Benzoic Ester Research Articles

Synthesis and biological evaluation of new hydrazone

Synthesis of new hydrazone derivatives, starting from 2-(3,4-Dichloro-benzoyl)-benzoic acid to 2-(3,4-Dichloro-benzoyl)-benzoic acid ethyl ester than converted into 2-(3,4-Dichloro-benzoyl)-benzoic acid hydrazide with substituted aromatic ketones. The structures of the newly synthesized compounds were confirmed by analytical and spectral analysis of IR, 1H NMR and MASS spectroscopy. The in-vitro antibacterial screening of synthesized compounds was performed against the following standard bacterial strains Escherichia coli (MTCC 1573), and staphylococcus aureus (MTCC 1430). Compound 2-(3,4-dichloro-bezoyl)-benzoic acid [1-(4-bromo-phenyle)-ethyledene]-hydrazide (BP-10), gives the highest activity on Escherichia coli (MTCC 1573) and staphylococcus aureus (MTCC 1430). The in-vitro anthelmintic activity was evaluated on Adult earthworms (Pheretima posthuma). Compound 2-(3,4-dichloro-bezoyl)-benzoic acid (2-oxo-1,2-diphynyl-ethylidene)-hydrazide (BP-7), and 2-(3,4-dichloro-bezoyl)-benzoic acid (2-oxo-1,4-chlorophenyle-ethylidene)-hydrazide (BP-13), gives the highest activity and other is gives the moderate activity against Adult earthworms (Pheretima posthuma).

Structure of Nanotubes Self-Assembled from a Monoamide Organogelator.

Some organic compounds are known to self-assemble into nanotubes in solutions, but the packing of the molecules into the walls of the tubes is known only in a very few cases. Herein, we study two compounds forming nanotubes in alkanes. They bear a secondary alkanamide chain linked to a benzoic acid propyl ester (HUB-3) or to a butyl ester (HUB-4). They gel alkanes for concentrations above 0.2 wt.%. The structures of these gels, studied by freeze fracture electron microscopy, exhibit nanotubes: for HUB-3 their external diameters are polydisperse with a mean value of 33.3 nm; for HUB-4, they are less disperse with a mean value of 25.6 nm. The structure of the gel was investigated by small- and wide-angle X-ray scattering. The evolution of the intensities show that the tubes are metastable and transit slowly toward crystals. The intensities of the tubes of HUB-4 feature up to six oscillations. The shape of the intensities proves the tubular structure of the aggregates, and gives a measurement of 20.6 nm for the outer diameters and 11.0 nm for the inner diameters. It also shows that the electron density in the wall of the tubes is heterogeneous and is well described by a model with three layers.

High-efficient decomplexation of Cu-HA by discharge plasma: Process and mechanisms

It is difficult to remove heavy metals-humid acid (HA) complexes with stable properties by traditional precipitation method, and they can bring potential threats to human health. The decomplexation of heavy metal-HA complex (Cu-HA as a model) was explored using non-thermal plasma (NTP) in this study, and influences of coexisting ions on Cu-HA decomplexation were assessed. High-efficient Cu-HA decomplexation performance was obtained by the NTP oxidation, and it reached 89.3% in a treatment period of 15 min; and the pseudo-first order kinetics was suitable to describe this process. The presence of Fe2+ favored Cu-HA decomplexation process via displacement and Fenton-like effects. Whereas some amounts of Cl−, NO3− and SO42− with low dosages promoted this process. Active species including O3, O2− and OH played primary roles in Cu-HA decomplexation, but the role of high-energy electrons could be neglected. NTP oxidation broke the chromophoric group, CuO, CuN, and unsaturated bonds of the Cu-HA complex. Some decomplexation intermediates including benzoic acids, amines, esters, and phenols were generated. Meanwhile, the precipitation processes were analyzed via energy dispersive X-ray, X-ray photoelectron spectrum, thermal stability, fourier transform infrared spectroscopy, and X-ray diffraction.

