Allyl isothiocyanate

Structural formula
General
Surname	Allyl isothiocyanate
other names	Allyl mustard oil; allyl mustard essential oil; 3-isothiocyanato-1-propene;
Molecular formula	C 4 H 5 NS
Brief description	colorless to yellowish liquid with a pungent sharp to tear-irritating odor
External identifiers / databases
EC number	200-309-2
ECHA InfoCard	100,000.281
PubChem	5971
Wikidata	Q419406
properties
Molar mass	99.16 g mol −1
Physical state	liquid
density	1.02 g cm −3
Melting point	−80 ° C
boiling point	151 ° C
Vapor pressure	5.21 hPa (20 ° C)
solubility	poor in water (2 g l −1 at 20 ° C)
Refractive index	1.5306 (20 ° C)
safety instructions
H and P phrases	H: 226-301-310-330-315-319-335-410
	P: 210-280-304 + 340-310-332 + 313-337 + 313-309 + 310
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Allyl isothiocyanate ( AITC ) is formed during the enzymatic conversion of the mustard oil glycoside sinigrin , which is the main component of the mustard oil of black mustard ( Brassica nigra ) with a content of over 95% . It is therefore also known as allyl mustard oil. Allyl isothiocyanate - among other ingredients - is responsible for the pungent taste of mustard , horseradish and wasabi .

Allyl isothiocyanate (below, marked in blue ) is formed during the hydrolysis of sinigrin , a plant ingredient (e.g. garlic mustard or black mustard).

properties

The substance is a colorless to slightly yellowish, steam-volatile and optically inactive oil with a pungent odor. It is sparingly soluble in water, but can be mixed with the organic solvents ethanol, diethyl ether and benzene. Allyl isothiocyanate is very reactive. Allyl isothiocyanate is hydrolyzed to allylamine in just a few minutes by cold water . It is sensitive to light, air, heat and heavy metals. When standing for a long time, it breaks down to form an orange-red colored substance.

use

Mutagenic insecticide

Sprout inhibitors for wheat, peas, rapeseed, lettuce (food products such as Japanese tube horseradish)

Flavor for food, e.g. B. Fruit mustard sauce

Synthesis of warfare agents

Fighting cancer: In one study, mustard seed powder was highly effective against bladder cancer cells in vitro . Since allyl isothiocyanate is excreted in the urine, application of the powder in vivo in bladder cancer seems promising.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on allyl isothiocyanate in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-12.
↑ Jonathan Clayden, Nick Greeves, Stuart Warren, Peter Wothers: Organic Chemistry , Oxford University Press, 2001, ISBN 978-0-19-850346-0 , pp. 1367-1368.
↑ Otto-Albrecht Neumüller (Ed.): Römpps Chemie-Lexikon. Volume 1: A-Cl. 8th revised and expanded edition. Franckh'sche Verlagshandlung, Stuttgart 1979, ISBN 3-440-04511-0 , p. 141.
↑ Arup Bhattacharya, Yun Li, Kristina L. Wade, Joseph D. Paonessa, Jed W. Fahey, and Yuesheng Zhang: Allyl Isothiocyanate-Rich Mustard Seed Powder Inhibits Bladder Cancer Growth and Muscle Invasion . In: Carcinogenesis . 32, No. 1, January 2011. doi : 10.1093 / carcin / bgq202 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on allyl isothiocyanate in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .

[CRC90_3_12-2] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-12.

[Clayden-3] Jonathan Clayden, Nick Greeves, Stuart Warren, Peter Wothers: Organic Chemistry , Oxford University Press, 2001, ISBN 978-0-19-850346-0 , pp. 1367-1368.

[RÖMPP-4] Otto-Albrecht Neumüller (Ed.): Römpps Chemie-Lexikon. Volume 1: A-Cl. 8th revised and expanded edition. Franckh'sche Verlagshandlung, Stuttgart 1979, ISBN 3-440-04511-0 , p. 141.

[5] Arup Bhattacharya, Yun Li, Kristina L. Wade, Joseph D. Paonessa, Jed W. Fahey, and Yuesheng Zhang: Allyl Isothiocyanate-Rich Mustard Seed Powder Inhibits Bladder Cancer Growth and Muscle Invasion . In: Carcinogenesis . 32, No. 1, January 2011. doi : 10.1093 / carcin / bgq202 .