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Xylitol is a natural sugar derived from plants, fruits and vegetables, whose antimicrobial properties are described in the literature. This study aimed to evaluate the antimicrobial effectiveness of C-8 xylitol monoester, for its use as a preservative in cosmetic formulations. The minimum inhibitory concentration (MIC) was determined by the broth macrodilution method, and the antimicrobial effectiveness of C-8 xylitol monoester was determined by using challenge test method. The results obtained in the determination of minimum inhibitory concentration are between 1.0% and 1.25% for Staphylococcus aureus, Escherichia coli and Candida albicans and between 1.0% and 1.5% for Pseudomonas aeruginosa and Aspergillus niger. The amount of 1% of C-8 xylitol monoester was added to the lotion used in the challenge test, observing a rapid decline in the number of CFU g(-1) in stages of evaluation after contamination of the product by all bacteria. The same occurs in relation to C. albicans, which shows a 90% reduction in the number of CFU g(-1). Regarding A. niger, similar reduction is observed when pH value of the lotion is adjusted from 5.5 to 7.0. The results indicate that under the tests conditions, C-8 xylitol monoester has antimicrobial activity and could be considered as an alternative preservative for cosmetic formulations.

A series of novel xylitan derivatives derived from xylitol were synthesized using operationally simple procedures. A xylitan acetonide was the key intermediate used to prepare benzoate, arylsulfonate esters and 1,2,3-triazole derivatives of xylitan. These compounds were evaluated for their in vitro anti-Trypanosoma cruzi activity against trypomastigote and amastigote forms of the parasite in T. cruzi-infected cell lineages. Benznidazole was used as positive control against T. cruzi and cytotoxicity was determined in mammalian L929 cells. The arylsulfonate xylitan derivative bearing a nitro group displayed the best activity of all the compounds tested, and was slightly more potent than the reference drug benznidazole. The importance of the isopropylidene ketal moiety was established and the greater lipophilicity of these compounds suggests enhancement in cell penetration.

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Neutral and charge tagged reagents were used to investigate the mechanism of the classical Morita-Baylis-Hillman (MBH) reaction as well as its aza-version using mass spectrometry with electrospray ionization (ESI-MS). The use of an acrylate (activated alkene) with a methylimidazolium ion as a charge tag eliminates the requirement for adding acids as ESI(+) additives, which are normally used to favor protonation and therefore detection of reaction partners (reagents, intermediates, and products) by ESI(+)-MS. For both charge tagged reactions (MBH/aza-MBH), most reactants, intermediates, and the final adducts were efficiently detected in the form of abundant doubly and singly charged ions. Characterization of the reactions partners was performed via both tandem mass spectrometry (ESI(+)-MS/MS) and accurate m/z measurements. The charge tagged reactions also showed faster conversion rates when compare to the neutral reaction, indicating a dualistic role for the charge tagged acrylate. It acts as both the reagent and a cocatalyst due to the inherent ionic-coordination nature of the methylimidazolium ion, which stabilizes the zwitterionic intermediates and reagents through different types of coordination ion pairs. Hemiacetal intermediates for the rate-limiting proton transfer step were also intercepted and characterized for both classical and aza-MBH charge tagged reactions.

The Morita-Baylis-Hillman (MBH) reaction has been stablished as an important CÀ C bond-forming transformation between carbonyl-containing compounds and activated olefins. However, the slow reaction rate usually observed with electron-rich electrophilic partners hinders a more widespread use of this reaction. In order to overcome this drawback, the effects of several Brønsted acids on the rate of DABCO-catalyzed MBH reactions were evaluated. The protocol is operationally simple, involving neat and open-flask conditions, and is compatible with a wide range of reagents. We suggest a general acid catalysis mechanism to be responsible for the rate increase. The synthetic versatility of the MBH adducts is exemplified with a two-steps diastereoselective synthesis of the natural product (�)-sitophilure. We hope this acid-mediated protocol to have potential use as a general methodology for the MBH reaction.

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Ions under Solvent-Free Conditions. -The efficiency of InCl 3 as the catalyst for the nucleophilic addition of enol ethers as 1,3-dicarbonyl compounds to N-acyliminium and oxocarbenium ion precursors is demonstrated. -(DE GODOY, L. A. F.; CAMILO, N. S.; PILLI*, R. A.; Tetrahedron Lett. 47 (2006) 45, 7853-7856; Inst. Quim., Univ. Estadual Campinas, 13084 Campinas, Sao Paulo, Brazil; Eng.) -Mais 07-088