# Glucotropaeolin

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{{Chembox
<!-- Images -->
| ImageFile = Glucotropaeolin.svg
| ImageSize = 200px
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<!-- Names -->
| IUPACName = 1-''S''-[(1''Z'')-2-Phenyl-''N''-(sulfooxy)ethanimidoyl]-1-thio-beta-<small>D</small>-glucopyranose
| OtherNames = Benzyl glucosinolate
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| Section1 = {{Chembox Identifiers
| CASNo = 499-26-3
<!-- CAS shows E isomer but natural product is Z -->
| PubChem = 6537197
| ChemSpiderID = 5020503
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| KEGG = C02153
| ChEBI = 17127
| Beilstein = 61369
| SMILES = c1ccc(cc1)C/C(=N/OS(=O)(=O)O)/S[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI=1S/C14H19NO9S2/c16-7-9-11(17)12(18)13(19)14(23-9)25-10(15-24-26(20,21)22)6-8-4-2-1-3-5-8/h1-5,9,11-14,16-19H,6-7H2,(H,20,21,22)/b15-10-/t9-,11-,12+,13-,14+/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey=QQGLQYQXUKHWPX-RFEZBLSLSA-N
  }}
| Section2 = {{Chembox Properties
| C=14|H=19|N=1|O=9|S=2
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| Section3 = {{Chembox Hazards
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'''Glucotropaeolin''' or '''benzyl glucosinolate''' is a [glucosinolate](/source/glucosinolate) found in [cruciferous vegetable](/source/cruciferous_vegetable)s, particularly [garden cress](/source/garden_cress).<ref>{{Cite web | url = http://lpi.oregonstate.edu/mic/dietary-factors/phytochemicals/isothiocyanates | title = Isothiocyanates | publisher = Linus Pauling Institute, Oregon State University}}</ref>  Upon enzymatic activity, it is transformed into [benzyl isothiocyanate](/source/benzyl_isothiocyanate), which contributes to the characteristic flavor of these [brassicas](/source/brassicas).
==Occurrence==
The compound was first reported in 1899, after its isolation from ''[Tropaeolum majus](/source/Tropaeolum_majus)'', a nasturtium species.<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 |article-number=112100 |pmid=31771793 |s2cid=208318505 }}</ref>{{rp|Section 2}} Glucotropaeolin is now known to occur widely in other [brassica families](/source/brassica) including [Caricaceae](/source/Caricaceae), [Phytolaccaceae](/source/Phytolaccaceae), [Resedaceae](/source/Resedaceae), [Salvadoraceae](/source/Salvadoraceae) and [Tovariaceae](/source/Tovariaceae).<ref>{{cite journal |doi=10.1016/S0031-9422(00)00316-2 |title=The chemical diversity and distribution of glucosinolates and isothiocyanates among plants |year=2001 |last1=Fahey |first1=Jed W. |last2=Zalcmann |first2=Amy T. |last3=Talalay |first3=Paul |journal=Phytochemistry |volume=56 |issue=1 |pages=5–51 |pmid=11198818 }}</ref>

==Structure==
thumb|left|E isomer
The chemical structure of glucotropaeolin was confirmed by [total synthesis](/source/total_synthesis) in 1957. This showed that it is a glucose derivative with [β-<small>D</small>-glucopyranose](/source/pyranose) configuration. At that time it was unclear whether the C=N bond was in the [Z form](/source/E%E2%80%93Z_notation), with sulfur and oxygen substituents on the same side of the double bond, or the alternative E form in which they are on opposite sides. The suggestion was made that the Z form was more likely, based on the known decomposition to [benzyl isothiocyanate](/source/benzyl_isothiocyanate) by a mechanism analogous to the [Lossen rearrangement](/source/Lossen_rearrangement).<ref name=Ettlinger>{{cite journal |doi=10.1021/ja01564a066 |title=First Synthesis of a Mustard Oil Glucoside; the Enzymatic Lossen Rearrangement |year=1957 |last1=Ettlinger |first1=Martin G. |last2=Lundeen |first2=Allan J. |journal=Journal of the American Chemical Society |volume=79 |issue=7 |pages=1764–1765 }}</ref> However, when an identical product was obtained by an alternative route in 1963, it was pointed out that the E form would be expected to rearrange in a similar way.<ref name=Benn>{{cite journal |doi=10.1139/v63-415 |title=A New Mustard Oil Glucoside Synthesis: The Synthesis of Glucotropaeolin |year=1963 |last1=Benn |first1=M. H. |journal=Canadian Journal of Chemistry |volume=41 |issue=11 |pages=2836–2838 |doi-access=free }}</ref> The matter was settled by X-ray crystallography and other spectroscopic studies and it is now known that all natural [glucosinolates](/source/glucosinolates) are of Z form.<ref name=pmid31771793/>
==Synthesis==
===Biosynthesis===
Glucotropaeolin is biosynthesised from the amino acid [phenylalanine](/source/phenylalanine) in a multi-step pathway.<ref name=pmid31771793/>
===Laboratory synthesis===
The first laboratory syntheses served to confirm the compound's structure.<ref name=Ettlinger/><ref name=Benn/> Later work allowed many glucosinolates including this benzyl derivative to be made. These processes are more efficient than isolating pure materials from the plants in which they are naturally found.<ref name=pmid31771793/>{{rp|Section 3}}
==Function==
{{Main|Glucosinolate}}
The natural role of glucosinolates are as plant defense compounds. The enzyme [myrosinase](/source/myrosinase) removes the glucose group in glucotropaeolin to give an intermediate which spontaneously rearranges to [benzyl isothiocyanate](/source/benzyl_isothiocyanate). This is a reactive material which is toxic to many insect predators and its production is triggered when the plant is damaged.<ref>{{cite journal |doi=10.1016/j.phytochem.2008.03.006 |title=β-Glucosidases as detonators of plant chemical defense |year=2008 |last1=Morant |first1=Anne Vinther |last2=Jørgensen |first2=Kirsten |last3=Jørgensen |first3=Charlotte |last4=Paquette |first4=Suzanne Michelle |last5=Sánchez-Pérez |first5=Raquel |last6=Møller |first6=Birger Lindberg |last7=Bak |first7=Søren |journal=Phytochemistry |volume=69 |issue=9 |pages=1795–1813 |pmid=18472115 }}</ref> This effect has been called the [mustard oil bomb](/source/mustard_oil_bomb).<ref>{{cite journal |doi=10.1016/S0015-3796(80)80059-X |title="Die Senfolbombe": Zur Kompartimentierung des Myrosinasesystems |year=1980 |last1=Matile |first1=Ph. |journal=Biochemie und Physiologie der Pflanzen |volume=175 |issue=8–9 |pages=722–731 }}</ref> At concentrations typically found in foods, the glucosinolates are not toxic to humans and can be useful flavor components.<ref>{{cite journal |doi=10.1080/10408398209527361 |title=Glucosinolates and their breakdown products in food and food plants |year=1983 |last1=Fenwick |first1=G. Roger |last2=Heaney |first2=Robert K. |last3=Mullin |first3=W. John |last4=Vanetten |first4=Cecil H. |journal=C R C Critical Reviews in Food Science and Nutrition |volume=18 |issue=2 |pages=123–201 |pmid=6337782 }}</ref>
==References==
{{reflist}}

{{Cruciferous Biochemistry}}

Category:Glucosinolates
Category:Benzyl compounds

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Adapted from the Wikipedia article [Glucotropaeolin](https://en.wikipedia.org/wiki/Glucotropaeolin) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Glucotropaeolin?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.