(±)-α-Lipoic acid
SIGMA/T1395 - BioReagent, suitable for cell culture, ≥99%
Synonym: Thioctic acid; (±)
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: T1395-1G
This image depicts SKU: T1395-1G
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: T1395-5G
This image depicts SKU: T1395-5G
| assay | ≥99% |
| InChI | 1S/C8H14O2S2/c9-8(10)4-2- |
| InChI key | AGBQKNBQESQNJD-UHFFFAOYSA |
| product line | BioReagent |
| Quality Level | 200  |
| SMILES string | OC(=O)CCCCC1CCSS1 |
| solubility | ethanol: 50 mg/mL |
| technique(s) | cell culture | mammalian: suitable |
| Application: | Lipoic acid has been used: • for induction of eryptosis in erythrocytes • as a constituent in NS21 media for neuronal cultures • to evaluate its effect on liver energy metabolism by high performance liquid chromatography (HPLC) and assessing mitochondrial function by mitochondrial gene expression studies in lipopolysaccharide (LPS) pre-treated mice • to elucidate its effect on paraquat poisoning in lungs |
| 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 (LA), a nutritional component found in vegetables and meat, has both antioxidant and oxidant properties. LA exerts therapeutic potential to many diseases like liver cirrhosis, heavy metal poisoning, and diabetic polyneuropathy. LA exerts apoptotic potential in cancer cells either by oxidative stress related pathway or by activation of caspases. LA improves mitochondrial function and plays a key role in mitochondrial energy metabolism. |
| Other Notes: | Oxidized form |
| Packaging: | 1, 5 g in poly bottle |
| Symbol |   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 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 2 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Purity | ≥99% |
| UNSPSC | 12352207 |