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10031-82-0 Usage


4-Ethoxybenzaldehyde, also known as p-Ethoxybenzaldehyde, is a flavoring ingredient with a sweet, floral, and anise odor and a similar taste. It is a clear yellow to light brown liquid and has been reported to be found in black tea. 4-Ethoxybenzaldehyde can be used as an anti-inflammatory and prostaglandin E2 suppressor, making it useful in reducing facial erythema and as a skin lightening agent.


Used in Pharmaceutical Industry:
4-Ethoxybenzaldehyde is used as an anti-inflammatory and prostaglandin E2 suppressor for its potential therapeutic effects in reducing inflammation and suppressing the production of prostaglandin E2, a molecule involved in various inflammatory processes.
Used in Cosmetics Industry:
4-Ethoxybenzaldehyde is used as a skin lightening agent for its ability to reduce facial erythema and promote an even skin tone. Its anti-inflammatory properties also contribute to its effectiveness in this application.
Used in Flavor and Fragrance Industry:
4-Ethoxybenzaldehyde is used as a flavoring ingredient due to its sweet, floral, and anise odor and taste, adding unique and pleasant flavors to various products in this industry.


By ethylation of p-hydroxybenzaldehyde using aluminum chloride catalyst.


Makino, Elizabeth T., et al. "Evaluation of a hydroquinone-free skin brightening product using in vitro inhibition of melanogenesis and clinical reduction of ultraviolet-induced hyperpigmentation." Journal of drugs in dermatology: JDD 12.3 (2013): s16-20. Draelos, Zoe Diana, and Bryan B. Fuller. "Efficacy of 1% 4‐Ethoxybenzaldehyde in Reducing Facial Erythema." Dermatologic surgery31.s1 (2005): 881-886. Cadby, P. "Estimating intakes of flavouring substances." (1996): 453-460.

Check Digit Verification of cas no

The CAS Registry Mumber 10031-82-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,0,0,3 and 1 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 10031-82:
40 % 10 = 0
So 10031-82-0 is a valid CAS Registry Number.

10031-82-0 Well-known Company Product Price

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  • Alfa Aesar

  • (A11987)  4-Ethoxybenzaldehyde, 97+%   

  • 10031-82-0

  • 25g

  • 282.0CNY

  • Detail
  • Alfa Aesar

  • (A11987)  4-Ethoxybenzaldehyde, 97+%   

  • 10031-82-0

  • 100g

  • 796.0CNY

  • Detail
  • Alfa Aesar

  • (A11987)  4-Ethoxybenzaldehyde, 97+%   

  • 10031-82-0

  • 500g

  • 3620.0CNY

  • Detail



According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017


1.1 GHS Product identifier

Product name 4-Ethoxybenzaldehyde

1.2 Other means of identification

Product number -
Other names para-ethoxybenzaldehyde

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:10031-82-0 SDS

10031-82-0Relevant articles and documents

Synthesis of aromatic aldehydes by oxidative hydroxymethylation

Branytska, Oiena,Neumann, Ronny

, p. 1575 - 1576 (2004)

A new high yield method for the synthesis of aromatic aldehydes has been developed. The procedure is based on an acid catalyzed hydroxymethylation of an arene substrate by paraformaldehyde with concurrent selective oxidation of the intermediate aromatic carbinol by 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) to the aldehyde product.

Mesomorphism dependence on molecular rigidity and flexibility

Ranchchh, Avani R.,Bhoya

, p. 43 - 51 (2018)

A novel homologous series of liquid crystalline properties is synthesized and studied with a view to understand the effect of molecular structure on its thermotropic properties. Novel homologous series consisted of thirteen homologs. All the homologs are enantiotropically smectogenic with absence of nematic property even in the monotropic condition. Textures of the homologs as observed through an optical hot stage polarizing microscopy. The mesophase temperature range vary minimum from 6.0°C to a maximum 37.0°C at the methyloxy and propyloxy derivatives of a series respectively with its thermal stability (Sm–I) 127.0°C. Transition curves of a phase diagram behaved in normal manner. Odd–even effect is observed for Sm–I transition curve.

