Allyl isothiocyanate Allyl isothiocyanate Space-filling model of allyl isothiocyanate Names Preferred IUPAC name 3-Isothiocyanatoprop-1-ene
Other namesSynthetic mustard oil
Identifiers ChEBI ChEMBL ChemSpider ECHA InfoCard 100.000.281 EC Number KEGG RTECS number UNII UN number 1545 InChI=1S/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2
Y Key: ZOJBYZNEUISWFT-UHFFFAOYSA-N
Y InChI=1/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2
Key: ZOJBYZNEUISWFT-UHFFFAOYAS
Properties C 4 H 5 N S Molar mass −1 Density 1.013–1.020 g/cm3 Melting point −102 °C (−152 °F; 171 K) Boiling point 148 to 154 °C (298 to 309 °F; 421 to 427 K) Hazards GHS labellingDanger H226, H301, H310, H315, H319, H330, H335, H410 P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501 Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Allyl isothiocyanate (AITC ) is a naturally occurring unsaturatedisothiocyanate . The colorless oil is responsible for the pungent taste ofcruciferous vegetables such asmustard ,radish ,horseradish , andwasabi . Thispungency and thelachrymatory effect of AITC are mediated through theTRPA1 andTRPV1 ion channels.[ 1] [ 2] [ 3] [ 4]
Biosynthesis and biological functions [ edit ] Allyl isothiocyanate can be obtained from the seeds ofblack mustard (Rhamphospermum nigrum ) or brownIndian mustard (Brassica juncea ). When thesemustard seeds are broken, theenzyme myrosinase is released and acts on aglucosinolate known assinigrin to give allyl isothiocyanate.[ 5] herbivores ; since it is harmful to the plant itself,[citation needed 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.[ 6] : 105
The compound has been shown to strongly repelfire ants (Solenopsis invicta ).[ 7] [ 6] : 118–120
Production and applications [ edit ] Allyl isothiocyanate is produced commercially by the reaction ofallyl chloride andpotassium thiocyanate :[ 4]
CH2 =CHCH2 Cl + KSCN → CH2 =CHCH2 NCS + KCl The product obtained in this fashion is sometimes known assynthetic mustard oil . Allyl thiocyanate isomerizes to the isothiocyanate:[ 8]
CH2 =CHCH2 SCN → CH2 =CHCH2 NCS Allyl isothiocyanate can also be liberated by drydistillation of the seeds. The product obtained in this fashion is known asvolatile oil of mustard .
It is used principally as aflavoring agent in foods. Synthetic allyl isothiocyanate is used as aninsecticide , as an anti-mold agent[ 9] bacteriocide ,[ 10] nematicide , and is used in certain cases for crop protection.[ 4] [ 11] [ 12]
Hydrolysis of allyl isothiocyanate givesallylamine .[ 13]
Allyl isothiocyanate has anLD50 of 151 mg/kg and is alachrymator (similar to tear gas or mace).[ 4]
Based onin vitro animal models , allyl isothiocyanate exhibits many of the desirable attributes of a cancer chemopreventive agent.[ 14]
^ Everaerts, W.; Gees, M.; Alpizar, Y. A.; Farre, R.; Leten, C.; Apetrei, A.; Dewachter, I.; van Leuven, F.; Vennekens, R. (2011)."The Capsaicin Receptor TRPV1 is a Crucial Mediator of the Noxious Effects of Mustard Oil" .Current Biology .21 (4):316– 321.Bibcode :2011CBio...21..316E .doi :10.1016/j.cub.2011.01.031 PMID 21315593 .S2CID 13151479 . ^ Brône, B.; Peeters, P. J.; Marrannes, R.; Mercken, M.; Nuydens, R.; Meert, T.; Gijsen, H. J. (2008). "Tear gasses CN, CR, and CS are potent activators of the human TRPA1 receptor".Toxicology and Applied Pharmacology 231 (2):150– 156.Bibcode :2008ToxAP.231..150B .doi :10.1016/j.taap.2008.04.005 .PMID 18501939 . ^ Ryckmans, T.; Aubdool, A. A.; Bodkin, J. V.; Cox, P.; Brain, S. D.; Dupont, T.; Fairman, E.; Hashizume, Y.; Ishii, N.; et al. (2011). "Design and Pharmacological Evaluation ofPF-4840154 , a Non-Electrophilic Reference Agonist of the TrpA1 Channel".Bioorganic & Medicinal Chemistry Letters .21 (16):4857– 4859.doi :10.1016/j.bmcl.2011.06.035 .PMID 21741838 . ^a b c d Romanowski, F.; Klenk, H. "Thiocyanates and Isothiocyanates, Organic".Ullmann's Encyclopedia of Industrial Chemistry doi :10.1002/14356007.a26_749 .ISBN 978-3-527-30673-2 ^ Blažević, Ivica; Montaut, Sabine; Burčul, Franko; Olsen, Carl Erik; Burow, Meike; Rollin, Patrick; Agerbirk, Niels (2020)."Glucosinolate structural diversity, identification, chemical synthesis and metabolism in plants" .Phytochemistry .169 : 112100.Bibcode :2020PChem.169k2100B .doi :10.1016/j.phytochem.2019.112100 PMID 31771793 .S2CID 208318505 . ^a b