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

MedKoo CAT#: 529607

CAS#: 2257-09-2

Description: Phenylethyl isothiocyanate is an HDAC inhibitor potentially for the treatment of benign prostatic hypertrophy.

Chemical Structure

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Phenylethyl isothiocyanate
CAS# 2257-09-2
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 529607
Name: Phenylethyl isothiocyanate
CAS#: 2257-09-2
Chemical Formula: C9H9NS
Exact Mass: 163.05
Molecular Weight: 163.238
Elemental Analysis: C, 66.22; H, 5.56; N, 8.58; S, 19.64

Price and Availability

Size Price Availability Quantity
5g USD 250
10g USD 450
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Synonym: JC-5411; JC5411; JC 5411; purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.

IUPAC/Chemical Name: (2-isothiocyanatoethyl)benzene

InChi Key: IZJDOKYDEWTZSO-UHFFFAOYSA-N

InChi Code: InChI=1S/C9H9NS/c11-8-10-7-6-9-4-2-1-3-5-9/h1-5H,6-7H2

SMILES Code: S=C=NCCC1=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:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: 2-Phenylethyl isothiocyanate is a potent antifungal agent.
In vitro activity: The results indicated that PEITC (phenylethyl isothiocyanate) decreased the cell viability and inhibited the protein levels and expressions of IL-1β, IL-6, and TNF-α genes at the transcriptional level in GBM 8401 cells. PEITC inhibited the binding of NF-κB on promoter site of DNA in GBM 8401 cells. PEITC also altered the protein expressions of protein kinase B (Akt), extracellular signal-regulated kinase (ERK), and NF-κB signaling pathways. The inflammatory responses in human glioblastoma cells may be suppressed by PEITC through the phosphoinositide 3-kinase (PI3K)/Akt/NF-κB signaling pathway. Reference: Glioblastoma Cells through the PI3K/Akt/NF-κB Signaling Pathway In Vitro. https://pubmed.ncbi.nlm.nih.gov/35368876/
In vivo activity: This study focused to research on the effect of PEITC (phenylethyl isothiocyanate) against renal toxicity caused by CP and its relationship to the Nrf2 signaling mechanism. Thirty female Wistar albino rats were allocated to three groups: control (n = 10), CP (n = 10), and PEITC-pretreated group (150 µmol/kg b.w. orally; n = 10). Pretreatment with PEITC ameliorated kidney tissue injury. The renal protective effect of the PEITC was supported by the histological analysis of the kidney. PEITC prevented CP-induced nephrotoxicity by decreasing oxidative damage through Nrf2 and SIRT1 activation and NF-κB inhibition. Reference: Exp Biol Med (Maywood). 2023 Jan;248(2):157-164. https://pubmed.ncbi.nlm.nih.gov/36598044/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 30.0 183.78
DMSO 65.0 398.19
Ethanol 30.0 183.78

Preparing Stock Solutions

The following data is based on the product molecular weight 163.24 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. Zhang M, Li Y, Bi Y, Wang T, Dong Y, Yang Q, Zhang T. 2-Phenylethyl Isothiocyanate Exerts Antifungal Activity against Alternaria alternata by Affecting Membrane Integrity and Mycotoxin Production. Toxins (Basel). 2020 Feb 15;12(2):124. doi: 10.3390/toxins12020124. PMID: 32075318; PMCID: PMC7077316. 2. Hsu SY, Lee SC, Liu HC, Peng SF, Chueh FS, Lu TJ, Lee HT, Chou YC. Phenethyl Isothiocyanate Suppresses the Proinflammatory Cytokines in Human Glioblastoma Cells through the PI3K/Akt/NF-κB Signaling Pathway In Vitro. Oxid Med Cell Longev. 2022 Mar 25;2022:2108289. doi: 10.1155/2022/2108289. PMID: 35368876; PMCID: PMC8975692. 3. Uyumlu AB, Satılmış B, Atıcı B, Taşlıdere A. Phenethyl isothiocyanate protects against cyclophosphamide-induced nephrotoxicity via nuclear factor E2-related factor 2 pathway in rats. Exp Biol Med (Maywood). 2023 Jan;248(2):157-164. doi: 10.1177/15353702221139206. Epub 2023 Jan 4. PMID: 36598044; PMCID: PMC10041055. 4. Haloi P, Chawla S, Konkimalla VB. Thermosensitive smart hydrogel of PEITC ameliorates the therapeutic efficacy in rheumatoid arthritis. Eur J Pharm Sci. 2023 Feb 1;181:106367. doi: 10.1016/j.ejps.2022.106367. Epub 2022 Dec 23. PMID: 36572358.
In vitro protocol: 1. Zhang M, Li Y, Bi Y, Wang T, Dong Y, Yang Q, Zhang T. 2-Phenylethyl Isothiocyanate Exerts Antifungal Activity against Alternaria alternata by Affecting Membrane Integrity and Mycotoxin Production. Toxins (Basel). 2020 Feb 15;12(2):124. doi: 10.3390/toxins12020124. PMID: 32075318; PMCID: PMC7077316. 2. Hsu SY, Lee SC, Liu HC, Peng SF, Chueh FS, Lu TJ, Lee HT, Chou YC. Phenethyl Isothiocyanate Suppresses the Proinflammatory Cytokines in Human Glioblastoma Cells through the PI3K/Akt/NF-κB Signaling Pathway In Vitro. Oxid Med Cell Longev. 2022 Mar 25;2022:2108289. doi: 10.1155/2022/2108289. PMID: 35368876; PMCID: PMC8975692.
In vivo protocol: 1. Uyumlu AB, Satılmış B, Atıcı B, Taşlıdere A. Phenethyl isothiocyanate protects against cyclophosphamide-induced nephrotoxicity via nuclear factor E2-related factor 2 pathway in rats. Exp Biol Med (Maywood). 2023 Jan;248(2):157-164. doi: 10.1177/15353702221139206. Epub 2023 Jan 4. PMID: 36598044; PMCID: PMC10041055. 2. Haloi P, Chawla S, Konkimalla VB. Thermosensitive smart hydrogel of PEITC ameliorates the therapeutic efficacy in rheumatoid arthritis. Eur J Pharm Sci. 2023 Feb 1;181:106367. doi: 10.1016/j.ejps.2022.106367. Epub 2022 Dec 23. PMID: 36572358.

