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Merck

T1395

(±)-α-Lipoic acid

BioReagent, suitable for cell culture, ≥99%

Sinónimos:

Thioctic acid, (±)-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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Acerca de este artículo

Fórmula empírica (notación de Hill):
C8H14O2S2
Número CAS:
Peso molecular:
206.33
UNSPSC Code:
12352207
NACRES:
NA.71
PubChem Substance ID:
EC Number:
214-071-2
Beilstein/REAXYS Number:
81853
MDL number:
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Nombre del producto

(±)-α-Lipoic acid, BioReagent, suitable for cell culture, ≥99%

InChI key

AGBQKNBQESQNJD-UHFFFAOYSA-N

InChI

1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)

SMILES string

OC(=O)CCCCC1CCSS1

product line

BioReagent

assay

≥99%

technique(s)

cell culture | mammalian: suitable

solubility

ethanol: 50 mg/mL

Quality Level

Gene Information

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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 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.

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

pictograms

Exclamation markEnvironment

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Stimulation of suicidal erythrocyte death by alpha-lipoic acid
Bhavsar SK, et al.
Cellular Physiology and Biochemistry, 26(6), 859-868 (2010)
Effect of SP-A/B in lipoic acid on acute paraquat poisoning
Li SP, et al.
World journal of emergency medicine, 5(1), 57-62 (2014)
alpha-Lipoic acid attenuates LPS-induced liver injury by improving mitochondrial function in association with GR mitochondrial DNA occupancy
Liu Z, et al.
Biochimie, 116, 52-60 (2015)
Yucui Chen et al.
Journal of neuroscience methods, 171(2), 239-247 (2008-05-13)
In vitro culturing of primary neurons is a mainstay of neurobiological research. Many of these culture paradigms have taken advantage of defined culture media rather than serum additives that contain undefined survival factors to facilitate experimental manipulations and interpretation of
Michela Rosini et al.
European journal of medicinal chemistry, 46(11), 5435-5442 (2011-09-20)
Lipoic acid (LA) is a natural antioxidant. Its structure was previously combined with that of the acetylcholinesterase inhibitor tacrine to give lipocrine (1), a lead compound multitargeted against Alzheimer's disease (AD). Herein, we further explore LA as a privileged structure

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