Allyl isothiocyanate

Allyl isothiocyanate
Names
	Preferred IUPAC name 3-Isothiocyanatoprop-1-ene
	Other names Synthetic mustard oil
Identifiers
CAS Number	57-06-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:73224 ;
ChEMBL	ChEMBL233248 ;
ChemSpider	21105854 ;
ECHA InfoCard	100.000.281
EC Number	200-309-2;
IUPHAR/BPS	2420;
KEGG	D02818 ; C19317;
PubChem CID	5971;
RTECS number	NX8225000;
UNII	BN34FX42G3 ;
UN number	1545
CompTox Dashboard (EPA)	DTXSID3020047 ;
	InChI InChI=1S/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2 Key: ZOJBYZNEUISWFT-UHFFFAOYSA-N ; InChI=1/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2 Key: ZOJBYZNEUISWFT-UHFFFAOYAS;
	SMILES C=CCN=C=S;
Properties
Chemical formula	C4H5NS
Molar mass	99.15 g·mol−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 labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H301, H310, H315, H319, H330, H335, H410
Precautionary statements	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). verify (what is ?) Infobox references

Allyl isothiocyanate (AITC) is a naturally occurring unsaturated isothiocyanate. The colorless oil is responsible for the pungent taste of cruciferous vegetables such as mustard, radish, horseradish, and wasabi. This pungency and the lachrymatory effect of AITC are mediated through the TRPA1 and TRPV1 ion channels.^[1]^[2]^[3] It is slightly soluble in water, but more soluble in most organic solvents.^[4]

^ 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 of PF-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.
^ Romanowski, F.; Klenk, H. "Thiocyanates and Isothiocyanates, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_749. ISBN 978-3527306732.