Synonym
Alyssin; 5-Methylsulfinylpentyl isothiocyanate; 5-Methylsulfinylpentyl ITC
IUPAC/Chemical Name
1-isothiocyanato-5-(methylsulfinyl)pentane
InChi Key
IUUQPVQTAUKPPB-UHFFFAOYSA-N
InChi Code
InChI=1S/C7H13NOS2/c1-11(9)6-4-2-3-5-8-7-10/h2-6H2,1H3
SMILES Code
O=S(CCCCCN=C=S)C
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
191.30
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.
| 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 |
1: Pocasap P, Weerapreeyakul N, Thumanu K. Alyssin and Iberin in Cruciferous Vegetables Exert Anticancer Activity in HepG2 by Increasing Intracellular Reactive Oxygen Species and Tubulin Depolymerization. Biomol Ther (Seoul). 2019 Nov 1;27(6):540-552. doi: 10.4062/biomolther.2019.027. PMID: 31405267; PMCID: PMC6824623.
2: Misiewicz I, Skupinska K, Kasprzycka-Guttman T. Differential response of human healthy lymphoblastoid and CCRF-SB leukemia cells to sulforaphane and its two analogues: 2-oxohexyl isothiocyanate and alyssin. Pharmacol Rep. 2007 Jan- Feb;59(1):80-7. PMID: 17377210.
3: Nowicki D, Krause K, Szamborska P, Żukowska A, Cech GM, Szalewska-Pałasz A. Induction of the Stringent Response Underlies the Antimicrobial Action of Aliphatic Isothiocyanates. Front Microbiol. 2021 Jan 14;11:591802. doi: 10.3389/fmicb.2020.591802. PMID: 33584562; PMCID: PMC7874123.
4: Lubelska K, Misiewicz-Krzemińska I, Milczarek M, Krzysztoń-Russjan J, Anuszewska E, Modzelewska K, Wiktorska K. Isothiocyanate-drug interactions in the human adenocarcinoma cell line Caco-2. Mol Cell Biochem. 2012 Aug;367(1-2):19-29. doi: 10.1007/s11010-012-1314-y. Epub 2012 Apr 18. PMID: 22527941.
5: Kim MJ, Kim SH, Lim SJ. Comparison of the apoptosis-inducing capability of sulforaphane analogues in human colon cancer cells. Anticancer Res. 2010 Sep;30(9):3611-9. PMID: 20944144.
6: Fahey JW, Stephenson KK, Wade KL, Talalay P. Urease from Helicobacter pylori is inactivated by sulforaphane and other isothiocyanates. Biochem Biophys Res Commun. 2013 May 24;435(1):1-7. doi: 10.1016/j.bbrc.2013.03.126. Epub 2013 Apr 11. PMID: 23583386; PMCID: PMC4618678.
7: Milczarek M, Mielczarek L, Lubelska K, Dąbrowska A, Chilmonczyk Z, Matosiuk D, Wiktorska K. In Vitro Evaluation of Sulforaphane and a Natural Analog as Potent Inducers of 5-Fluorouracil Anticancer Activity. Molecules. 2018 Nov 21;23(11):3040. doi: 10.3390/molecules23113040. PMID: 30469330; PMCID: PMC6278648.
8: Skupinska K, Misiewicz-Krzeminska I, Stypulkowski R, Lubelska K, Kasprzycka- Guttman T. Sulforaphane and its analogues inhibit CYP1A1 and CYP1A2 activity induced by benzo[a]pyrene. J Biochem Mol Toxicol. 2009 Jan-Feb;23(1):18-28. doi: 10.1002/jbt.20259. PMID: 19202560.
9: Skupinska K, Misiewicz-Krzeminska I, Lubelska K, Kasprzycka-Guttman T. The effect of isothiocyanates on CYP1A1 and CYP1A2 activities induced by polycyclic aromatic hydrocarbons in Mcf7 cells. Toxicol In Vitro. 2009 Aug;23(5):763-71. doi: 10.1016/j.tiv.2009.04.001. Epub 2009 Apr 9. PMID: 19362136.
10: Kim SH, Singh SV. D,L-Sulforaphane causes transcriptional repression of androgen receptor in human prostate cancer cells. Mol Cancer Ther. 2009 Jul;8(7):1946-54. doi: 10.1158/1535-7163.MCT-09-0104. Epub 2009 Jul 7. PMID: 19584240; PMCID: PMC2779717.
