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T5625

Sigma-Aldrich

(±)-α-Lipoic acid

synthetic, ≥99% (titration), powder

Synonyme(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

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 :
12352106
ID de substance PubChem :
57654679
Nomenclature NACRES :
NA.77

Source biologique

synthetic

Niveau de qualité

200

Description

Oxidized form

Pureté

≥99% (titration)

Forme

powder

Solubilité

ethanol: soluble 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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Application

α-LA can reinstate endothelial activities and alleviate oxidative stress in high-fat fed diabetic rats4. It has also been used to analyze ROS production in astrocytes5.

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.

Notes préparatoires

(±)-α-Lipoic acid (α-LA) is soluble in ethanol at 50 mg/ml

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)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Daniely V S Costa et al.
Pharmaceuticals (Basel, Switzerland), 13(11) (2020-11-07)
Irinotecan, an anticancer drug, induces diarrhea and intestinal inflammation, resulting in an increase in the cost of care and in treatment delays. In this study, we investigated whether alpha-lipoic acid (α-LA) could improve irinotecan-mediated intestinal inflammation, diarrhea and dysmotility. Intestinal
Massimo Dal Monte et al.
Diagnostics (Basel, Switzerland), 10(3) (2020-03-07)
Melatoninergic agents are known to reduce intraocular pressure (IOP). The present study was performed to evaluate the effect of nanomicellar formulations of melatoninergic agents on IOP in the rat. Tonometry was used to measure IOP in eyes instilled with melatonin
Reda Hassan Elbakary et al.
Journal of microscopy and ultrastructure, 8(2), 42-50 (2020-08-09)
Polychlorinated biphenyl (PCB) is considered one of the environmental pollutants. It is used as hydraulic coils in vacuum pumps, pesticides transformers, heat-exchange systems, capacitors and as additives in adhesive inks, paints, plastics, copying paper and sealants. Alpha lipoic acid (ALA)
C M Sena et al.
British journal of pharmacology, 153(5), 894-906 (2007-10-02)
This study was conducted to investigate the effects of alpha-lipoic acid (alpha-LA) on endothelial function in diabetic and high-fat fed animal models and elucidate the potential mechanism underlying the benefits of alpha-LA. Plasma metabolites reflecting glucose and lipid metabolism, endothelial
Maria C N Marchetto et al.
Cell stem cell, 3(6), 649-657 (2008-12-02)
Amyotrophic lateral sclerosis (ALS) is a neurodegenerative disease characterized by motor neuron death. ALS can be induced by mutations in the superoxide dismutase 1 gene (SOD1). Evidence for the non-cell-autonomous nature of ALS emerged from the observation that wild-type glial
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