Table of Contents Categories
Allyl isothiocyanate
Topic: Chemistry
From HandWiki - Reading time: 8 min
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| Names | |
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| Preferred IUPAC name
3-Isothiocyanatoprop-1-ene | |
| Other names
Synthetic mustard oil
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| UNII | |
| UN number | 1545 |
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| 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 pictograms |    
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| GHS Signal word | 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+310, P302+350, P302+352, P303+361+353, P304+340, P305+351+338, P310, P312, P320, P321 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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| 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]
Biosynthesis and biological functions
Allyl isothiocyanate can be obtained from the seeds of black mustard (Rhamphospermum nigrum) or brown Indian mustard (Brassica juncea). When these mustard seeds are broken, the enzyme myrosinase is released and acts on a glucosinolate known as sinigrin to give allyl isothiocyanate.[5] This serves the plant as a defense against herbivores; since it is harmful to the plant itself,[6] it is stored in the harmless form of the glucosinolate, separate from the myrosinase enzyme. When an animal chews the plant, the allyl isothiocyanate is released, repelling the animal. Human appreciation of the pungency is learned.[7]: 105
The compound has been shown to strongly repel fire ants (Solenopsis invicta).[8] AITC vapor is also used as an antimicrobial and shelf life extender in food packaging.[7]: 118–120
Production and applications
Allyl isothiocyanate is produced commercially by the reaction of allyl chloride and potassium thiocyanate:[4]
- CH2=CHCH2Cl + KSCN → CH2=CHCH2NCS + KCl
The product obtained in this fashion is sometimes known as synthetic mustard oil. Allyl thiocyanate isomerizes to the isothiocyanate:[9]
- CH
2=CHCH
2SCN → CH
2=CHCH
2NCS
Allyl isothiocyanate can also be liberated by dry distillation of the seeds. The product obtained in this fashion is known as volatile oil of mustard.
It is used principally as a flavoring agent in foods. Synthetic allyl isothiocyanate is used as an insecticide, as an anti-mold agent [10] bacteriocide,[11] and nematicide, and is used in certain cases for crop protection.[4] It is also used in fire alarms for the deaf.[12][13]
Hydrolysis of allyl isothiocyanate gives allylamine.[14]
Safety
Allyl isothiocyanate has an LD50 of 151 mg/kg and is a lachrymator (similar to tear gas or mace).[4]
Oncology
Based on in vitro experiments and animal models, allyl isothiocyanate exhibits many of the desirable attributes of a cancer chemopreventive agent.[15]
See also
- Mustard plaster, traditional home remedy
- Piperine, the piquant chemical in black pepper
- Capsaicin, the piquant chemical in chili peppers
- Allicin, the piquant flavor chemical in raw garlic
References
- ↑ Everaerts, W.; Gees, M.; Alpizar, Y. A.; Farre, R.; Leten, C.; Apetrei, A.; 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. Bibcode: 2011CBio...21..316E.
- ↑ 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.2008.04.005. PMID 18501939. Bibcode: 2008ToxAP.231..150B.
- ↑ Ryckmans, T. 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.
- ↑ 4.0 4.1 4.2 4.3 Romanowski, F.; Klenk, H.. "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_749.
- ↑ Blažević, Ivica; Montaut, Sabine; Burčul, Franko; Olsen, Carl Erik; Burow, Meike; Rollin, Patrick; Agerbirk, Niels (2020). "Glucosinolate structural diversity, identification, chemical synthesis and metabolism in plants". Phytochemistry 169. doi:10.1016/j.phytochem.2019.112100. PMID 31771793. Bibcode: 2020PChem.169k2100B.
- ↑ Li, Yingbin; Lu, Daqing; Xia, Yan; Xu, Xinjing; Huang, Huichuan; Mei, Xinyue; Yang, Min; Li, Jianqiang et al. (2023-09-30). "Effects of allyl isothiocyanate fumigation on medicinal plant root knot disease control, plant survival, and the soil bacterial community". BMC Microbiology 23 (1): 278. doi:10.1186/s12866-023-02992-w. ISSN 1471-2180. PMID 37775764. "Allyl isothiocyanate (AITC) [...] has been used in agriculture because of its fungicidal [...] bactericidal, nematocidal [able to destroy nematodes], and herbicidal [able to destroy plants] biological activities.".
- ↑ 7.0 7.1 Melton, Laurence, ed (2019). The Encyclopedia of Food Chemistry. Netherlands: Elsevier. ISBN 978-0-12-814045-1.
- ↑ Hashimoto, Yoshiaki; Yoshimura, Masashi; Huang, Rong-Nan (2019). "Wasabi versus red imported fire ants: Preliminary test of repellency of microencapsulated allyl isothiocyanate against Solenopsis invicta (Hymenoptera: Formicidae) using bait traps in Taiwan". Applied Entomology and Zoology 54 (2): 193–196. doi:10.1007/s13355-019-00613-5. Bibcode: 2019AppEZ..54..193H. https://oist.repo.nii.ac.jp/?action=repository_uri&item_id=1557.
- ↑ Emergon, David W. (1971). "The Preparation and Isomerization of Allyl Thiocyanate. An Organic Chemistry Experiment". Journal of Chemical Education 48 (1): 81. doi:10.1021/ed048p81. Bibcode: 1971JChEd..48...81E.
- ↑ US Patent No. 8691042
- ↑ Masuda, Shuichi; Masuda, Hideki; Shimamura, Yuko; Sugiyama, Chitose; Takabayashi, Fumiyo (April 2017). "Improvement Effects of Wasabi (Wasabia japonica) Leaves and Allyl Isothiocyanate on Stomach Lesions of Mongolian Gerbils Infected with Helicobacter pylori". Natural Product Communications 12 (4): 595–598. doi:10.1177/1934578X1701200431. PMID 30520603.
- ↑ US patent 20100308995A1, Hideaki Goto, Tomo Sakai, Koichiro Mizoguchi, Yukinobu Tajima, Makoto Imai, "Odor generation alarm and method for informing unusual situation", issued 2015-06-24
- ↑ Phillipson, Tacye (29 August 2018). "Why would you want a wasabai fire alarm?". https://blog.nms.ac.uk/2018/08/29/why-would-you-want-a-wasbai-fire-alarm/.
- ↑ Leffler, M. T. (1938). "Allylamine". Organic Syntheses 18: 5. http://www.orgsyn.org/demo.aspx?prep=CV2P0024.; Collective Volume, 2, pp. 24
- ↑ Zhang, Y (2010). "Allyl isothiocyanate as a cancer chemopreventive phytochemical". Molecular Nutrition & Food Research 54 (1): 127–35. doi:10.1002/mnfr.200900323. PMID 19960458.
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