2589-73-3

Usage

Uses

Used in Surfactant Industry:
4-Hydroxyoctanophenone is used as an intermediate in the synthesis of 4-Octylphenol Monoethoxylate, which is a widely used nonionic surfactant. Nonionic surfactants are essential in various applications due to their ability to reduce surface tension between two liquids or a liquid and a solid, making them valuable in industries such as detergents, cleaning products, and personal care products.
In the synthesis process, 4-Hydroxyoctanophenone reacts with ethylene oxide to form 4-Octylphenol Monoethoxylate. This nonionic surfactant is favored for its low toxicity, biodegradability, and effectiveness in various formulations, contributing to its widespread use in the surfactant industry.

InChI:InChI=1/C14H20O2/c1-2-3-4-5-6-7-14(16)12-8-10-13(15)11-9-12/h8-11,15H,2-7H2,1H3

Upstream product

• 5457-78-3 phenyl octanoate 
• 111-64-8 n-octanoic acid chloride 
• 108-95-2 phenol 
• 7446-70-0 aluminium trichloride 
• 630-20-6 1,1,1,2-tetrachoroethane 
• 102946-00-9 1-(4-octanoyloxy-phenyl)-octan-1-one 
• 98-95-3 nitrobenzene 
• 7705-08-0 iron(III) chloride 
• 75-15-0 carbon disulfide 
• 7550-45-0 titanium tetrachloride 
• 7646-78-8 tin(IV) chloride 
• 101-84-8 diphenylether 
• 106-41-2 4-bromo-phenol 
• 124-13-0 Octanal 

Downstream Products

• 102240-72-2 nicotinic acid-[1-(4-hydroxy-phenyl)-octylidenehydrazide] 
• 102240-70-0 isonicotinic acid-[1-(4-hydroxy-phenyl)-octylidenehydrazide] 
• 949-13-3 2-octylphenol 
• 1806-26-4 p-Octylphenol 
• 6814-22-8 4-octylhexanol 
• 3226-27-5 1-(2-hydroxy-phenyl)-octan-1-one 
• 17765-30-9 1-(4-hydroxy-phenyl)-octan-1-one-(2,4-dinitro-phenylhydrazone) 
• 17744-54-6 1-(2-hydroxy-phenyl)-octan-1-one-(2,4-dinitro-phenylhydrazone) 
• 102946-00-9 1-(4-octanoyloxy-phenyl)-octan-1-one 
• 80417-30-7 4-Ethoxy-benzoic acid 4-octanoyl-phenyl ester 
• 80417-26-1 4-Methoxy-benzoic acid 4-octanoyl-phenyl ester 
• 15234-81-8 2-Methyl-2-(4-octanoyl-phenoxy)-propionic acid 
• 15234-79-4 (4-Octanoyl-phenoxy)-acetic acid 
• 74604-19-6 2-hydroxy-5-octylacetophenone 

Relevant academic research and scientific papers

Visible Light-Mediated [2 + 2] Cycloaddition Reactions of 1,4-Quinones and Terminal Alkynes

A single-step synthesis of 4-hydroxy-functionalized bi-aryl and aryl/alkyl ketones via oxidative coupling of terminal alkynes with benzoquinones is reported. Furthermore, with naphthoquinones, owing to the cross-resonance of carbonyl with the aromatic ring, alkene-alkyne cycloaddition is more favored to give four-membered carbocyclic adducts, thereby precluding the requirement of preactivated alkynes.

Iron(III)-Catalyzed Hydration of Unactivated Internal Alkynes in Weak Acidic Medium, under Lewis Acid-Assisted Br?nsted Acid Catalysis

Alkylarylalkynes are converted with full regioselectivity into the corresponding arylketones by formal hydration of the triple bond under weak acidic conditions, at times and temperatures (≤95 °C) comparable to those used for terminal alkynes. The process catalyzed by Fe2(SO4)3nH2O in glacial acetic acid exhibits good functional group compatibility, including that with bulky triple bond substituents, and can be extended to the one-pot transformation of aryltrimethylsilylacetylenes into acetyl derivatives via a desilylation-hydration sequence. The overall reactivity pattern along with proton affinity data indicate that the triple bond is activated by proton transfer rather than by π-interaction with the metal ion. This mechanistic feature, at variance with that of noble metal catalysts, accounts for the total regioselectivity and the insensitivity to steric hindrance exhibited by the Fe2(SO4)3nH2O/AcOH catalytic system. (Figure presented.).

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 critical micelle concentration of a series of gemini alkylphenol polyoxyethylene nonionic surfactants

A series of gemini n-alkylphenol polyoxyethylene surfactants (GAP) were successfully synthesized and their molecular structure were confirmed by NMR and FTIR spectrum. Using the same synthesis route, a Gemini nonylphenol polyoxyethylene surfactant (GNP) was synthesized using an industrial nonylphenol product and paraformaldehyde, and its molecular structure was also characterized by 1H-NMR and FTIR spectra. The optimal reaction conditions were established. The critical micelle concentration (CMC) values of GAP were determined by means of Wilhelmy plate method and steady-state fluorescence probe method. The experimental results show how the lengths of the hydrophilic polyoxyethylene chain and the hydrophobic tail alter the CMC values. The CMC values of the GAP are found to be much lower than those of corresponding conventional single tail nonionic surfactants of the polyethoxylated alkylphenol type, which indicates that the gemini species exhibit a better surface activity. AOCS 2011.

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.

Palladium(0) nanoparticle-catalyzed sp2 C-H activation: A convenient route to alkyl-aryl ketones by direct acylation of aryl bromides and iodides with aldehydes

Palladium(0) nanoparticles efficiently catalyze aliphatic aldehyde C-H functionalization by aryl halides to produce alkyl-aryl ketones in good yields. A wide range of substituted aryl and hetero-aryl bromides/iodides and open-chain aldehydes of varied chain length participated in this reaction.

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.

Novel inhibitors of the enzyme estrone sulfatase (ES)

We report the initial results of our study into a series of simple 4-sulfamated phenyl alkyl ketones as potential inhibitors of the enzyme estrone sulfatase. The results of the study show that these compounds are potent inhibitors, possessing greater inhibitory activity than COUMATE, but weaker activity than EMATE. Furthermore, the compounds are observed to be irreversible inhibitors.

Hydrophobicity, a physicochemical factor in the inhibition of the enzyme estrone sulfatase (ES)

We report the initial structure-activity relationship study (SAR) (in particular log P) of a series of compounds based upon 4-sulfamated phenyl ketones as potent inhibitors of the enzyme estrone sulfatase (ES). The results of the study show that these compounds are irreversible inhibitors of ES and that they are more potent than COUMATE, but weaker than EMATE. Analysis of the SAR data shows a strong correlation between IC50 and log P but also supports our previous study, which suggests a very strong relationship between pKa and IC50.

Cytotoxicity and antiestrogenicity of a novel series of basic diphenylethylenes

On the premise that it is necessary to develop antiestrogens with a higher cytotoxic component in order to reduce the risks of the development of heterogeneous malignant cell populations in breast cancer, we studied a novel series of basic diphenylethylenes, for the most part devoid of estrogenic activity, with low antiestrogenicity but much enhanced cytotoxicity compared to the reference drug tamoxifen. The main structural features associated with cytotoxicity were E isomery, substituents of five to eight carbons on the ethylene bond, and dibasicity.