Benzyl isothiocyanate

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

MedKoo CAT#: 571298

CAS#: 622-78-6

Description: Benzyl isothiocyanate is an antineoplastic that inhibits carcinogen-induced neoplasia and also promotes urinary bladder carcinoma. It also suppresses growth of mammary tumor progression.

Chemical Structure

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Benzyl isothiocyanate
CAS# 622-78-6
Instruction

Theoretical Analysis

MedKoo Cat#: 571298
Name: Benzyl isothiocyanate
CAS#: 622-78-6
Chemical Formula: C8H7NS
Exact Mass: 149.03
Molecular Weight: 149.210
Elemental Analysis: C, 64.40; H, 4.73; N, 9.39; S, 21.49

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Benzyl isothiocyanate; Tromacaps

IUPAC/Chemical Name: Benzene, (isothiocyanatomethyl)-

InChi Key: MDKCFLQDBWCQCV-UHFFFAOYSA-N

InChi Code: InChI=1S/C8H7NS/c10-7-9-6-8-4-2-1-3-5-8/h1-5H,6H2

SMILES Code: S=C=NCC1=CC=CC=C1

Appearance: Solid powder

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 149.21 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:

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1: Dufour V, Stahl M, Rosenfeld E, Stintzi A, Baysse C. Insights into the mode of action of benzyl isothiocyanate on Campylobacter jejuni. Appl Environ Microbiol. 2013 Nov;79(22):6958-68. doi: 10.1128/AEM.01967-13. Epub 2013 Sep 6. PubMed PMID: 24014524; PubMed Central PMCID: PMC3811535.

2: De Nicola GR, Montaut S, Rollin P, Nyegue M, Menut C, Iori R, Tatibouët A. Stability of benzylic-type isothiocyanates in hydrodistillation-mimicking conditions. J Agric Food Chem. 2013 Jan 9;61(1):137-42. doi: 10.1021/jf3041534. Epub 2012 Dec 18. PubMed PMID: 23214966.

3: Tang Y, Abe N, Yoshimoto M, Zhu B, Murata Y, Nakamura Y. Benzyl isothiocyanate inhibits IL-13 expression in human basophilic KU812 cells. Biosci Biotechnol Biochem. 2015;79(1):159-63. doi: 10.1080/09168451.2014.963503. Epub 2014 Sep 25. PubMed PMID: 25253661.

4: Lawson AP, Long MJC, Coffey RT, Qian Y, Weerapana E, El Oualid F, Hedstrom L. Naturally Occurring Isothiocyanates Exert Anticancer Effects by Inhibiting Deubiquitinating Enzymes. Cancer Res. 2015 Dec 1;75(23):5130-5142. doi: 10.1158/0008-5472.CAN-15-1544. Epub 2015 Nov 5. PubMed PMID: 26542215; PubMed Central PMCID: PMC4668232.

5: Kim M, Cho HJ, Kwon GT, Kang YH, Kwon SH, Her S, Park T, Kim Y, Kee Y, Park JH. Benzyl isothiocyanate suppresses high-fat diet-stimulated mammary tumor progression via the alteration of tumor microenvironments in obesity-resistant BALB/c mice. Mol Carcinog. 2015 Jan;54(1):72-82. doi: 10.1002/mc.22159. Epub 2014 Apr 11. PubMed PMID: 24729546.

6: Rao CV. Benzyl isothiocyanate: double trouble for breast cancer cells. Cancer Prev Res (Phila). 2013 Aug;6(8):760-3. doi: 10.1158/1940-6207.CAPR-13-0242. Epub 2013 Jul 10. PubMed PMID: 23842793.

7: Wolf MA, Claudio PP. Benzyl isothiocyanate inhibits HNSCC cell migration and invasion, and sensitizes HNSCC cells to cisplatin. Nutr Cancer. 2014;66(2):285-94. doi: 10.1080/01635581.2014.868912. Epub 2014 Jan 21. PubMed PMID: 24447182; PubMed Central PMCID: PMC3943495.

8: Li W, Liu X, Yang Q, Zhang N, Du Y, Zhu H. Preparation and characterization of inclusion complex of benzyl isothiocyanate extracted from papaya seed with β-cyclodextrin. Food Chem. 2015 Oct 1;184:99-104. doi: 10.1016/j.foodchem.2015.03.091. Epub 2015 Mar 28. PubMed PMID: 25872431.

9: Agerbirk N, De Nicola GR, Olsen CE, Müller C, Iori R. Derivatization of isothiocyanates and their reactive adducts for chromatographic analysis. Phytochemistry. 2015 Oct;118:109-15. doi: 10.1016/j.phytochem.2015.06.004. Epub 2015 Sep 2. PubMed PMID: 26342619.

