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(S)-Goitrin

CAS# 500-12-9

(S)-Goitrin

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Chemical structure

(S)-Goitrin

3D structure

Chemical Properties of (S)-Goitrin

Cas No. 500-12-9 SDF Download SDF
PubChem ID 7568320.0 Appearance Powder
Formula C5H7NOs M.Wt 129.18
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (5S)-5-ethenyl-1,3-oxazolidine-2-thione
SMILES C=CC1CNC(=S)O1
Standard InChIKey UZQVYLOFLQICCT-BYPYZUCNSA-N
Standard InChI InChI=1S/C5H7NOS/c1-2-4-3-6-5(8)7-4/h2,4H,1,3H2,(H,6,8)/t4-/m0/s1
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.

(S)-Goitrin Dilution Calculator

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(S)-Goitrin Molarity Calculator

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Preparing Stock Solutions of (S)-Goitrin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 7.7411 mL 38.7057 mL 77.4114 mL 154.8227 mL 193.5284 mL
5 mM 1.5482 mL 7.7411 mL 15.4823 mL 30.9645 mL 38.7057 mL
10 mM 0.7741 mL 3.8706 mL 7.7411 mL 15.4823 mL 19.3528 mL
50 mM 0.1548 mL 0.7741 mL 1.5482 mL 3.0965 mL 3.8706 mL
100 mM 0.0774 mL 0.3871 mL 0.7741 mL 1.5482 mL 1.9353 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 (S)-Goitrin

Stereospecific Assay of (R)- and (S)-Goitrin in Commercial Formulation of Radix Isatidis by Reversed Phase High-Performance Liquid Chromatography.[Pubmed:28894621]

J Anal Methods Chem. 2017;2017:2810565.

Radix isatidis (Banlangen) is a widely used traditional Chinese medicine for treating fever and removing toxic heat. Pharmacological studies have indicated that (R)-goitrin (epigoitrin) is one of the main constituents accounting for its antiviral activity, while (S)-Goitrin (goitrin) is known as an antithyroid factor. To better control the quality of radix isatidis and its formulations, it is imperative to enantiomerically determine the contents of R- and S-goitrin. In this study, an enantioselective method based on reversed phase chromatography was developed for the assay of (R, S)-goitrin enantiomers. Optimum separation was obtained on an S-Chiral A column (4.6 mm x 250 mm, 5 mum) using methanol/water (30 : 70, v/v) as the mobile phase. After validation, the method was applied to quantify the enantiomers in Banlangen granules, which is the most prescribed commercial formulation of radix isatidis. Compared to enantioselective resolution approaches based on normal phase chromatography, the new method could be conveniently performed using regular reversed phase high-performance liquid chromatography (RP-HPLC) equipment and was found to be more suitable for the enantioselective quality control of water-extracted and soluble medicines.

Improved Chiral Separation of (R,S)-Goitrin by SFC: An Application in Traditional Chinese Medicine.[Pubmed:27022502]

J Anal Methods Chem. 2016;2016:5782942.

Like chemical drugs, research and development of herbal medicine also have a need to resolve enantiomers. To help illustrating the antiviral bioactivity of Isatidis Radix, a widely used traditional Chinese medicine (TCM), supercritical fluid chromatography (SFC) was used for analytical and preparative separation of (R,S)-goitrin, which was reported as the active ingredient of the herbal. Improved resolution was achieved on Chiralpak IC column, using acetonitrile as the organic modifier, representing a tenfold increase in speed, compared to the previous normal phase HPLC (NPLC) method. The newly developed chromatographic method was validated in terms of linearity, precision, limit of detection (LOD), and limit of quantitation (LOQ). Scale-up purification of (R)-goitrin and (S)-Goitrin was performed on a preparative column with >90% total recovery. The absolute stereochemical assignment of the purified isomers was determined through optical rotation study. This attempt explored SFC's application in chiral research of traditional Chinese medicine.

Biotransformation of glucosinolates epiprogoitrin and progoitrin to (R)- and (S)-Goitrin in Radix isatidis.[Pubmed:22023255]

J Agric Food Chem. 2011 Dec 14;59(23):12467-72.

Radix isatidis is an important traditional Chinese medicine with antiviral efficacy. (R)- and (S)-Goitrin are its main bioactive constituents in the 2010 edition of the Chinese Pharmacopoeia. (R)- and (S)-Goitrin are the breakdown products of epiprogoitrin and progoitrin from R. isatidis. The biotransformation of glucosinolates epiprogoitrin and progoitrin to (R)- and (S)-Goitrin, however, is still unclear. In the current paper, the biotransformation of glucosinolates was studied. First, the high-performance liquid chromatography methods to analyze glucosinolates and their breakdown products were developed. Then, the biotransformation of individual glucosinolates such as epiprogoitrin and progoitrin was investigated under different pH conditions. Lastly, their biotransformation under five extraction environments was studied. The results showed that (R)- and (S)-Goitrin were the most noteworthy breakdown products. Their relative transformation rates were about 70-80%, and the influence of different extraction environments on the transformation rate was not significant. These results would serve as a theoretical basis for industrial production and quality control and would be helpful for further studies on the biotransformation of glucosinolates.

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