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MedKoo Cat#: 540121 | Name: Erucin
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Description:

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

Erucin is a sulforaphane analog and telomerase inhibitor found in cruciferous vegtables. It induces phase II enzyme activity, suppresses cellular proliferation in hepatocellular carcinoma cells, prevents 6-OHDA-induced neurodegenration, and inhibits LPS-stimulated pro inflammatory cytokine expression in vivo.

Chemical Structure

Erucin
Erucin
CAS#4430-36-8

Theoretical Analysis

MedKoo Cat#: 540121

Name: Erucin

CAS#: 4430-36-8

Chemical Formula: C6H11NS2

Exact Mass: 161.0333

Molecular Weight: 161.28

Elemental Analysis: C, 44.68; H, 6.87; N, 8.68; S, 39.76

Price and Availability

Size Price Availability Quantity
50mg USD 450.00 2 weeks
250mg USD 1,450.00 2 weeks
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Synonym
Erucin; ERU; MTBITC;
IUPAC/Chemical Name
(4-isothiocyanatobutyl)(methyl)sulfane
InChi Key
IHQDGXUYTSZGOG-UHFFFAOYSA-N
InChi Code
InChI=1S/C6H11NS2/c1-9-5-3-2-4-7-6-8/h2-5H2,1H3
SMILES Code
CSCCCCN=C=S
Appearance
Liquid
Purity
>98% (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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
An isothiocyanate with neuroprotective and antioxidant effects.
In vitro activity:
The administration of HG-induced apoptosis both in HASMCs and HUVECs. In HASMCs, HG evoked an increase in the fluorescence index (FI) linked to the caspase 3/7 activity by 26.88 ± 7.94% compared to vehicle-treated cells. Pre-incubation of erucin prevented this change, particularly at the top concentration used (% increase vs. vehicle-treated cells in: erucin 0.3 µM + HG-treated cells: 19.41 ± 2.33; erucin 1 µM + HG-treated cells: 20.64 ± 1.83; erucin 3 µM + HG-treated cells: 5.24 ± 4.22) (Figure 3a). In HUVECs, exposure to HG induced a significant increase in caspase 3/7 activation by 15.96 ± 1.95% vs. the vehicle-treated cells, while this effect was fully inhibited by the pre-incubation with erucin 3 µM (Figure 3b). Reference: Antioxidants (Basel). 2021 Jun; 10(6): 961. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8232611/
In vivo activity:
Erucin was able to protect the rats against DMBA-induced histopathological changes in the lungs and stomach. No changes were observed in the kidney following treatment with DMBA or erucin. Reference: Turk Patoloji Derg. 2017;33(2):150-156. https://pubmed.ncbi.nlm.nih.gov/28272652/
Solvent mg/mL mM
Solubility
DMSO 14.0 86.81
DMF 12.0 74.40
Ethanol 16.0 99.21
Ethanol:PBS (pH 7.2) (1:50) 0.0 0.12
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 161.28 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:
1. Martelli A, Piragine E, Gorica E, Citi V, Testai L, Pagnotta E, Lazzeri L, Pecchioni N, Ciccone V, Montanaro R, Di Cesare Mannelli L, Ghelardini C, Brancaleone V, Morbidelli L, Calderone V. The H2S-Donor Erucin Exhibits Protective Effects against Vascular Inflammation in Human Endothelial and Smooth Muscle Cells. Antioxidants (Basel). 2021 Jun 15;10(6):961. doi: 10.3390/antiox10060961. PMID: 34203803; PMCID: PMC8232611. 2. Citi V, Piragine E, Pagnotta E, Ugolini L, Di Cesare Mannelli L, Testai L, Ghelardini C, Lazzeri L, Calderone V, Martelli A. Anticancer properties of erucin, an H2 S-releasing isothiocyanate, on human pancreatic adenocarcinoma cells (AsPC-1). Phytother Res. 2019 Mar;33(3):845-855. doi: 10.1002/ptr.6278. Epub 2019 Jan 10. PMID: 30632211. 3. Mannan R, Arora R, Bhushan S, Sharma S, Bhasin T, Arora S. Bioprotective Efficacy of Erucin Against 7,12-Dimethylbenz(α)anthracene-Induced Microstructural Changes in Male Wistar Rats. Turk Patoloji Derg. 2017;33(2):150-156. English. doi: 10.5146/tjpath.2016.01381. PMID: 28272652. 4. Herz C, Hertrampf A, Zimmermann S, Stetter N, Wagner M, Kleinhans C, Erlacher M, Schüler J, Platz S, Rohn S, Mersch-Sundermann V, Lamy E. The isothiocyanate erucin abrogates telomerase in hepatocellular carcinoma cells in vitro and in an orthotopic xenograft tumour model of HCC. J Cell Mol Med. 2014 Dec;18(12):2393-403. doi: 10.1111/jcmm.12412. Epub 2014 Sep 25. PMID: 25256442; PMCID: PMC4302645.
