8545. Sinigrin
Nomenclature
CAS number: 3952-98-5
1-Thio-β-d-glucopyranose 1-[N-(sulfooxy)-3-butenimidate]
monopotassium salt; sinigroside; myronate potassium; potassium myronate; allyl glucosinolate. C10H16KNO9S2; mol wt 397.46.
C 30.22%, H 4.06%, K 9.84%, N 3.52%, O 36.23%, S 16.13%.
Description and references
A β-glucopyranoside isolated from black mustard seeds and from the horseradish root Alliaria officinalis Andrz., Cruciferae: A. Bussy, J. Pharm. Chim. 26, 39 (1840); Gadamer, Arch. Pharm. 235, 44 (1897); Stoll, Seebeck, Helv. Chim. Acta 31, 1432 (1948). Structure: Ettlinger, Lundeen, J. Am. Chem. Soc. 78, 4173 (1956); 79, 1764 (1957). Hydrolysis: Ettlinger et al., Proc. Natl. Acad. Sci. USA 47, 1875 (1961). Crystal structure: Waser, Watson, Nature 198, 1297 (1963). Synthesis: Benn, Ettlinger, Chem. Commun. 1965, 445; A. Kjaer, Acta Chem. Scand. 22, 3324 (1968).
Derivative
Monohydrate.Properties
Crystals, mp 127-129°. When anhydr mp 179°. [α]D18 -16.4°. Freely sol in water, hot alcohol; insol in benzene, chloroform, ether.Derivative
Tetraacetate.C18H24KNO13S2; mol wt 565.61.
C 38.22%, H 4.28%, K 6.91%, N 2.48%, O 36.77%, S 11.34%.