Yuzu ( Citrus junos Sieb. ex Tanaka), a tree-grown fruit similar to a kind of sour orange, is widely used in Japanese food/cooking for its pleasant flavor. To clarify the odor-active volatiles that differentiate yuzu from other citrus fruits, sensory evaluations were conducted on yuzu peel oil. The results revealed that the polar part of yuzu peel oil was the source of the characteristic aroma of fresh yuzu fruit. By aroma extract dilution analysis (AEDA) of the polar volatile part of yuzu peel oil, seven odorants were newly identified as odor-active volatiles in yuzu peel oil in the highest flavor dilution (FD) factors of 128 and 32: oct-1-en-3-one, (E)-non-4-enal, (E)-dec-4-enal, 4-methyl-4-mercaptopentan-2-one, (E)-non-6-enal, (6Z,8E)-undeca-6,8,10-trien-3-one (Yuzunone), and (6Z,8E)-undeca-6,8,10-trien-4-ol (Yuzuol). Among the most odor-active volatiles in yuzu, (E)-non-6-enal and Yuzunone were identified for the first time solely in yuzu peel oil and not in the peel of other citrus species, and Yuzuol was identified for the first time in nature. Sensory evaluation of yuzu aroma reconstitutions revealed that the newly identified compound, Yuzunone, contributes greatly to the distinct yuzu aroma.
A chiral titanium complex, Ti(O-i-Pr)(4)/BINOL/tert-butylcatechol, catalyzes enantioselective addition reaction of ketene silyl acetals to nitrones to give optically active beta-amino acid derivatives which are biologically active compounds and useful synthetic intermediates of natural products and pharmaceuticals such as beta-lactam antibiotics. The combined process of catalytic oxidation of secondary amines and enantioselective carbon-carbon bond formation of nitrones thus obtained with ketene silyl acetals provides a useful two-step method for the synthesis of optically active beta-amino acid derivatives and related nitrogen compounds.
Galbanum oil is composed of monoterpenes in large amounts and pyrazines in small amounts. Although the monoterpenes are the main components of galbanum oil, they hardly contribute to the distinct galbanum aroma. The scanty amounts of pyrazines, in contrast, contribute significantly to the aroma. Considering the complexity and potency of the odor, the essential oil was assumed to contain so far not identified compounds with high odor contribution. By the gas chromatography-mass spectrometry-olfactometry (GC-MS-O) analysis of galbanum oil, fruity-green-balsamic notes were detected at two different retention times. The mass spectra (MS) of the newly discovered notes were elucidated by conducting multidimensional (MD) GC-MS-O. By analyzing the MS data, six chemical structures were proposed: (6E/Z,8E)-undeca-6,8,10-trien-2-one, (6E/Z,8E)-undeca-6,8,10-trien-3-one, and (6E/Z,8E)-undeca-6,8,10-trien-4-one. The compounds were then synthesized in an attempt to match the MS, retention indices (RI), and odor qualities. The MD-GC-MS-O analyses of the candidate compounds led to the identification of the novel key aroma compounds (6Z,8E)-undeca-6,8,10-trien-3-one and (6Z,8E)-undeca-6,8,10-trien-4-one in galbanum oil.
The purpose of this study was to elucidate the effect of high-temperature storage on the stability of ranitidine, specifically with respect to the potential formation of N-nitrosodimethylamine (NDMA), which is classified as a probable human carcinogen. Commercially available ranitidine reagent powders and formulations were stored under various conditions, and subjected to LC-MS/MS analysis. When ranitidine tablets from two different brands (designated as tablet A and tablet B) were stored under accelerated condition (40 °C with 75% relative humidity), following the drug stability guidelines issued by the International Conference on Harmonisation (ICH-Q1A), for up to 8 weeks, the amount of NDMA in them substantially increased from 0.19 to 116 ppm and from 2.89 to 18 ppm, respectively. The formation of NDMA that exceeded the acceptable daily intake limit (0.32 ppm) at the temperature used under accelerated storage conditions clearly highlights the risk of NDMA formation in ranitidine formulations when extrapolated to storage under ambient conditions. A forced-degradation study under the stress condition (60 °C for 1 week) strongly suggested that environmental factors such as moisture and oxygen are involved in the formation of NDMA in ranitidine formulations. Storage of ranitidine tablets and reagent powders at the high temperatures also increased the amount of nitrite, which is considered one of the factors influencing NDMA formation. These data indicate the necessity of controlling/monitoring stability-related factors, in addition to controlling impurities during the manufacturing process, in order to mitigate nitrosamine-related health risks of certain pharmaceuticals.
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