27893-41-0

Usage

Uses

Used in Fragrance and Flavoring Industry:
4-N-Heptyloxybenzaldehyde is used as a key ingredient in the creation of fragrances and flavoring agents due to its distinctive aromatic properties. It contributes to the development of complex scents and tastes in a variety of consumer products, enhancing their appeal and marketability.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 4-N-Heptyloxybenzaldehyde serves as an intermediate in the synthesis of various medicinal compounds. Its unique chemical structure allows it to be a building block for the development of new drugs, potentially leading to advancements in healthcare and treatment options.
Used in Agrochemical Industry:
4-N-Heptyloxybenzaldehyde is also utilized in the agrochemical industry, where it plays a role in the production of pesticides, herbicides, and other agricultural chemicals. Its involvement in these processes helps to improve crop yields and protect plants from pests and diseases, contributing to global food security and agricultural sustainability.

InChI:InChI=1/C14H20O2/c1-2-3-4-5-6-11-16-14-9-7-13(12-15)8-10-14/h7-10,12H,2-6,11H2,1H3

Upstream product

• 4282-40-0 1-Iodoheptane 
• 123-08-0 4-hydroxy-benzaldehyde 
• 629-04-9 1-Bromoheptane 
• 773101-88-5 2-(p-heptoxyphenyl)-1,3-dioxolane 
• 123732-04-7 4-n-heptyloxybromobenzene 
• 68-12-2 N,N-dimethyl-formamide 
• 629-06-1 1-Chloroheptane 

Downstream Products

• 61440-52-6 4-heptyloxybenzyl alcohol 
• 99163-26-5 4,4'-Di-n-Heptyloxybenzalazine 
• 114468-27-8 (E)-N-Phenyl-4-heptyloxybenzaldimin 
• 70262-79-2 N-(4-heptyloxy-benzylidene)-p-phenetidine 
• 71299-68-8 4-heptyloxy-benzaldehyde (4-oxo-thiazolidin-2-ylidene)-hydrazone 
• 60625-42-5 p-Heptyloxybenzyliden-p'-aminozimtsaeure-R-2-chlorpropylester 
• 71299-77-9 4-methoxy-benzaldehyde [5-(4-heptyloxy-benzylidene)-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 61440-55-9 p-{[p-(Heptyloxy)benzyl]amino}benzoic Acid 
• 61440-54-8 ethyl p-{[p-(heptyloxy)benzyl]amino}benzoate 
• 90863-30-2 2-(4-Heptyloxy-phenyl)-5-hexadecyloxy-[1,3]dioxane 
• 81220-98-6 2-(4-Heptyloxy-phenyl)-5-hexadecyloxy-[1,3]dioxane 
• 74800-52-5 5-Butyl-2-(4-heptyloxy-phenyl)-[1,3]dioxane 
• 81221-03-6 5-Butyl-2-(4-heptyloxy-phenyl)-[1,3]dioxane 
• 75552-41-9 2-(4-Heptyloxy-phenyl)-5-hexyl-[1,3]dioxane 

Relevant academic research and scientific papers

pH-Tolerant giant vesicles composed of cationic lipids with imine linkages and oleic acids

Giant vesicles (GVs) have attracted attention as functional materials because they can encapsulate both hydrophilic and hydrophobic compounds. For next generation functional GVs, both tolerance and stimuli-sensitivity are needed. So far, vesicles tolerant to acidic or basic conditions were generated using a mixture of cationic lipids and fatty acids. Here, to create functional GVs that are tolerant to a wide pH range but sensitively respond at below a specific pH, the behaviour of GVs composed of a cationic lipid with an imine bond and oleic acid was investigated. Even though the GVs prepared by the film swelling method were tolerant to strongly acidic conditions, GVs without oleic acid gradually shrank, accompanied by the generation of oil droplets at the same pH. 1H NMR analysis revealed that during hydration of the film, the imine bond hydrolysed to provide a cationic surfactant and an oil component in the presence of oleic acid due to its own Lewis basicity, suggesting the dissociation of oleic acid. The results of fluorescence spectroscopy using an environment-responsive probe and IR spectroscopy indicated that the GV tolerance originated from the intermolecular interactions of cationic lipids and anionic oleate. This journal is

Lipophilic tail modifications of 2-(hydroxymethyl)pyrrolidine scaffold reveal dual sphingosine kinase 1 and 2 inhibitors

