Skip to Content
MilliporeSigma
All Photos(6)

Key Documents

View All Documentation

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)

Sign Into View Organizational & Contract Pricing
All Photos(6)

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)

Looking for similar products? Visit Product Comparison Guide

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000422297
0000422296
0000422296
0000422297
0000413537

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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)
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
Fatma M Ghoneim et al.
Biology, 9(9) (2020-08-23)
Sodium valproate (VPA) is an antiepileptic drug (AED) licensed for epilepsy and used during pregnancy in various indications. Alpha-lipoic acid (ALA) is a natural compound inducing endogenous antioxidant production. Our study aimed to investigate the effect of prenatal administration of
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
View All Related Papers

Articles

DISCOVER Bioactive Small Molecules for Nitric Oxide & Cell Stress Research

DISCOVER Bioactive Small Molecules for Nitric Oxide & Cell Stress Research

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.

Questions

1–2 of 2 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service