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'''異硫氰酸烯丙酯 (Allyl isothiocyanate, AITC)''' 是一種[[有機硫化合物]],其化學式為CH<sub>2</sub>CHCH<sub>2</sub>NCS。 |
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'''異硫氰酸烯丙酯'''(Allyl isothiocyanate, AITC),是一種[[有機硫化合物]],其化學式為CH<sub>2</sub>CHCH<sub>2</sub>NCS。 |
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異硫氰酸烯丙酯是一種無色的油脂,芥菜,蘿蔔,辣根,芥末的刺激性味道都是來自於此化合物。這種辛辣的味道以及催淚的效果是通過[[TRPA1]]和[[TRPV1]]離子通道介導的。<ref>{{cite journal | last1 = Everaerts | first1 = W. | last2 = Gees | first2 = M. | last3 = Alpizar | first3 = Y. A. | last4 = Farre | first4 = R. | last5 = Leten | first5 = C. | last6 = Apetrei | first6 = A. | last7 = Dewachter | first7 = I. | last8 = van Leuven | first8 = F. | last9 = Vennekens | first9 = R. | displayauthors=8| title = The Capsaicin Receptor TRPV1 is a Crucial Mediator of the Noxious Effects of Mustard Oil | journal = Current Biology | year = 2011 | volume = 21 | issue = 4 | pages = 316–321 | pmid = 21315593 | doi = 10.1016/j.cub.2011.01.031 }}</ref><ref name="pmid18501939">{{cite journal | author = Brône, B.; Peeters, P. J.; Marrannes, R.; Mercken, M.; Nuydens, R.; Meert, T.; Gijsen, H. J. | title = Tear gasses CN, CR, and CS are potent activators of the human TRPA1 receptor | journal = [[Toxicology and Applied Pharmacology]] | year = 2008 | volume = 231 | issue = 2 | pages = 150–156 | pmid = 18501939 | doi = 10.1016/j.taap.2008.04.00 }}</ref><ref name="pmid21741838">{{cite journal | author = Ryckmans, T.; Aubdool, A. A.; Bodkin, J. V.; Cox, P.; Brain, S. D.; Dupont, T.; Fairman, E.; Hashizume, Y.; Ishii, N. et al. | title = Design and Pharmacological Evaluation of [[PF-4840154]], a Non-Electrophilic Reference Agonist of the TrpA1 Channel | journal = Bioorganic and Medicinal Chemistry Letters | year = 2011 | volume = 21 | issue = 16 | pages = 4857–4859 | pmid = 21741838 | doi = 10.1016/j.bmcl.2011.06.035 }}</ref>異硫氰酸烯丙酯微溶於水,但易溶於大多數的有機溶劑。<ref name=Ullmann>{{ Ullmann | author = Romanowski, F.; Klenk, H. | title = Thiocyanates and Isothiocyanates, Organic | doi = 10.1002/14356007.a26_749 }}</ref> |
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異硫氰酸烯丙酯是一種無色的油脂,[[芥菜]]、[[蘿蔔]]、[[辣根]]、[[芥末]]的刺激性味道都是來自於此化合物。這種辛辣的味道以及催淚的效果是通過[[TRPA1]]和[[TRPV1]]離子通道介導的。<ref>{{cite journal | last1 = Everaerts | first1 = W. | last2 = Gees | first2 = M. | last3 = Alpizar | first3 = Y. A. | last4 = Farre | first4 = R. | last5 = Leten | first5 = C. | last6 = Apetrei | first6 = A. | last7 = Dewachter | first7 = I. | last8 = van Leuven | first8 = F. | last9 = Vennekens | first9 = R. | displayauthors=8| title = The Capsaicin Receptor TRPV1 is a Crucial Mediator of the Noxious Effects of Mustard Oil | journal = Current Biology | year = 2011 | volume = 21 | issue = 4 | pages = 316–321 | pmid = 21315593 | doi = 10.1016/j.cub.2011.01.031 }}</ref><ref name="pmid18501939">{{cite journal | author = Brône, B.; Peeters, P. J.; Marrannes, R.; Mercken, M.; Nuydens, R.; Meert, T.; Gijsen, H. J. | title = Tear gasses CN, CR, and CS are potent activators of the human TRPA1 receptor | journal = [[Toxicology and Applied Pharmacology]] | year = 2008 | volume = 231 | issue = 2 | pages = 150–156 | pmid = 18501939 | doi = 10.1016/j.taap.2008.04.00 }}</ref><ref name="pmid21741838">{{cite journal | author = Ryckmans, T. |author2=Aubdool, A. A. |author3=Bodkin, J. V. |author4=Cox, P. |author5=Brain, S. D. |author6=Dupont, T. |author7=Fairman, E. |author8=Hashizume, Y. |author9=Ishii, N. |display-authors=etal | title = Design and Pharmacological Evaluation of [[PF-4840154]], a Non-Electrophilic Reference Agonist of the TrpA1 Channel | journal = Bioorganic and Medicinal Chemistry Letters | year = 2011 | volume = 21 | issue = 16 | pages = 4857–4859 | pmid = 21741838 | doi = 10.1016/j.bmcl.2011.06.035 }}</ref>異硫氰酸烯丙酯微溶於水,但易溶於大多數的有機溶劑。