13037-86-0

Usage

Uses

Used in Pharmaceutical Industry:
4-Heptyloxyphenol is used as a steroidogenic factor-1 (SF-1) agonist for its potential role in modulating the secretion of estradiol and oxytocin (OT) from granulosa cells. This application is particularly relevant in the study and treatment of hormonal imbalances and related conditions.
Used in Veterinary Medicine:
In veterinary medicine, 4-Heptyloxyphenol is used to treat bovine luteal cells. Its agonistic effect on SF-1 may contribute to the regulation of reproductive hormones in cattle, potentially improving reproductive health and productivity in the livestock industry.
These applications highlight the versatility of 4-Heptyloxyphenol in different fields, emphasizing its importance as a compound with significant therapeutic and physiological implications.

Biological Activity

Selective inverse agonist at the orphan nuclear receptor steroidogenic factor-1 (SF-1) (IC 50 = 50-100 nM).? Displays no activity at estrogen, LRH-1, ROR, ERR or Nurr receptors. Inhibits SFRE-mediated transcription.

InChI:InChI=1/C13H20O2/c1-2-3-4-5-6-11-15-13-9-7-12(14)8-10-13/h7-10,14H,2-6,11H2,1H3

Upstream product

• 123-31-9 hydroquinone 
• 111-70-6 n-heptan1ol 
• 629-04-9 1-Bromoheptane 

Downstream Products

• 102841-35-0 Benzene-1,2,4-tricarboxylic acid tris-(4-heptyloxy-phenyl) ester 
• 127109-50-6 (2R,3S)-(-)-4-heptyloxyphenyl-3--oxirane-2-carboxylate 
• 131889-34-4 4-((S)-2-Ethoxy-propoxy)-benzoic acid 4-heptyloxy-phenyl ester 
• 102101-55-3 C₄₆H₅₈O₈ 
• 82356-02-3 4-(4-Propyl-bicyclo[2.2.2]oct-1-yl)-benzoic acid 4-heptyloxy-phenyl ester 
• 82356-08-9 4-(4-Pentyl-bicyclo[2.2.2]oct-1-yl)-benzoic acid 4-heptyloxy-phenyl ester 
• 82356-12-5 4-(4-Hexyl-bicyclo[2.2.2]oct-1-yl)-benzoic acid 4-heptyloxy-phenyl ester 
• 82356-16-9 4-(4-Heptyl-bicyclo[2.2.2]oct-1-yl)-benzoic acid 4-heptyloxy-phenyl ester 
• 82928-27-6 4-Pentyl-bicyclo[2.2.2]octane-1-carboxylic acid 3-chloro-4-(4-heptyloxy-phenoxycarbonyl)-phenyl ester 
• 81978-09-8 7-Butyl-9,10-dihydro-phenanthrene-2-carboxylic acid 4-heptyloxy-phenyl ester 
• 81990-75-2 7-Pentyl-9,10-dihydro-phenanthrene-2-carboxylic acid 4-heptyloxy-phenyl ester 
• 102101-62-2 C₅₀H₆₆O₈ 

Relevant academic research and scientific papers

Allylphenols as a new class of human 15-lipoxygenase-1 inhibitors

In this study, a series of mono- and diallylphenol derivative were designed, synthesized, and evaluated as potential human 15-lipoxygenase-1 (15-hLOX-1) inhibitors. Radical scavenging potency of the synthetic allylphenol derivatives was assessed and the results were in accordance with lipoxygenase (LOX) inhibition potency. It was found that the electronic natures of allyl moiety and para substituents play the main role in radical scavenging activity and subsequently LOX inhibition potency of the synthetic inhibitors. Among the synthetic compounds, 2,6-diallyl-4-(hexyloxy)phenol (42) and 2,6-diallyl-4-aminophenol (47) showed the best results for LOX inhibition (IC50 = 0.88 and 0.80 μM, respectively).

Novel macro metallomesogens derived from simple dihydroxy benzenes

A series of tetradentate Schiff base metallomesogenic diols and their model compounds were synthesized from two simple dihydroxy benzenes. The metallomesogenic diol was constructed from three ring containing mesogen linked through ester and azomethine with terminal hydroxy group. This upon complexation with copper(II) formed metallomesogenic diol with varing terminal chain length. The related model metallomesogenic compounds were also synthesized with varying chain length with terminal methyl group and compared the properties with metallomesogenic diols. Extensive characterization of all metallomesogenic compounds and intermediates were carried out by FT-IR, 1H & 13C NMR, EPR, VSM, Mass (EI and FAB) and UV-Vis spectroscopy. Hot stage polarizing microscope, Differential scanning calorimetry was used to ensure the phase characteristics such as nature of phase, melting and clearing temperatures and phase range. The appearance of enantiotropic smectic A phases indicated high molecular polarizability of the core due to the metal ion. The role of copper(II) ion on mesogens were discussed.

