The structure of glycerol acetals

Stefanović, Gj.; Petrovic, Dan

doi:10.1016/s0040-4039(01)89888-9

Cited by 7 publications

(3 citation statements)

References 5 publications

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“…As expected from previous investigations, − the GC–MS and NMR analyses of the products obtained from glycerol revealed the formation of several cyclic products, whose actual distribution was found to depend on the nature of the starting carbonyl material. In detail, although ketones gave the five-membered cyclic derivative (1,3-dioxolane, Figure , general structure 27 ) in a nearly exclusive manner, the aldehydes provided a mixture of the former and its six-membered isomer (1,3-dioxane, general structure 28 ) in comparable amounts.…”

Section: Resultssupporting

confidence: 85%

Cyclic Acetals as Novel Long-Lasting Mosquito Repellents

Iovinella

Mandoli

Luceri

et al. 2023

J. Agric. Food Chem.

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The use of skin repellents against hematophagous mosquitoes is an important personal protection practice wherever these insects are abundant and where they are vectors of diseases. DEET and Icaridin are the major synthetic insect repellents in commercial formulations and are considered the most effective. Here, we tested against the mosquito Aedes albopictus several cyclic hydroxyacetals synthesized by acetalization of commercially available aliphatic carbonyl compounds (ranging from C3 to C15) with either glycerol, 1,1,1-trismethyloletane, or 1,1,1-trismethylolpropane and compared their efficacy with commercial repellents. We found that several hydroxyacetals were comparable with DEET and Icaridin both in terms of the required dose and repellence duration, while a few performed better. For those most active, toxicity was investigated, finding that a few of them were less cytotoxic than DEET and less prone to permeate through cell layers. Therefore, such results indicate that novel safe mosquito repellents could be developed among cyclic hydroxyacetals.

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Section: Resultssupporting

confidence: 85%

Cyclic Acetals as Novel Long-Lasting Mosquito Repellents

Iovinella

Mandoli

Luceri

et al. 2023

J. Agric. Food Chem.

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“…As expected, 33 13 C NMR analysis of the sample revealed the presence of six distinct acetal compounds, whose C2 carbon atoms were found to resonate in the δ C = 101–105 ppm region. Based on previous spectroscopic studies on glycerol acetals of long‐chain aldehydes, 34 , 35 the NMR constants recorded for the sample were consistent with a mixture of trans and cis 1,3‐dioxolane and 1,3‐dioxane derivatives (Fig. 1 ), whose relative content was roughly estimated to be ≈3.0:1.9:1.4:1.0 by least‐square fitting of the intensities of selected 13 C NMR resonances (Supporting Information Fig.…”

Section: Resultsmentioning

confidence: 99%

Advances in mosquito repellents: effectiveness of citronellal derivatives in laboratory and field trials

Iovinella

Caputo²,

Cobre³

et al. 2022

Pest Management Science

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BACKGROUND: Several essential oils, including citronella (lemongrass, Cymbopogon sp., Poaceae), are well-known mosquito repellents. A drawback of such products is their limited protection time resulting from the high volatility of their active components. In particular, citronella oil protects for <2 h, although formulations with fixatives can increase this time.RESULTS: We synthesized hydroxylated cyclic acetals of citronellal, the main component of citronella, to obtain derivatives with lower volatility and weaker odour. The crude mixture of isomers obtained in the reaction was tested under laboratory conditions for its repellency against two mosquito species, the major malaria vector Anopheles gambiae and the arbovirus vector Aedes albopictus, and found to be endowed with longer protection time with respect to DEET (N,N-diethyl-meta-toluamide) at the same concentration. Formulated products were tested in a latin square human field trial, in an area at a high density of A. albopictus for 8 h from the application. We found that the performance of the citronellal derivatives mixture is comparable (95% protection for ≤3.5 h) with those of the most widespread synthetic repellents DEET and Icaridin, tested at a four-fold higher doses.CONCLUSIONS: Modifying the hydrophilicity and volatility of natural repellents is a valuable strategy to design insect repellents with a long-lasting effect.

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“…One of the first manuscripts on acetalization reactions was published at the end of the 19 th century and it is reported by Aksnes et al (Aksnes et al, 1965). However, all these pioneering works are related to the isolation and identification of the different acetal isomers (Aksnes et al 1965;Aksnes et al, 1966;Stefanovic et al, 1967). It must be remarked the important role that glycerol can play in the field of bio-additives.…”

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confidence: 99%