Mesomorphism and flexibility of alkyl chains in chalcone esters


, p. 95 - 102 (2016)

A novel homologous series of chalconyl ester liquid crystals (LCs): RO?C6H4–CH:CH–COO?C6H4–CO?CH:CH?C6H4–OC10H21 (n) (para) has been synthesized and studied with a view to understanding and establishing the relationship between molecular structure and LC properties with reference to flexibility of the terminal chain. The novel series consists of eleven homologs (C1–C16). The C1 and C2 homologs are nonliquid crystals and the rest of the homologs (C3–C16) are enantiotropic nematic without exhibition of smectic mesophase. Transition and melting temperatures were determined by an optical polarizing microscope equipped with a heating stage. Textures of nematic phases are threaded or Schlieren. Cr-N/I transition curve adopts a zigzag path in a normal manner with overall descending behaviors. The N-I transition curve exhibits a sharp and shorter odd-even effect from C3 to C6 and it diminishes from and beyond C6 for higher homologs of longer n-alkyl chain (R) in more or less or negligible deviating manner from normal descending tendency. Thermal stability for the nematic is 116.4°C and mesophase length ranges from 19°C to 67°C at the C3 and C12 homolog respectively. The LC properties of present novel series are compared with structurally similar analogous series to derive group efficiency order.

Mesomorphism dependence of a terminal or lateral alkoxy group

Solanki, Ravindra,Patel

, p. 50 - 57 (2016)

A novel homologous series of thermotropic mesomorphs has been synthesized and studied with a view to understanding and establishing the effect of molecular structure on mesomorphic properties with reference to rigidity and flexibility of the homologues series: RO-C6H4-CH?CH-CO-C6H4-OC18H37(n). The novel homologous series comprises 13 novel homologues (C1 to C18), from which 11 homologues are enantiotropically mesogenic (C3 to C18). Smectogenic mesophase commences from C7 homologue, and nematogenic mesophase is exhibited by C3 to C18 homologues in enantiotropic manner. Thus, C7 to C18 homologues are enantiotropically smectogenic plus nematogenic. Textures of smectic phase are of the type A or C, and that of nematic phase are threaded or Schlieren as confirmed through an optical polarizing microscope equipped with a heating stage. Transition curve of a phase diagram behaved in a normal manner except N-I transition curve, which shows minor deviating trend (C12 to C18) from expected normal behavior. An odd-even effect is exhibited by N-I and Sm-N transition curves. Analytical, spectral, and thermal data confirm the molecular structures of novel homologues. Thermal stabilities for smectic and nematic are 52.7°C and 66.6°C, respectively, whose total mesophase lengths range from 12.0°C to 28.0°C. Thus, novel series of chalcones is a low melting series whose mesogenic transition temperatures vary between 38.0 and 86.0°C.

N-methyl morpholine chlorochromate: An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds


, p. 2638 - 2645 (2008)

Instantaneous generation of N-methyl morpholine chlorochromate (NMMCC) is an efficient reagent for oxidation of primary and secondary alcohols to the corresponding carbonyl compounds. The comparison of reaction time and product yield was studied with novel NMMCC and other chlorochromate reagents and shows that the presented method requires less reaction time with good yield at laboratory temperature. The synthesis of reagent, formation of toxic and hazardous chromylchloride have been avoided, and also use of NMMCC under microwave irradiation for oxidation leads to fast reaction time and success of the strategy. Copyright Taylor & Francis Group, LLC.

Solvent-free Williamson synthesis: An efficient, simple, and convenient method for chemoselective etherification of phenols and bisphenols

Massah, Ahmad R.,Mosharafian, Masumeh,Momeni, Ahamad R.,Aliyan, Hamid,Naghash, H. Javaherian,Adibnejad, Mohamad

, p. 1807 - 1815 (2007)

Etherification of phenols with dimethyl- and diethylsulfates and benzyl chloride was performed efficiently in the presence of a suitable solid base, NaHCO3 or K2CO3, under solvent-free conditions. The reaction proceeded rapidly at low temperature, and the corresponding ethers were obtained with high purity and excellent yield. Selective etherification of electron-poor phenols in the presence of electron-rich ones and also selective mono-etherification of bisphenols are the noteworthy advantages of this method. This method is environmentally friendly. Copyright Taylor & Francis Group, LLC.

