Abstract
This article deals with the identification and characterization of process-related impurities of trans-resveratrol (3,5,4′-trihydroxystilbene), which exhibits several health benefits, including cancer prevention. During the synthesis of the bulk drug resveratrol, three new impurities were observed. The impurities were detected using the high-performance liquid chromatographic (HPLC) method, whose area percentages ranged from 0.05 to 0.3%. A systematic study was carried out to characterize them. These impurities were isolated by preparative HPLC and characterized by spectral data, subjected to co-injection in HPLC, and were found to be matching with the impurities present in the sample. LC-MS was performed to identify the mass of these impurities. Based on their spectral data (IR, NMR, and Mass), these impurities were characterized as 2-benzyl-5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol [Impurity-B], 3-(benzyloxy)-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenol [Impurity-C], 5-{(E)-2-[4-(benzyloxy)phenyl]ethenyl}benzene-1,3-diol [Impurity-D). These compounds are not reported earlier as process-related impurities.
Highlights
Resveratrol (3,5,4'-trihydroxystilbene) is a naturally-occurring phytoalexin produced by various plants in response to environmental stress or pathogenic attack
These impurities are required in pure form to check the HPLC method performance in areas such as specificity, linearity, range, accuracy, precision, limit of detection (LOD), limit of quantification (LOQ), robustness, system suitability testing, and relative response factor (RRF) [8]
We have identified the following five impurities in the samples analyzed: Identification and Characterization of Process-Related Impurities of Trans-Resveratrol (Z)-5-[2-(4-Hydroxphenyl)ethenyl]benzene-1,3-diol [cis-resveratrol [Impurity-A], 2-Benzyl-5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol [Impurity-B], 3-(Benzyloxy)-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenol [Impurity-C], 5-{(E)-2-[4-(Benzyloxy)phenyl]ethenyl}benzene-1,3-diol [Impurity-D); 1,3-(Dibenzyloxy)-5-[(E)-2-(4-benzyloxyphenyl)ethenyl)benzene [Impurity-E]
Summary
Resveratrol (3,5,4'-trihydroxystilbene) is a naturally-occurring phytoalexin produced by various plants in response to environmental stress or pathogenic attack. During the analysis of laboratory batches of resveratrol, three impurities were observed by the HPLC method (Figure 1). The structure of the three isolated impurities (Figure 2) related to the process is identified/characterized by the various characterization techniques such as UV, IR, NMR & Mass, and chromatographically by HPLC spiking studies.
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