Flow Reactor Synthesis of Bio-Based Polyol from Soybean Oil for the Production of Rigid Polyurethane Foam

In this study, a complex ring-opening agent including benzoic acid pentaerythritol ester bearing aromatic group and pentaerythritol monolaurate bearing pending chain was applied in the ring-opening...

Evaluation of the potential aphrodisiac activity of sesquiterpenoids from roots of Ferula huber-morathii Peşmen in male rats

Ethnopharmacological relevanceSeveral species of Ferula L. genus have been used in traditional Turkish medicine as aphrodisiac to treat male sexual dysfunction. Especially, roots and oleo gum resin of F. elaeochytris Korovin, F. communis L., F. assa-foetida L. and F. gummosa Boiss. were claimed to be used for aphrodisiac activity, menstrual regulation and treatment of gastric pain in Anatolia. Ferula L. is represented by 23 taxa in Turkey, 13 of which are endemic species. F. huber-morathii Peşmen (FHM), an endemic plant, is popularly known as ‘‘helizan, çağşır’’. Aim of the studyThis study aimed to isolate sesquiterpenoids from the roots of Ferula huber-morathii (FHM) and to confirm their aphrodisiac potential in male rats. Material and methodsIn a preliminary experiment, the effects of aqueous (H2O) and chloroform (CHCl3) extracts of FHM were tested for their potential aphrodisiac activities in male rats. Then, sesquiterpene derivatives were isolated from the active chloroform extract of FHM roots (FHM-R) and characterized (TLC, 1D, 2D NMR, HR-MS and CD). Moreover, some of the isolates with adequate quantities were evaluated for their possible aphrodisiac effects on male rats. Single doses (10 mg/kg BW) of sildenafil citrate (SC, positive control), gummosin, mogoltavidin, deacetylkellerin, ferukrin acetate with kellerin, elaeochytrin-A and ferutinin were administered orally by gavages to male Wistar albino rats. Mount latency (ML), mount frequency (MF), intromission latency (IL), intromission frequency (IF), ejaculation latency (EL) and postejaculatory interval (PEI) were studied. In addition, copulatory efficiency (CE) and intercopulatory efficiency (ICE) were calculated. ResultsThe preliminary experiment revealed that the chloroform extract was the main source of the active compounds as it showed the higher aphrodisiac activity while the aqueous extract was found to be inactive. Eleven sesquiterpene derivatives, viz. gummosin, mogoltavidin, farnesiferol A, deacetylkellerin, ferukrin acetate, kellerin, teuclatriol, feruhermonin C, ferutinin, elaeochytrin A and teferidin, were isolated from the FHM-CHCl3 extract. Oral administration of deacetylkellerin, elaeochytrin-A and ferutinin significantly increased MF and IF. The ML and IL were significantly reduced, and ejaculation latencies were prolonged. Administration of these sesquiterpenoids also reduced the PEI. The present results revealed that ferutinin was the most effective aphrodisiac compound compared to other sesquiterpenoids. The results of 10 mg/kg of ferutinin are comparable to SC, the positive control. The results revealed that gummosin, mogoltavidin and ferukrin acetate with kellerin did not significantly alter the aphrodisiac parameters. ConclusionsThis study has established that the CHCl3 extract of FHM root contains sesquiterpene derivatives, especially coumarin ethers and benzoic esters. Findings of the present study demonstrate that the chloroform extract and some of the sesquiterpene derivatives significantly stimulates sexual behavior in male rats, thus suggesting that F. huber-morathii possesses an aphrodisiac activity.