Mesomorphic study of novel chalconyl-ester-based nonisomeric series: Synthesis and characterization

Sharma, Vinay S.,Patel

, p. 13 - 27 (2017)

A newly designed homologues series: 3-(3-(4-(Dimethylamino) phenyl) acrylonyl) phenyl 3-(4-n-alkoxyphenyl) acrylate has been synthesized and studied through chalconyl ester linking group at (meta) position. The series consists of 13 compounds, in which C1 to C4 homologue are nonliquid crystal, while C5 to C18 exhibit nematic phase, and C12 to C18 shows smectic and nematic phase with enantiotropically manner. Mesophase image of present compounds are rod like, needle and threaded type textures investigated by POM. All this compounds were characterized by elemental analysis, FT-IR and 1H NMR. The mesomorphism is measured by POM, DSC, and molecular packing is determined by XRD technique. The following synthesized chalconyl ester-based compounds C5 to C12 shows antibacterial as well as antifungal activity compared with corresponding standard drugs. Analytical and spectral data confirmed the molecular structures of homologous series.

Intermolecular C–O Coupling Using Hemicucurbituril Supported Ionic Liquid Phase Catalyst

Kurane, Rajanikant,Bansode, Prakash,Khanapure, Sharanabasappa,Kale, Dolly,Salunkhe, Rajashri,Rashinkar, Gajanan

, p. 2485 - 2494 (2016)

Abstract: Hemicucurbituril supported ionic liquid phase catalyst (HmCucSILP) has been synthesized by anchoring multilayer of ionic liquid ([Bmim]Cl) containing Pd(OAc)2 and X-phos on the surface of hemicucurbit[6]uril. The HmCucSILP was effectively employed in intermolecular C–O coupling of aryl halides with sodium alkoxides for the synthesis of alkyl aryl ethers. Graphical Abstract: [Figure not available: see fulltext.]

Study the effects of terminal side chain and –nitro group on mesomorphic behaviour of cinnamate-chalconyl based liquid crystal

Sharma, Vinay S.,Patel

, p. 1 - 12 (2017)

The influence of the terminal side chain and lateral nitro on mesomorphism due to the flexibility and polarity of lateral group is investigated. A new homologues series is synthesized to accomplish this aim. The C1 to C3 homologue are nonmesomorphic, while the rest of the homologues exhibit enantiotropic nematic and smectic properties. The texture of the nematic mesophase is of threaded, Schlieren and droplets type. All these compounds were characterized by elemental analyses and spectroscopic techniques of FTIR and 1H Nuclear magnetic resonance (NMR). The phase behaviour was studied by polarizing optical microscopy (POM), differential scanning calorimetry (DSC), and X-ray diffraction techniques.

Synthesis and mesomorphic properties of new chalconyl-ester based liquid crystals: The effect of tail group

Sharma, Vinay S.,Vekariya, Rajesh H.,Sharma, Anuj S.,Patel

, p. 10 - 22 (2017)

A new homologous series viz. 4-(3-(3, 4-dioctadecyloxy) phenyl)-3- oxoprop-1-en-1-yl) phenyl-3-(4-n-alkoxy phenyl) cinnamate) based on two linking groups have been synthesized and characterized. The mesomorphic properties of these compounds were observed by optical polarized light microscopy (POM) and confirmed by differential scanning calorimetry (DSC). All synthesized compounds exhibited LC behaviour except compound C1. Thermal stability of smectic and nematic phase of present series are 79.0°C and 120.0°C whose temperature range is vary from 14 to 20°C and 24 to 56°C respectively. The mesomorphic properties of present series were compared with other structurally related mesogenic homologous series to evaluate the effects of tail group on mesomorphism.

