Iberin
featured

    WARNING: This product is for research use only, not for human or veterinary use.

Hodoodo CAT#: H540215

CAS#: 505-44-2

Description: Iberin is a sulforaphane homolog and antioxidant. It induces phase II enzyme activity and suppresses CDK expression, inducing apoptosis in cancer cells.

Chemical Structure

img
Iberin
CAS# 505-44-2
Instruction

Theoretical Analysis

Hodoodo Cat#: H540215
Name: Iberin
CAS#: 505-44-2
Chemical Formula: C5H9NOS2
Exact Mass: 163.01
Molecular Weight: 163.253
Elemental Analysis: C, 36.79; H, 5.56; N, 8.58; O, 9.80; S, 39.28

Price and Availability

Size Price Availability Quantity
5mg USD 350 2 Weeks
10mg USD 600 2 Weeks
Bulk inquiry

Synonym: 1-Isothiocyanato-3-(methylsulfinyl)propane; 3-Methylsulfinylpropyl isothiocyanate; 3-Methylsulphinylpropylisothiocyanate; Iberin

IUPAC/Chemical Name: 1-isothiocyanato-3-(methylsulfinyl)propane

InChi Key: LELAOEBVZLPXAZ-UHFFFAOYSA-N

InChi Code: InChI=1S/C5H9NOS2/c1-9(7)4-2-3-6-5-8/h2-4H2,1H3

SMILES Code: S=C=NCCCS(C)=O

Appearance: A solution in ethanol

Purity: >95% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 163.25 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Tan SY, Liu Y, Chua SL, Vejborg RM, Jakobsen TH, Chew SC, Li Y, Nielsen TE, Tolker-Nielsen T, Yang L, Givskov M. Comparative systems biology analysis to study the mode of action of the isothiocyanate compound Iberin on Pseudomonas aeruginosa. Antimicrob Agents Chemother. 2014 Nov;58(11):6648-59. doi: 10.1128/AAC.02620-13. Epub 2014 Aug 25. PubMed PMID: 25155599; PubMed Central PMCID: PMC4249438.

2: Ernst IM, Palani K, Esatbeyoglu T, Schwarz K, Rimbach G. Synthesis and Nrf2-inducing activity of the isothiocyanates iberverin, iberin and cheirolin. Pharmacol Res. 2013 Apr;70(1):155-62. doi: 10.1016/j.phrs.2013.01.011. Epub 2013 Feb 9. PubMed PMID: 23403058.

3: Jakobsen TH, Bragason SK, Phipps RK, Christensen LD, van Gennip M, Alhede M, Skindersoe M, Larsen TO, Høiby N, Bjarnsholt T, Givskov M. Food as a source for quorum sensing inhibitors: iberin from horseradish revealed as a quorum sensing inhibitor of Pseudomonas aeruginosa. Appl Environ Microbiol. 2012 Apr;78(7):2410-21. doi: 10.1128/AEM.05992-11. Epub 2012 Jan 27. PubMed PMID: 22286987; PubMed Central PMCID: PMC3302586.

4: Traka MH, Chambers KF, Lund EK, Goodlad RA, Johnson IT, Mithen RF. Involvement of KLF4 in sulforaphane- and iberin-mediated induction of p21(waf1/cip1). Nutr Cancer. 2009;61(1):137-45. doi: 10.1080/01635580802348641. PubMed PMID: 19116884.

5: Jadhav U, Ezhilarasan R, Vaughn SF, Berhow MA, Mohanam S. Iberin induces cell cycle arrest and apoptosis in human neuroblastoma cells. Int J Mol Med. 2007 Mar;19(3):353-61. PubMed PMID: 17273780; PubMed Central PMCID: PMC2435066.

6: Jadhav U, Ezhilarasan R, Vaughn SF, Berhow MA, Mohanam S. Dietary isothiocyanate iberin inhibits growth and induces apoptosis in human glioblastoma cells. J Pharmacol Sci. 2007 Feb;103(2):247-51. PubMed PMID: 17310076.

7: Shibata T, Nakashima F, Honda K, Lu YJ, Kondo T, Ushida Y, Aizawa K, Suganuma H, Oe S, Tanaka H, Takahashi T, Uchida K. Toll-like receptors as a target of food-derived anti-inflammatory compounds. J Biol Chem. 2014 Nov 21;289(47):32757-72. doi: 10.1074/jbc.M114.585901. Epub 2014 Oct 7. PubMed PMID: 25294874; PubMed Central PMCID: PMC4239626.

