Glucotropaeolin

Glucotropaeolin
Names

IUPAC name 1-S-[(1E)-2-Phenyl-N-(sulfooxy)ethanimidoyl]-1-thio-beta-D-glucopyranose
Other names Benzylglucosinolate
Identifiers
CAS Number	499-26-3
3D model (JSmol)	Interactive image
ChemSpider	7827528
InChI 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
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
Properties
Chemical formula	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

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.

Refs

Cruciferous biochemistry
Types of compounds	Phenylthiocarbamide (PTC/PTU) Thiocyanates Nitriles Indoles Gibberellin
Glucosinolates	Glucobrassicin Glucocapparin Glucoraphanin Gluconasturtiin Glucotropaeolin Progoitrin Sinigrin Sinalbin
Isothiocyanates (ITC, mustard oils)	Sulforaphane (SFN) Raphanin Allyl isothiocyanate (AITC) Methyl isothiocyanate (MITC) Benzyl isothiocyanate (BITC) Fluorescein isothiocyanate (FITC) Phenyl isothiocyanate (PITC) Phenethyl isothiocyanate (PEITC) 6-MITC
Bioactive metabolites	Goitrin Indole-3-carbinol
Brassicaceae (Cruciferous vegetables): Brassica Raphanus Cruciferous Biochemistry genera (list)

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