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T1395

Sigma-Aldrich

(±)-α-Lipoic acid

suitable for cell culture, BioReagent, ≥99%

Synonym(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

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:
12352207
PubChem Substance ID:
24899963
NACRES:
NA.71

product line

BioReagent

Assay

≥99%

technique(s)

cell culture | mammalian: suitable

solubility

ethanol: 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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General description

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

Biochem/physiol Actions

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.

Other Notes

Oxidized form

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
View All Related Papers

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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