Stepwise degradation of hydroxyl compounds to aldehydes: Via successive C-C bond cleavage

Liu, Mingyang,Zhang, Zhanrong,Shen, Xiaojun,Liu, Huizhen,Zhang, Pei,Chen, Bingfeng,Han, Buxing

, p. 925 - 928 (2019)

Stepwise degradation of hydroxyl compounds to aldehydes via successive cleavage of C-C bonds was achieved by using a bimetallic catalytic system (PdCl2 + CuCl) without any ligands and additives. The broad applicability is expanded to a diverse range of aromatic, aliphatic, primary and secondary alcohols, as well as lignin model compounds.

Mesomorphism and molecular flexibility in novel chalconyl derivatives with two phenyl rings

Sharma, Vinay S.,Jain,Patel

, p. 68 - 76 (2016)

A novel chalconyl liquid crystalline (LC) homologous series with two phenyl rings and one central bridge RO?C6H4?CH=CH–CO?C6H4(O?C18H37) (meta) has been synthesized and studied with a view to understanding and establishing the effects of molecular structure on thermotropic LC behaviors or properties. Homologous series of present investigation (C1–C18) consists of thirteen homologues, and thermotropic mesomorphism for nematic and smectic commences from C3 and C6 homologues respectively. The C3, C4, and C5 homologues are enantiotropically nematic, whereas, the homologues from C6 to C18 are monotropically smectic plus nematic. Melting points and transition temperatures were determined using a polarizing optical microscope (POM) equipped with a heating stage. The textures of the nematic phase are threaded or Schlieren and that of a smectic phase are fan shaped of smectic-A or smectic-C type. The Cr?I/M, N?I/I?N, and N-Sm transition curves behave in the normal manner, and the Cr-I/M exhibits an odd-even effect. Analytical, thermal, and spectral data confirm the molecular structures. Thermal stabilities of smectic and nematic are low. Mesophase lengths are very short, ranging between 1–8°C and 14°C. The novel compounds are compared with a known series.

Gadolinium Complex of 1,4,7,10-Tetraazacyclododecane-1,4,7-Trisacetic Acid (DO3A)-Ethoxybenzyl (EOB) Conjugate as a New Macrocyclic Hepatobiliary MRI Contrast Agent

Baek, Ah Rum,Kim, Hee-Kyung,Park, Subin,Lee, Gang Ho,Kang, Hyo Jeung,Jung, Jae-Chang,Park, Joon-Suk,Ryeom, Hun-Kyu,Kim, Tae-Jeong,Chang, Yongmin

, p. 4861 - 4868 (2017)

We report the synthesis of a macrocyclic Gd chelate based on a 1,4,7,10-Tetraazacyclododecane-1,4,7-Trisacetic acid (DO3A) coordinationn cage bearing an ethoxybenzyl (EOB) moiety and discuss its use as a T1 hepatobiliary magnetic resonance imaging (MRI) contrast agent. The new macrocyclic liver agent shows high chelation stability and high r1 relaxivity compared with linear-Type Gd chelates, which are the current clinically approved liver agents. Our macrocyclic, liver-specific Gd chelate was evaluated in vivo through biodistribution analysis and liver MRI, which demonstrated its high tumor detection sensitivity and suggested that the new Gd complex is a promising contrast agent for liver cancer imaging.

Mesomorphism Dependence on Molecular Flexibility and Molecular Rigidity


, p. 46 - 54 (2015)

A novel liquid crystal (LC) homologues series of ethylene derivatives was synthesized and evaluated for mesomorphic properties. Mesomorphism commences from sixth member of the series. Textures of the nematic phase are threaded or Schlieren and those of the smectic phase are of the focal conic fan type. The N-I and Sm-N transition curves of the phase diagram exhibit odd-even effects and behave in a normal manner. The average thermal stabilities of the smectic and nematic are 113.4°C and 123.2°C with mesogenic phase lengths varying between 3.3°C and 8.1°C and 4.5°C to 13.5°C, respectively. The LC behavior of the novel series is compared with a structurally similar known series.

Room temperature aerobic oxidation of alcohols using CuBr2 with TEMPO and a tetradentate polymer based pyridyl-imine ligand

Hu, Zhenzhong,Kerton, Francesca M.

