Glucotropaeolin

Glucotropaeolin (benzylglucosinolate) is a glucosinolate found in cruciferous vegetables, particularly garden cress.[1] Upon enzymatic activity, it is transformed into benzyl isothiocyanate (BITC). Isothiocyanates are being studied for their toxicity to cancer, which is more generally sensitive to toxins than healthy cells.

Glucotropaeolin
Names
IUPAC name
1-S-[(1E)-2-Phenyl-N-(sulfooxy)ethanimidoyl]-1-thio-beta-D-glucopyranose
Other names
Benzylglucosinolate
Identifiers
3D model (JSmol)
61369
ChEBI
ChemSpider
KEGG
  • InChI=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
    Key: QQGLQYQXUKHWPX-BXLHIMNRSA-N
  • 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
Properties
C14H19NO9S2
Molar mass 409.42 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Refs
  1. "Isothiocyanates". Linus Pauling Institute, Oregon State University.
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