The sphingosine 1-phosphate (S1P) signaling pathway is an attractive target for pharmacological manipulation due to its involvement in cancer progression and immune cell chemotaxis. The synthesis of S1P is catalyzed by the action of sphingosine kinase 1 or 2 (SphK1 or SphK2) on sphingosine and ATP. While potent and selective inhibitors of SphK1 or SphK2 have been reported, development of potent dual SphK1/SphK2 inhibitors are still needed. Towards this end, we report the structure–activity relationship profiling of 2-(hydroxymethyl)pyrrolidine-based inhibitors with 22d being the most potent dual SphK1/SphK2 inhibitor (SphK1 Ki = 0.679 μM, SphK2 Ki = 0.951 μM) reported in this series. 22d inhibited the growth of engineered Saccharomyces cerevisiae and decreased S1P levels in histiocytic lymphoma myeloid cell line (U937 cells), demonstrating inhibition of SphK1 and 2 in vitro. Molecular modeling studies of 22d docked inside the Sph binding pocket of both SphK1 and SphK2 indicate essential hydrogen bond between the 2-(hydroxymethyl)pyrrolidine head to interact with aspartic acid and serine residues near the ATP binding pocket, which provide the basis for dual inhibition. In addition, the dodecyl tail adopts a “J-shape” conformation found in crystal structure of sphingosine bound to SphK1. Collectively, these studies provide insight into the intermolecular interactions in the SphK1 and 2 active sites to achieve maximal dual inhibitory activity.

Synthesis and determination of thermotropic liquid crystalline behavior of cinnamaldehyde-based molecules with two schiff base linking units

A series of liquid crystal molecules with two Schiff base linking units and a cinnamaldehyde core with different terminal groups were synthesized and characterized. The intermediates of 4-heptyloxybenzaldehyde (1a) and 4-dodeyloxybenzaldehyde (1b) were synthesized through the alkylation of 4-hydroxybenzaldehyde with a series of bromoalkane. A condensation reaction of cinnamaldehyde, 1,4-phenylenediamine and a series of substituted benzaldehydes with different terminal groups such as bromo, chloro, hydroxy, cinnamaldehyde, hydrogen, methoxy, heptyloxy and dodecyloxy produced a series of new cinnamaldehyde-based compounds, 2-9, respectively. All these compounds were characterized using Fourier transform infrared (FTIR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy, and CHN elemental analysis. The liquid crystal properties of these compounds were determined using polarized optical microscopy (POM), and their transitions were further confirmed using differential scanning calorimetry (DSC). Compounds with chloro, bromo, methoxy, heptyloxy, and dodecyloxy substituents are mesogenic compounds with nematic phase behavior. However, the other compounds were found to be non-mesogenic without any mesophase transitions. The structure-property relationship was investigated in order to study the effect of different terminal groups and Schiff base linking units on the liquid crystalline behavior of these compounds.

1,3-Oxazine-2-one derived dual-targeted molecules against replicating and non-replicating forms of Mycobacterium tuberculosis

The high mortality rate and increasing prevalence of resistant Mtb are the major concerns for the Tuberculosis (TB) treatment in this century. To curtail the prevalence of resistant Mtb, we have prepared 1,3-oxazine-2-one based dual targeted molecules. Compound 67 and 68 were found to be equally active against replicating and non-replicatiing form of Mtb (MICMABA 3.48 and 2.97 μg/ml; MICLORA 2.94 and 2.15 μg/ml respectively). They had found to suppress the biosynthesis of alfa, methoxy and keto-mycolate completely, as well as inhibit enzymatic activity of MenG (IC50 = 9.11 and 6.25 μg/ml respectively for H37Ra; IC50 = 11.76 and 10.88 μg/ml respectively for M smegmatis).

Synthesis and mesomorphic properties of coumarin derivatives with chalcone and imine linkages

We report here design and synthesis of two new mesogenic homologous series of coumarin derivatives consisting of chalcone and imine central linkages along with terminal n-alkoxy chain. All the compounds were synthesized and characterized by combination of elemental analysis and standard spectroscopic methods. All compounds were screened under polarising optical microscope (POM) for liquid crystalline properties, thermogram of all compounds were studied using differential scanning calorimetry (DSC) to get phase transition temperatures, enthalpy and entropy. X-ray single crystal study of n-octyloxy coumarin derivative 16 g was resolved with imine central linkage, which showed linear rod like geometry.