, p. 332 - 339 (2012)

A series of tetradentate pyridyl-imine terminated Schiff-base ligands has been investigated for their ability in the catalytic oxidation of alcohols when combined with copper bromide (CuBr2) and 2,2,6,6- tetramethylpiperidyl-1-oxy (TEMPO). Analogous bidentate ligands showed poorer catalytic activity and the ratio of Cu:ligand was of crucial importance in maintaining high yields. The polydimethylsiloxane (PDMS) derived pyridyl-imine terminated ligand combined with copper(II) ions affords an effective and selective catalyst for aerobic oxidations of primary and secondary alcohols under aqueous conditions. Preliminary mechanistic studies suggest that bimetallic complexes may be playing a role in the catalytic transformation.

“Dependence of Mesomorphism in Combination with Fluoro and Chloro Groups”

Ranchchh, Avani R.,Tharesha, Bhavna R.,Bhoya

, p. 49 - 58 (2018)

A novel azoester homologous series with chloro lateral group and a fluoro terminal end group was synthesized and characterized for mesomorphic properties. It consists of thirteen azo ester derivatives from trans-4-n-alkoxy cinnamic acid with 4-hydroxy-3-chloro phenyl azo-3-chloro-4-fluoro benzene. Mesomorphic property commences from C4homologue as smectic.C1 to C3 member of the series are non-mesomorphic. C4 to C18 homologous are enantiotropic smectic A phase. The nematic mesophase is totally absent. Texture and transition temperatures of the homologues are determined by an optical polarizing microscopy equipped with heating stage. 1H NMR, IR spectra, mass spectra, of some member is included. The spectroscopic analysis supports the molecular structure. A phase diagram is used to illustrate the mesomorphic behaviour across the series. Mesophaselength for smectic is varying from18.0°C to 69.00C. Mesomorphic properties of the novel azoester series are compared with structurally similar series.

Dependence of mesomorphism on molecular rigidity of chalconyl liquid crystals with two phenyl rings

Sharma, Vinay S.,Patel

, p. 19 - 27 (2016)

A novel homologues series: RO-C6H4?CH=CH?CO?C6H4?OC16H33(n) (meta) of chalcones with two phenyl rings is synthesized and studied with a view to understanding and establishing the relationship between molecular structure and mesogenic behavior. The series consists of 13 homologues (C1 to C18). Mesomorphism commences from the second member of the series. C2 to C6 homologues are enantiotropicnematic and the rest of the homologues (C7 to C8) are monotropicnematic plus monotropicsmectic. C1 homologue is nonmesogenic. Transition temperatures were determined by an optical polarizing microscope (POM) equipped with a heating stage. Textures of nematic and smectic phases are threaded, Schlieren or smectic-A, respectively, as judged directly from the heating top of microscopic observations. Thermal, analytical and spectral data confirms the molecular structures. Thermal stabilities for smectic and nematic are few (1 or 2°C) degrees and 72.6°C, respectively. The mesophase lengths are relatively shorter with low mesomorphic transition temperatures (44.0°C to 85.0°C).

Nighttime tropospheric chemistry: Kinetics and product studies in the reaction of 4-Alkyl- and 4-Alkoxytoluenes with NO3 in gas phase

Bolzacchini, Ezio,Meinardi, Simone,Orlandi, Marco,Rindone, Bruno,Hjorth, Jens,Restelli, Gianbattista

, p. 461 - 468 (1999)

Alkylbenzenes are important constituents of gasoline and industrial solvents and contribute to the formation of tropospheric ozone. The removal of these compounds from the troposphere is due to reaction with OH during the day and with NO3 during the night. Five para-substituted toluenes are reacted with the nitrate radical in gas phase. Samples to be used for product analysis were preconcentrated and analyzed by GC-MSD analysis with the use of a reference curve. The yields of methanol, ethanol, and formaldehyde were determined by FTIR analysis of the reaction mixture in the chamber. Carbonyl compounds, benzyl alcohols, and nitroderivatives were formed. In the case of the alkoxytoluenes, products were also an alkanol, benzyl alcohols, and nitrophenols. Indirect rate constants measurements were performed by comparing by FTIR measurements the decay of the aromatic compound under investigation to that of a reference compound, with a known rate constant for the reaction with NO3 added to the gas mixture. Wall loss constants were evaluated by FTIR. A Hammett correlation with ρ = - 4.3 ± 0.6; r2-= 0.87 was obtained. This and the kinetic isotope effect of 1.5-1.8 suggest a reaction mechanism occurring via an addition-elimination pathway.

