isosafrole and piperonal

Piperonal is a compound of key industrial importance due to its attractive olfactory and biological properties. It has been shown that among the fifty-six various fungal strains tested, the ability to cleave the toxic isosafrole into piperonal through alkene cleavage is mainly found in strains of the genus

Topics: Biotransformation; Trametes

Topics: Benzaldehydes; Benzodioxoles; Candida; Escherichia coli; Formate Dehydrogenases; Fungal Proteins; Metabolic Engineering; NAD; Oxygenases; Safrole

Safrole, the main compound in the essential oil of several plants of the Laurel family (Lauraceae), and its secondary product piperonylmethylketone are the predominantly used precursors for the illicit synthesis of 3,4-methylenedioxymethamphetamine (MDMA) which is, in turn, the most common active ingredient in Ecstasy tablets. Analytical methods with adequate capacity to identify links and origin of precursors, such as safrole, provide valuable information for drug-related police intelligence. Authentic sassafras oil samples from police seizures were subjected to comparative analysis based on their chemical profiles obtained by comprehensive two-dimensional gas chromatography time-of-flight mass spectrometry (GC × GC-TOFMS). The enhanced separation power and increased sensitivity of GC × GC allowed for the detection of minor compounds present in the essential oils which were of particular interest in case of very pure samples whose impurity profiles were not very pronounced. Discrimination of such samples was still possible even in the absence of characteristic main compounds.

Topics: Allylbenzene Derivatives; Benzaldehydes; Benzodioxoles; Benzyl Compounds; Cyclohexane Monoterpenes; Dioxolanes; Eugenol; Forensic Toxicology; Gas Chromatography-Mass Spectrometry; Hallucinogens; Illicit Drugs; Molecular Structure; Monoterpenes; N-Methyl-3,4-methylenedioxyamphetamine; Phenols; Plant Oils; Pyrogallol; Safrole; Sassafras

The biotransformation of isosafrole by Cladosporium sphaerospermum yielded piperonal, which is a compound of great commercial importance in the flavor and fragrance industries. The experiments were performed in 500-mL conical flasks containing 100 mL of Czapek-modified medium in an orbital shaker with controlled agitation and temperature. Spores of C. sphaerospermum were used as inocula, and after 96 h of incubation the substrate was added to the culture. Samples of 2 mL were withdrawn at 24-h intervals and analyzed by gas chromatography, (GC) and/or GC/MS spectroscopy.

Topics: Benzaldehydes; Benzodioxoles; Biotransformation; Chromatography, Gas; Cladosporium; Gas Chromatography-Mass Spectrometry; Isomerism; Oxidation-Reduction; Safrole

Eighteen methylenedioxyphenyl (MDP) compounds, including some commonly inhaled by people, were tested for the ability to inhibit rabbit nasal microsomal cytochrome P-450-dependent hexamethylphosphoramide (HMPA) N-demethylase. For comparison, liver microsomes were also used. Nasal cytochrome P-450 from rabbits metabolized MDP compounds to form cytochrome P-450-metabolite (P-450-MI) complexes as indicated by difference spectra in the Soret region. Several of the MDP compounds were potent inhibitors of nasal P-450-dependent N-demethylase. If inhibition of nasal P-450 also occurs in vivo after inhibiting MDP compounds are inhaled, the metabolism of concurrently or subsequently inhaled compounds may be altered.

Topics: Animals; Benzaldehydes; Benzodioxoles; Carcinogens; Cytochrome P-450 Enzyme Inhibitors; Dealkylation; Dioxoles; Liver; Male; Nose; Oxidoreductases, N-Demethylating; Phenols; Piperonyl Butoxide; Rabbits; Safrole

The genotoxicity of safrole, 9 compounds that are structurally similar to safrole (anethole, cinnamaldehyde, cinnamyl alcohol, estragole, methyl eugenol, eugenol, isoeugenol, isosafrole, piperonal), 5 essential oils, cassia oil, cinnamon bark oil, clove oil, fennel oil) which contain the chemicals tested, and 1 oleoresin was studies in 3 microbial test systems. Only anethole showed mutagenicity in the Ames Salmonella reversion assay. All chemicals except anethole, estragole and isosafrole were positive in the Bacillus subtilis DNA-repair test (Rec assay) without S9. All samples tested were negative in the Escherichia coli WP2 uvrA reversion test. The essential oils and pimenta oleoresin were positive in the DNA-repair test. The results obtained are discussed in relation to the nature of the problems encountered with each test method.

Topics: 1-Propanol; Allylbenzene Derivatives; Animals; Anisoles; Bacillus subtilis; Benzaldehydes; Benzodioxoles; Dioxoles; DNA Repair; Escherichia coli; Eugenol; Mutagenicity Tests; Oils, Volatile; Propanols; Rats; Safrole; Salmonella typhimurium