Palladium(0)‐Catalyzed Rearrangement of Allylic Esters

AbstractThe palladium‐catalyzed transposition of allylic esters is usually performed with a rather high loading of a palladium(II) catalyst. In the present investigation, a palladium(0) catalyst is developed for rearranging methyl 2‐acyloxybut‐3‐enoates into the corresponding methyl 4‐acyloxycrotonates. The transformation is performed at room temperature with 2% of Pd(PPh3)4 and gives good yields with acetate, benzoate and propanoate esters. Methyl 2‐(methoxycarbonyloxy)but‐3‐enoate, on the other hand, is rearranged into methyl 4‐methoxycrotonate due to decarboxylation of the released methyl carbonate into methoxide. The mechanism for the transposition of methyl 2‐acetoxybut‐3‐enoate was investigated in two separate crossover experiments and shown to proceed by formation of the intermediate π‐allyl palladium(II) complex, which is then attacked by acetate in an intermolecular fashion.

Photosensitive bent-core nematic liquid crystals with various linking units in the side arms: Structure-properties relationships

We present two isomeric series of photosensitive bent-core liquid crystals possessing a lateral chlorine atom in the central resorcinol unit and various linking units in the side arms. With the aim to tune properties of the nematic phase, we have varied the type of the linking unit in the lengthening arm with rising rigidity from benzoate ester, biphenyl, cinnamate, Schiff base to stilbene moieties. In addition to that, we have changed the position of the lateral substituent (chlorine) as well. The mesomorphic properties of the materials have been determined from differential scanning calorimetry, polarizing optical microscopy, dielectric spectroscopy and X-ray studies. We show that synergy of the linking unit with the effect of the lateral substituent gives rise to broad temperature range of mesophases — the nematic phase as well as a SmCP phase. Thanks to the presence of the photosensitive group in the molecular structure, we have been able to transform both mesophases to the isotropic phase under UV light. The chemical structure–mesomorphic properties relationships are discussed with the aid of ab initio calculations and the results presented in context with experimental data. • Two series of 4-chlororesorcinol-based photosensitive bent-core nematogens are presented. • Mutual position of chlorine atom on the central core and the azo group is crucial for mesomorphic behaviour. • Broad stable nematic phase below 100 °C and switchable SmC A P A phase are observed. • Photosensitivity of bulk mesophases is documented by X-ray profile and polarizing microscopy measurements.

Design and synthesis of anti-convulsant and anti-bacterial activity of new hydrazone derivatives

Synthesis of new hydrazone derivatives, starting from 2-(3, 4-Dichloro-benzoyl)-benzoic acid to 2-(3, 4-dichloro-benzoyl) - benzoic acid ethyl ester than converted into 2- (3, 4-Dichloro-benzoyl)-benzoic acid hydrazide with a substituted aldehyde. The structure of newly synthesized compounds was confirmed by analytical and spectral analysis IR, 1HNMR and MASS. For docking study, we took structures of ligand compounds (i.e. AK-series Compounds) and target protein structures into ‘pdb’ file format. Three compounds as possible anti-convulsant AK-1, AK-2 &Ak-4 were considered for compounds Ak-1 was not found suitable for anti-convulsant activity; while AK-2 & AK-4 have the capacity to show anti-convulsant activity with lesser affinity than controls. As an overall conclusion, except Ak-1, other compounds can be further used for anti- convulsant activity. Anti-convulsant activities were performed on rats by using maximal Electroshock Seizure test and minimal Neurotoxicity. Compound 2- (3, 4 – Dichloro-benzoyl)-benzoic acid (4- chloro-benzylidene) (AK-2) shows good anti-convulsant activity. The in-vitro antibacterial strains Escherichia coli MTCC 1573), and staphylococcus aureus (MTCC 1430), were used. Compound 2-(3, 4-Dichloro-benzoyl)-benzoic acid (2-notro-benzylidene-hydrazide (AK-1) gives the highest activity against Escherichia coli (MTCC 1573) and Staphylococcus aureus (MTCC-1430).

Novel isatin-indole derivatives as potential inhibitors of chorismate mutase (CM): their synthesis along with unexpected formation of 2-indolylmethylamino benzoate ester under Pd-Cu catalysis.