Dependence of mesomorphism on flexibility of lateral and terminal groups of chalconyl esters

Patel, Priya K.,Shah

, p. 1 - 9 (2016)

A novel liquid crystalline homologous series of chalconyl vinyl esters with a lateral bromo substituent RO─C6H4─CH═CH─COO─C6H3─(Br)─CO-CH═CH─C6H4─C12H25(n) has been synthesized and studied with a view to understanding and establishing the relation between the molecular structure and liquid crystal (LC) behavior in terms of molecular flexibility of the lateral and terminal groups. The novel homologous series consists of thirteen (C1–C18) homologues, whose enantiotropic nematic and smectic mesomorphism commences from the C4, (C4–C18) and the C5, (C5–C18) homologue, respectively. The rest of the homologues (C1, C2, C3) are nonliquid crystals (NLC). Mesomorphism and transition temperatures were examined using an optical polarising microscope (POM) equipped with a heating stage. Textures of nematic phase are threaded or Schlieren and those of the Smectic-A or Smectic-C are focal conic. Analytical, thermal and spectral data supported molecular structures of the novel homologues. Thermal for smectic and nematic are 87.5°C and 101.1°C, respectively, whose, total mesophase length ranges from 17°C to 30°C at C14 and C7 homologue, respectively. The mesomorphic transition temperature ranges are between 70°C and 113°C.

Reductant-directed formation of PS-PAMAM-supported gold nanoparticles for use as highly active and recyclable catalysts for the aerobic oxidation of alcohols and the homocoupling of phenylboronic acids

Zheng, Jie,Lin, Shengyue,Zhu, Xianhao,Jiang, Biwang,Yang, Zhen,Pan, Zhengying

, p. 6235 - 6237 (2012)

Polystyrene-polyamidoamine-supported gold nanoparticles were prepared using a reductant-directed formation strategy. The resulting catalysts exhibited excellent activities in the aerobic oxidation of benzyl alcohols and the homocoupling of phenylboronic acids under mild conditions and can be recycled at least 14 times without significant loss of activity. The Royal Society of Chemistry 2012.

Synthesis and study of mesomorphic properties in rod-like chalconyl compounds

Sharma, Vinay S.,Patel

, p. 52 - 61 (2017)

In order to investigate the influence of the central linking group and effect on flexibility on mesophase behavior of liquid crystal we have synthesized newly homologous series viz. 3-(4-Octyloxyphenyl)-1-(4′-n-alkoxy phenyl) prop-2-en-1-one (Series-l) consists of thirteen homologues (C1 to C8, C10, C12, C14, C16, C18). Textures of a nematic phases are threaded or Schlieren type. The textures of smectic and nematic phase are directly judged from the heating and cooling condition. Group efficiency order for mesophases is derived on the basis of thermal stabilities from the comparative study of thermometric data determined from structurally analogous series. A transition curve as depicted in a phase diagram behaves in normal manner. Structural and conformational characterization of these new compounds had achieved by 1H NMR, 13C NMR, IR, and elemental analysis.

Mesomorphism dependence on central bridge and tail ended polar group

Ranchchh, Avani R.,Chavda, Kavita,Bhanderi, Roshani,Patel, Suman,Bhoya

, p. 33 - 42 (2018)

A novel azoester homologous series of laterally and terminally substituted viz, RO–C6H4–CH=CH–COO–C6H3–(CH3) –N=N–C6H4–Cl is synthesized, characterized and studied with a view to understand and establish the relation between molecular structure and thermotropic liquid crystalline property of its homologs. Series consists of twelve homologs. LC properties commence from very first member of a series and continue up to last homolog as enantiotropic nematic with absence of smectic property even in the monotropic condition. Transition temperatures of homologs were determined by polarizing optical microscopy equipped with a heating stage. The transition curves Cr?N and N?I behaved in normal manner. Thermal stability for nematic is 196.7?C whose mesophaselength ranges from 35°C to 131°C.