10: Zhu Y, Liu A, Zhang X, Qi L, Zhang L, Xue J, Liu Y, Yang P. The effect of benzyl isothiocyanate and its computer-aided design derivants targeting alkylglycerone phosphate synthase on the inhibition of human glioma U87MG cell line. Tumour Biol. 2015 May;36(5):3499-509. doi: 10.1007/s13277-014-2986-6. Epub 2014 Dec 28. PubMed PMID: 25542233.

11: Abe N, Hou DX, Munemasa S, Murata Y, Nakamura Y. Nuclear factor-kappaB sensitizes to benzyl isothiocyanate-induced antiproliferation in p53-deficient colorectal cancer cells. Cell Death Dis. 2014 Nov 20;5:e1534. doi: 10.1038/cddis.2014.495. PubMed PMID: 25412312; PubMed Central PMCID: PMC4260753.

12: Sahu RP. Expression of the platelet-activating factor receptor enhances benzyl isothiocyanate-induced apoptosis in murine and human melanoma cells. Mol Med Rep. 2015 Jul;12(1):394-400. doi: 10.3892/mmr.2015.3371. Epub 2015 Feb 18. PubMed PMID: 25695262; PubMed Central PMCID: PMC4438923.

13: Giacoppo S, Galuppo M, De Nicola GR, Iori R, Bramanti P, Mazzon E. 4(α-l-rhamnosyloxy)-benzyl isothiocyanate, a bioactive phytochemical that attenuates secondary damage in an experimental model of spinal cord injury. Bioorg Med Chem. 2015 Jan 1;23(1):80-8. doi: 10.1016/j.bmc.2014.11.022. Epub 2014 Nov 22. PubMed PMID: 25497964.

14: Liu Y, Zhang L, Meng Y, Huang L. Benzyl isothiocyanate inhibits breast cancer cell tumorigenesis via repression of the FoxH1-Mediated Wnt/β-catenin pathway. Int J Clin Exp Med. 2015 Oct 15;8(10):17601-11. eCollection 2015. PubMed PMID: 26770350; PubMed Central PMCID: PMC4694250.

15: Kim SH, Singh SV. The role of polycomb group protein Bmi-1 and Notch4 in breast cancer stem cell inhibition by benzyl isothiocyanate. Breast Cancer Res Treat. 2015 Feb;149(3):681-92. doi: 10.1007/s10549-015-3279-5. Epub 2015 Feb 8. PubMed PMID: 25663545; PubMed Central PMCID: PMC4329083.

16: Zhu Y, Zhang L, Zhang GD, Wang HO, Liu MY, Jiang Y, Qi LS, Li Q, Yang P. Potential mechanisms of benzyl isothiocyanate suppression of invasion and angiogenesis by the U87MG human glioma cell line. Asian Pac J Cancer Prev. 2014;15(19):8225-8. PubMed PMID: 25339010.

17: Yeh YT, Hsu YN, Huang SY, Lin JS, Chen ZF, Chow NH, Su SH, Shyu HW, Lin CC, Huang WT, Yeh H, Chih YC, Huang YH, Su SJ. Benzyl isothiocyanate promotes apoptosis of oral cancer cells via an acute redox stress-mediated DNA damage response. Food Chem Toxicol. 2016 Nov;97:336-345. doi: 10.1016/j.fct.2016.09.028. Epub 2016 Sep 28. PubMed PMID: 27693243.

18: Waterman C, Cheng DM, Rojas-Silva P, Poulev A, Dreifus J, Lila MA, Raskin I. Stable, water extractable isothiocyanates from Moringa oleifera leaves attenuate inflammation in vitro. Phytochemistry. 2014 Jul;103:114-122. doi: 10.1016/j.phytochem.2014.03.028. Epub 2014 Apr 11. PubMed PMID: 24731259; PubMed Central PMCID: PMC4071966.

19: Galuppo M, Giacoppo S, Iori R, De Nicola GR, Milardi D, Bramanti P, Mazzon E. 4(α-L-RHAMNOSYLOXY)-BENZYL ISOTHIOCYANATE, A BIOACTIVE PHYTOCHEMICAL THAT DEFENDS CEREBRAL TISSUE AND PREVENTS SEVERE DAMAGE INDUCED BY FOCAL ISCHEMIA/REPERFUSION. J Biol Regul Homeost Agents. 2015 Apr-Jun;29(2):343-56. PubMed PMID: 26122222.

20: Kasiappan R, Jutooru I, Karki K, Hedrick E, Safe S. Benzyl Isothiocyanate (BITC) Induces Reactive Oxygen Species-dependent Repression of STAT3 Protein by Down-regulation of Specificity Proteins in Pancreatic Cancer. J Biol Chem. 2016 Dec 30;291(53):27122-27133. doi: 10.1074/jbc.M116.746339. Epub 2016 Nov 15. PubMed PMID: 27875298; PubMed Central PMCID: PMC5207142.