Allyl isothiocyanate

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					Allyl isothiocyanate
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Allyl isothiocyanate (AITC) is the organosulfur compound with the formula                              Allyl isothiocyanate
CH2 CHCH 2 NCS. This colorless oil is responsible for the pungent taste of
mustard, horseradish, and wasabi. This pungency and the lachrymatory effect of
AITC is mediated through the TRPA1 and TRPV1 ion channels.[1][2][3] It is
slightly soluble in water, but well soluble in most organic solvents. [4]

                  Contents
 1 Biosynthesis and biological functions
 2 Commercial and other applications
 3 Safety
 4 References
                                                                                                              IUPAC name
 5 See also
                                                                                                     3-Isothiocyanato-1-propene

                                                                                                              Other names
Biosynthesis and biological functions
                                                                                                           synthetic mustard oil
Allyl isothiocyanate comes from the seeds of black mustard (Brassica nigra) or
                                                                                                                 Identifiers
brown Indian mustard (Brassica juncea). When these mustard seeds are broken,
                                                                                           CAS number         57-06-7
the enzyme myrosinase is released and acts on a glucosinolate known as sinigrin
                                                                                           PubChem            5971
to give allyl isothiocyanate.
                                                                                           ChemSpider         21105854
Allyl isothiocyanate serves the plant as a defense against herbivores; since it is         UNII               BN34FX42G3
harmful to the plant itself, it is stored in the harmless form of the glucosinolate,       KEGG               D02818
separate from the myrosinase enzyme. When an animal chews the plant, the allyl             ChEMBL             CHEMBL233248
isothiocyanate is released, repelling the animal.                                          Jmol-3D            Image 1
                                                                                           images
Commercial and other applications                                                                                 SMILES
                                                                                           C=CCN=C=S
Allyl isothiocyanate is produced commercially by the reaction of allyl chloride and
                                                                                                                     InChI
potassium thiocyanate:[4]
                                                                                           InChI=1S/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2
   CH2 =CHCH 2 Cl + KSCN → CH2 =CHCH 2 NCS + KCl.                                          Key: ZOJBYZNEUISWFT-UHFFFAOYSA-N
The product obtained in this fashion is sometimes known as synthetic mustard oil.          InChI=1/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2
Allyl isothiocyanate can also be liberated by dry distillation of the seeds. The           Key: ZOJBYZNEUISWFT-UHFFFAOYAS
product obtained in this fashion is known as volatile oil of mustard and is usually
                                                                                                                 Properties
around 92% pure. It is used principally as a flavoring agent in foods. Synthetic
                                                                                           Molecular          C4 H5 NS
allyl isothiocyanate is used as an insecticide, bacteriocide [5] , and nematocide,         formula
and is used in certain cases for crop protection.[4]                                       Molar mass         99.15 g mol−1

Hydrolysis of allyl isothiocyanate gives allyl amine.[6]                                   Density            1.013–1.020 g/cm3
                                                                                           Melting point      −102 °C, 171 K, -152 °F
Safety                                                                                     Boiling point      148-154 °C, 421-427 K, 298-
Allyl isothiocyanate is fairly toxic with LD50 of 151 mg/kg and is a dangerous                                309 °F

lachrymator.[4]                                                                                             (verify) (what is:   / ?)
                                                                                           Except where noted otherwise, data are given for
References                                                                                    materials in their standard state (at 25 °C,
                                                                                                                100 kPa)
   1. ^ Everaerts, W.; Gees, M.; Alpizar, Y. A.; Farre, R.; Leten, C.; Apetrei, A.;                       Infobox references
      Dewachter, I.; van Leuven, F. et al. (2011). "The Capsaicin Receptor TRPV1 is a
      Crucial Mediator of the Noxious Effects of Mustard Oil". Current Biology 21 (4): 316–321. doi:10.1016/j.cub.2011.01.031           .
     PMID 21315593 .
  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.
     doi:10.1016/j.taap.2008.04.00 . 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
     and Medicinal Chemistry Letters 21 (16): 4857–4859. doi:10.1016/j.bmcl.2011.06.035 . PMID 21741838 .
  4. ^ a b c d Romanowski, F.; Klenk, H. (2005), "Thiocyanates and Isothiocyanates, Organic", Ullmann's Encyclopedia of Industrial
     Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a26_749
  5. ^ Shin, I. S.; Masuda, H.; Naohide, K. (2004). "Bactericidal Activity of Wasabi (Wasabia japonica) against Helicobacter pylori".
     International Journal of Food Microbiology 94 (3): 255–261. doi:10.1016/S0168-1605(03)00297-6 . PMID 15246236 . edit
  6. ^ Leffler, M. T. (1938), "Allylamine"   , Org. Synth. 18: 5; Coll. Vol. 2: 24

See also
  Piperine, the active piquant chemical in black pepper
  Capsaicin, the active piquant chemical in chili peppers
  Allicin, the active piquant flavor chemical in raw garlic


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posted:9/15/2012
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