2-Aryl benzazole derived new class of anti-tubercular compounds: Endowed to eradicate mycobacterium tuberculosis in replicating and non-replicating forms

The high mortality rate and the increasing prevalence of Mtb resistance are the major concerns for the Tuberculosis (TB) treatment in this century. To counteract the prevalence of Mtb resistance, we have synthesized 2-aryl benzazole based dual targeted molecules. Compound 9m and 9n were found to be equally active against replicating and non-replicating form of Mtb (MIC(MABA) 1.98 and 1.66 μg/ml; MIC(LORA) 2.06 and 1.59 μg/ml respectively). They arrested the cell division (replicating Mtb) by inhibiting the GTPase activity of FtsZ with IC50 values 45 and 64 μM respectively. They were also capable of kill Mtb in non-replicating form by inhibiting the biosynthesis of menaquinone which was substantiated by the MenG inhibition (IC50 = 11.62 and 7.49 μM respectively) followed by the Vit-K2 rescue study and ATP production assay.

Synthesis and characterization of 1,4-phenylenediamine derivatives containing hydroxyl and cyclotriphosphazene as terminal group

A series of compounds with two Schiff base linking units and four different substituents (heptyl, dodecyl, methoxy and chloro) have been successfully synthesized. Further reactions form new monosubstituted cyclotriphosphazene based molecules with different substituents. These compounds were characterized using FT-IR (Fourier Transform Infrared), NMR (Nuclear Magnetic Resonance) and CHN elemental analysis. The transition mesophase(s) of these compounds were determined using POM (Polarized Optical Microscope) and DSC (Differential Scanning Calorimetry). Two compounds with heptyl and dodecyl substituents were found to be mesogenic with smectic C phases while monosubstituted cyclotriphosphazene compounds of the same substituents (heptyl and dodecyl chains) were also found to be mesogenic. Cyclotriphosphazene compounds with heptyl chain shows smectic C and nematic phases while compound with dodecyl chain shows only the nematic phase. However, compounds with methoxy and chloro substituents were found to be non-mesogenic.

“Effect of the linking unit on the calamitic-shaped liquid crystal: a comparative study of two homologous series of benzoate and cinnamate linked compounds”

Two homologous series based on three linking groups have been synthesized and well characterized by elemental analyses and spectroscopic techniques such as Fourier transform infrared [FT-IR] and proton magnetic resonance magnetic resonance [1H NMR] spectroscopy. The mesomorphic properties of these compounds were observed by using optical polarized microscopy (POM) and confirmed by differential scanning calorimetry (DSC) analysis. In this present investigation, we have synthesized two homologous series viz. (E)-4-(3-(4-(tetra decanoyloxy) phenyl) acryloyl) phenyl-4-n-alkoxy benzoate (Series-1) and 4-((E)-3-(4-(((E)-3-(4-n-alkoxy phenyl) acryloyl) oxy) phenyl)-3-oxo prop-1-en-1-yl) phenyl tetradecanoate (Series-2). Both of the series are differing with respect to the first linking group. All the homologous in following series displays LC properties on heating as well as cooling condition except first four homologous (C1 to C4) in series-1 and six homologous (C1 to C6) in series-2. To get more insights, the HOMO, LUMO studies are carried out which supports intramolecular charge transfer interactions in this class of mesogens.

Mesomorphism behaviour and photoluminescent properties of new asymmetrical 1,2-di(4-alkoxybenzylidene) hydrazines

{1-[4-(n-Alkoxy)]-2-(4’-decyloxy)benzylidene}hydrazines (n-alkoxy = O(CH2)nH, n = 1–9, 12, 16 or 18), an asymmetrical series of 1,2-disubstituted hydrazines, were prepared in a simple two-step procedure as a part of our continuing work in evaluating hydrophobic azine compounds as photoluminescent liquid crystalline materials. The compounds were characterized spectroscopically and their liquid crystalline behaviour and luminescent properties were evaluated using polarized light optical microscopy, differential scanning calorimetry and X-ray powder diffraction techniques. The studies revealed that all of these compounds are liquid crystalline materials exhibiting photoluminescent properties in the crystalline and liquid crystal states.

Liquid Crystalline Properties of 4,4'-methylenebis(N-(4-Alkanoxybenzylidene)aniline): Synthesis, Characterization, and Theoretical study

The paper presents six homologues series of Schiff bases ether compounds distinguished by the length of terminal alkoxy groups which substituted on a side benzene nucleus. The above structures were demonstrated through the use of spectroscopic techniques, like FT- IR and1H-NMR. Polarized hot stage optical microscopy was used to study both mesomorphic properties and phase transitions. The results showed that out of the six compounds only three (B2, B3 and B4) were pure (marble) nematic mesophase, while no liquid crystal properties for (B5, B6 and B7) compounds. The theoretical study for the electronic structures was intended to study the effects of alkyl chain length on the electronic structure by using Gaussian program, DFT and 6-31G as basis set. The theoretical results indicate that there is no effect to the terminal substituted alkoxy groups on the HOMO energies but there is an effect on LUMO energies through decreasing energy for the prepared compounds.