<ref name=Ullmann>{{ Ullmann | author = Romanowski, F.; Klenk, H. | title = Thiocyanates and Isothiocyanates, Organic | doi = 10.1002/14356007.a26_749 }}</ref> |
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== 生物合成和生物功能 == |
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== 生物合成和生物功能 == |
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以這種方式獲得的產物有時被稱為合成[[芥子油]]。異硫氰酸烯丙酯也可以藉由種子的[[乾餾]]來獲得,以這種方式獲得的產物被稱為芥末精油,通常純度約為92%,主要用於食品中的調味劑。 |
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以這種方式獲得的產物有時被稱為合成[[芥子油]]。異硫氰酸烯丙酯也可以藉由種子的[[乾餾]]來獲得,以這種方式獲得的產物被稱為芥末精油,通常純度約為92%,主要用於食品中的調味劑。 |
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人工合成的異硫氰酸烯丙酯可以用於當作殺蟲劑或是殺菌劑。<ref>{{cite pmid|15246236}}</ref>並在某些情況下用於保護[[農作物]]。<ref name=Ullmann/> |
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人工合成的異硫氰酸烯丙酯可以用於當作殺蟲劑或是殺菌劑。<ref>{{cite journal|title=Bactericidal activity of wasabi (Wasabia japonica) against Helicobacter pylori|pages=255–261|issn=0168-1605|journal=International Journal of Food Microbiology|volume=94|issue=3|date=2004-08-01|doi=10.1016/S0168-1605(03)00297-6|url=https://www.ncbi.nlm.nih.gov/pubmed/15246236|accessdate=2019-02-12|author=Il Shik Shin, Hideki Masuda, Kinae Naohide|pmid=15246236|archive-date=2020-04-10|archive-url=https://web.archive.org/web/20200410161018/https://www.ncbi.nlm.nih.gov/pubmed/15246236}}</ref>並在某些情況下用於保護[[農作物]]。<ref name=Ullmann/> |
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[[水解]]異硫氰酸烯丙酯可以得到[[烯丙基胺]]。<ref>{{OrgSynth | author = Leffler, M. T. | title = Allylamine | volume = 18 | pages = 5 | collvol = 2 | collvolpages = 24 | year = 1938 | prep = CV2P0024 }}</ref> |
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[[水解]]異硫氰酸烯丙酯可以得到[[烯丙基胺]]。<ref>{{OrgSynth | author = Leffler, M. T. | title = Allylamine | volume = 18 | pages = 5 | collvol = 2 | collvolpages = 24 | year = 1938 | prep = CV2P0024 }}</ref> |
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== 腫瘤 == |
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== 腫瘤 == |
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在[[體外實驗]]以及[[動物實驗]]中,顯示出異硫氰酸烯丙酯具有許多[[腫瘤]]的[[化學預防劑]]的特徵,<ref>{{cite pmid|19960458}}</ref> |
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在[[體外實驗]]以及[[動物實驗]]中,顯示出異硫氰酸烯丙酯具有許多[[腫瘤]]的[[化學預防劑]]的特徵,<ref>{{cite journal|title=Allyl isothiocyanate as a cancer chemopreventive phytochemical|pages=127–135|issn=1613-4133|journal=Molecular Nutrition & Food Research|volume=54|issue=1|date=2010-01|doi=10.1002/mnfr.200900323|url=https://www.ncbi.nlm.nih.gov/pubmed/19960458|accessdate=2019-02-12|author=Yuesheng Zhang|pmid=19960458|pmc=2814364|archive-date=2020-04-10|archive-url=https://web.archive.org/web/20200410161023/https://www.ncbi.nlm.nih.gov/pubmed/19960458}}</ref> |
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== 參考文獻 == |
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== 參考文獻 == |