Melton, Laurence, ed. (2019).The Encyclopedia of Food Chemistry . Netherlands: Elsevier.ISBN 978-0-12-814045-1 ^ Hashimoto, Yoshiaki; Yoshimura, Masashi; Huang, Rong-Nan (2019). "Wasabi versus red imported fire ants: Preliminary test of repellency of microencapsulated allyl isothiocyanate against Solenopsis invicta (Hymenoptera: Formicidae) using bait traps in Taiwan".Applied Entomology and Zoology .54 (2):193– 196.Bibcode :2019AppEZ..54..193H .doi :10.1007/s13355-019-00613-5 . ^ Emergon, David W. (1971). "The Preparation and Isomerization of Allyl Thiocyanate. An Organic Chemistry Experiment".Journal of Chemical Education .48 (1): 81.Bibcode :1971JChEd..48...81E .doi :10.1021/ed048p81 . ^ US Patent No. 8691042 ^ Masuda, Shuichi; Masuda, Hideki; Shimamura, Yuko; Sugiyama, Chitose; Takabayashi, Fumiyo (April 2017)."Improvement Effects of Wasabi (Wasabia japonica) Leaves and Allyl Isothiocyanate on Stomach Lesions of Mongolian Gerbils Infected with Helicobacter pylori" .Natural Product Communications .12 (4):595– 598.doi :10.1177/1934578X1701200431 PMID 30520603 .S2CID 54567566 . ^ US patent 20100308995A1 , Hideaki Goto, Tomo Sakai, Koichiro Mizoguchi, Yukinobu Tajima, Makoto Imai, "Odor generation alarm and method for informing unusual situation", issued 2015-06-24 ^ Phillipson, Tacye (29 August 2018)."Why would you want a wasabai fire alarm?" .National Museums Scotland Blog . Retrieved10 March 2022 . ^ Leffler, M. T. (1938)."Allylamine" .Organic Syntheses 18 : 5 Collected Volumes , vol. 2, p. 24^ Zhang, Y (2010)."Allyl isothiocyanate as a cancer chemopreventive phytochemical" .Molecular Nutrition & Food Research .54 (1):127– 35.doi :10.1002/mnfr.200900323 .PMC 2814364 PMID 19960458 .
TRPA
Activators 4-Hydroxynonenal 4-Oxo-2-nonenal 5,6-EET 12S-HpETE 15-Deoxy-Δ12,14 -prostaglandin J2 α-Sanshool (ginger ,Sichuan andmelegueta peppers )Acrolein Allicin (garlic )Allyl isothiocyanate (mustard ,radish ,horseradish ,wasabi )AM404 ASP-7663 Bradykinin Cannabichromene (cannabis )Cannabidiol (cannabis )Cannabigerol (cannabis )Cinnamaldehyde (cinnamon )CR gas (dibenzoxazepine; DBO) CS gas (2-chlorobenzal malononitrile) Cuminaldehyde (cumin )Curcumin (turmeric )Dehydroligustilide (celery )Diallyl disulfide Dicentrine (Lindera Farnesyl thiosalicylic acid Formalin Gingerols (ginger )Hepoxilin A3 Hepoxilin B3 Hydrogen peroxide Icilin Isothiocyanate JT-010 Ligustilide (celery ,Angelica acutiloba Linalool (Sichuan pepper ,thyme )Methylglyoxal Methyl salicylate (wintergreen )N-Methylmaleimide Nicotine (tobacco )Oleocanthal (olive oil )Paclitaxel (Pacific yew )Paracetamol (acetaminophen) PF-4840154 Phenacyl chloride Polygodial (Dorrigo pepper )Shogaols (ginger ,Sichuan andmelegueta peppers )Tear gases Tetrahydrocannabinol (cannabis )Tetrahydrocannabiorcol Thiopropanal S-oxide (onion )Umbellulone (Umbellularia californica )WIN 55,212-2 Blockers
TRPC
TRPM
TRPML
TRPP
TRPV
Activators 2-APB 5,6-EET 9-HODE 9-oxoODE 12S-HETE 12S-HpETE 13-HODE 13-oxoODE 20-HETE α-Sanshool (ginger ,Sichuan andmelegueta peppers )Allicin (garlic )AM404 Anandamide Bisandrographolide (Andrographis paniculata Camphor (camphor laurel ,rosemary ,camphorweed ,African blue basil ,camphor basil )Cannabidiol (cannabis )Cannabidivarin (cannabis )Capsaicin (chili pepper )Carvacrol (oregano ,thyme ,pepperwort ,wild bergamot , others)DHEA Diacyl glycerol Dihydrocapsaicin (chili pepper )Estradiol Eugenol (basil ,clove )Evodiamine (Euodia ruticarpa Gingerols (ginger )GSK1016790A Heat Hepoxilin A3 Hepoxilin B3 Homocapsaicin (chili pepper )Homodihydrocapsaicin (chili pepper )Incensole (incense )Lysophosphatidic acid LowpH (acidic conditions) Menthol (mint )N-Arachidonoyl dopamine N-Oleoyldopamine N-Oleoylethanolamide Nonivamide (PAVA) (PAVA spray )Nordihydrocapsaicin (chili pepper )Paclitaxel (Pacific yew )Paracetamol (acetaminophen) Phenylacetylrinvanil Phorbol esters (e.g.,4α-PDD )Piperine (black pepper ,long pepper )Polygodial (Dorrigo pepper )Probenecid Protons RhTx Rutamarin (Ruta graveolens Resiniferatoxin (RTX) (Euphorbia resinifera /pooissonii Shogaols (ginger ,Sichuan andmelegueta peppers )Tetrahydrocannabivarin (cannabis )Thymol (thyme ,oregano )Tinyatoxin (Euphorbia resinifera /pooissonii Tramadol Vanillin (vanilla )Zucapsaicin Blockers
CAR Tooltip Constitutive androstane receptor PXR Tooltip Pregnane X receptor