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1: Freitas E, Aires A, de Santos Rosa EA, Saavedra MJ. Antibacterial activity and synergistic effect between watercress extracts, 2-phenylethyl isothiocyanate and antibiotics against 11 isolates of Escherichia coli from clinical and animal source. Lett Appl Microbiol. 2013 Oct;57(4):266-73. doi: 10.1111/lam.12105. PubMed PMID: 23682789.

2: Kleszczyński K, Ernst IM, Wagner AE, Kruse N, Zillikens D, Rimbach G, Fischer TW. Sulforaphane and phenylethyl isothiocyanate protect human skin against UVR-induced oxidative stress and apoptosis: role of Nrf2-dependent gene expression and antioxidant enzymes. Pharmacol Res. 2013 Dec;78:28-40. doi: 10.1016/j.phrs.2013.09.009. PubMed PMID: 24121007.

3: Li Q, Zhan M, Chen W, Zhao B, Yang K, Yang J, Yi J, Huang Q, Mohan M, Hou Z, Wang J. Phenylethyl isothiocyanate reverses cisplatin resistance in biliary tract cancer cells via glutathionylation-dependent degradation of Mcl-1. Oncotarget. 2016 Mar 1;7(9):10271-82. doi: 10.18632/oncotarget.7171. PubMed PMID: 26848531; PubMed Central PMCID: PMC4891119.

4: Ernst IM, Wagner AE, Schuemann C, Storm N, Höppner W, Döring F, Stocker A, Rimbach G. Allyl-, butyl- and phenylethyl-isothiocyanate activate Nrf2 in cultured fibroblasts. Pharmacol Res. 2011 Mar;63(3):233-40. doi: 10.1016/j.phrs.2010.11.005. PubMed PMID: 21109004.

5: Li RW, Li C, Wang TT. Transcriptomic alterations in human prostate cancer cell LNCaP tumor xenograft modulated by dietary phenethyl isothiocyanate. Mol Carcinog. 2013 Jun;52(6):426-37. doi: 10.1002/mc.21873. PubMed PMID: 22308101.

6: Welte CU, de Graaf RM, van den Bosch TJ, Op den Camp HJ, van Dam NM, Jetten MS. Plasmids from the gut microbiome of cabbage root fly larvae encode SaxA that catalyses the conversion of the plant toxin 2-phenylethyl isothiocyanate. Environ Microbiol. 2016 May;18(5):1379-90. doi: 10.1111/1462-2920.12997. PubMed PMID: 26234684.

7: Wu WJ, Zhang Y, Zeng ZL, Li XB, Hu KS, Luo HY, Yang J, Huang P, Xu RH. β-phenylethyl isothiocyanate reverses platinum resistance by a GSH-dependent mechanism in cancer cells with epithelial-mesenchymal transition phenotype. Biochem Pharmacol. 2013 Feb 15;85(4):486-96. doi: 10.1016/j.bcp.2012.11.017. PubMed PMID: 23219523.