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*[[辣椒素]], 一種在[[辣椒]]中的化學物質 |
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*[[辣椒素]], 一種在[[辣椒]]中的化學物質 |
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*[[大蒜素]], 一種在未煮熟的[[大蒜]]中的化學物質 |
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*[[大蒜素]], 一種在未煮熟的[[大蒜]]中的化學物質 |
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{{异生素敏感受体调节剂}} |
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[[Category:抗生素]] |
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[[Category:抗生素]] |
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[[Category:異硫氰酸酯]] |
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[[Category:異硫氰酸酯]] |
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[[Category:辛味]] |
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[[Category:辛味]] |
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[[Category:烯丙酯]] |
異硫氰酸烯丙酯(Allyl isothiocyanate, AITC),是一種有機硫化合物,其化學式為CH2CHCH2NCS。
異硫氰酸烯丙酯是一種無色的油脂,芥菜、蘿蔔、辣根、芥末的刺激性味道都是來自於此化合物。這種辛辣的味道以及催淚的效果是通過TRPA1和TRPV1離子通道介導的。[1][2][3]異硫氰酸烯丙酯微溶於水,但易溶於大多數的有機溶劑。[4]
生物合成和生物功能
[编辑]
異硫氰酸烯丙酯主要來自於黑芥菜(Brassica nigra)或印度芥菜(Brassica juncea)的種子。當這些芥菜種子被破壞後,黑芥子酶會被釋放,並且作用在硫代葡萄糖苷(黑芥子硫苷酸钾)上產生出異硫氰酸烯丙酯。
異硫氰酸烯丙酯是植物用於對抗草食動物的防禦化學物質,但因為它本身也對植物具有危害,所以平時以無害的形式儲存,當植物被動物咀嚼時,經由酵素的作用才釋放出異硫氰酸烯丙酯抵抗動物的攝食。
異硫氰酸烯丙酯可藉由烯丙基氯和硫氰酸鉀的反應進行商業化生產:[4]
- CH2=CHCH2Cl + KSCN → CH2=CHCH2NCS + KCl
以這種方式獲得的產物有時被稱為合成芥子油。異硫氰酸烯丙酯也可以藉由種子的乾餾來獲得,以這種方式獲得的產物被稱為芥末精油,通常純度約為92%,主要用於食品中的調味劑。
人工合成的異硫氰酸烯丙酯可以用於當作殺蟲劑或是殺菌劑。[5]並在某些情況下用於保護農作物。[4]
水解異硫氰酸烯丙酯可以得到烯丙基胺。[6]
異硫氰酸烯丙酯可作為一種催淚瓦斯,並且半數致死量為151 mg/kg。[4]
在體外實驗以及動物實驗中,顯示出異硫氰酸烯丙酯具有許多腫瘤的化學預防劑的特徵,[7]
- ^ Everaerts, W.; Gees, M.; Alpizar, Y. A.; Farre, R.; Leten, C.; Apetrei, A.; Dewachter, I.; van Leuven, F.; et al. The Capsaicin Receptor TRPV1 is a Crucial Mediator of the Noxious Effects of Mustard Oil. Current Biology. 2011, 21 (4): 316–321. PMID 21315593. doi:10.1016/j.cub.2011.01.031.
- ^ Brône, B.; Peeters, P. J.; Marrannes, R.; Mercken, M.; Nuydens, R.; Meert, T.; Gijsen, H. J. Tear gasses CN, CR, and CS are potent activators of the human TRPA1 receptor. Toxicology and Applied Pharmacology. 2008, 231 (2): 150–156. PMID 18501939. doi:10.1016/j.taap.2008.04.00.
- ^ Ryckmans, T.; Aubdool, A. A.; Bodkin, J. V.; Cox, P.; Brain, S. D.; Dupont, T.; Fairman, E.; Hashizume, Y.; Ishii, N.; et al. Design and Pharmacological Evaluation of PF-4840154, a Non-Electrophilic Reference Agonist of the TrpA1 Channel. Bioorganic and Medicinal Chemistry Letters. 2011, 21 (16): 4857–4859. PMID 21741838. doi:10.1016/j.bmcl.2011.06.035.
- ^ 4.0 4.1 4.2 4.3 Romanowski, F.; Klenk, H., Thiocyanates and Isothiocyanates, Organic, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a26_749
- ^ Il Shik Shin, Hideki Masuda, Kinae Naohide. Bactericidal activity of wasabi (Wasabia japonica) against Helicobacter pylori. International Journal of Food Microbiology. 2004-08-01, 94 (3): 255–261 [2019-02-12]. ISSN 0168-1605. PMID 15246236. doi:10.1016/S0168-1605(03)00297-6. (原始内容存档于2020-04-10).
- ^ Leffler, M. T. (1938). "Allylamine". Org. Synth. 18: 5; Coll. Vol. 2: 24.
- ^ Yuesheng Zhang. Allyl isothiocyanate as a cancer chemopreventive phytochemical. Molecular Nutrition & Food Research. 2010-01, 54 (1): 127–135 [2019-02-12]. ISSN 1613-4133. PMC 2814364 . PMID 19960458. doi:10.1002/mnfr.200900323. (原始内容存档于2020-04-10).