Condensation Reaction of Glycerol and Carbonyl Compounds: Synthesis, Characterization, and Derivatization for Liquid Crystals

Kautz, Jacqueline; Feltrin, Willian; Sales, Eric Souza; Eifler‐Lima, Vera Lucia; Merlo, Aloir A.

doi:10.5935/0100-4042.20150111

Cited by 2 publications

(3 citation statements)

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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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“…21,22 Glycerol is a low-cost byproduct obtained from the transesterification of vegetable oils or animal fats. 23 This polyol, also known as propane-1,2,3-triol, is a colorless, odorless, sweet, and viscous liquid, which can be obtained from natural or synthetic sources. 23 Glycerol is widely used in the pharmaceutical, food, cosmetic, and polymer industries.…”

Section: ■ Introductionmentioning

confidence: 99%

“…23 This polyol, also known as propane-1,2,3-triol, is a colorless, odorless, sweet, and viscous liquid, which can be obtained from natural or synthetic sources. 23 Glycerol is widely used in the pharmaceutical, food, cosmetic, and polymer industries. Furthermore, the byproduct has also been widely used in organic synthesis as a model structure for the development of bioactive molecules.…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis and Fungicide Activity onAsperisporium caricaeof Glycerol Derivatives Bearing 1,2,3-Triazole Fragments

Lima

Teixeira

Moraes

et al. 2023

J. Agric. Food Chem.

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In agriculture, the control of fungal infections is essential to improve crop quality and productivity. This study describes the preparation and fungicidal activity evaluation of 12 glycerol derivatives bearing 1,2,3-triazole fragments. The derivatives were prepared from glycerol in four steps. The key step corresponded to the Cu(I)-catalyzed alkyne−azide cycloaddition (CuAAC) click reaction between the azide 4-(azidomethyl)-2,2-dimethyl-1,3-dioxolane (3) and different terminal alkynes (57−91% yield). The compounds were characterized by infrared spectroscopy, nuclear magnetic resonance ( 1 H and 13 C), and high-resolution mass spectrometry. The in vitro assessment of the compounds on Asperisporium caricae, that is, the etiological agent of papaya black spot, at 750 mg L −1 showed that the glycerol derivatives significantly inhibited conidial germination with different degrees of efficacy. The most active compound 4-(3-chlorophenyl)-1-((2,2-dimethyl-1,3-dioxolan-4-yl) methyl)-1H-1,2,3-triazole (4c) presented a 91.92% inhibition. In vivo assays revealed that 4c reduced the final severity (70.7%) and area under the disease severity progress curve of black spots on papaya fruits 10 days after inoculation. The glycerol-bearing 1,2,3-triazole derivatives also present agrochemicallikeness properties. Our in silico study using molecular docking calculations show that all triazole derivatives bind favorably to the sterol 14α-demethylase (CYP51) active site at the same region of the substrate lanosterol (LAN) and fungicide propiconazole (PRO). Thus, the mechanism of action of the compounds 4a−4l may be the same as the fungicide PRO, blocking the entrance/ approximation of the LAN into the CYP51 active site by steric effects. The reported results point to the fact that the glycerol derivatives may represent a scaffold to be explored for the development of new chemical agents to control papaya black spot.

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Condensation Reaction of Glycerol and Carbonyl Compounds: Synthesis, Characterization, and Derivatization for Liquid Crystals

Cited by 2 publications

References 0 publications

Cyclic Acetals as Novel Long-Lasting Mosquito Repellents

Cyclic Acetals as Novel Long-Lasting Mosquito Repellents

Synthesis and Fungicide Activity onAsperisporium caricaeof Glycerol Derivatives Bearing 1,2,3-Triazole Fragments

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