214-071-2
MDL Number: MFCD00005474
Linear Formula: C8H14O2S2
Product Type: Chemical
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: 62320-25G-F
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: 62320-5G-F
| assay | ≥98.0% |
| ≥98.0% (HPLC) | |
| form | solid |
| ign. residue | ≤0.1% |
| InChI | 1S/C8H14O2S2/c9-8(10)4-2- |
| InChI key | AGBQKNBQESQNJD-UHFFFAOYSA |
| loss | ≤0.2% loss on drying |
| mp | 60-62 °C |
| Quality Level | 200  |
| SMILES string | OC(=O)CCCCC1CCSS1 |
| storage temp. | 2-8°C |
| 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. |
| 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. |
| 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. |
| Packaging: | 5, 25 g in glass bottle |
| Symbol |   GHS07,GHS09 |
| Signal word | Warning |
| Hazard statements | H302 - H315 - H317 - H319 - H411 |
| Precautionary statements | P273 - P280 - P301 + P312 + P330 - P302 + P352 - P305 + P351 + P338 |
| Hazard Codes | Xn |
| Risk Statements | 22 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 2 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Purity | ≥98.0% (HPLC); ≥98.0% |
| mp | 60-62 °C |
| Storage Temp. | 2-8°C |
| UNSPSC | 12352100 |