In vitro protocol:
1. Martelli A, Piragine E, Gorica E, Citi V, Testai L, Pagnotta E, Lazzeri L, Pecchioni N, Ciccone V, Montanaro R, Di Cesare Mannelli L, Ghelardini C, Brancaleone V, Morbidelli L, Calderone V. The H2S-Donor Erucin Exhibits Protective Effects against Vascular Inflammation in Human Endothelial and Smooth Muscle Cells. Antioxidants (Basel). 2021 Jun 15;10(6):961. doi: 10.3390/antiox10060961. PMID: 34203803; PMCID: PMC8232611. 2. Citi V, Piragine E, Pagnotta E, Ugolini L, Di Cesare Mannelli L, Testai L, Ghelardini C, Lazzeri L, Calderone V, Martelli A. Anticancer properties of erucin, an H2 S-releasing isothiocyanate, on human pancreatic adenocarcinoma cells (AsPC-1). Phytother Res. 2019 Mar;33(3):845-855. doi: 10.1002/ptr.6278. Epub 2019 Jan 10. PMID: 30632211.
In vivo protocol:
1. Mannan R, Arora R, Bhushan S, Sharma S, Bhasin T, Arora S. Bioprotective Efficacy of Erucin Against 7,12-Dimethylbenz(α)anthracene-Induced Microstructural Changes in Male Wistar Rats. Turk Patoloji Derg. 2017;33(2):150-156. English. doi: 10.5146/tjpath.2016.01381. PMID: 28272652. 2. Herz C, Hertrampf A, Zimmermann S, Stetter N, Wagner M, Kleinhans C, Erlacher M, Schüler J, Platz S, Rohn S, Mersch-Sundermann V, Lamy E. The isothiocyanate erucin abrogates telomerase in hepatocellular carcinoma cells in vitro and in an orthotopic xenograft tumour model of HCC. J Cell Mol Med. 2014 Dec;18(12):2393-403. doi: 10.1111/jcmm.12412. Epub 2014 Sep 25. PMID: 25256442; PMCID: PMC4302645.
1: Martelli A, Piragine E, Citi V, Testai L, Pagnotta E, Ugolini L, Lazzeri L, Di Cesare Mannelli L, Manzo OL, Bucci M, Ghelardini C, Breschi MC, Calderone V. Erucin exhibits vasorelaxing effects and antihypertensive activity by H2 S-releasing properties. Br J Pharmacol. 2020 Feb;177(4):824-835. doi: 10.1111/bph.14645. Epub 2019 Apr 15. PMID: 30825379; PMCID: PMC7024703. 2: Mashhoor MV, Moharramipour S, Mikani A, Mehrabadi M. Erucin modulates digestive enzyme release via crustacean cardioactive peptide in the elm leaf beetle Xanthogaleruca luteola (Coleoptera: Chrysomelidae). J Insect Physiol. 2021 Apr;130:104196. doi: 10.1016/j.jinsphys.2021.104196. Epub 2021 Feb 2. PMID: 33545106. 3: Melchini A, Traka MH. Biological profile of erucin: a new promising anticancer agent from cruciferous vegetables. Toxins (Basel). 2010 Apr;2(4):593-612. doi: 10.3390/toxins2040593. Epub 2010 Apr 5. PMID: 22069601; PMCID: PMC3153205. 4: Guerreiro Í, Vidovic B, Costa JG, Martins M, Ferreira S, Oliveira NG, Saraiva N, Fernandes AS. The Dietary Isothiocyanate Erucin Reduces Kidney Cell Motility by Disturbing Tubulin Polymerization. Mol Nutr Food Res. 2023 Feb;67(3):e2200581. doi: 10.1002/mnfr.202200581. Epub 2022 Dec 15. PMID: 36415106; PMCID: PMC10077903. 5: Ciccone V, Piragine E, Gorica E, Citi V, Testai L, Pagnotta E, Matteo R, Pecchioni N, Montanaro R, Di Cesare Mannelli L, Ghelardini C, Brancaleone V, Morbidelli L, Calderone V, Martelli A. Anti-Inflammatory Effect of the Natural H2S-Donor Erucin in Vascular Endothelium. Int J Mol Sci. 2022 Dec 9;23(24):15593. doi: 10.3390/ijms232415593. PMID: 36555238; PMCID: PMC9778978. 6: Martelli A, Piragine E, Gorica E, Citi V, Testai L, Pagnotta E, Lazzeri L, Pecchioni N, Ciccone V, Montanaro R, Di Cesare Mannelli L, Ghelardini C, Brancaleone V, Morbidelli L, Calderone V. The H2S-Donor Erucin Exhibits Protective Effects against Vascular Inflammation in Human Endothelial and Smooth Muscle Cells. Antioxidants (Basel). 2021 Jun 15;10(6):961. doi: 10.3390/antiox10060961. PMID: 34203803; PMCID: PMC8232611. 