Acid Decyl Ester Research Articles

GC-MS and Antibacterial Potential of Methanolic Extract Hyphaene Thebaica L. Fruit Pulp against Antibiotics-resistant Pathogens

Methanol extract obtained from the fruits of Hyphaene thebaica (doum fruit) was chemically analyzed using GC-MS (gas chromatography-mass spectrometry). Up to thirty compounds were identified in the extract. Acetic acid decyl ester (36.80%), n-Hexadecenoic acid (5.14%),1H-Purine-2,6-dione, 3,7-dihydro-1-methyl (4.24%), 2-Furancarboxaldehyde, 5-(2-hydroxy-2-phenylacetyl)-dimethylhydrazone (4.67%), Propanoic acid 3,3′-dithiobis (3.52%) and [1,2,4] Triazolo[1,5-a]pyrimidin-7-ol were major components. The antibacterial potential of the extract against six clinical bacterial isolates resistant to antibiotics was also investigated, using various in vitro assays including well diffusion, minimal inhibitory and minimal bactericidal concentration. It was found that, the methanol extract of doum fruit was characterized by antibacterial action toward one Gram-positive ß-lactamase bacteria (Staphylococcus aureus), and one Gram-negative Multidrug-resistant bacteria (Proteus mirabilis). The other four bacterial strains showed no susceptibility towards the extract. The study suggests future additional biochemical and microbiological investigations in order to understand the mechanism of action of the bioactive molecules as antimicrobial agents.

Synthesis of Dendrimer‐Like Helical Poly(Phenyl Isocyanide)s Using Air‐Stable Palladium Complexes with Double Arms

AbstractA new stepwise iterative method is developed for the synthesis of well‐defined dendrimer‐like helical poly(phenyl isocyanide)s (PPIs). The method mainly involves the following three reaction steps in an iterative process: 1) the polymerization of decyl 4‐isocyanobenzoate (monomer 1) or 4‐isocyanobenzoyl‐2‐aminoisobutyric acid decyl ester (monomer 2) to afford the polymer, 2) reacting one pentafluorophenyl (PFP) ester‐functionalized phenyl isocyanide (monomer 3) at the end of the polymer, followed by the treating of PPh3 to remove the ‐Pd(PEt3)2Cl groups, and 3) the transesterification reaction of the PFP group with hydroxyl functionalized palladium catalyst (catalyst 1) to introduce two ‐Pd(PEt3)2Cl groups at the end of the polymer, which can be used as the next initiating site. Repeating the above three reaction steps, (1), (2) and (3), enables the synthesis of high‐generation and high‐molecular‐weight dendrimer‐like helical PPIs. In practice, a series of dendrimer‐like helical poly‐1ns and poly‐2ms up to the fourth generation (4G) are successfully synthesized. The molecular weight (Mn) of the final 4G dendrimer‐like poly‐1ns and poly‐2ms is 49.4 and 66.5 kDa, respectively and they are both with narrow molecular weight distribution.

Effect of pretreatment and low‐temperature low humidity drying on quality characteristics of coriander foliage

AbstractPretreatment followed by low‐temperature low humidity drying was explored for efficient dehydration of coriander foliage to retain its quality characteristics. Newton, Page, Handerson & Pabis, Logarithmic & Midilli and Kucuk models were used to study the drying kinetics. Hygienic shelf‐stable green dried coriander foliage (HSSGDCF) obtained was evaluated for their flavour, physico‐chemical, microbial and sensory qualities during storage at ambient (65% RH, 27 ± 1°C) and accelerated (92% RH, 37 ± 1°C) conditions for 90 days. Logarithmic model with higher (R2 = 0.9997) and lower root mean square error value (0.0050) showed the best‐fitted model. Major volatiles identified in HSSGDCF were decanal (5.103%), 2‐decenal (10.021%), dodecanal (7.314%), 2‐dodecenal (7.684%), tetradecanal (8.509%), 13‐tetradecenal (19.393%) and decanoic acid decyl ester (6.051%). Degradation of chlorophyll, carotenoid and colour values were higher at 37 ± 1°C during storage. HSSGDCF was found to be microbiologically safe and sensorily acceptable at the end of 90 days at 27 ± 1°C.

