Alpha-(3,4,5-trimethoxybenzylidene)-beta-methoxypropylnitrile is a nitrile-containing impurity arising from condensation between 3,4,5-trimethoxybenzaldehyde and 3-methoxyacrylonitrile. Its structure features a conjugated enone system bridging a trimethoxyphenyl ring and a methoxy-substituted nitrile chain, conferring rigidity and hydrophobic character. This impurity likely forms during alkylation steps in the synthesis of the parent pharmaceutical agent, where methoxy-directed electrophilic substitution occurs. Serves as an HPLC reference standard for quantitative impurity profiling in drug substance batches.
On Request[2H]C([2H])([2H])OC1=C(C=C(C=C1OC)/C=C(/COC)\C#N)OC
InChI=1S/C14H17NO4/c1-16-9-11(8-15)5-10-6-12(17-2)14(19-4)13(7-10)18-3/h5-7H,9H2,1-4H3/b11-5+/i4D3
RMKSZKNEPFLURM-VVJDSYHOSA-N