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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/REAXYS Number:
81853
EC Number:
214-071-2
MDL number:
MFCD00005474
UNSPSC Code:
12352106
PubChem Substance ID:
57654679
NACRES:
NA.77
Pricing and availability is not currently available.

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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1 of 4

This Item
623201368201PHR2561
(±)-α-Lipoic acid synthetic, ≥99% (titration), powder

T5625

(±)-α-Lipoic acid

(±)-α-Lipoic acid ≥98.0%

62320

(±)-α-Lipoic acid

Alpha Lipoic Acid United States Pharmacopeia (USP) Reference Standard

1368201

Alpha Lipoic Acid

Alpha Lipoic Acid

PHR2561

Alpha Lipoic Acid

assay

≥99% (titration)

assay

≥98.0% (HPLC)

assay

-

assay

-

form

powder

form

solid

form

-

form

powder

Quality Level

200

Quality Level

200

Quality Level

-

Quality Level

300

solubility

ethanol: soluble 50 mg/mL

solubility

water: 0.87 g/L at 22 °C

solubility

-

solubility

-

biological source

synthetic

biological source

-

biological source

-

biological source

-

description

Oxidized form

description

-

description

-

description

Pharmaceutical Secondary Standard; Certified Reference Material

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

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

  • Specification Sheet

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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
    View All Related Papers

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