A series of novel isatin–indole derivatives has been designed as potential inhibitors of chorismate mutase (CM) that is known to be present in bacteria, fungi and higher plants but not in human. The design was supported by in silico docking studies that predicted strong interactions of these molecules with CM. The target compounds were synthesized via the one-pot coupling/cyclization method involving the reaction of an isatin based terminal alkyne with 2-iodosulfanilides under Pd–Cu catalysis. A number of isatin–indole derivatives were prepared using this method. A side product e.g. 2-indolylmethylamino benzoate ester derivative was obtained as a result of isatin ring opening (ethanolysis) of products in certain cases. Additionally, regioselective reduction of selected compounds afforded the corresponding C-3 hydroxy derivatives. All isatin–indole derivatives showed good to high inhibition of CM in vitro among which two compounds (3e and 3f) showed inhibition at nanomolar concentration.

Synthesis of 1-(2-Methoxybenzyl)-1,10-phenanthrolin-1-ium Bromide from Gandapura Oil

This study describes simple synthetic method to prepare 1-(2-methoxybenzyl)-1,10-phenanthrolin-1-ium bromide from gandapura oil. The salt were synthesized in four steps. Initially, commercial gandapura oil was directly subjected to the alkylation reaction under basic condition using dimethyl sulfate to give methyl 2-methxybenzoate in 86% yield. Next, the produced benzoate ester was reduced by LiAlH4 to produce 2-methoxybenzyl alcohol in 67% yield. The treatment of benzyl alcohol with phosphorus tribromide under solvent free condition produced the corresponding benzyl bromide (in 67% yield), which was directly introduced into bimolecular nucleophilic substitution reaction with 1,10-phenantroline monohydrate to finally give the desired product in 63% yield.

In situ formation of thymol-based hydrophobic deep eutectic solvents: Application to antibiotics analysis in surface water based on liquid-liquid microextraction followed by liquid chromatography

A simple and ecofriendly sample preparation method was developed for quantifying fluoroquinolone (FQ) antibiotics in surface water. Seventeen combinations of monoterpenes (menthol, thymol, and camphor), fatty acids (heptanoic, octanoic, nonanoic, and decanoic acids), and a benzoate ester (salol) were utilized for the in situ formation of hydrophobic deep eutectic solvents (hDESs) for liquid-liquid microextraction (LLME). The hDES comprising thymol and heptanoic acid (HA) exhibited the highest extraction efficiency for ofloxacin, norfloxacin, ciprofloxacin, and enrofloxacin. Optimization via the one-variable-at-a-time strategy revealed that a 2:1 ratio of thymol to HA yielded the highest efficiency for antibiotic extraction at pH 4−7. Further, response surface methodology-based optimization suggested that the optimal extraction conditions involved the use of appropriate amounts of thymol and HA to generate 100 μL of hDES in 10 mL of aqueous sample with incubation at 52 °C for 5 min, followed by automated shaking for 1 min. The collected hDES phase was diluted and subjected to liquid chromatography-ultraviolet detection analysis. The established method based on in situ formation of hDES coupled with shaker-assisted LLME (in situ hDES-SA-LLME) was validated. The method was specific and showed good linearity in the 15-3000 ng mL−1 concentration range (r2 ≥ 0.9997), with a limit of detection of 3.0 ng mL−1, limit of quantification of 9.0 ng mL−1, accuracy of 84.1–113.65%, and intra-day and inter-day precision of ≤7.78% RSD and ≤7.91% RSD, respectively. The method was successfully applied to three different types of real surface water samples. Without toxic volatile organic solvents, the developed method allows for safe and rapid, yet reliable, analysis of FQ antibiotics.

