Allyl isothiocyanate

Allyl isothiocyanate
Allyl isothiocyanate
Space-filling model of allyl isothiocyanate
Names
Preferred IUPAC name
3-Isothiocyanatoprop-1-ene
Other names
Synthetic mustard oil
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.281 Edit this at Wikidata
EC Number
  • 200-309-2
KEGG
RTECS number
  • NX8225000
UNII
UN number 1545
  • InChI=1S/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2 checkY
    Key: ZOJBYZNEUISWFT-UHFFFAOYSA-N checkY
  • InChI=1/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2
    Key: ZOJBYZNEUISWFT-UHFFFAOYAS
  • C=CCN=C=S
Properties
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:
GHS02: FlammableGHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
Danger
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).
☒N verify (what is checkY☒N ?)

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]

  1. ^ 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.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.