7: Takagi T, Inoue H, Fujii S, Takahashi N, Uehara M. Erucin inhibits osteoclast formation via suppressing cell-cell fusion molecule DC-STAMP without influencing mineralization by osteoblasts. BMC Res Notes. 2022 Mar 16;15(1):105. doi: 10.1186/s13104-022-05988-3. PMID: 35296341; PMCID: PMC8925049. 8: Azarenko O, Jordan MA, Wilson L. Erucin, the major isothiocyanate in arugula (Eruca sativa), inhibits proliferation of MCF7 tumor cells by suppressing microtubule dynamics. PLoS One. 2014 Jun 20;9(6):e100599. doi: 10.1371/journal.pone.0100599. PMID: 24950293; PMCID: PMC4065051. 9: Shimoyama M, Hosokawa Y, Hosokawa I, Ozaki K, Hosaka K. Effects of erucin on inflammatory mediators and antioxidant enzymes' expression in TNF-α-stimulated human oral epithelial cells. Immunopharmacol Immunotoxicol. 2023 Aug 30:1-6. doi: 10.1080/08923973.2023.2250551. Epub ahead of print. PMID: 37624680. 10: Bello I, Smimmo M, d'Emmanuele di Villa Bianca R, Bucci M, Cirino G, Panza E, Brancaleone V. Erucin, an H2S-Releasing Isothiocyanate, Exerts Anticancer Effects in Human Triple-Negative Breast Cancer Cells Triggering Autophagy-Dependent Apoptotic Cell Death. Int J Mol Sci. 2023 Apr 5;24(7):6764. doi: 10.3390/ijms24076764. PMID: 37047736; PMCID: PMC10095418. 11: Cho HJ, Lee KW, Park JH. Erucin exerts anti-inflammatory properties in murine macrophages and mouse skin: possible mediation through the inhibition of NFκB signaling. Int J Mol Sci. 2013 Oct 15;14(10):20564-77. doi: 10.3390/ijms141020564. PMID: 24132147; PMCID: PMC3821631. 12: Abbaoui B, Lucas CR, Riedl KM, Clinton SK, Mortazavi A. Cruciferous Vegetables, Isothiocyanates, and Bladder Cancer Prevention. Mol Nutr Food Res. 2018 Sep;62(18):e1800079. doi: 10.1002/mnfr.201800079. Epub 2018 Aug 29. PMID: 30079608; PMCID: PMC6196731. 13: Lv C, Zhang Y, Zou L, Sun J, Song X, Mao J, Wu Y. Simultaneous Hydrolysis and Extraction Increased Erucin Yield from Broccoli Seeds. ACS Omega. 2021 Feb 22;6(9):6385-6392. doi: 10.1021/acsomega.0c06319. PMID: 33718729; PMCID: PMC7948436. 14: Mannan R, Arora R, Bhushan S, Sharma S, Bhasin T, Arora S. Bioprotective Efficacy of Erucin Against 7,12-Dimethylbenz(α)anthracene-Induced Microstructural Changes in Male Wistar Rats. Turk Patoloji Derg. 2017;33(2):150-156. English. doi: 10.5146/tjpath.2016.01381. PMID: 28272652. 15: Gründemann C, Garcia-Käufer M, Lamy E, Hanschen FS, Huber R. 4-Methylthiobutyl isothiocyanate (Erucin) from rocket plant dichotomously affects the activity of human immunocompetent cells. Phytomedicine. 2015 Mar 15;22(3):369-78. doi: 10.1016/j.phymed.2014.12.012. Epub 2015 Jan 28. PMID: 25837274. 16: Hu X, Xiao Y, Sun J, Ji B, Luo S, Wu B, Zheng C, Wang P, Xu F, Cheng K, Hua H, Li D. New possible silver lining for pancreatic cancer therapy: Hydrogen sulfide and its donors. Acta Pharm Sin B. 2021 May;11(5):1148-1157. doi: 10.1016/j.apsb.2020.10.019. Epub 2020 Oct 31. PMID: 34094825; PMCID: PMC8144891. 17: Maresca DC, Conte L, Romano B, Ianaro A, Ercolano G. Antiproliferative and Proapoptotic Effects of Erucin, a Diet-Derived H2S Donor, on Human Melanoma Cells. Antioxidants (Basel). 2022 Dec 26;12(1):41. doi: 10.3390/antiox12010041. PMID: 36670903; PMCID: PMC9854590. 18: 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. doi: 10.1021/jf048153j. PMID: 15740016. 19: Lamy E, Oey D, Eißmann F, Herz C, Münstedt K, Tinneberg HR, Mersch- Sundermann V. Erucin and benzyl isothiocyanate suppress growth of late stage primary human ovarian carcinoma cells and telomerase activity in vitro. Phytother Res. 2013 Jul;27(7):1036-41. doi: 10.1002/ptr.4798. Epub 2012 Sep 5. PMID: 22949403. 20: Kaur H, Kaur K, Singh A, Bedi N, Singh B, Alturki MS, Aldawsari MF, Almalki AH, Haque S, Lee HJ, Yadav DK, Arora S. Frankincense oil-loaded nanoemulsion formulation of paclitaxel and erucin: A synergistic combination for ameliorating drug resistance in breast cancer: In vitro and in vivo study. Front Pharmacol. 2022 Oct 18;13:1020602. doi: 10.3389/fphar.2022.1020602. PMID: 36330087; PMCID: PMC9623270.