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Sinigrin monohydrate

CAS# 64550-88-5

Sinigrin monohydrate

Catalog No. BCN2595----Order now to get a substantial discount!

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Quality Control of Sinigrin monohydrate

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Chemical structure

Sinigrin monohydrate

3D structure

Chemical Properties of Sinigrin monohydrate

Cas No. 64550-88-5 SDF Download SDF
PubChem ID 23670774 Appearance Powder
Formula C10H18KNO10S2 M.Wt 415.5
Type of Compound Miscellaneous Storage Desiccate at -20°C
Synonyms (-)-Sinigrin,monohydrate
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name potassium;[(Z)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylbut-3-enylideneamino] sulfate;hydrate
SMILES C=CCC(=NOS(=O)(=O)[O-])SC1C(C(C(C(O1)CO)O)O)O.O.[K+]
Standard InChIKey IUBVMJHASFBYGW-YEIBXKIESA-M
Standard InChI InChI=1S/C10H17NO9S2.K.H2O/c1-2-3-6(11-20-22(16,17)18)21-10-9(15)8(14)7(13)5(4-12)19-10;;/h2,5,7-10,12-15H,1,3-4H2,(H,16,17,18);;1H2/q;+1;/p-1/b11-6-;;/t5-,7-,8+,9-,10+;;/m1../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.

Source of Sinigrin monohydrate

The seeds of Lepidium apetalum

Biological Activity of Sinigrin monohydrate

DescriptionSinigrin has antimicrobial activity. Sinigrin also exerts important anti-proliferative activities in carcinogen-induced hepatocarcinogenesis in rats.
Targetsp53 | Bcl-2/Bax | Caspase | Antifection
In vitro

Use of a nanoparticulate carboxymethyl cellulose film containing sinigrin as an antimicrobial precursor to kill Escherichia coli O157:H7 on fresh beef.[Pubmed: 25976711]

Lett Appl Microbiol. 2015 May 15.


METHODS AND RESULTS:
Nanocomposite carboxymethyl cellulose films containing Sinigrin (SNG) were prepared by stirring 2% (w/v) carboxymethyl cellulose (CMC) and 2% (w/v) glycerol (as a plasticizer) in distilled water with or without SNG (an antimicrobial precursor) as a 99% pure reagent (pSNG) or as a crude extract (cSNG). These films plus normal CMC film with or without SNG were tested on Escherichia coli O157:H7- inoculated beef for antimicrobial activity. Beef pieces measuring 6 × 5 × 2 cm(3) (L × W × H) were dipped in an E. coli O157:H7 broth suspension containing >8 log10 CFU ml(-1) and were drained for 3 min over a sterile cloth. They were wrapped in CMC or NCMC films, placed in a high oxygen barrier film (Deli *1), vacuum-packaged and stored at 8°C for 5, 8, 12 and 18 days.
CONCLUSIONS:
The CMC and NCMC films without SNG were not antimicrobial against E. coli O157:H7; however, NCMC and CMC films with SNG were highly antimicrobial. After 5 days at 8°C, E. coli O157:H7 was reduced more than 4 log10 by the NCMC•pSNG film and this reduction remained almost the same until 18 days at 8°C when E. coli O157:H7 was reduced >5 log10 CFU g(-1) meat.

In vivo

Anti-proliferative activities of sinigrin on carcinogen-induced hepatotoxicity in rats.[Pubmed: 25329483]

PLoS One. 2014 Oct 20;9(10):e110145.

Liver cancer is one of the leading causes of cancer death worldwide. A very high incidence of new liver cancer cases is diagnosed every year, and metastasis has been found to correlate to poor prognoses in humans. Better treatments for liver cancer are thus clearly needed. Sinigrin is one of the major ingredients present in Brassica nigra, which has been used in combination with other herbs for treatment of various diseases.
METHODS AND RESULTS:
The anti-proliferative activities of Sinigrin were studied in a model of carcinogen-induced hepatotoxicity in rats. Rats were orally administered with Sinigrin on a daily basis for three months before sacrifice. Sinigrin was found to significantly inhibit the proliferation of liver tumor cells; the number of surface tumors in the rat liver was dramatically reduced. Sinigrin induced apoptosis of liver cancer cells through up-regulation of p53 and down-regulation of Bcl-2 family members and caspases. Our findings indicated that the liver functions were gradually restored after treatment with Sinigrin and that the agent did not cause liver toxicity. Cell cycle analysis indicated that Sinigrin caused cell cycle arrest in G0/G1 phase.
CONCLUSIONS:
The results suggest that Sinigrin exerts important anti-proliferative activities in carcinogen-induced hepatocarcinogenesis in rats, and highlight the potential of Sinigrin as an anti-cancer agent for liver cancer.

