α-Lipoic Acid

Modify Date: 2024-01-02 12:17:48

α-Lipoic Acid structure	Common Name	α-Lipoic Acid
	CAS Number	1077-28-7	Molecular Weight	206.326
	Density	1.2±0.1 g/cm3	Boiling Point	362.5±11.0 °C at 760 mmHg
	Molecular Formula	C₈H₁₄O₂S₂	Melting Point	60-62ºC
	MSDS	Chinese USA	Flash Point	173.0±19.3 °C
	Symbol	GHS07	Signal Word	Warning

Use of α-Lipoic Acid

α-Lipoic Acid is an antioxidant, which is an essential cofactor of mitochondrial enzyme complexes. α-Lipoic Acid inhibits NF-κB-dependent HIV-1 LTR activation.

Name	DL-Thioctic Acid
Synonym	More Synonyms

Description	α-Lipoic Acid is an antioxidant, which is an essential cofactor of mitochondrial enzyme complexes. α-Lipoic Acid inhibits NF-κB-dependent HIV-1 LTR activation.
Related Catalog	Signaling Pathways >> Anti-infection >> HIV Signaling Pathways >> Metabolic Enzyme/Protease >> Mitochondrial Metabolism Natural Products >> Acids and Aldehydes Research Areas >> Cancer Research Areas >> Inflammation/Immunology Research Areas >> Infection
Target	NF-κB HIV Mitochondrial bioenergetics
In Vitro	The long terminal repeat (LTR) of HIV-1 is the target of cellular transcription factors such as NF-κB, and serves as the promoter-enhancer for the viral genome when integrated in host DNA[1]. α-Lipoic Acid (Alpha-Lipoic acid, ALA), a naturally occurring dithiol compound, plays an essential role in mitochondrial bioenergetics. α-Lipoic Acid reduces lipid accumulation in the liver by regulating the transcriptional factors SREBP-1, FoxO1, and Nrf2, and their downstream lipogenic targets via the activation of the SIRT1/LKB1/AMPK pathway. Treatment of cells with α-Lipoic Acid (250, 500 and 1000 μM) significantly increases the NAD+/NADH ratio in HepG2 cells (P<0.05 or P<0.01). Treatment with α-Lipoic Acid (50, 125, 250 and 500 μM) increases SIRT1 activity in HepG2 cells. α-Lipoic Acid (50, 125, 250, 500 and 1000 μM) increases phosphorylation of AMPK and acetyl-CoA carboxylase (ACC) in HepG2 cells in a dose-dependent fashion[1].
In Vivo	C57BL/6J mice, divided into four groups, are fed an high-fat diet (HFD) for 24 weeks to induce nonalcoholic fatty liver disease (NAFLD) followed by daily administration of α-Lipoic Acid. Then, the effects of α-Lipoic Acid on hepatic lipid accumulation in long-term HFD-fed mice are assessed. Administration of α-Lipoic Acid (100 mg/kg or 200 mg/kg) markedly reduces visceral fat mass in mice. In addition, α-Lipoic Acid (100 mg/kg or 200 mg/kg) treatment inhibits the appetite and causes a dramatic weight loss (all P<0.05)[1].
Cell Assay	The human hepatocellular carcinoma (HepG2) cell line is cultured in Dulbecco's modified Eagle's medium containing 10% fetal bovine serum at 37°C and 5% CO2. HepG2 cells are treated with AMPK inhibitor (CC, 20 μM, 0.5 h), SIRT1 inhibitor (NA, 10 mM, 12 or 24 h), and AMPK activator (AICAR, 2 mM, 1 h), Palmitate (PA, 125 μM, 12 h) and α-Lipoic Acid (250 μM, 6 or 12 h)[1].
Animal Admin	Mice[1] Male C57BL/6J mice (6-week-old; body weight: 22-24 g) are allowed ad libitum access to normal diet and water for 2 weeks before dividing into four groups (n=8): normal diet (ND) (10% energy from fat), high-fat diet (HFD) (60% energy from fat) and HFD plus α-Lipoic Acid (100 mg/kg or 200 mg/kg). After 24 weeks of treatment, blood samples are collected after the eyeballs of the mice are extracted for serum preparation by centrifugation at 2000×g for 10 min at 4°C. The liver tissues are harvested in liquid nitrogen and stored at -80°C.
References	[1]. Xiao L, et al. Activity of the dietary antioxidant ergothioneine in a virus gene-based assay for inhibitors of HIV transcription. Biofactors. 2006;27(1-4):157-65. [2]. Yang Y, et al. Alpha-lipoic acid improves high-fat diet-induced hepatic steatosis by modulating the transcription factors SREBP-1, FoxO1 and Nrf2 via the SIRT1/LKB1/AMPK pathway. J Nutr Biochem. 2014 Nov;25(11):1207-1217. [3]. Lei D, et al. Synergistic neuroprotective effect of rasagiline and idebenone against retinal ischemia-reperfusion injury via the Lin28-let-7-Dicer pathway. Oncotarget. 2018 Jan 30;9(15):12137-12153.

