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Merck
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Autres documents

T1395

Sigma-Aldrich

(±)-α-Lipoic acid

suitable for cell culture, BioReagent, ≥99%

Synonyme(s) :

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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About This Item

Formule empirique (notation de Hill):
C8H14O2S2
Numéro CAS:
1077-28-7
Poids moléculaire :
206.33
Numéro Beilstein :
81853
Numéro CE :
214-071-2
Numéro MDL:
MFCD00005474
Code UNSPSC :
12352207
ID de substance PubChem :
24899963
Nomenclature NACRES :
NA.71

Gamme de produits

BioReagent

Pureté

≥99%

Technique(s)

cell culture | mammalian: suitable

Solubilité

ethanol: 50 mg/mL

Chaîne SMILES 

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)

Clé InChI

AGBQKNBQESQNJD-UHFFFAOYSA-N

Informations sur le gène

human ... ACHE(43) , BCHE(590)
rat ... Adra1a(29412) , Adra1b(24173) , Adra1d(29413)

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Description générale

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.

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

Actions biochimiques/physiologiques

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.

Autres remarques

Oxidized form

Pictogrammes

Exclamation markEnvironment
GHS07,GHS09

Mention d'avertissement

Warning

Mentions de danger

H302,H315,H317,H319,H411

Classification des risques

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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)
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)
Stimulation of suicidal erythrocyte death by alpha-lipoic acid
Bhavsar SK, et al.
Cellular Physiology and Biochemistry, 26(6), 859-868 (2010)
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
Afficher tous les articles scientifiques apparentés

Articles

Lipoic (Thioctic) Acid, in Cell Culture

How lipoic acid (thioctic acid) and other cell culture components affect the performance of serum-free, protein-free cell culture systems used for biomanufacturing heterologous proteins including monoclonal antibodies.

Mitochondrial Stress and ROS

Oxidative stress is mediated, in part, by reactive oxygen species produced by multiple cellular processes and controlled by cellular antioxidant mechanisms such as enzymatic scavengers or antioxidant modulators. Free radicals, such as reactive oxygen species, cause cellular damage via cellular.

Dietary Antioxidants

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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