Novel hydroxy- and methyl-terminated triaromatic schiff base compounds: Synthesis and mesogenic properties

A series of Schiff base hydroxy-mesogens and their model compounds have been synthesized. The mesogen is constructed from three-ring-containing mesogens linked through ester and azomethine groups with a terminal hydroxy group. The related model compounds were also synthesized with varying chain length with a terminal methyl group and their properties were compared with that of hydroxy mesogens. Extensive characterization of all mesogenic compounds was carried out by Fourier-transform IR, 1H and 13C NMR and mass spectroscopy. The phase characteristics such as nature of phase, melting and clearing temperatures and phase range were evaluated using a hot-stage optical polarizing microscope and differential scanning calorimetry. The appearance of enantiotropic smectic phases is due to the high molecular polarizability of the triaromatic core with azomethine and ester linkages. CSIRO 2010.

Synthesis of Y-Shaped liquid crystals and the influence of their structure on the phase behavior

A series of the Y-shaped liquid crystalline (LC) materials based on central 1,2,4-benzenetricarboxylic core was synthesized with variation of the arm length (two or three para-linked phenyl rings) in the Y-shaped mesogen and their dipole architecture (ether or ester terminal and linked groups). Our results indicate that main relationships between molecular structure and mesomorphic behavior well known for the calamitic LC are valid for the Y-shaped compounds too. Smectic mesophases might be obtained by lengthening the mesogen with an additional aromatic core in the arm or with an alkyl chain at the tail. The substitution of the alkoxy terminal groups on to alkanoyl also leads to the enhanced smectic behavior of the Y-shaped molecules. Taylor & Francis Group, LLC.

Dipole architecture of molecules and mesomorphic behavior of liquid crystals with rigid T-shaped mesogenic fragment

A number of liquid crystalline polyesters having a rigid T-shaped mesogenic fragment and differing in dipole architecture were synthesized and examined by polarizing optical microscopy, differential scanning calorimetry, and IR and 1H NMR spectroscopy. The thermal stability of the mesophase in the given series of compounds was shown to increase with extension of arms in the T-shaped mesogenic fragment, as well as on replacement of the terminal ester groups (COOAlk) therein by ether moieties (OAlk). Such replacement also enhances smectogenic properties.

Synthesis of 4-[(1R,4R)-3-oxo-p-menthan-2-ylidenemethyl]benzoic acid and its esters

Carbonylation of (E)-2-(4-halobenzylidene)-p-menthan-3-ones, catalyzed by PdCl2(PPh3)2, gave a distereometric mixure of 4-[(1R,4R)- and (1R,4S)-3-oxo-p-menthan-2-ylidenemethyl]benzoic acids, whose reaction with phenols gave 1R,4R diastereomers of the corresponding esters. 2005 Pleiades Publishing, Inc.

O-MONOALKYLATION OF HYDROQUINONE BY ALCOHOLS

The dependence of the initial rate of O-monoalkylation of hydroquinone by alcohols on the F constant of the alcohol radical has the following form: w0*104 = 21(F + 1.28)-5 + 0.44.The previously unknown steric constants F for hexyl, heptyl, cyclohexyl, and 2-ethoxyethyl radicals were determined by means of this relationship.

A Protection-Deprotection Method for the Synthesis of Substituted Benzoyloxybenzoates

Common syntheses of phenyl benzoyloxybenzoates generally produce products in low yields.A variety of synthetic pathways were employed in an attempt to increase the overall yield of the final product.It was found that catalytic agents such as boron trifluo

LIQUID CRYSTALLINE PROPERTIES OF 4-N-ALKOXYPHENYL 4-NITROBENZOATES.

Twelve 4-alkoxyphenyl esters of 4-nitrobenzoic acid were synthesized. The mesophases were identified and the transition temperatures and enthalpies determined. The above series shows considerable similarity to the reverse analogues, i. e. , the 4-nitro-phenyl 4-n-alkoxybenzoates.