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beta-Lipoic acid

CAS# 6992-30-9

beta-Lipoic acid

2D Structure

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beta-Lipoic acid

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Chemical Properties of beta-Lipoic acid

Cas No. 6992-30-9 SDF Download SDF
PubChem ID 5319044 Appearance Powder
Formula C8H14O3S2 M.Wt 222.32
Type of Compound Miscellaneous Storage Desiccate at -20°C
Synonyms Protogen-B;5-(1-oxodithiolan-3-yl)pentanoic acid
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 5-(1-oxodithiolan-3-yl)pentanoic acid
SMILES C1CS(=O)SC1CCCCC(=O)O
Standard InChIKey HRIQWEOKIFSCBV-UHFFFAOYSA-N
Standard InChI InChI=1S/C8H14O3S2/c9-8(10)4-2-1-3-7-5-6-13(11)12-7/h7H,1-6H2,(H,9,10)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

beta-Lipoic acid Dilution Calculator

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beta-Lipoic acid Molarity Calculator

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Preparing Stock Solutions of beta-Lipoic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.498 mL 22.4901 mL 44.9802 mL 89.9604 mL 112.4505 mL
5 mM 0.8996 mL 4.498 mL 8.996 mL 17.9921 mL 22.4901 mL
10 mM 0.4498 mL 2.249 mL 4.498 mL 8.996 mL 11.2451 mL
50 mM 0.09 mL 0.4498 mL 0.8996 mL 1.7992 mL 2.249 mL
100 mM 0.045 mL 0.2249 mL 0.4498 mL 0.8996 mL 1.1245 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on beta-Lipoic acid

Lipoic acid favors thiolsulfinate formation after hypochlorous acid scavenging: a study with lipoic acid derivatives.[Pubmed:8031117]

Arch Biochem Biophys. 1994 Jul;312(1):114-20.

Lipoic acid, the oxidized form of 6,8-dimercapto-octanoic acid has a strained cyclic disulfide in a 1,2-dithiolane ring. Recently its antioxidant activity gained attention. Hypochlorous acid (HOCl) is an oxidant produced by neutrophils. A prominent effect of HOCl is the inactivation of alpha-1-antiproteinase. Due to this inactivation, the ability of alpha-1-antiproteinase to inhibit elastase is lost. The resulting higher activity of elastase is held responsible for tissue damage in lung emphysema. We studied the HOCl scavenging capability of three metabolites of lipoic acid: tetranor-, bisnor-, and beta-Lipoic acid. To obtain some insight on the molecular basis of HOCl scavenging 1,2-dithiane-4,5-diol, cystine, lipoic acid methyl ester, and lipoamide were also included in the study. The extent of alpha-1-antiproteinase inactivation by HOCl in the presence of scavenger was taken as a parameter to quantify the scavenging activity. It was found that lipoic acid, tetranor- and bisnorlipoic acid, lipoic acid methyl ester, and lipoamide all showed the same activity toward HOCl. beta-Lipoic acid, 1,2-dithiane-4,5-diol and cystine were less active. The products of lipoic acid after reaction with HOCl were studied using GC/MS. Indications for thiolsulfinate formation were found by comparing these products with the GC/MS profile of beta-Lipoic acid. Thiolsulfinate formation may also be suggested in the reaction of tetranor- and bisnorlipoic acid and lipoic acid methyl ester with HOCl. The present results show an antioxidant activity of the metabolites tetranor- and bisnorlipoic acid. The 1,2-dithiolane ring may enhance the reactivity toward HOCl compared to less strained disulfides, resulting in the formation a thiolsulfinate.

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