Nutraceutical Potential and Antipsychotic Activity of Local Dry Fruit Waste – Juglans regia

Aim: To identify the biologically active components in shells of Juglans regia and study its nutraceutical potential and antipsychotic activity for effective waste management.
 Study Design: Biochemical and in vivo analyses of plant extract using established protocols. 
 Place and Duration of Study: Sample extraction at Department of Food Science and technology, School of Biotechnology and Bioinformatics, DY Patil deemed to be University, Navi Mumbai, India; sample components identification at Sophisticated Analytical Instrument facility (SAIF), Indian Institute of Technology (IIT), Mumbai, India; and in vivo studies for antipsychotic activity using Caenorhabditis elegans at Department of Life Science and Biochemistry, St. Xavier’s College, Mumbai, India between November 2018 and May 2019.
 Methodology: The shells of Juglans regia were milled and the extract was prepared using Soxhlet extraction at 60oC using methanol as solvent. The GCMS analysis of the extract was carried out using a GC JEOL – The Accu TOF. Antipsychotic activity was studied using pharyngeal pumping assay in Caenorhabditis elegans.
 Results: GC-MS analysis of methanolic extract of shells of Juglans regia revealed the presence of Tridecanoic acid, Acetoxyacetic acid, nonyl ester, 2-hexenal, 2-ethyl, Eicosanoic acid, phenylmethyl ester, Undecane, Benzeneacetic acid decyl ester, (1-pentyl-allyoxymethoxy-methyl)-benzene), 9,12-octadecadienoic acid(Z,Z), phenylmethyl ester, Benzyl oxytridecanoic acid, 6,9,12- octadecatrienoic acid, phenylmethyl ester (Z,Z), 9- octadecanoic acid (Z), phenylmethyl ester, 9,12,15- octadecatrienoic acid, Z [(trimethyl (sil)oxy, 1 – trimethyl (sily)oxy] ethyl ester (Z,Z,Z). Furthermore, behavioural assay done using Caenorhabditis elegans as a model organism showed that the sample exerted antipsychotic activity at lowest concentration.
 Conclusion: The shells of Juglans regia being a natural source, can be used as an alternative to the synthetic antipsychotic drugs that have side effects. Our current work suggests that the walnut shells that end up into trash bins are an excellent source of effective natural biologically active compounds.

Growth Inhibition of Human Breast and Prostate Cancer Cells by Cinnamic Acid Derivatives and Their Mechanism of Action

Cancer is the leading cause of death and there is a particularly pressing need to develop effective treatments for breast and prostate cancer. In the current study, we show the inhibitory effects of cinnamic acid derivatives, including caffeic acid phenethyl ester (CAPE, 1), on the growth of breast and prostate cancer cells. Among the compounds examined, 3,4,5-trihydroxycinnamic acid decyl ester (6) showed the most potent inhibition of cancer cell growth by the induction of apoptosis. Compound 6 could be a new anti-cancer agent for use against breast and prostate cancer.

Solvent-controlled reversible switching between adsorbed self-assembled nanoribbons and nanotubes.

We have demonstrated that solutions of 3,5-bis-(5-hexylcarbamoylpentyloxy)-benzoic acid decyl ester (BHPB-10) can form metastable nanostructures on solid substrates and in the bulk. BHPB-10 is an achiral molecule involving several distinct, strongly interacting groups (SIGs), one aromatic-ester ring and two amide groups per molecule. Specific solvents affect the interactions between particular SIGs, thus promoting various nano-structures: lamellae, nanoribbons, helical ribbons, or nanotubes. In cyclohexane, a solvent allowing for both inter-amide hydrogen bonds and mutual attraction of rings, the formation of nanotubes with a diameter of 28 ± 5 nm was observed in the bulk and on surfaces. By contrast, in cyclohexanone, which suppresses inter-amide hydrogen bonds, flat nanoribbons with a specific width of 12 ± 4 nm were formed on solid substrates after drying. By annealing in cyclohexane vapor, we followed the process of switching surface structures from nanoribbons to nanotubes and observed helical ribbons as the precursor of nanotubes. We also turned nanotubes back into nanoribbons by adding cyclohexanone, thus demonstrating reversible switching along the route: tubes → lamellae → flat ribbons → helical ribbons → tubes. We propose models explaining the observed nanostructures and their transformations, including the origin of spontaneous chirality of the helical ribbons. Our findings on the self-assembly in the achiral BHPB-10 solutions provide insight into the influence of complementary inter-molecular specific SIG-based interactions and demonstrate an effective route for tailoring the shape and size of nanostructures derived from the same building unit.