Thermoresponsive Dendronized Poly(phenylacetylene)s Showing Tunable Helicity

Switching the macromolecular helicity of poly(phenylacetylene)s (PPAs) through external achiral stimuli provides convenient possibilities in designing smart chiral materials. Herein, a series of PPAs carrying dendritic oligoethylene glycol (OEG) pendants were synthesized with different linkages between the backbone and dendron pendants, including benzamide (PPA-AC), inverted acylamide (PPA-AM), diamide (PPA-dAM), benzoate (PPA-ES), and benzyl ester (PPA-OEG). The periphery of the OEG dendrons is capped with either an ethoxy (PPA-ACe) or a methoxy group (PPA-ACm) to afford the PPAs with different overall hydrophilicity. These dendronized PPAs inherit unprecedented thermoresponsiveness from the dendritic OEGs and show characteristic thermally induced phase transitions with cloud points (Tcps) in the range 30–54 °C. Hydrogen bonding interactions between neighboring repeating units were found to play a key role in transferring chirality from pendants to polymer backbone. Dependent on the linkages, these PPAs behave differently about helix–helix transitions driven by the thermally induced collapse of the pendanted OEG dendrons. Interestingly, dendronized homopolymer with methoxy terminals (PPA-ACm) shows radial amphiphilicity in aqueous solutions, which renders the polymer a different chiroptical property. For comparison, chiroptical properties of these polymers were also investigated in organic solvents. Furthermore, coordination with Ba2+ was found to mediate the chiroptical properties of these dendronized PPAs in aqueous solutions, which can be surprisingly shielded by OEG dendrons below their Tcps.

Hydrogen Sulfide Mediated Tandem Reaction of Selenenyl Sulfides and Its Application in Fluorescent Probe Development

A unique reaction between H2S and a selenenyl sulfide containing benzoate ester template was discovered. This reaction could be specifically triggered by H2S and lead to ester bond cleavage. The reaction was not affected by the presence of thiols such as glutathione and cysteine. With this reaction, a series of fluorescent probes were synthesized and evaluated. The probes exhibited high sensitivity/selectivity for H2S in both buffers and cells.

Electron-induced ionization of undeuterated and deuterated benzoic acid isopropyl esters and nicotinic acid isopropyl esters: Some implications for the mechanism of the McLafferty rearrangement.

Electron ionization mass spectra, ionization, and appearance energies and bond energies (as dissociation energies) are reported for benzoic acid-1-methyl-ethyl ester (BAIPE), benzoic acid-1-deutero-1-methyl-ethyl ester (BAIPED1), benzoic acid-2,2,2-trideutero-1-trideuteromethyl-ethyl ester (BAIPED6) as well as nicotinic acid-1-methyl-ethyl ester (NAIPE), nicotinic acid-1-deutero-1-methyl-ethyl ester (NAIPED1), and nicotinic acid-2,2,2-trideutero-1-trideuteromethyl-ethyl ester (NAIPED6). Ionization energies of 9.39 eV for BAIPE, 9.40 eV for BAIPED1, 9.26 eV for BAIPED6 as well as 9.70 eV for NAIPE, 9.79 eV for NAIPED1, and 9.65 eV for NAIPED6 were determined. A gas-phase formation enthalpy of = (-4.10 ± 0.1) eV for BAIPE is calculated as well as = (-3.35 ± 0.1) eV for NAIPE. Molecular ions show two main fragmentation pathways. The first is a classical McLafferty rearrangement, characterized by the transfer of one γ-hydrogen atom from the isopropyl ester chain leading to the ions of the corresponding acid and neutral propene. The second is the double hydrogen transfer from the ester chain leading to the formation of the protonated acid and a C3H5√ allyl radical. For BAIPE, both hydrogen atoms originate from the methyl groups of the aliphatic chain with a probability of ≥98%, whereas the C-1-hydrogen is transferred with a probability of ≤2%. For NAIPE, both hydrogen atoms originate from the methyl groups of the aliphatic chain with a probability of 90%. Experimental proton affinities of PA = (8.75 ± 0.2) eV for benzoic acid and PA = (8.43 ± 0.2) eV for nicotinic acid are derived. For the protonation of the carbonyl group, B3LYP DFT calculations yielded PA = 8.66 eV for benzoic acid and PA = 8.41 eV for nicotinic acid. The overall fragmentation mechanism is explained with the initial formation of a 1,5-distonic ion by transfer of the first hydrogen. For the transfer of the second hydrogen, an intermediate ion/neutral complex is formulated.

