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Allyl isothiocyanate
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{{chembox |Verifiedfields = changed |Watchedfields = changed |verifiedrevid = 477314225 |Name = Allyl isothiocyanate |ImageFile = Allyl-isothiocyanate-2D-skeletal.png |ImageSize = 200px |ImageName = Allyl isothiocyanate |ImageFile1 = Allyl-isothiocyanate-3D-vdW.png |ImageSize1 = 150px |ImageName1 = Space-filling model of allyl isothiocyanate |PIN = 3-Isothiocyanatoprop-1-ene |OtherNames = Synthetic mustard oil |Section1={{Chembox Identifiers |IUPHAR_ligand = 2420 |UNII_Ref = {{fdacite|correct|FDA}} |UNII = BN34FX42G3 |ChEBI_Ref = {{ebicite|changed|EBI}} |ChEBI = 73224 |KEGG_Ref = {{keggcite|correct|kegg}} |KEGG = D02818 |KEGG1=C19317 |InChI = 1/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2 |InChIKey = ZOJBYZNEUISWFT-UHFFFAOYAS |StdInChI_Ref = {{stdinchicite|correct|chemspider}} |StdInChI = 1S/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2 |StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |StdInChIKey = ZOJBYZNEUISWFT-UHFFFAOYSA-N |CASNo_Ref = {{cascite|correct|CAS}} |CASNo = 57-06-7 |ChEMBL_Ref = {{ebicite|correct|EBI}} |ChEMBL = 233248 |ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |ChemSpiderID = 21105854 |SMILES = C=CCN=C=S |PubChem = 5971 |EINECS = 200-309-2 |RTECS = NX8225000 |UNNumber = 1545 }} |Section2={{Chembox Properties |C=4|H=5|N=1|S=1 |Density = 1.013β1.020 g/cm<sup>3</sup> |MeltingPtC = β102 |BoilingPtC = 148 to 154 }} |Section7={{Chembox Hazards |GHSPictograms = {{GHS02}}{{GHS06}}{{GHS07}}{{GHS09}} |GHSSignalWord = Danger |HPhrases = {{H-phrases|226|301|310|315|319|330|335|410}} |PPhrases = {{P-phrases|210|233|240|241|242|243|260|261|262|264|270|271|273|280|284|301+310|302+350|302+352|303+361+353|304+340|305+351+338|310|312|320|321|322|330|332+313|337+313|361|362|363|370+378|391|403+233|403+235|405|501}} }} }} '''Allyl isothiocyanate''' ('''AITC''') is a naturally occurring unsaturated [[isothiocyanate]]. The colorless oil is responsible for the pungent taste of [[cruciferous vegetables]] such as [[mustard (condiment)|mustard]], [[radish]], [[horseradish]], and [[wasabi]]. This [[pungency]] and the [[tears|lachrymatory effect]] of AITC are mediated through the [[TRPA1]] and [[TRPV1]] ion channels.<ref>{{cite journal | last1 = Everaerts | first1 = W. | last2 = Gees | first2 = M. | last3 = Alpizar | first3 = Y. A. | last4 = Farre | first4 = R. | last5 = Leten | first5 = C. | last6 = Apetrei | first6 = A. | last7 = Dewachter | first7 = I. | last8 = van Leuven | first8 = F. | last9 = Vennekens | first9 = R.| title = The Capsaicin Receptor TRPV1 is a Crucial Mediator of the Noxious Effects of Mustard Oil | journal = Current Biology | year = 2011 | volume = 21 | issue = 4 | pages = 316β321 | pmid = 21315593 | doi = 10.1016/j.cub.2011.01.031 | s2cid = 13151479 | doi-access = free| bibcode = 2011CBio...21..316E }}</ref><ref name="pmid18501939">{{cite journal |author1=BrΓ΄ne, B. |author2=Peeters, P. J. |author3=Marrannes, R. |author4=Mercken, M. |author5=Nuydens, R. |author6=Meert, T. |author7=Gijsen, H. J. | title = Tear gasses CN, CR, and CS are potent activators of the human TRPA1 receptor | journal = [[Toxicology and Applied Pharmacology]] | year = 2008 | volume = 231 | issue = 2 | pages = 150β156 | pmid = 18501939 | doi = 10.1016/j.taap.2008.04.005 |bibcode=2008ToxAP.231..150B }}</ref><ref name="pmid21741838">{{cite journal |author1=Ryckmans, T. |author2=Aubdool, A. A. |author3=Bodkin, J. V. |author4=Cox, P. |author5=Brain, S. D. |author6=Dupont, T. |author7=Fairman, E. |author8=Hashizume, Y. |author9=Ishii, N. | title = Design and Pharmacological Evaluation of [[PF-4840154]], a Non-Electrophilic Reference Agonist of the TrpA1 Channel | journal = Bioorganic & Medicinal Chemistry Letters | year = 2011 | volume = 21 | issue = 16 | pages = 4857β4859 | pmid = 21741838 | doi = 10.1016/j.bmcl.2011.06.035 |display-authors=etal}}</ref> It is slightly soluble in water, but more soluble in most organic solvents.<ref name=Ullmann>{{Ullmann | author = Romanowski, F. |author2=Klenk, H. | title = Thiocyanates and Isothiocyanates, Organic | doi = 10.1002/14356007.a26_749}}</ref>
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