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Merck
CN

T1395

(±)-α-Lipoic acid

BioReagent, suitable for cell culture, ≥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
UNSPSC Code:
12352207
NACRES:
NA.71
PubChem Substance ID:
24899963
EC Number:
214-071-2
Beilstein/REAXYS Number:
81853
MDL number:
MFCD00005474

Key Documents

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Product Name

(±)-α-Lipoic acid, BioReagent, suitable for cell culture, ≥99%

Quality Level

200

InChI key

AGBQKNBQESQNJD-UHFFFAOYSA-N

InChI

1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)

SMILES string

OC(=O)CCCCC1CCSS1

product line

BioReagent

assay

≥99%

technique(s)

cell culture | mammalian: suitable

solubility

ethanol: 50 mg/mL

Gene Information

human ... ACHE(43), BCHE(590)
rat ... Adra1a(29412), Adra1b(24173), Adra1d(29413)

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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 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.

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.

Other Notes

Oxidized form

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

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000499355
0000499355
0000481769
0000481769
0000481767

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Stimulation of suicidal erythrocyte death by alpha-lipoic acid
Bhavsar SK, et al.
Cellular Physiology and Biochemistry, 26(6), 859-868 (2010)
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)
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)
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
Jorgelindo da Veiga Moreira et al.
Scientific reports, 9(1), 3153-3153 (2019-03-01)
In the recent years, cancer research succeeded with sensitive detection methods, targeted drug delivery systems, and the identification of a large set of genes differently expressed. However, although most therapies are still based on antimitotic agents, which are causing wide
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Articles

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.

Mitochondrial Stress and ROS

Cellular oxidative stress is countered by enzymatic scavengers and antioxidant modulators against reactive oxygen species damage.

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.

线粒体应激和ROS

氧化应激，在一部分上，是由多种细胞过程产生的活性氧介导，并由诸如酶清除剂或抗氧化剂调节剂等细胞抗氧化剂机制所控制的。自由基，如活性氧，会通过细胞引起细胞损伤。

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