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Allyl isothiocyanate
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==Biosynthesis and biological functions== Allyl isothiocyanate can be obtained from the seeds of [[Rhamphospermum nigrum|black mustard]] (''Rhamphospermum nigrum'') or brown [[Brassica juncea|Indian mustard]] (''Brassica juncea''). When these [[mustard seed]]s are broken, the [[enzyme]] [[myrosinase]] is released and acts on a [[glucosinolate]] known as [[sinigrin]] to give allyl isothiocyanate.<ref name=pmid31771793>{{cite journal |doi=10.1016/j.phytochem.2019.112100 |doi-access=free |title=Glucosinolate structural diversity, identification, chemical synthesis and metabolism in plants |year=2020 |last1=Blažević |first1=Ivica |last2=Montaut |first2=Sabine |last3=Burčul |first3=Franko |last4=Olsen |first4=Carl Erik |last5=Burow |first5=Meike |last6=Rollin |first6=Patrick |last7=Agerbirk |first7=Niels |journal=Phytochemistry |volume=169 |page=112100 |pmid=31771793 |bibcode=2020PChem.169k2100B |s2cid=208318505 }}</ref> This serves the plant as a defense against [[herbivore]]s; since it is harmful to the plant itself,<ref>{{Cite journal |last1=Li |first1=Yingbin |last2=Lu |first2=Daqing |last3=Xia |first3=Yan |last4=Xu |first4=Xinjing |last5=Huang |first5=Huichuan |last6=Mei |first6=Xinyue |last7=Yang |first7=Min |last8=Li |first8=Jianqiang |last9=Zhu |first9=Shusheng |last10=Liu |first10=Yixiang |last11=Zhang |first11=Zhiping |date=2023-09-30 |title=Effects of allyl isothiocyanate fumigation on medicinal plant root knot disease control, plant survival, and the soil bacterial community |journal=BMC Microbiology |volume=23 |issue=1 |pages=278 |doi=10.1186/s12866-023-02992-w |doi-access=free |issn=1471-2180 |pmc=10542678 |pmid=37775764 |quote=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. }}</ref> 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.<ref name=EFC>{{Cite book |editor-last=Melton |editor-first=Laurence |title=The Encyclopedia of Food Chemistry |publisher=Elsevier |year=2019 |isbn=978-0-12-814045-1 |location=Netherlands }}</ref>{{rp|105}} The compound has been shown to strongly repel [[Red imported fire ant|fire ants]] (''Solenopsis invicta'').<ref>{{cite journal | doi = 10.1007/s13355-019-00613-5 | title = Wasabi versus red imported fire ants: Preliminary test of repellency of microencapsulated allyl isothiocyanate against Solenopsis invicta (Hymenoptera: Formicidae) using bait traps in Taiwan | date = 2019 | last1 = Hashimoto | first1 = Yoshiaki | last2 = Yoshimura | first2 = Masashi | last3 = Huang | first3 = Rong-Nan | journal = Applied Entomology and Zoology | volume = 54 | issue = 2 | pages = 193–196 | bibcode = 2019AppEZ..54..193H | url = https://oist.repo.nii.ac.jp/?action=repository_uri&item_id=1557 }}</ref> AITC vapor is also used as an antimicrobial and shelf life extender in food packaging.<ref name=EFC/>{{rp|118–120}}
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