Insulated Molecular Wires: Sheathing Semiconducting Polymers with Organic Nanotubes through Heterogeneous Nucleation

Insulated molecular wires formed from organic molecules may have promising applications in organic and flexible electronic devices. Here, the authors provide compelling evidence of the formation of insulated molecular wires by sheathing conducting regioregular poly(3‐butylthiophene‐2,5‐diyl) (P3BT) fibrils with insulating nanotubes from 3,5‐bis‐(5‐hexylcarbamoylpentyloxy)‐benzoic acid decyl ester molecules through a nucleation and growth process. For dilute systems, conducting atomic force microscopy together with force–distance curves and current–voltage spectroscopy are concomitantly performed to sense current from the topmost surface to the core of the composite fibrils at controlled tip indentation depths. Results show that current is sensed only when the core of the nanocomposite fibrils is reached which indicates the presence of an insulating layer around the semiconducting P3BT fibrils. The existence of this molecular nanocomposite is further supported by neutron scattering experiments carried out on more concentrated systems at different temperatures.

Helix-Sense-Selective and Enantiomer-Selective Living Polymerization of Phenyl Isocyanide Induced by Reusable Chiral Lactide Using Achiral Palladium Initiator

Polymerization of phenyl isocyanide using achiral Pd(II) initiator with the presence of chiral l- or d-lactide (l-LA or d-LA) as additive was found to proceed in helix-sense-selective manner. The polymerization of achiral phenyl isocyanide, 4-isocyanobenzoyl-2-aminoisobutyric acid decyl ester (1) by this method produced optically active helical poly-1m(L), whose chirality was solely come from the helical conformation without containing of any other chiral atoms. The added chiral LA can be facilely recovered and reused in the helix-sense-selective polymerizations without significantly loss of its chiral induction, and the chiral economy of the polymerization is high. When enantiomerically pure phenyl isocyanide bearing an R- or S-alanine pendent with a long n-decyl chain (1r or 1s) were polymerized by this method, the polymerization was found to proceed in a highly enantiomer-selective manner with one of the enantiomers preferentially polymerized over the antipode by a factor of 3.6. Single-handed helical ...

Effects of side chains with similar lengths and different structures of polyimides on liquid crystal alignment behavior

Polyimides (PI) with different side chains in structure were synthesized by copolycondensation of pyromelliticmdianhydride (PMDA) with 3,5-diamino-(4′-methane acid hexyl ester) phenyl-benzamide (C6-PDA), (4-butoxybiphenol)-3′, 5′-diaminobenzoate (C4-BBDA) and 3, 5-diamino-benzoic acid decyl ester (C10-DA) named PI-PDA, PI-C4, PI-DA, respectively. The lengths of side chains of PI-PDA and PI-DA are as similar as that of PI-C4. Through the pretilt angle tests it is demonstrated that neither the structure of side chains nor the rubbing process could make an obvious difference on vertical alignment property when the lengths of the side chains are similar, standing at around 1.6 nm. The measurement of surface energy of PI surfaces further proved this result. The result of the X-ray photo-electron spectroscope measurement indicated that the side chains of PIs stretched out from the polymer bulk phase and accumulated on the surface.

One‐pot synthesis of conjugated poly(3‐hexylthiophene)‐b‐poly(phenyl isocyanide) hybrid rod–rod block copolymers and its self‐assembling properties

ABSTRACTIn this article, the synthesis of a series of conjugated rod–rod block copolymers based on poly(3‐hexylthiophene) (P3HT) and poly(phenyl isocyanide) (PPI) building blocks in a single pot is presented. Ni‐catalyzed Grignard metathesis polymerization of 2,5‐dibromo‐3‐hexylthiophene and subsequent addition of 4‐isocyanobenzoyl‐2‐aminoisobutyric acid decyl ester in the presence of Ni(dppp)Cl2 as a single catalyst afford P3HT‐b‐PPI with tunable molecular weights and compositions. In solid state, microphase separation occurred as differential scanning calorimetric analysis of P3HT‐b‐PPI revealed two glass transition temperatures. In solutions, the copolymers can self‐assemble into spherical aggregates with P3HT core and PPI shell in tetrahydrofuran and exhibit amorphous state in CHCl3. However, atomic force microscopy revealed that the block copolymers self‐assemble into nanofibrils on the substrate. These unique features warrant the resultant conjugated rod–rod copolymers' potential study in organic photovoltaic and other electronic devices. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 2939–2947

Chemical and biological characterisation of solvent extracts and essential oils from leaves and fruit of two Australian species of Pittosporum (Pittosporaceae) used in aboriginal medicinal practice

