22 August 2013 (online)
Methallyl isothiocyanate (MAITC) is a flammable, colorless liquid with a boiling point of 169–170 °C (760 mm), a flash point of 57 °C, and a density of 0.993 g/cm3 at 25 °C. It has a special, onion-like odor and is insoluble in water. MAITC is a lachrymator and may be harmful if inhaled, swallowed, and absorbed through the skin; it may cause respiratory tract, skin and eye irritation.
MAITC is commercially available and can be synthesized by the reaction of methallyl chloride with an alkali metal thiocyanate or with ammonium thiocyanate to give methallyl thiocyanate which readily rearranges under heating (usually with distillation) to the desired product (Scheme ). In addition, it is the product of the reaction of thiocyanogen with isobutylene.
Recent literature has shown the anti-inflammatory action of MAITC through (i) the irreversible inhibition of the macrophage migration inhibitory factor and (ii) the inhibition of the caspase-1 activity through the inhibition of intracellular calcium levels. Polymerized MAITC is used to obtain oral care compositions comprising a polymeric dye.
MAITC has several applications in organic synthesis because of two highly reactive centers which provide the basis for numerous applications of the compound as an organic intermediate. MAITC is a versatile building block in the hands of the organic chemist because of the ease with which reactions can be initiated at either center without losing the reactive possibilities of the other center.
- 1 Bruson HA, Eastes JW. J. Am. Chem. Soc. 1937; 59: 2011
- 2 Skorobogatova EV, Kartashov VR. Russ. Chem. Rev. 1998; 67: 423
- 3 Ouertatani-Sakouhi H, El-Turk F, Fauvet B, Roger T, Le RoyD, Karpinar DP, Leng L, Bucala R, Zweckstetter M, Calandra T, Lashuel HA. Biochemistry 2009; 48: 9858
- 4 Han N.-R, Kim I.-K, Kim H.-M, Jeong H.-J. Biochimie 2012; 94: 816
- 5 Batchelor SN, Joiner A, Meng S, Philpotts CJ, Tao Q, Wang J. US 20120093905, 2012
- 6 Richter C, Klatt K, Feuerer A, Schulze K. J. Prakt. Chem. 1992; 334: 60
- 7 Gunnlaugsson T, Veale E. EP 2251687, 2010
- 8 Merla B, Frank R, Bahrenberg G, Schroeder W, Zemolka S. US 7696238, 2010
- 9 Schick H, Frank R, Reich M, Jostock R, Bahrenberg G, Theil F, Henkel B. EP 2292625, 2011
- 10 Stefanska J, Szulczyk D, Koziol AE, Miroslaw B, Kedzierska E, Fidecka S, Busonera B, Sanna G, Giliberti G, La CollaP, Struga M. Eur. J. Med. Chem. 2012; 55: 205
- 11 Naidu NB, Sorenson ME, Ueda Y, Matiskella JD, Walker MA. US 7902182, 2011
- 12 Hanyu N, Saito T, Shibata T, Sato K, Ogino K. EP 2251001, 2010
- 13 Kochikyan TV, Samvelyan MA, Arutyunyan EV, Arutyunyan VS, Avetisyan AA, Malakyan MG, Vardevanyan LA, Badzhinyan SA. Pharm. Chem. J. 2011; 44: 525
- 14 Hassan AA, Shawky AM. J. Heterocycl. Chem. 2011; 48: 495
- 15 Williams MS, Jackson R, Andrus R. US 7435774, 2008