Second-Generation Synthesis of the Northern Fragment of Mandelalide A: Role of π-Stacking on Sharpless Dihydroxylation of cis-Enynes.

The development of a π-stacking-based approach for increased stereoselectivity in Sharpless asymmetric and diastereomeric dihydroxylation of cis-enynes is disclosed. The use of neighboring, electron-rich benzoate esters proved key to the success of this process. Density functional theory study suggests that the substrate benzoate ester group rigidifies the dihydroxylation transition states by forming a favorable π-stacking interaction in both Major-TS and Minor-TS. The energetic preference for the Major-TS was found in part because of the favorable eclipsing conformation of the alkene substituent as opposed to the disfavored bisecting conformation found in the Minor-TS. The application to a second-generation synthesis of the C15-C24 northern portion of mandelalide A is demonstrated.

Emissive Enhancement of the Singlet Oxygen Chemiluminescence Probe after Binding to Bovine Serum Albumin.

A chemiluminescence probe for singlet oxygen 1O2 (SOCL) was investigated in phosphate buffer saline (PBS), either in the absence of proteins or containing bovine serum albumin (BSA). In the protein-free PBS, the reactivity of SOCL for methylene blue (MB)-photosensitized 1O2 was found to be moderate or low. The reaction yield increased with temperature and/or concentration of dissolved molecular oxygen. Unexpectedly, the presence of BSA boosted both the emissive nature and the thermal stability of the phenoxy-dioxetane intermediate formed in the chemiexcitation pathway. Isothermal titration calorimetry showed that SOCL has a moderate binding affinity for BSA and that entropy forces drive the formation of the SOCL-BSA complex. A model with two identical and independent binding sites was used to fit the binding isotherm data. Co-operative binding was observed when MB was present. Local viscosity factors and/or conformational restrictions of the BSA-bound SOCL phenoxy-dioxetane were proposed to contribute to the formation of the highly emissive benzoate ester during the chemically initiated electron exchange luminescence (CIEEL) process. These results led us to conclude that hydrophobic interactions of the SOCL with proteins can modify the emissive nature of its phenoxy-dioxetane, which should be taken into account when using SOCL or its cell-penetrating peptide derivative in living cells.

Ion-Selective Electrodes Based on Polyvinyl Chloride Modified by p-(Trifluoroacetyl)Benzoate Groups

Ion-selective electrodes (ISEs), reversible to hydrophilic sulfate, hydrophosphate, and sulfide ions, are developed based on modified polyvinyl chloride (MPVC), combining the functions of a polymer matrix and a neutral carrier. A procedure for the synthesis of MPVC is described, which consists in grafting p-(trifluoroacetyl)benzoate groups to PVC. Previously, ISEs of this type contained PVC as a basis and p-(trifluoroacetyl)benzoic acid heptyl ester (p-TFABAHE). The use of MPVC significantly increases the lifetime of these ISEs by preventing changes associated both with the dissolution of p-TFABAHE (for -SE and S2–-SE, working in alkaline media) and with the crystallization of the hydrate form of p-TFABAHE on the surface of the -SE membranes working in acidic media.

Synthesis, crystal structure and optical properties of a series of dipyrrins bearing peripheral coordinating groups and their BODIPYs and Zn(II) complexes

A series of dipyrrins bearing peripheral coordinating units has been prepared by Knoevenagel condensation of the appropriate aldehyde with 5-aryl-1,3,7,9-tetramethyldipyrrin derivatives (aryl = mesityl or 4-(4-pyridyl)phenyl). Pyridine, benzoic ester and benzonitrile moieties have thus been appended on the bis-pyrrolic backbone via vinylic junctions. These compounds have been fully characterized in solution by 1H-, 13C NMR and UV–Visible spectroscopies, by mass spectrometry and, in the solid state, by single-crystal X-Ray diffraction. For all dipyrrins, an intramolecular hydrogen bond between the two pyrrolic rings and a trans organization around the vinylic junctions are observed. The coordination propensity of these ligands has been explored by preparation of the corresponding B(III) and Zn(II) complexes, showing emission in DMF solution.

