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Merck

T5625

Sigma-Aldrich

(±)-α-Lipoic acid

synthetic, ≥99% (titration), powder

Synonym(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

Empirical Formula (Hill Notation):
C8H14O2S2
CAS Number:
1077-28-7
Molecular Weight:
206.33
Beilstein:
81853
EC Number:
214-071-2
MDL number:
MFCD00005474
UNSPSC Code:
12352106
PubChem Substance ID:
57654679
NACRES:
NA.77

Key Documents

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biological source

synthetic

Quality Level

200

description

Oxidized form

Assay

≥99% (titration)

form

powder

solubility

ethanol: soluble 50 mg/mL

SMILES string

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)

InChI key

AGBQKNBQESQNJD-UHFFFAOYSA-N

Gene Information

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.

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.

Preparation Note

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

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H315,H317,H319,H411

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD6561V
SLCL6411
WXBD5705V
WXBD5201V
WXBC4682V

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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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