Structure and generation mechanism of a novel degradation product formed by oxidatively induced coupling of miconazole nitrate with butylated hydroxytoluene in a topical ointment studied by HPLC-ESI-MS and organic synthesis
✍ Scribed by Fa Zhang; Mathews Nunes
- Publisher
- John Wiley and Sons
- Year
- 2004
- Tongue
- English
- Weight
- 164 KB
- Volume
- 93
- Category
- Article
- ISSN
- 0022-3549
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✦ Synopsis
In a petrolatum based topical ointment formulation containing miconazole nitrate (1) as the active ingredient and 2,6-di-t-butyl-4-methylphenol (BHT) as a vehicle antioxidant, an oxidatively induced coupling reaction between miconazole nitrate and BHT occurred to form a novel adduct 1-
. The structure of 2 was established using high-performance liquid chromatography coupled with electrospray ionization mass spectrometry and was confirmed by comparing with a synthesized reference compound. The reaction proceeded through a quinone methide intermediate from BHT. Two synthetic methods were established for preparing 2.