:Phenethyl isothiocyanate

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 480479568

| ImageFile = Phenethyl isothiocyanate.svg

| ImageSize = 150px

| ImageFileL2 = Phenethyl isothiocyanate-3D-balls-by-AHRLS-2012.png

| ImageSizeL2 = 150px

| ImageFileR2 = Phenethyl isothiocyanate-3D-vdW-by-AHRLS-2012.png

| ImageSizeR2 = 150px

| PIN = (2-Isothiocyanatoethyl)benzene

| OtherNames = Phenylethyl isothiocyanate; Phenethyl mustard oil

|Section1={{Chembox Identifiers

| Abbreviations = PEITC

| CASNo = 2257-09-2

| CASNo_Ref = {{cascite|changed|??}}

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 151649

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 351346

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = 6U7TFK75KV

| PubChem = 16741

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 15870

| SMILES = S=C=N/CCc1ccccc1

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

| InChIKey = IZJDOKYDEWTZSO-UHFFFAOYAB

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C9H9NS/c11-8-10-7-6-9-4-2-1-3-5-9/h1-5H,6-7H2

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = IZJDOKYDEWTZSO-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| C=9 | H=9 | N=1 | S=1

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

}}

Phenethyl isothiocyanate (PEITC) is a naturally occurring isothiocyanate whose precursor, gluconasturtiin is found in some cruciferous vegetables,{{cite web | url = http://www.cancer.gov/dictionary?cdrid=44447 | title = Dictionary of Cancer Terms: PEITC | publisher = National Cancer Institute}} especially watercress.

PEITC has been studied for its potential for chemoprevention of cancers,{{Cite journal | pmid = 20013083 | year = 2010 | last1 = Cheung | first1 = KL | last2 = Kong | first2 = AN | title = Molecular targets of dietary phenethyl isothiocyanate and sulforaphane for cancer chemoprevention | volume = 12 | issue = 1 | pages = 87–97 | doi = 10.1208/s12248-009-9162-8 | pmc = 2811646 | journal = The AAPS Journal}}{{cite journal |author1=Kwon, Ki Han |author2=Xu, Changjiang |author3=Keum, Young-Sam |author4=Khor, Tin Oo |author5=Kim, Jung-Hwan |author6=Huang, Mou-Tuan |author7=Reddy, Bandaru S. |author8=Li, Wenge |author9=Kong, Ah-Ng Tony | title = Natural dietary phytochemicals: a promising future for cancer prevention and treatment of earlier lesion | journal = Cancer: Disease Progression and Chemoprevention | year = 2007 | pages = 109–126}} such as prostate cancer.{{Cite journal | pmid = 20664922 | year = 2010 | last1 = Wang | first1 = LG | last2 = Chiao | first2 = JW | title = Prostate cancer chemopreventive activity of phenethyl isothiocyanate through epigenetic regulation (review) | volume = 37 | issue = 3 | pages = 533–9 | journal = International Journal of Oncology | doi=10.3892/ijo_00000702| doi-access = free }}

In terms of biosynthesis, PEITC is produced from gluconasturtiin by the action of the enzyme myrosinase.

References

{{Reflist}}

Category:Isothiocyanates

Category:Phenyl compounds

{{Cruciferous Biochemistry}}