Drapeau, Jeremy and Rossano, Manon and Touraud, Didier and Obermayr, Ulla and Geier, Martin and Rose, Andreas and Kunz, Werner (2011) Green synthesis of para-Menthane-3,8-diol from Eucalyptus citriodora: Application for repellent products. COMPTES RENDUS CHIMIE, 14 (7-8). pp. 629-635. ISSN 1631-0748,
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A simple and efficient method was developed for the synthesis of para-Menthane-3,8-diol (PMD), a well-known repellent active against mosquitoes, from Eucalyptus citriodora essential oil by a treatment of citric acid in a biphasic medium (H2O/essential oil). The E. citriodora contains as main component (+)-citronellal (74% in the present case), which cyclises (Prins reaction) to form cis/trans PMD isomers. As an example, an emulsion containing an aqueous solution of 7% citric acid and E. citriodora oil at 500, conducted after 15 h stirring to 82% conversion of (+)-citronellal with a selectivity of 80% with the remaining presence of monoterpenes and sesquiterpenes in the medium. Investigations of lasting protection on human volunteers are carried out using a cage test bioassay protocol and Aedes aegypti mosquitoes. At 20% in (PrOH)-Pr-i, the new reaction mixture showed a complete protection of 303 min compared to 22 min with the pure essential oil. The modified oil was compared with N,N-diethyl-m-methylbenzamide (DEET), the most popular active used in repellent formulations. Thermogravimetric analyses (TGA) of E. citriodora, the modified oil, PMD, DEET, and (+)-citronellal were performed and showed a slow evaporation rate for PMD and DEET as well as for the modified oil, which may explain their long lasting protection action. (C) 2011 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | INSECT REPELLENTS; FIELD-EVALUATION; N,N-DIETHYL-M-TOLUAMIDE DEET; BOLIVIAN AMAZON; ESSENTIAL OILS; ANOPHELES; P-MENTHANE-3,8-DIOLS; FORMULATION; MOSQUITOS; CULICIDAE; Mosquitoes; Aedes Aegypti; Repellent; Eucalyptus citriodora; para-Menthane-3.8-diol |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Physikalische und Theoretische Chemie > Chair of Chemistry VI - Physical Chemistry (Solution Chemistry) > Prof. Dr. Werner Kunz |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 08 Jun 2020 06:24 |
| Last Modified: | 08 Jun 2020 06:24 |
| URI: | https://pred.uni-regensburg.de/id/eprint/20564 |
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