A new fluorinated chalcone (E)-3-(2,6-difluorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one was synthesized in 90% yield and crystallized by a slow evaporation technique. Its full structural characterization and purity were determined by scanning electron microscopy, infrared spectroscopy, gas chromatography-mass spectrometry, ¹H, ¹³C and ¹⁹F nuclear magnetic resonance, thermal gravimetric analysis (TGA), differential scanning calorimetry (DSC), Raman microspectroscopy, UV-Vis absorption spectroscopy, single crystal X-ray diffraction (XRD) and Hirshfeld surface (HS) analysis. The fluorinated chalcone crystallized in centrosymmetric space group P2₁/c stabilized by the C–H⋯O and C–H⋯F interactions and the π⋯π contact. The crystalline environment was simulated through the supermolecule approach where a bulk with 378 000 atoms was built. The electric parameters were calculated at the DFT/CAM-B3LYP/6-311++G(d,p) level as function of the electric field frequency. The macroscopic parameters such as linear refractive index and third-order nonlinear susceptibility (χ⁽³⁾) were calculated, and the results were compared with experimental data obtained from the literature. The χ⁽³⁾-value for the chalcone crystal is 369.294 × 10⁻²² m² V⁻², higher than those obtained from a few similar types of molecule, showing that the chalcone crystal can be considered as a nonlinear optical material. Also, molecular theoretical calculations such as infrared spectrum assignments, frontier molecular orbital analysis and MEP were implemented, revealing that the most positive region is around the hydrogen atoms of the aromatic rings, and electrophilic attack occurs on the carbonyl group.

Microwave-assisted extraction of volatile oils (MAE) potentially offers a more efficient and bio-sustainable method than conventional extraction by Clevenger apparatus (CE). This study aimed to optimise the MAE of the volatile oil from Pterodon emarginatus fruits and characterise the volatile compounds. A 2³ full-factorial central composite design and response surface methodology were used to evaluate the effects of time (min), moisture (%) and microwave power (W) on the extraction yield. The process optimisation was based on the desirability function approach. The reaction time and moisture conditions were standardised in these analyses. The volatile oil composition was analysed by Gas Chromatography/Mass Spectrometry (GC/MS) in order to compare techniques extractions influences. Microwave irradiation showed excellent performance for extraction of the volatile oil from Pterodon emarginatus and there were some advantages in compare to conventional method with respect to the time (14 times), energy (6 times), reagents amounts and waste formation. About chemical composition presents significant differences with the type of extraction. Caryophyllene (25.65%) and trans-α-bisabolol (6.24%) were identified as major components in MAE sample while caryophyllene (6.75%) and γ-elemene (7.02%) are the components with higher relative percentage in CE samples. The microwaves assisted process shown an increase of economic interested compounds present in volatile oil.

In the present study, we developed a green epoxidation approach for the synthesis of the diastereomers of (−)-isopulegol benzyl ether epoxide using molecular oxygen as the oxidant and a hybrid manganese(III)-porphyrin magnetic reusable nanocomposite as the catalyst. High activity, selectivity, and stability were obtained, with up to four recycling cycles without the loss of activity and selectivity for epoxide. The anticancer effect of the newly synthesized isopulegol epoxide diastereomers was evaluated on a human osteosarcoma cell line (MG-63); both diastereomers showed similar in vitro potency. The measured IC₅₀ values were significantly lower than those reported for other monoterpene analogues, rendering these epoxide isomers as promising anti-tumor agents against low prognosis osteosarcoma.

Studies have previously shown that anthracene and naphthalene derivatives serve as compounds for trapping and chemically generating singlet molecular oxygen [O₂(¹Δ_g)], respectively. Simple and efficient synthetic routes to anthracene and naphthalene derivatives are needed, for improved capture and release of O₂(¹Δ_g) in cellular environments. Because of this need, we have synthesized a dihydroxypropyl amide naphthlene endoperoxide as a O₂(¹Δ_g) donor, as well as five anthracene derivatives as O₂(¹Δ_g) acceptor. The anthracene derivatives bear dihydroxypropyl amide, ester, and sulfonate ion end groups connected to 9,10-positions by way of unsaturated (vinyl) and saturated (ethyl) bridging groups. Heck reactions were found to yield these six compounds in easy-to-carry out 3-step reactions in yields of 50–76%. Preliminary results point to the potential of the anthracene compounds to serve as O₂(¹Δ_g) acceptors and would be amenable for future use in biological systems to expand the understanding of O₂(¹Δ_g) in biochemistry.

The development of photoprotective agents presents a growing interest due to skin disorders, e.g., cancer. In order to obtain natural-based compounds with potential photoprotective activity, we promote the synthesis and extensive characterization of a butylchalcone derivative (E)-3-(4-butylphenyl)-1-(4-methylphenyl)-prop-2-en-1-one (BMP). Moreover, we carried out a comparative analysis of two chalcones bearing a methyl (BMP) and bromo (BBP) substituent groups (at para position), on respective electronic structures and supramolecular arrangement, using density functional theory (DFT). Through theoretical calculations carried out by DFT, it was possible to verify its antioxidant property by the mechanisms of free radical scavenging, H-atom transfer (HAT), and one-electron transfer (ET), and their stabilities. Finally, from the analysis of chalcone’s electronic transitions in the excited state calculated by the time-dependent (TD)-DFT method as well as UV-vis absorption spectra of the BMP and BBP (200–390 nm), it is possible to highlight their potential use as organic photoprotective agents.