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Chemistry of Essential Oils
Published in K. Hüsnü Can Başer, Gerhard Buchbauer, Handbook of Essential Oils, 2020
Reduction of the side chain of ferulic acid (36) leads to an important family of essential oil components, shown in Figure 6.11. The key material is eugenol (53), which is widespread in its occurrence. It is found in spices such as clove, cinnamon, and allspice, herbs such as bay and basil, and in flower oils including rose, jasmine, and carnation. Isoeugenol (54) is found in basil, cassia, clove, nutmeg, and ylang ylang. Oxidative cleavage of the side chain of shikimates to give benzaldehyde derivatives is common and often significant, as it is in this case, where the product is vanillin (55). Vanillin is the key odor component of vanilla and is therefore of considerable commercial importance. It also occurs in other sources such as jasmine, cabreuva, and the smoke of agar wood. The methyl ether of eugenol, methyl eugenol (56), is very widespread in nature, which, since it is the subject of some toxicological safety issues, creates difficulties for the essential oils business. The oils of some Melaleuca species contain up to 98% methyl eugenol, and it is found in a wide range of species including pimento, bay, tarragon, basil, and rose. The isomer, methyl isoeugenol (57), occurs as both (E)- and (Z)-isomers, the former being slightly commoner. Typical sources include calamus, citronella, and some narcissus species. Oxidative cleavage of the side chain in this set of substances produces veratraldehyde (58), a relatively rare natural product. Formation of the methylenedioxy ring, via methylenecaffeic acid (37), gives safrole (59), the major component of sassafras oil. The toxicity of safrole has led to a ban on the use of sassafras oil by the perfumery industry. Isosafrole (60) is found relatively infrequently in nature. The corresponding benzaldehyde derivative, heliotropin (61), also known as piperonal, is the major component of heliotrope.
In vitro anticancer potentiality and molecular modelling study of novel amino acid derivatives based on N1,N3-bis-(1-hydrazinyl-1-oxopropan-2-yl) isophthalamide
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2019
Asmaa F. Kassem, Gaber O. Moustafa, Eman S. Nossier, Hemat S. Khalaf, Marwa M. Mounier, Suliman A. Al-Yousef, Sabry Y. Mahmoud
The condensation of the hydrazide 4 with 4-chlorobenzaldehyde or 4-fluorobenzaldehyde took place through refluxing in ethanol containing glacial acetic acid. This produced substituted hydrazides 10 and 11 (Scheme 3). 1H-NMR of hydrazones 10 and 11 illustrated the characteristic signal of NH in the range δ 8.72–8.81, as well as signal of -N = CH at 8.50 and 8.55, respectively. The mass spectrum of 10 and 11 revealed a characteristic peaks equal to its molecular weights at m/z = (581 and 548) and base beak at m/z = (368 and 339), respectively. On the contrary, N1,N3-bis (1-hydrazinyl-1-oxopropan-2-yl) isophthalamide (4) was reacted with 4-Anisaldehyde or Veratraldehyde to give the corresponding hydrazide derivatives 12 and 13, respectively (Scheme 3), and its structures were proven under the basis of their spectral data.
Evaluation of hazards of electronic -cigarette’s liquid refill on testes of mice, complemented by histopathological and chromatographic analysis
Published in Ultrastructural Pathology, 2023
Raghda Elsherif, Nora Z. Abdellah, Ola A. Hussein, Eman S. Shaltout
Analysis of the e-liquid in the present study showed the presence of the flavors: vanillin, ethyl vanillin acetal, ethyl vanillin, and veratraldehyde propylene glycol acetal. In accordance with the present results, an analysis of 28 different e-liquids by GC/MS demonstrated that vanillin, ethyl vanillin, ethyl maltol, and menthol were the most commonly detected flavors.22 It was reported that the concentrations of some flavors are high enough to be of toxicological concern. Furthermore, the flavoring aldehydes are perceived as irritants of the respiratory tract mucosa.23