14392-69-9

Usage

Uses

Used in Pharmaceutical and Biochemical Research:
4-HYDROXYNONANOPHENONE is used as a key intermediate in the synthesis and biochemical evaluation of a series of methanesulfonate derivatives of 4-hydroxyphenyl ketone. These derivatives serve as probes for investigating the active site of type 3 of the 17β-hydroxysteroid dehydrogenase family of enzymes. This application is particularly relevant in the fields of pharmaceuticals and biochemistry, where understanding enzyme mechanisms and developing targeted therapies are of great importance.

InChI:InChI=1/C15H22O2/c1-2-3-4-5-6-7-8-15(17)13-9-11-14(16)12-10-13/h9-12,16H,2-8H2,1H3

Upstream product

• 764-85-2 Nonanoyl chloride 
• 108-95-2 phenol 

Downstream Products

• 104-40-5 4-Nonylphenol 
• 20683-52-7 C₁₅H₂₀Br₂O₂ 
• 1337918-11-2 4-nonanoylphenyl trifluoromethanesulfonate 
• 38444-38-1 4-Butoxy-benzoic acid 4-nonyl-phenyl ester 
• 93913-80-5 (E)-1-(2'-Hydroxy-5'-nonylphenyl)-1-ethanone oxime 
• 115851-77-9 2-hydroxy-5-nonylacetophenone 

Relevant academic research and scientific papers

Synthesis, biochemical evaluation and rationalisation of a series of 3,5- dibromo derivatives of 4-hydroxyphenyl ketone-based compounds as probes of the active site of type 3 of 17β-hydroxysteroid dehydrogenase (17β-hsd3) and the role of hydrogen bonding interaction in the inhibition of 17β-HSD3

We report the synthesis, evaluation and rationalisation of the inhibitory activity of a series of 3,5-dibromo derivatives of 4-hydroxyphenyl ketone as probes of the active site of the type 3 of 17β-hydroxysteroid dehydrogenase (17β-HSD3). The results support the important role of hydrogen bonding interaction in the inhibition of 17β-HSD3.

Synthesis and biochemical evaluation of a series of trifluoromethanesulfonate derivatives of 4 hydroxyphenyl ketones - Probes of the active site of type 1 and 3 of the 17β-hydroxysteroid dehydrogenase family of enzymes

In an effort to aid the design of 'dual-inhibitors' of types 1 and 3 of the 17β-hydroxysteroid dehydrogenase (17β-HSD), we report the synthesis, biochemical evaluation and rationalisation of the inhibitory activity of trifluoromethanesulfonate derivatives of 4-hydroxyphenyl ketone-based compounds which were found to be weak inhibitors of types 1 and 3.

Synthesis, biochemical evaluation and rationalisation of the inhibitory activity of a series of 4-hydroxyphenyl ketones as potential inhibitors of 17β-hydroxysteroid dehydrogenase type 3 (17β-HSD3)

We report the preliminary results of the synthesis and biochemical evaluation of a number of 4-hydroxyphenyl ketones as inhibitors of the isozyme of the enzyme 17β-hydroxysteroid dehydrogenase (17β-HSD) responsible for the conversion of androstenedione (AD) to testosterone (T), more specifically type 3 (17β-HSD3). The results of our study suggest that we have synthesised compounds which are, in general, potent inhibitors of 17β-HSD3, in particular, we discovered that 1-(4-hydroxy-phenyl)-nonan-1-one (8) was the most potent (IC50 = 2.86 ± 0.03 μM). We have therefore provided good lead compounds in the synthesis of novel non-steroidal inhibitors of 17β-HSD3.

Biodegradation of Nonionic Surfactants. I. Biotransformation of 4-(1-Nonyl)phenol by a Candida maltosa Isolate

Results are reported concerning biodegradation of 4-(1-nonyl)phenol by cultures of a Candida maltosa strain isolated from aerobic sludge samples collected at a depuration plant treating wastewaters from a textile industry. The yeast was able to utilize 4-(1-nonyl)phenol as a sole carbon and energy source. Preliminary attempts to draw the actual metabolic pathway evidenced microbial attack on the alkyl chain with the production of 4-acetylphenol. To the best of our knowledge this is the first report describing a microorganism capable of attacking nonylphenol in axenic culture and at the same time allowing for the identification of its degradation products.

Synthesis, Spectral Data and Extraction of Copper by 1-(2'-Hydroxy-5'-alkylphenyl)-1-alkanone Oximes

1-(2'-Hydroxy-5'-alkylphenyl)-1-ethanone oximes with a normal alkyl group containing 2 to 12 carbon atoms and 1-(2'-hydroxy-5'-methylphenyl)-1-alkanone oximes containing 1 to 11 carbon atoms in the hydrocarbon chain were synthesized.Spectral data (u.v., i.r., n.m.r. and 13C) of oximes are reported.Four of these oximes were used for copper extraction from acidic solution.The results obtained indicate, that these oximes are better extractants than alkyl derivatives of 2-hydroxybenzophenone oximes.

The Effect of Carbonyl Containing Groups in the Terminal Chains on Mesomorphic Properties in Aromatic Esters and Thioesters. I. α-Keto Groups on the Phenolic End

The effect of inserting a ketone group in the α-position of the alkyl chain on the phenolic end of 4,4'-disubstituted phenylbenzoates and di-(4'-substituted phenyl)-trans-cyclohexane-1,4-dicarboxylates on mesomorphic properties as compared to those properties observed for the corresponding alkyl compounds was determined.Transition tempetatures were higher and mesophase ranges usually wider in the α-keto compounds in both series.Nematic phases were observed in both series, but a strong preference for a single smectic phase predominated with this being a smectic A phase in the phenylbenzoates and a smectic C phase in the cyclohexane diesters.A variety of crystal changes and a few complex melting transition were also observed in the cyclohexane diesters. - Keywords: liquid crystals; x-ray; phenylbenzoates; phase transistors; trans-cyclohexane-1,4-dicarboxylates.

RECHERCHES SUR LES SUBSTANCES MESOGENES-VIII; PREPARATION ET PROPERTIES MESOMORPHES DE SERIES ISOMETRIQUES

The synthesis and the mesomorphic properties of various series of isometric mesogenic compounds are described.It is confirmed that isometric mesogenic molecules may be nematogenic and/or smectogenic according to the position of the polar rigid core.