Linamarin
Title: Linamarin
CAS Registry Number: 554-35-8
CAS Name: 2-(b-D-Glucopyranosyloxy)-2-methylpropanenitrile
Additional Names: phaseolunatin
Molecular Formula: C10H17NO6
Molecular Weight: 247.25
Percent Composition: C 48.58%, H 6.93%, N 5.66%, O 38.83%
Literature References: From the seed skins or embryos of flax: Jorissen, Hairs, Bull. Acad. Roy. Sci. Belg. [3] 21, 529 (1891); André et al., Compt. Rend. 231, 590 (1950); Lüdtke, Biochem. Z. 323, 428 (1953). Synthesis: Fischer, Anger, Ber. 52, 854 (1919). Biosynthesis in white clover: Butler, Butler, Nature 187, 780 (1960).
Properties: Bitter needles, mp 142-143°. [a]D18 -29°. Freely sol in water, cold alcohol, hot acetone; slightly in hot ethyl acetate, ether, benzene, chloroform. Practically insol in petr ether. Evolves HCN with linseed meal but not with emulsin.
Melting point: mp 142-143°
Optical Rotation: [a]D18 -29°
 
Derivative Type: Tetraacetate
Molecular Formula: C18H25NO10
Molecular Weight: 415.39
Percent Composition: C 52.05%, H 6.07%, N 3.37%, O 38.52%
Properties: Needles from alcohol, mp 140-141°. [a]D14 -10.8° (acetone). Sol in acetone, ethyl acetate, chloroform, glacial acetic acid, benzene, warm methanol and ethanol. Practically insol in petr ether.
Melting point: mp 140-141°
Optical Rotation: [a]D14 -10.8° (acetone)

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