Sinigrin monohydrate Dilution Calculator

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Sinigrin monohydrate Molarity Calculator

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Preparing Stock Solutions of Sinigrin monohydrate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.4067 mL 12.0337 mL 24.0674 mL 48.1348 mL 60.1685 mL
5 mM 0.4813 mL 2.4067 mL 4.8135 mL 9.627 mL 12.0337 mL
10 mM 0.2407 mL 1.2034 mL 2.4067 mL 4.8135 mL 6.0168 mL
50 mM 0.0481 mL 0.2407 mL 0.4813 mL 0.9627 mL 1.2034 mL
100 mM 0.0241 mL 0.1203 mL 0.2407 mL 0.4813 mL 0.6017 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 Sinigrin monohydrate

Use of a nanoparticulate carboxymethyl cellulose film containing sinigrin as an antimicrobial precursor to kill Escherichia coli O157:H7 on fresh beef.[Pubmed:25976711]

Lett Appl Microbiol. 2015 Aug;61(2):139-45.

UNLABELLED: Nanocomposite carboxymethyl cellulose films containing sinigrin (SNG) were prepared by stirring 2% (w/v) carboxymethyl cellulose (CMC) and 2% (w/v) glycerol (as a plasticizer) in distilled water with or without SNG (an antimicrobial precursor) as a 99% pure reagent (pSNG) or as a crude extract (cSNG). These films plus normal CMC film with or without SNG were tested on Escherichia coli O157:H7- inoculated beef for antimicrobial activity. Beef pieces measuring 6 x 5 x 2 cm(3) (L x W x H) were dipped in an E. coli O157:H7 broth suspension containing >8 log10 CFU ml(-1) and were drained for 3 min over a sterile cloth. They were wrapped in CMC or NCMC films, placed in a high oxygen barrier film (Deli *1), vacuum-packaged and stored at 8 degrees C for 5, 8, 12 and 18 days. The CMC and NCMC films without SNG were not antimicrobial against E. coli O157:H7; however, NCMC and CMC films with SNG were highly antimicrobial. After 5 days at 8 degrees C, E. coli O157:H7 was reduced more than 4 log10 by the NCMC*pSNG film and this reduction remained almost the same until 18 days at 8 degrees C when E. coli O157:H7 was reduced >5 log10 CFU g(-1) meat. SIGNIFICANCE AND IMPACT OF THE STUDY: Transparent nanoparticulate carboxymethyl cellulose (CMC) films containing sinigrin (SNG), an antimicrobial precursor, controlled surface contamination of packaged fresh beef by the pathogen Escherichia coli O157:H7 when stored at 8 degrees C. Films with nanoparticulation that carried pure SNG or the naturally occurring SNG in Oriental mustard were significantly more antimicrobial than similar films without nanoparticulation. As films without sinigrin were not antimicrobial, the combinations studied showed that nanoparticulation of the packaging film enhanced delivery of the antimicrobial incorporated within the film.

Anti-proliferative activities of sinigrin on carcinogen-induced hepatotoxicity in rats.[Pubmed:25329483]

PLoS One. 2014 Oct 20;9(10):e110145.

Liver cancer is one of the leading causes of cancer death worldwide. A very high incidence of new liver cancer cases is diagnosed every year, and metastasis has been found to correlate to poor prognoses in humans. Better treatments for liver cancer are thus clearly needed. Sinigrin is one of the major ingredients present in Brassica nigra, which has been used in combination with other herbs for treatment of various diseases. The anti-proliferative activities of sinigrin were studied in a model of carcinogen-induced hepatotoxicity in rats. Rats were orally administered with sinigrin on a daily basis for three months before sacrifice. Sinigrin was found to significantly inhibit the proliferation of liver tumor cells; the number of surface tumors in the rat liver was dramatically reduced. Sinigrin induced apoptosis of liver cancer cells through up-regulation of p53 and down-regulation of Bcl-2 family members and caspases. Our findings indicated that the liver functions were gradually restored after treatment with sinigrin and that the agent did not cause liver toxicity. Cell cycle analysis indicated that sinigrin caused cell cycle arrest in G0/G1 phase. The results suggest that sinigrin exerts important anti-proliferative activities in carcinogen-induced hepatocarcinogenesis in rats, and highlight the potential of sinigrin as an anti-cancer agent for liver cancer.

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