Ethnopharmacological significanceAlthough no known medicinal use for Pittosporum undulatum Vent. (Pittosporaceae) has been recorded, anecdotal evidence suggests that Australian Aboriginal people used Pittosporum angustifolium Lodd., G. Lodd. & W. Lodd. topically for eczema, pruritis or to induce lactation in mothers following child-birth and internally for coughs, colds or cramps. Aims of the studyEssential oil composition and bioactivity as well as differential solvent extract antimicrobial activity from Pittosporum angustifolium are investigated here first, to partially describe the composition of volatiles released in traditional applications of Pittosporum angustifolium for colds or as a lactagogue, and second to investigate antibacterial activity related to topical applications. Essential oils were also investigated from Pittosporum undulatum Vent., first to enhance essential oil data produced in previous studies, and second as a comparison to Pittosporum angustifolium. Materials and methodsEssential oils were hydrodistilled from fruit and leaves of both species using a modified approach to lessen the negative (frothing) effect of saponins. This was achieved by floating pumice or pearlite obsidian over the mixture to crush the suds formed while boiling. Essential oil extracts were analysed using GC–MS, quantified using GC-FID then screened for antimicrobial activity using a micro-titre plate broth dilution assay (MIC). Using dichloromethane, methanol, hexane and H2O as solvents, extracts were produced from leaves and fruit of Pittosporum angustifolium and screened for antimicrobial activity and qualitative phytochemical character. ResultsAlthough the essential oil from leaves and fruit of Pittosporum undulatum demonstrated some component variation, the essential oil from fruits of Pittosporum angustifolium had major constituents that strongly varied according to the geographical location of collection, suggesting the existence of at least two chemotypes; one with high abundance of acetic acid decyl ester. This chemotype had high antimicrobial activity whilst the other chemotype had only moderate antimicrobial activity against the three microbial species investigated here. This result may support the occurrence of geographical specificity with regard to ethnopharmacological use. Antimicrobial activity screening of the solvent extracts from Pittosporum angustifolium revealed the leaves to be superior to fruit, with water being the most suitable extraction solvent. ConclusionTo the best of our knowledge, this study constitutes the first time essential oils, and solvent extracts from the fruits of Pittosporum angustifolium, have been examined employing comprehensive chemical and biological analysis. The essential oil composition presented in this paper, includes components with structural similarity as chemosemiotic compounds involved in mother–infant identification, which may have significance with regard to traditional applications as a lactagogue.

Structure and chemical analysis of the metathoracic scent glands of Carpocoris fuscispinus (Boheman, 1851) (Heteroptera: Pentatomidae) from Turkey

Metathoracic scent glands (MTGs) of Carpocoris fuscispinus (Boheman, 1851) (Heteroptera: Pentatomidae) were studied in adult females and males. Structures of the glands were investigated using scanning electron microscopy, and the volatile fraction was analyzed by gas chromatography-mass spectrometry. MTGs of C. fuscispinus have many features in common: a large, median reservoir and paired lateral glands opening laterally at each anterior margin forming evaporation areas composed of mushroom-like structures, which are diagnostic for species-level taxonomy. In the MTGs of C. fuscispinus, 24 and 21 compounds were detected in females and males, respectively. Most of the chemical compounds are qualitatively similar in each male and female but differ in quantity. In the MTG analysis of females, n-tridecane (57.76%) was most abundant, and bromoacetic acid decyl ester (0.04%) was least abundant. In males, n-tridecane (49.26%) was most abundant, and 2,3-dihydroxypropyl ester (0.06%) was least abundant in all samples.

Sheathing Polymer Gels Fibrils with Nanotubules

AbstractThe aim of this preliminary study is to master the making of nanocomposites by physical processes. In particular, the sheathing of polymer fibrils by self‐assembled nanotubules is examined. Nanotubules recently prepared from 3,5‐Bis‐(5‐hexylcarbamoyl‐pentyloxy)‐benzoic acid decyl ester have been used for sheathing fibrils obtained by thermoreversible gelation of isotactic polystyrene. Investigations have been carried out by means of atomic force microscopy (AFM).

Formation of Helical Mesopores in Organic Polymer Matrices

Self-assembled helices were used as templates to form helical mesopores in a polymeric matrix. The template was formed from the self-association of 3,5-bis(5-hexylcarbamoylpentyloxy)benzoic acid decyl ester in ethylene glycol diacrylate. The monomer was photopolymerized, and the resulting resin was extracted to remove the template. The helical shape of the pores was proven by TEM and tomographic studies. The ability to form material with high specific areas using tubular templates from the same molecules was also shown.

