Methyl Isoeugenol Research Articles

Floral fragrances in Cimicifuga: Chemical polymorphism and incipient speciation in Cimicifuga simplex

Floral fragrances in four species of Cimicifuga (Ranunculaceae) were collected by sorption and analyzed by gas chromatography-mass spectrometry. One pollination morph in C. simplex was found to contain three benzenoid compounds absent in the two other morphs. Two of these substances — methyl anthranilate and isoeugenol — induce behavioural modification in pollinating butterflies. The function of a range of terpenes present in small amounts in all analyzed species is unknown, but they may be involved in herbivore deterrence.

Semiochemical attractants ofDiabrotica undecimpunctata howardi barber, southern corn rootworm, andDiabrotica virgifera virgifera leconte, the western corn rootworm (Coleoptera: Chrysomelidae)

During the summers of 1984 and 1985, a variety of structurally related benzenoid compounds was evaluated in sweet corn plots as attractants for adult southern corn rootworms (SCR), western com rootworms (WCR), and northern corn rootworms (NCR). Field response to the volatiles was measured by beetle counts on baited cylindrical sticky traps placed inside the corn plots at a height of l m above ground level. SCR adults were attracted late in the season (last week of August through September, 1984 and 1985) to numerous aromatic compounds, including phenylacetaldehyde, benzyl acetone, phenethyl alcohol, phenyl acetate, indole, veratrole, methyl eugenol, methyl isoeugenol, eugenol, and isoeugenol. Although many compounds attracted SCR adults late in the season, only veratrole, phenylacetaldehyde, and chavicol were significantly active in early and middle August 1985. WCR adults were attracted to a different group of compounds, namely estragole,trans-anethole, and indole. Estragole (4-methoxy-1-allylbenzene) was an effective WCR attractant from corn tasseling in early August 1985, until the end of the trapping period in late September and early October 1985. Indole andtrans-anethole (4-methoxy-1-propenylbenzene) were less effective attractants than estragole and were most active at the beginning and/or end of the corn season. Traps baited with 100 mg of estragole caught an average of 20 times more WCR adults than unbaited control traps, and the females outnumbered the males in the baited traps. Estragole dosage tests were conducted in three sweet corn plots on different dates in 1985 and the minimum effective dose ranged between 5 and 30 mg/trap. Field tests with structural analogs revealed the importance of the site of unsaturation in the allylic side chain of estragole and the effect of different ring substituents on WCR response. The phenylpropanoids, eugenol and isoeugenol, significantly attracted NCR adults, even though these beetles were in low abundance in the test corn plots. Field tests indicate there is no cross-species response by WCR and NCR adults to their related phenylpropanoid attractants. However, in late August, SCR adults do respond to some WCR and NCR attractants (indole and several eugenol analogs). Electroantennographic analysis of SCR males revealed they can perceive peripherally a wide range of benzenoid compounds.

Factors influencing conjugation of phenolic compounds with the epsilon-amino group.

ABSTRACTFactors influencing the conjugation potency of eugenol (E), isoeugenol (IE), methyl isoeugenol (MIE), and acetyl isoeugenol (AIE) with [l‐14C]ɛ‐aminocaproic acid are investigated. The conjugation reaction for IE is accelerated in the presence of H2O2‐peroxidase and inhibited under anaerobic conditions by nitrogen gas flow. An oxidation reaction is found to be necessary for the conjugation of IE with ɛ‐aminocaproic acid. Immediately after mixing the phenolic compounds with [1‐14C]ɛ‐aminocaproic acid and H2O2‐peroxidase, the main conjugates are 7.7% for IE, 2.1% for E, 0.7% for AIE, and 0.2% for MIE. IE, which is a potent sensitizer in vivo, produces the greatest amount of conjugates while MIE, which is negative in vivo, produces almost no conjugates. AIE and E, both mild sensitizers in vivo, produce less conjugates than IE.

Influence of vehicles on penetration through human epidermis of benzyl alcohol, isoeugenol and methyl isoeugenol.

ABSTRACTThe influence of 5 liquid, 6 cosmetic and 2 ointment vehicles on the penetration of benzyl alcohol, isoeugenol and methyl isoeugenol through human epidermis was studied. Benzyl alcohol penetrated most rapidly from almost all vehicles. Among liquid vehicles, liquid paraffin provided the best penetration for the 3 compounds. As the ratio of water to ethanol increased in ethanol/water solutions, the penetration of each compound increased. Among cosmetic and ointment vehicles, lotion and milky lotion afforded maximum penetration of each compound with the exception of milky lotion in the case of benzyl alcohol. Macrogol ointment provided the poorest penetration results for the 3 compounds tested.

Sensitization potency of some phenolic compounds--with special emphasis on the relationship between chemical structure and allergenicity.

AbstractSkin irritability and sensitization potency of 14 phenolic compounds were studied on guinea pigs. When 10% preparations of each compound were used for induction, and 1% preparations were used for the challenge, the sensitization frequencies were 80% for isoeugenol and isosafro eugenol, 67% for isohomogenol, 40% for acetyl isoeugenol, 20% for eugenol, and 5% for dihydro eugenol. No animals were sensitized by methyl eugenol, acetyl eugenol, methyl isoeugenol or benzyl isoeugenol. The sensitization frequency was 80% for catechol, 89% for guaethol, 14% for p‐n‐propyl phenol, and 0% for phenol.The frequency of positive allergic reactions to patch tests on patients with cosmetic dermatitis was 2.6% for eugenol and 5.2% for isoeugenol. The frequency of cross reactions on patients sensitive to isoeugenol was also studied.The relationship between chemical structures and sensitization potencies as well as other factors influencing the results of patch tests on patients are discussed.

Temperature effects on essential oil composition of citronella selections

Four citronella [Cymbopogon nardus (L.) Rendle] selections indigenous to Sri Lanka were grown for 90 days at 27/21° or 32/27°C daylnight temperatures in controlled environments. Leaves were harvested and oil extracted by steam distillation. Analysis for chemical constituents was carried out by gas liquid chromatography. Growing temperatures affected oil composition with the response to temperature differing among selections. The commercially desired constituent. citronellal, was higher at 27/21°C than at 32/27°C in all selections, whereas the commercially undesirable constituent borneol was higher at 32/27°C than at 27/ 21°C. The production of total monoterpene hydrocarbons was enhanced at 27/ 21°C in selections C-4 and C-8 compared to 32/27°C. The level of methyl isoeugenol differed among selections.

Varietal differences in the constituents of citronella oil

Gas chromatography of citronella oil showed that the Ceylon variety (Lenabatu) contained large amounts of monoterpene hydrocarbons, while the Java variety (Mahapengiri) contained only small amounts, mainly limonene. Both types contained comparable amounts of geraniol, and the Java type more of citronellol and citronellal. In addition the Ceylon type contained tricyclene, methyl eugenol, methyl isoeugenol, eugenol and l-borneol. The GLC profiles enable the identification of the type of oil and the detection of kerosene as a possible adulterant. The variety that grows wild in Ceylon (Mana) was quite different to both cultivated types.