| Revision as of 04:44, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 451364369 of page Allyl_isothiocyanate for the Chem/Drugbox validation project (updated: ''). |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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|Verifiedfields = changed |
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|Watchedfields = changed |
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| verifiedrevid = 413309467 |
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|verifiedrevid = 477314225 |
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| Name = Allyl isothiocyanate |
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| ImageFile = Allyl-isothiocyanate-2D-skeletal.png |
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|Name = Allyl isothiocyanate |
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|ImageFile = Allyl-isothiocyanate-2D-skeletal.png |
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| ImageSize = 120px |
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|ImageSize = 200px |
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| ImageName = Allyl isothiocyanate |
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|ImageName = Allyl isothiocyanate |
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| ImageFile1 = Allyl-isothiocyanate-3D-vdW.png |
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|ImageFile1 = Allyl-isothiocyanate-3D-vdW.png |
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| ImageSize1 = 120px |
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|ImageSize1 = 150px |
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| ImageName1 = Space-filling model of allyl isothiocyanate |
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|ImageName1 = Space-filling model of allyl isothiocyanate |
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|PIN = 3-Isothiocyanatoprop-1-ene |
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| IUPACName = 3-Isothiocyanato-1-propene |
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| OtherNames = synthetic mustard oil |
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|OtherNames = Synthetic mustard oil |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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|IUPHAR_ligand = 2420 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = BN34FX42G3 |
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|UNII = BN34FX42G3 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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|ChEBI_Ref = {{ebicite|changed|EBI}} |
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| KEGG = D02818 |
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|ChEBI = 73224 |
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| InChI = 1/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2 |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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| InChIKey = ZOJBYZNEUISWFT-UHFFFAOYAS |
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|KEGG = D02818 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|KEGG1=C19317 |
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| StdInChI = 1S/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2 |
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|InChI = 1/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = ZOJBYZNEUISWFT-UHFFFAOYSA-N |
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|InChIKey = ZOJBYZNEUISWFT-UHFFFAOYAS |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI = 1S/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2 |
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| CASNo = 57-06-7 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey = ZOJBYZNEUISWFT-UHFFFAOYSA-N |
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| ChEMBL = 233248 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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|CASNo = 57-06-7 |
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| ChemSpiderID = 21105854 |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| SMILES = C=CCN=C=S |
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| PubChem = 5971 |
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|ChEMBL = 233248 |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChemSpiderID = 21105854 |
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|SMILES = C=CCN=C=S |
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|PubChem = 5971 |
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|EINECS = 200-309-2 |
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|RTECS = NX8225000 |
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|UNNumber = 1545 |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=4|H=5|N=1|S=1 |
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|C=4|H=5|N=1|S=1 |
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| Density = 1.013–1.020 g/cm<sup>3</sup> |
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|Density = 1.013–1.020 g/cm<sup>3</sup> |
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| MeltingPtC = −102 |
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|MeltingPtC = −102 |
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|BoilingPtC = 148 to 154 |
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| BoilingPtCL = 148 |
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| BoilingPtCH = 154 |
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}} |
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}} |
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}} |
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|Section7={{Chembox Hazards |
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|GHSPictograms = {{GHS02}}{{GHS06}}{{GHS07}}{{GHS09}} |
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|GHSSignalWord = Danger |
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|HPhrases = {{H-phrases|226|301|310|315|319|330|335|410}} |
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|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}} |
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}} |
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}} |
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'''Allyl isothiocyanate''' ('''AITC''') is a naturally occurring unsaturated ]. The colorless oil is responsible for the pungent taste of ] such as ], ], ], and ]. This ] and the ] of AITC are mediated through the ] and ] 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 = 316–321 | 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=Brône, 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 = ] | year = 2008 | volume = 231 | issue = 2 | pages = 150–156 | 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 ], a Non-Electrophilic Reference Agonist of the TrpA1 Channel | journal = Bioorganic & Medicinal Chemistry Letters | year = 2011 | volume = 21 | issue = 16 | pages = 4857–4859 | 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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==Biosynthesis and biological functions== |