Self‐Assembled Nanotubes in Organic Solvents

AbstractSelf‐assembled nanotubes are formed spontaneously in alkane solvents by a simple diamide compound: the 3,5‐Bis‐(5‐hexylcarbamoyl‐pentyloxy)‐benzoic acid decyl ester (BHPB‐10). The tubular shape was proved by freeze fracture TEM and by SANS techniques. The tubes have a mean radius of 121 Å and a length of the order of a micron. BHPB‐14, a homologue of this compound, bearing a longer ester chain (C14 instead of C10), self‐assemble into flat ribbons under the same conditions. FTIR and UV spectroscopy showed that H‐bonds between amide groups and π‐π interaction between aromatic groups are involved in both kinds of aggregates and in the solid state as well. The nanotubes feature specific interactions between the ester carbonyls. Hence we show that ester, by its length and by the interactions between carbonyls determines the formation of nanotubes.

Caffeic Acid Decyl Ester: An Antioxidant Principle from Phleum pratense

The isolation, comprehensive structure elucidation, and assessment of the free radical scavenging activity of caffeic acid decyl ester (1) from the seeds of Phleum pratense have been described. The RC50 value of this compound in the DPPH assay was found to be 3.60 × 10−3 mg/mL, whereas that of positive control, trolox, was 3.07 × 10−3 mg/mL.

Biocatalytical synthesis and monolayer studies of multiple hydroxylated wax esters

AbstractThe continuous production of aleuritic acid decyl ester has been investigated with LipozymeTM as biocatalyst in a fixed‐bed reactor. To avoid the limiting effects of mean substrate solubility, the direct synthesis without organic solvents was chosen, whereby a yield of 90% was obtained depending on the residence time. A comparison of different reaction paths to synthesize a centrally dihydroxylated decyl ester indicated a preference for transesterification of the methyl ester. Under external compression, the interfacial behavior of several enzymatically produced hydroxy wax esters was determined with a Langmuir film balance to find a structure/efficiency relationship. Brewster‐angle microscopy allowed direct visualization of a wax ester monolayer at the air/water interface.

Synthesis and in Vitro Transdermal Penetration Enhancing Activity of Lactam N-Acetic Acid Esters

A homologous series of N-acetic acid esters of 2-pyrrolidinone and 2-piperidinone has been prepared and evaluated for its ability to enhance the skin content and flux of hydrocortisone 21-acetate in hairless mouse skin in vitro. Enhancement ratios (ER) were determined for flux (J), 24-hour diffusion cell receptor cell concentrations (Q24), and 24-h full-thickness mouse skin steroid content (SC) and compared to control values (no enhancer present). In addition, in an attempt to abrogate toxicity, these dermal penetration enhancers were designed to have the potential for biodegradation by dermal esterases. 2-Oxopyrrolidine-α-acetic acid dodecyl ester (5) showed the highest enhancement ratios for J(ER 67.33) and Q24 (ER 180.66). 2-Oxopiperidine-α-acetic acid decyl ester (10) showed a high Q24 (ER 162.07) but a lower J (ER 12.67). 2-Oxopyrrolidine-α-acetic acid decyl ester (3) showed the highest enhancement ratio for SC (ER 8.7). The ER Q24 for 3, 5 and 10, as well as other lactam N-acetic acid esters in this work, were significantly higher than the ER found using Azone as enhancer.†

Hydroxyl radical scavenging and antipsoriatic activity of benzoic acid derivatives

The hydroxyl radical scavenging and antipsoriatic activity of a number of lipophilic and hydrophilic benzoic acid derivatives was investigated. To quantify antioxidative effects, a newly introduced test system based on the diminution of the ESR signal of DMPO-OH (generated by Fenton's reagent) by the tested compounds was applied. It was found that the in vitro antioxidative (toward hydroxyl radical) activity of benzoic acid esters decreases with increasing chain length whereas the antisoriatic activity increases. This effect is discussed in terms of a larger lipophilicity of long-chain esters. Propyl gallate was found to be the most active ȮH scavenger since it is some orders of magnitude more efficient than “model” antioxidants like α-tocopherol or mannitol. The highest antipsoriatic activity was exhibited by hydroxy benzoic acid decyl ester.