8: Jakubikova J, Cervi D, Ooi M, Kim K, Nahar S, Klippel S, Cholujova D, Leiba M, Daley JF, Delmore J, Negri J, Blotta S, McMillin DW, Hideshima T, Richardson PG, Sedlak J, Anderson KC, Mitsiades CS. Anti-tumor activity and signaling events triggered by the isothiocyanates, sulforaphane and phenethyl isothiocyanate, in multiple myeloma. Haematologica. 2011 Aug;96(8):1170-9. doi: 10.3324/haematol.2010.029363. PubMed PMID: 21712538; PubMed Central PMCID: PMC3148911.

9: Su JC, Lin K, Wang Y, Sui SH, Gao ZY, Wang ZG. In vitro studies of phenethyl isothiocyanate against the growth of LN229 human glioma cells. Int J Clin Exp Pathol. 2015 Apr 1;8(4):4269-76. PubMed PMID: 26097624; PubMed Central PMCID: PMC4467011.

10: Huong LD, Shin JA, Choi ES, Cho NP, Kim HM, Leem DH, Cho SD. β-Phenethyl isothiocyanate induces death receptor 5 to induce apoptosis in human oral cancer cells via p38. Oral Dis. 2012 Jul;18(5):513-9. doi: 10.1111/j.1601-0825.2012.01905.x. PubMed PMID: 22309674.

11: Konsue N, Ioannides C. Phenethyl isocyanate is not the metabolite of phenethyl isothiocyanate responsible for mechanism-based inhibition of cytochrome P450. Arch Toxicol. 2010 Oct;84(10):751-9. doi: 10.1007/s00204-010-0522-z. PubMed PMID: 20140730.

12: Bolloskis MP, Carvalho FP, Loo G. Iron depletion in HCT116 cells diminishes the upregulatory effect of phenethyl isothiocyanate on heme oxygenase-1. Toxicol Appl Pharmacol. 2016 Apr 15;297:22-31. doi: 10.1016/j.taap.2016.02.024. PubMed PMID: 26945724.

13: Huong le D, Shim JH, Choi KH, Shin JA, Choi ES, Kim HS, Lee SJ, Kim SJ, Cho NP, Cho SD. Effect of β-phenylethyl isothiocyanate from cruciferous vegetables on growth inhibition and apoptosis of cervical cancer cells through the induction of death receptors 4 and 5. J Agric Food Chem. 2011 Aug 10;59(15):8124-31. doi: 10.1021/jf2006358. PubMed PMID: 21702500.

14: Eisa NH, ElSherbiny NM, Shebl AM, Eissa LA, El-Shishtawy MM. Phenethyl isothiocyanate potentiates anti-tumour effect of doxorubicin through Akt-dependent pathway. Cell Biochem Funct. 2015 Dec;33(8):541-51. doi: 10.1002/cbf.3153. PubMed PMID: 26548747.

15: Zheng L, Zheng F. Development and validation of an LC-APCI-MS/MS method for the determination of phenethyl isothiocyanate in human plasma. Biomed Chromatogr. 2015 Apr;29(4):619-25. doi: 10.1002/bmc.3323. PubMed PMID: 25209958.

16: Hu Y, Lu W, Chen G, Zhang H, Jia Y, Wei Y, Yang H, Zhang W, Fiskus W, Bhalla K, Keating M, Huang P, Garcia-Manero G. Overcoming resistance to histone deacetylase inhibitors in human leukemia with the redox modulating compound β-phenylethyl isothiocyanate. Blood. 2010 Oct 14;116(15):2732-41. doi: 10.1182/blood-2009-11-256354. PubMed PMID: 20566897; PubMed Central PMCID: PMC3324257.

17: Tsai JT, Liu HC, Chen YH. Suppression of inflammatory mediators by cruciferous vegetable-derived indole-3-carbinol and phenylethyl isothiocyanate in lipopolysaccharide-activated macrophages. Mediators Inflamm. 2010;2010:293642. doi: 10.1155/2010/293642. PubMed PMID: 20414337; PubMed Central PMCID: PMC2855117.

18: Hwang ES, Lee HJ. Effects of phenylethyl isothiocyanate and its metabolite on cell-cycle arrest and apoptosis in LNCaP human prostate cancer cells. Int J Food Sci Nutr. 2010 May;61(3):324-36. doi: 10.3109/09637481003639092. PubMed PMID: 20402549.

19: Qin CZ, Zhang X, Wu LX, Wen CJ, Hu L, Lv QL, Shen DY, Zhou HH. Advances in molecular signaling mechanisms of β-phenethyl isothiocyanate antitumor effects. J Agric Food Chem. 2015 Apr 8;63(13):3311-22. doi: 10.1021/jf504627e. Review. PubMed PMID: 25798652.

20: Gupta B, Chiang L, Chae K, Lee DH. Phenethyl isothiocyanate inhibits hypoxia-induced accumulation of HIF-1α and VEGF expression in human glioma cells. Food Chem. 2013 Dec 1;141(3):1841-6. doi: 10.1016/j.foodchem.2013.05.006. PubMed PMID: 23870899.