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Allyl isothiocyanate can be obtained from the seeds of ] (''Rhamphospermum nigrum'') or brown ] (''Brassica juncea''). When these ]s are broken, the ] ] is released and acts on a ] known as ] to give allyl isothiocyanate.<ref name=pmid31771793>{{cite journal |doi=10.1016/j.phytochem.2019.112100 |doi-access=free |title=Glucosinolate structural diversity, identification, chemical synthesis and metabolism in plants |year=2020 |last1=Blažević |first1=Ivica |last2=Montaut |first2=Sabine |last3=Burčul |first3=Franko |last4=Olsen |first4=Carl Erik |last5=Burow |first5=Meike |last6=Rollin |first6=Patrick |last7=Agerbirk |first7=Niels |journal=Phytochemistry |volume=169 |page=112100 |pmid=31771793 |bibcode=2020PChem.169k2100B |s2cid=208318505 }}</ref> This serves the plant as a defense against ]s; since it is harmful to the plant itself,{{Citation needed|date=June 2019}} it is stored in the harmless form of the glucosinolate, separate from the myrosinase enzyme. When an animal chews the plant, the allyl isothiocyanate is released, repelling the animal. Human appreciation of the pungency is learned.<ref name=EFC>{{Cite book |editor-last=Melton |editor-first=Laurence |title=The Encyclopedia of Food Chemistry |publisher=Elsevier |year=2019 |isbn=978-0-12-814045-1 |location=Netherlands }}</ref>{{rp|105}} |
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The compound has been shown to strongly repel ] (''Solenopsis invicta'').<ref>{{cite journal | doi = 10.1007/s13355-019-00613-5 | title = Wasabi versus red imported fire ants: Preliminary test of repellency of microencapsulated allyl isothiocyanate against Solenopsis invicta (Hymenoptera: Formicidae) using bait traps in Taiwan | date = 2019 | last1 = Hashimoto | first1 = Yoshiaki | last2 = Yoshimura | first2 = Masashi | last3 = Huang | first3 = Rong-Nan | journal = Applied Entomology and Zoology | volume = 54 | issue = 2 | pages = 193–196 | bibcode = 2019AppEZ..54..193H }}</ref> AITC vapor is also used as an antimicrobial and shelf life extender in food packaging.<ref name=EFC/>{{rp|118–120}} |
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==Production and applications== |
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Allyl isothiocyanate is produced commercially by the reaction of ] and ]:<ref name=Ullmann/> |
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:CH<sub>2</sub>=CHCH<sub>2</sub>Cl + KSCN → CH<sub>2</sub>=CHCH<sub>2</sub>NCS + KCl |
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The product obtained in this fashion is sometimes known as ''synthetic mustard oil''. |
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Allyl thiocyanate isomerizes to the isothiocyanate:<ref name=JCE>{{cite journal |doi=10.1021/ed048p81 |title=The Preparation and Isomerization of Allyl Thiocyanate. An Organic Chemistry Experiment |date=1971 |last1=Emergon |first1=David W. |journal=Journal of Chemical Education |volume=48 |issue=1 |page=81 |bibcode=1971JChEd..48...81E }}</ref> |
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:{{chem2|CH2\dCHCH2SCN -> CH2\dCHCH2NCS}} |
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Allyl isothiocyanate can also be liberated by dry ] of the seeds. The product obtained in this fashion is known as ]. |
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It is used principally as a ] agent in foods. Synthetic allyl isothiocyanate is used as an ], as an anti-mold agent <ref>US Patent No. 8691042</ref> <!--as an ], to ], and as a ].--> ],<ref>{{cite journal |last1=Masuda |first1=Shuichi |last2=Masuda |first2=Hideki |last3=Shimamura |first3=Yuko |last4=Sugiyama |first4=Chitose |last5=Takabayashi |first5=Fumiyo |title=Improvement Effects of Wasabi (Wasabia japonica) Leaves and Allyl Isothiocyanate on Stomach Lesions of Mongolian Gerbils Infected with Helicobacter pylori |journal=Natural Product Communications |date=April 2017 |volume=12 |issue=4 |pages=595–598 |doi=10.1177/1934578X1701200431 |pmid=30520603|s2cid=54567566 |doi-access=free }}</ref> and ], and is used in certain cases for crop protection.<ref name=Ullmann/> It is also used in fire alarms for the deaf.<ref>{{US patent reference|number= 20100308995A1|issue-date= 2015-06-24 |inventor= Hideaki Goto, Tomo Sakai, Koichiro Mizoguchi, Yukinobu Tajima, Makoto Imai| title= Odor generation alarm and method for informing unusual situation}}</ref><ref>{{cite web |last1=Phillipson |first1=Tacye |title=Why would you want a wasabai fire alarm? |url=https://blog.nms.ac.uk/2018/08/29/why-would-you-want-a-wasbai-fire-alarm/ |website=National Museums Scotland Blog |date=29 August 2018 |access-date=10 March 2022}}</ref> |
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Hydrolysis of allyl isothiocyanate gives ].<ref>{{OrgSynth | author = Leffler, M. T. | title = Allylamine | volume = 18 | pages = 5 | collvol = 2 | collvolpages = 24 | year = 1938 | prep = CV2P0024 }}</ref> |
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==Safety== |
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Allyl isothiocyanate has an ] of 151 mg/kg and is a ] (similar to tear gas or mace).<ref name=Ullmann/> |
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===Oncology=== |
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Based on '']'' experiments and ]s, allyl isothiocyanate exhibits many of the desirable attributes of a cancer chemopreventive agent.<ref>{{Cite journal |
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| pmid = 19960458 |
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| year = 2010 |
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| last1 = Zhang |
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| first1 = Y |
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| title = Allyl isothiocyanate as a cancer chemopreventive phytochemical |
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| journal = Molecular Nutrition & Food Research |
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| volume = 54 |
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| issue = 1 |
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| pages = 127–35 |
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| doi = 10.1002/mnfr.200900323 |
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| pmc = 2814364 |
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}}</ref> |
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== See also == |
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*], traditional home remedy |
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*], the piquant chemical in ] |
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*], the piquant chemical in ]s |
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*], the piquant flavor chemical in raw ] |
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== References == |
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{{reflist}} |
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{{Cruciferous Biochemistry}} |
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{{Transient receptor potential channel modulators}} |
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{{Xenobiotic-sensing receptor modulators}} |
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] |
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] |
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