Volatile non-intentionally added substances (NIAS) identified in recycled expanded polystyrene containers and their migration into food simulants

Abstract Recycled materials such as expanded polystyrene (EPS) are increasing in the food market and some hazardous chemicals may exist in recycled PS resins. Therefore, a method of solid-phase microextraction and gas chromatography coupled to mass spectrometry followed by chemometric tools applied to the data obtained allowed the identification of markers for virgin and recycled EPS. The multivariate statistical analysis was developed to characterize the profile of volatile organic compounds (VOCs) in virgin and recycled EPS containers, and identify the potential VOCs markers responsible for EPS containers discrimination. A total of 99 compounds were identified in virgin and recycled EPS containers. Among these, 17 compounds contributing the most to the discrimination, were selected based on their variables importance in the projection (VIP) values, including o-xylene, acetophenone, ethylbenzene, α-ethylstyrene, 2-phenylpropenal, propylbenzene, 2-phenyl-1-propene, undecanal, benzoic acid ethyl ester, 2-ethyl-1-hexanol, decanal, benzylcarboxaldehyde, isopropylbenzene, 2,4-diphenyl-1-butene, dodecanal, benzaldehyde and nonanal. To evaluate the health risk of EPS containers, migration tests from EPS containers into two food simulants (10% ethanol, 3% acetic acid) were conducted. It should be highlighted that high amount of styrene was detected. Nevertheless, analysed materials accomplish with current EU Regulation No.10/2011. The proposed method finds the differentiation markers and provides a reliable tool to discriminate virgin and recycled EPS containers, which could be an additional tool for quality control of EPS containers.

Development of C-Arylcalix[4]resorcinarenes and C-Arylcalix[4]pyrogallolarenes as Antioxidant and UV-B Protector

Indonesia is rich with essential oils such as anise and clove leave oils. In respect to explore the potential utilization of these resources, it has been conducted the transformation of p-hydroxybenzaldehyde and vanillin (4-hydroxy-3-methoxy benzaldehyde) respectively derived from anise oil and clove leaves oil to a series of C-arylcalix[4]resorcinarenes and C-arylcalix[4]pyrogallolarene macrocycles. Treatment of these aldehydes with resorcinol in the presence of HCl in absolute ethanol at reflux for 8 h afforded C-4-hydroxyphenylcalix[4]resorcinarene (3a) and C-4-hydroxy-3-methoxy phenyl-calix[4]resorcinarene (3b) in good yields. When the aldehydes were treated with pyrogallol under the similar condition, the products were C-4-hydroxyphenyl calix[4]pyrogallolarene (3c) and C-4-hydroxy-3-methoxyphenylcalix[4]pyrogallolarene (3d) which were also obtained in excellent yields. Treatment of these calix[4]resorcinarenes and calix[4]pyrogallolarenes with cinnamoyl chloride and benzoyl chloride in pyridine afforded the corresponding cinnamate esters and benzoate esters in high yields. The resulted C-arylcalix-[4]resorcinarenes and C-arylcalix[4]pyrogallol arenes were subjected to antioxidant activity test using DPPH method and showed strong activity with IC50 values of 15–80 μg/mL. In terms of the synthesized calix cinnamates, the compounds showed UV-B absorption with SPF values of 15–30 at a concentration of 25 ppm which demonstrate their potential to be applied as a UV-B protector. Furthermore, these compounds were also tested for their photostability on the UV-B region and the results showed that the compounds were still unstable under irradiation for 30 min.