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The essential oil composition of three spontaneous species growing in an abandoned mining of Elba island was analyzed by GC-MS. A total of 194 compounds were identified representing 73.7-100% of the whole oil composition. The essential oils of Cistus salvifolius and Dittrichia viscosa from this site showed different profiles in comparison with those from not polluted area, where oxygenated sesquiterpenes were the main class. Volatiles from D. viscosa growing in ex-mining area presented 10-epi-γ-eudesmol and α-eudesmol as main compounds while β-caryophyllene and limonene were the main ones in not polluted area. Ambroxide and ambrial were the most important compounds in the essential oil from C. salvifolius harvested in polluted area while nonanal and tridecanal were the main compounds in control samples. Oxygenated monoterpenes were the most abundant class from both Lavandula stoechas samples, with fenchone and camphor as main compounds.
soil pollution; volatile profile.
Chemical composition of essential oil from plants of abandoned mining site of Elba island
Laura Pistelli 1 2, Rose Vanessa Bandeira Reidel 3, Federico Parri 4, Elisabetta Morelli 5, Luisa Pistelli 1 2
Gibbs energies of complex formation between enantiomers of bicyclic terpenoid, fenchone, and naturally occurring cyclodextrins, βCD and γCD, were determined by means of 13 C and 1 H nuclear magnetic resonance (NMR) titration data. These results were compared with the corresponding data obtained previously for the diastereomeric fenchone/αCD complexes. The size of the inner cavity of host molecules significantly influences stoichiometry, association constants, and enantiomeric differentiation of the studied complexes. These complementary data allow us to discuss qualitatively the influence of the host size on the guest-host interactions. A method of the simultaneous use of titration data collected for several resonances of different isotopes in the determination of association constants was worked out and thoroughly analyzed. Comparison of the results of global data analyses with weighted means of individual ones revealed that both these approaches are equally trustworthy.
NMR enantiodifferentiation; association constants; global analysis of titration data; guest-host; inclusion complexes; terpenoids.
Size makes a difference: Chiral recognition in complexes of fenchone with cyclodextrins studied by means of NMR titration
Karolina Dudzik 1, Jacek Wojcik 2, Andrzej Ejchart 2, Michał Nowakowski 3
Background: The essential oil from Mesosphaerum sidifolium (L’Herit.) Harley & J.F.B.Pastore (syn. Hyptis umbrosa), Lamiaceae (EOM), and its major component, have been tested for toxicity and antitumor activity.
Methods: EOM was obtained from aerial parts of M. sidifolium subjected to hydro distillation, and gas chromatography-mass spectrometry was used to characterize the EOM chemical composition. The toxicity was evaluated using haemolysis assay, and acute toxicity and micronucleus tests. Ehrlich ascites carcinoma model was used to evaluate the in vivo antitumor activity and toxicity of EOM (50, 100 and 150 mg/kg), and fenchone (30 and 60 mg/kg) after 9 d of treatment.
Results: The EOM major components were fenchone (24.8%), cubebol (6.9%), limonene (5.4%), spathulenol (4.5%), β-caryophyllene (4.6%) and α-cadinol (4.7%). The HC50 (concentration producing 50% haemolysis) was 494.9 μg/mL for EOM and higher than 3000 μg/mL for fenchone. The LD50 for EOM was approximately 500 mg/kg in mice. The essential oil induced increase of micronucleated erythrocytes only at 300 mg/kg, suggesting moderate genotoxicity. EOM (100 or 150 mg/kg) and fenchone (60 mg/kg) reduced all analyzed parameters (tumor volume and mass, and total viable cancer cells). Survival also increased for the treated animals with EOM and fenchone. For EOM 150 mg/kg and 5-FU treatment, most cells were arrested in the G0/G1 phase, whereas for fenchone, cells arrested in the S phase, which represents a blockage in cell cycle progression. Regarding the toxicological evaluation, EOM induced weight loss, but did not induce hematological, biochemical or histological (liver and kidneys) toxicity. Fenchone induced decrease of AST and ALT, suggesting liver damage.
Conclusions: The data showed EOM caused in vivo cell growth inhibition on Ehrlich ascites carcinoma model by inducing cell cycle arrest, without major changes in the toxicity parameters evaluated. In addition, this activity was associated with the presence of fenchone, its major component.
Ehrlich ascites carcinoma; Fenchone; Genotoxicity; Hemolysis; Lamiaceae; Mesosphaerum sidifolium.
Toxicity and antitumor potential of Mesosphaerum sidifolium (Lamiaceae) oil and fenchone, its major component
Thaisa Leite Rolim 1, Deborah Ribeiro Pessoa Meireles 1, Tatianne Mota Batista 1, Tatyanna Kelvia Gomes de Sousa 1, Vivianne Mendes Mangueira 1, Renata Albuquerque de Abrantes 1, João Carlos Lima Rodrigues Pita 1, Aline Lira Xavier 1, Vicente Carlos Oliveira Costa 1, Leônia Maria Batista 1 2, Marcelo Sobral da Silva 1 2, Marianna Vieira Sobral 3 4
2017 Jul 3;