Density	1.2±0.1 g/cm3
Boiling Point	362.5±11.0 °C at 760 mmHg
Melting Point	60-62ºC
Molecular Formula	C₈H₁₄O₂S₂
Molecular Weight	206.326
Flash Point	173.0±19.3 °C
Exact Mass	206.043518
PSA	87.90000
LogP	2.16
Vapour Pressure	0.0±1.7 mmHg at 25°C
Index of Refraction	1.562
Storage condition	2-8°C
Stability	Stable. Incompatible with strong oxidizing agents.
Water Solubility	ethanol: 50 mg/mL \| 0.9 g/L (20 ºC)

α-Lipoic Acid MSDS(Chinese)

CHEMICAL IDENTIFICATION

RTECS NUMBER :: JP1192000

CHEMICAL NAME :: 1,2-Dithiolane-3-valeric acid, (+-)-

CAS REGISTRY NUMBER :: 1077-28-7

BEILSTEIN REFERENCE NO. :: 0081853

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C8-H14-O2-S2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 235 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 21,284,1971

Symbol	GHS07
Signal Word	Warning
Hazard Statements	H302
Precautionary Statements	P301 + P312 + P330
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes	Xn: Harmful;
Risk Phrases	R22
Safety Phrases	37/39-26-24/25-36
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	JP1192000
HS Code	2934999090

Precursor 7
CAS#:46236-19-5 methyl 5-(dithi... CAS#:138152-63-3 6,8-Dibromoctan... CAS#:100053-64-3 8-acetylsulfany... CAS#:88987-43-3 5-(2,2-dimethyl...
CAS#:462-20-4 Dihydrolipoic acid CAS#:35444-44-1 methyl adipoyl ... CAS#:104665-85-2 (R)-3-acetylsul...
DownStream 9
CAS#:940-69-2 Lipoamide CAS#:2387-23-7 1,3-Dicyclohexylurea CAS#:458529-20-9 N-(1-adamantane... CAS#:257926-20-8 5-(dithiolan-3-...
CAS#:244007-29-2 6,8-bis(3-phosp... CAS#:462-20-4 Dihydrolipoic acid CAS#:1892-29-1 2,2'-DITHIODIETHANOL CAS#:1200-22-2 lipoic acid
CAS#:111-41-1 2-(2-Aminoethyl...

HS Code	2934999090
Summary	2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Identification and Characterization of EDTA Test Strip Interfering Substances Using a Digital Color Detector.

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Rapid test strips for ethylenediaminetetraacetic acid (EDTA) can be used to verify correct specimen types for clinical assays which require, or cannot be performed on, plasma collection tubes containi...

Alpha-lipoic acid activates eNOS through activation of PI3-kinase/Akt signaling pathway.

Vascul. Pharmacol. 64 , 28-35, (2015)

Lipoic acid (LA) exerts therapeutic effects on cardiovascular diseases. However, the mechanisms underlying these therapeutic effects remain elusive. Endothelial nitric oxide synthase (eNOS) plays a cr...

All-trans retinoic acid prevents oxidative stress-induced loss of renal tight junction proteins in type-1 diabetic model.

J. Nutr. Biochem. 26 , 441-54, (2015)

We previously reported that diabetes decreased the expression of renal tight junction (TJ) proteins claudin-5 in glomerulus, and claudin-2 and occludin in proximal tubule through an oxidative stress d...

(S)-5-(1,2-Dithiolan-3-yl)pentanoic acid

Thioctic acid

5-[(3S)-Dithiolan-3-yl]pentanoic acid

(S)-6,8-Thioctic acid (S)-1,2-Dithiolane-3-pentanoic acid

DL-Thioctic acid

5-(1,2-Dithiolan-3-yl)pentanoic acid

DL-α-Lipoic acid

(±)-α-Lipoic acid

5-(dithiolan-3-yl)pentanoic acid

6,8-Dithiooctanoic acid

MFCD00005474

1,2-Dithiolane-3-pentanoic acid

(±)-1,2-Dithiolane-3-pentanoic acid

(±)-1,2-Dithiolane-3-valeric acid

6,8-Dihydrothioctic acid

lipoic acid

UNII:73Y7P0K73Y

DL-6,8-Thioctic acid

EINECS 214-071-2

α-Lipoic Acid

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China
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China
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China
Product Name: α-Lipoic Acid
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China
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China
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China
Product Name: DL-Thioctic Acid
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α-Lipoic Acid

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