Mesomorphism dependence on heterocyclic tail


, p. 30 - 37 (2016)

A novel homologous series of liquid crystal materials containing a heterocyclic ring was synthesized with a view to understanding and establishing the relation between liquid crystal (LC) properties and a molecular structure; and with a view to curing skin-related diseases following biological activity studies. The series consist of 13 (C1 to C18) members. All the members are liquid crystals. The C4 to C18 members are smectogenic of which C4 and C5 are monotropic and remaining members (C6 to C18) are enantiotropic in nature; whereas all C1 to C18 members are enantiotropically nematogenic. Hence the C1, C2, C3 members are only nematogenic and the rest of the homologues are smectogenic in addition to nematogenic. Transition temperatures were determined by an polarizing optical microscope equipped with heating stage. Analytical and spectral data confirmed the molecular structures of homologues. It is a middle ordered melting type series. LC properties of a series are compared with the structurally known series.

Dibenzazepine-linked isoxazoles: New and potent class of α-glucosidase inhibitors

Umm-E-Farwa,Ullah, Saeed,Khan, Maria Aqeel,Zafar, Humaira,Atia-tul-Wahab,Younus, Munisaa,Choudhary, M. Iqbal,Basha, Fatima Z.

supporting information, (2021/05/10)

α-Glucosidase inhibition is a valid approach for controlling hyperglycemia in diabetes. In the current study, new molecules as a hybrid of isoxazole and dibenzazepine scaffolds were designed, based on their literature as antidiabetic agents. For this, a series of dibenzazepine-linked isoxazoles (33–54) was prepared using Nitrile oxide-Alkyne cycloaddition (NOAC) reaction, and evaluated for their α-glucosidase inhibitory activities to explore new hits for treatment of diabetes. Most of the compounds showed potent inhibitory potency against α-glucosidase (EC enzyme (IC50 = 35.62 ± 1.48 to 333.30 ± 1.67 μM) using acarbose as a reference drug (IC50 = 875.75 ± 2.08 μM). Structure-activity relationship, kinetics and molecular docking studies of active isoxazoles were also determined to study enzyme-inhibitor interactions. Compounds 33, 40, 41, 46, 48–50, and 54 showed binding interactions with critical amino acid residues of α-glucosidase enzyme, such as Lys156, Ser157, Asp242, and Gln353.

Anticancer, antimicrobial activities of quinoline based hydrazone analogues: Synthesis, characterization and molecular docking

Katariya, Kanubhai D,Shah, Shailesh R.,Reddy, Dushyanth

supporting information, (2019/11/26)

Based on the biologically active heterocycle quinoline, a series (18a-p) of quinoline hydrazone analogues were prepared, starting from 6-bromo/6-chloro-2-methyl-quinolin-4-yl-hydrazines. For all the newly synthesized compounds cytotoxic activities were carried out at the National Cancer Institute (NCI), USA, against full NCI 60 human cancer cell lines. Amongst all the tested compounds, nine compounds (18b, 18d, 18e, 18f, 18g, 18h, 18i, 18j, 18l) exhibited important anti-proliferative activity at 10 μM concentration and were further screened at 10-fold dilutions of five different concentrations (0.01, 0.1, 1, 10 and 100 μM) with GI50 values ranging from 0.33 to 4.87 μM and LC50 values ranging from 4.67 μM to >100j μM. Further, the mean values of GI50, TGI and LC50 of the most potent compound 18j were compared with the clinically used anticancer agents bendamustine and chlorambucil, revealed that the quinolyl hydrazones holds promise as a potential anticancer agents. Further all the newly prepared compounds were screened for their antimicrobial activity. All the quinolyl hydrazones displayed good to excellent antimicrobial activity with MIC values ranging from 6.25 to 100 μg/mL against the tested pathogenic strains. Molecular docking of the synthesized compounds into the active binding site of human DNA topoisomerase I (htopoI) was carried out to predict the binding mode to the DNA topoisomerase I inhibitors. Hopefully in future, compounds based on quinoline core could be used as a lead compounds for designing new anticancer agents.

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