8: Wang W, Wang S, Howie AF, Beckett GJ, Mithen R, Bao Y. Sulforaphane, erucin, and iberin up-regulate thioredoxin reductase 1 expression in human MCF-7 cells. J Agric Food Chem. 2005 Mar 9;53(5):1417-21. PubMed PMID: 15740016.

9: Chambers KF, Bacon JR, Kemsley EK, Mills RD, Ball RY, Mithen RF, Traka MH. Gene expression profile of primary prostate epithelial and stromal cells in response to sulforaphane or iberin exposure. Prostate. 2009 Sep 15;69(13):1411-21. doi: 10.1002/pros.20986. PubMed PMID: 19489030.

10: Al Janobi AA, Mithen RF, Gasper AV, Shaw PN, Middleton RJ, Ortori CA, Barrett DA. Quantitative measurement of sulforaphane, iberin and their mercapturic acid pathway metabolites in human plasma and urine using liquid chromatography-tandem electrospray ionisation mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Dec 5;844(2):223-34. Epub 2006 Aug 23. PubMed PMID: 16931178.

11: Luang-In V, Narbad A, Nueno-Palop C, Mithen R, Bennett M, Rossiter JT. The metabolism of methylsulfinylalkyl- and methylthioalkyl-glucosinolates by a selection of human gut bacteria. Mol Nutr Food Res. 2014 Apr;58(4):875-83. doi: 10.1002/mnfr.201300377. Epub 2013 Oct 30. PubMed PMID: 24170324.

12: Jakubikova J, Bao Y, Bodo J, Sedlak J. Isothiocyanate iberin modulates phase II enzymes, posttranslational modification of histones and inhibits growth of Caco-2 cells by inducing apoptosis. Neoplasma. 2006;53(6):463-70. PubMed PMID: 17167713.

13: Wang N, Wang W, Liu C, Jin J, Shao B, Shen L. Inhibition of growth and induction of apoptosis in A549 cells by compounds from oxheart cabbage extract. J Sci Food Agric. 2016 Aug;96(11):3813-20. doi: 10.1002/jsfa.7575. Epub 2016 Feb 16. PubMed PMID: 26679410.

14: Oliviero T, Verkerk R, Vermeulen M, Dekker M. In vivo formation and bioavailability of isothiocyanates from glucosinolates in broccoli as affected by processing conditions. Mol Nutr Food Res. 2014 Jul;58(7):1447-56. doi: 10.1002/mnfr.201300894. Epub 2014 Mar 31. PubMed PMID: 24687744.

15: Slaby O, Sachlova M, Brezkova V, Hezova R, Kovarikova A, Bischofová S, Sevcikova S, Bienertova-Vasku J, Vasku A, Svoboda M, Vyzula R. Identification of microRNAs regulated by isothiocyanates and association of polymorphisms inside their target sites with risk of sporadic colorectal cancer. Nutr Cancer. 2013;65(2):247-54. doi: 10.1080/01635581.2013.756530. PubMed PMID: 23441612.

16: Wilson EA, Ennahar S, Marchioni E, Bergaentzlé M, Bindler F. Improvement in determination of isothiocyanates using high-temperature reversed-phase HPLC. J Sep Sci. 2012 Aug;35(16):2026-31. doi: 10.1002/jssc.201200071. Epub 2012 Jul 2. PubMed PMID: 22752995.

17: Ko MO, Kim MB, Lim SB. Relationship between Chemical Structure and Antimicrobial Activities of Isothiocyanates from Cruciferous Vegetables against Oral Pathogens. J Microbiol Biotechnol. 2016 Dec 28;26(12):2036-2042. doi: 10.4014/jmb.1606.06008. PubMed PMID: 27586534.

18: Steverding D, Michaels S, Read KD. In vitro and in vivo studies of trypanocidal activity of dietary isothiocyanates. Planta Med. 2014 Feb;80(2-3):183-6. doi: 10.1055/s-0033-1360262. Epub 2014 Jan 22. PubMed PMID: 24452460.

19: Barrera LN, Johnson IT, Bao Y, Cassidy A, Belshaw NJ. Colorectal cancer cells Caco-2 and HCT116 resist epigenetic effects of isothiocyanates and selenium in vitro. Eur J Nutr. 2013 Jun;52(4):1327-41. doi: 10.1007/s00394-012-0442-1. Epub 2012 Aug 26. PubMed PMID: 22923034.

20: Li D, Wu K, Howie AF, Beckett GJ, Wang W, Bao Y. Synergy between broccoli sprout extract and selenium in the upregulation of thioredoxin reductase in human hepatocytes. Food Chem. 2008 Sep 1;110(1):193-8. doi: 10.1016/j.foodchem.2008.01.032. Epub 2008 Feb 1. PubMed PMID: 26050183.