57103-47-6

Basic information

• Product Name: (2R)-2-(beta-D-glucopyranosyloxy)-3-methylbutanenitrile
• Synonyms: Butanenitrile, 2-(β-D-glucopyranosyloxy)-3-methyl-, (2R)-
• CAS NO: 57103-47-6
• Molecular Formula: C₁₁H₁₉NO₆
• Molecular Weight: 261.2717
• Mol File: 57103-47-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 479.1°C at 760 mmHg
• Flash Point: 243.5°C
• Density: 1.35g/cm³
• Vapor Pressure: 3.44E-11mmHg at 25°C
• Refractive Index: 1.54
• CAS DataBase Reference: (2R)-2-(beta-D-glucopyranosyloxy)-3-methylbutanenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-2-(beta-D-glucopyranosyloxy)-3-methylbutanenitrile(57103-47-6)
• EPA Substance Registry System: (2R)-2-(beta-D-glucopyranosyloxy)-3-methylbutanenitrile(57103-47-6)

Safety Data

• Hazardous Substances Data: 57103-47-6(Hazardous Substances Data)

Upstream product

• 625-28-5 Isovaleronitrile 
• 2280-44-6 D-Glucose 
• 15344-34-0 2-hydroxy-3-methylbutanenitrile 

Relevant articles and documents

Discrimination of the two diasteroisomeric glycosides heterodendrin and epi-heterodendrin by the combined use of NOE and molecular mechanics

The two glycosides (S)-heterodendrin and (R)-epi-heterodendrin were synthesized in a novel, one-step enzymatic synthesis, and separated by means of column chromatography.The 1H NMR spectra of the two diastereoisomers differ mainly in the chemical shift of H-2' of the side chain.At first sight the 1H NMR spectra do not allow a stereospecific assignment.It was found, however, that the NOE between the anomeric proton H-1 and H-2' of the side chain is considerably larger in epi-heterodendrin than in heterodendrin, which indicates on a time-averaged basis a smallerdistance between these two protons in epi-heterodendrin.This difference in conformational behaviour is correctly reproduced by molecular mechanics calculations, thereby offering a method for the discrimination of these two glycosides.Keywords: MM2; Cyanogenic glycoside; 3D structure; Conformational analysis; Glucosidase

Biosynthesis of cyanohydrin glucosides from unnatural nitriles in intact tissue of Passiflora morifolia and Turnera angustifolia

Passiflora morifolia, which under natural conditions contains cyanohydrin glucosides linamarin, lotaustralin and epilotaustralin, converted cyclopentanecarbonitrile, 2-cyclopentenecarbonitrile and 3- methylbutanenitrile into the corresponding cyanohydrin glucosides. Turnera angustifolia, which normally produces glucosides of cyclopentenone cyanohydrin, converted cyclopentanecarbonitrile, 2-methylpropanenitrile and 2-methylbutanenitrile, but not 3-methylbutanenitrile, into the corresponding cyanohydrin glucosides. Mixtures of epimers were produced when these glucosides contained chiral cyanohydrin carbon atoms. Feeding with cyclopentanecarbonitrile resulted in formation of 1-(β-D- glucopyranosyloxy)cyclopentanecarbonitrile, a saturated analogue of deidaclin and tetraphyllin A. Neither plant utilized cyclopropanecarbonitrile as substrate. The experiments demonstrate broad substrate specificity of nitrile hydroxylases present in these plants. A novel glycoside, 2-[6-O-(β-D- xylopyranosyl)-β-D-glucopyranosyloxy]propane (isopropyl primeveroside), was isolated from P. morifolia. The compound represents a rare example of natural isopropyl glycoside; its characterization included assignment of all 1H and (13C) NMR signals of the primeverosyl group using two-dimensional NMR methods. Biosynthesis of the isopropyl moiety of the primeveroside is unclear, but the formation of alcohols corresponding to natural cyanohydrins may be a previously unrecognized extension of the cyanohydrin biosynthesis pathway in higher plants.