14392-72-4

Usage

Uses

Used in Pharmaceutical Industry:
4-Hydroxyheptanophenone is used as a chemical intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drug compounds. Its unique structure and properties make it a promising candidate for creating innovative medications.
Used in Flavor and Fragrance Industry:
In the food and beverage industry, 4-Hydroxyheptanophenone is utilized as a flavor and fragrance ingredient, adding unique scents and tastes to various products. Its versatility allows it to enhance the sensory experience of a wide range of consumables.
Used in Fine Chemicals Production:
4-Hydroxyheptanophenone has potential applications in the production of fine chemicals, where its unique structure and properties can be leveraged to create high-quality specialty chemicals for various industries.
Overall, 4-Hydroxyheptanophenone is a multifaceted chemical with numerous potential uses across different industries, including pharmaceuticals, food and beverage, and fine chemicals production. Its unique structure and properties make it a valuable asset in the development of new compounds and products.

InChI:InChI=1/C13H18O2/c1-2-3-4-5-6-13(15)11-7-9-12(14)10-8-11/h7-10,14H,2-6H2,1H3

Upstream product

• 111-14-8 oenanthic acid 
• 108-95-2 phenol 
• 56052-14-3 heptanoic acid phenyl ester 
• 2528-61-2 Heptanoic acid chloride 
• 7446-70-0 aluminium trichloride 
• 98-95-3 nitrobenzene 
• 98-88-4 benzoyl chloride 
• 629-05-0 n-octyne 
• 106-51-4 p-benzoquinone 
• 629-08-3 heptanenitrile 
• 71597-85-8 (p-hydroxyphenyl)boronic acid 

Downstream Products

• 102011-49-4 nicotinic acid-[1-(4-hydroxy-phenyl)-heptylidenehydrazide] 
• 108984-69-6 isonicotinic acid-[1-(4-hydroxy-phenyl)-heptylidenehydrazide] 
• 106379-86-6 1-(4-hydroxy-phenyl)-heptan-1-ol 
• 20683-50-5 1-(3,5-dibromo-4-hydroxy-phenyl)-heptan-1-one 
• 58187-29-4 1-[4-(3-tert-Butylamino-2-hydroxy-propoxy)-phenyl]-heptan-1-one 
• 69287-13-4 1-(4-methoxyphenyl)-1-heptanone 
• 80417-23-8 4-Methoxy-benzoic acid 4-heptanoyl-phenyl ester 
• 187663-65-6 4-{(Z)-1-[4-(2-Diethylamino-ethoxy)-phenyl]-hept-1-enyl}-phenol 
• 38444-22-3 4'-heptylphenyl-4-butylbenzoate 
• 38444-23-4 4-Hexyl-benzoic acid 4-heptyl-phenyl ester 
• 38444-25-6 4-Butoxy-benzoic acid 4-heptyl-phenyl ester 
• 38444-24-5 4-Methoxy-benzoic acid 4-heptyl-phenyl ester 
• 1539285-80-7 C₁₄H₁₇F₃O₄S 
• 17403-97-3 4-(1-Hexylpent-1-enyl)-anisol 

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.

Nickel-Catalyzed Addition of Arylboronic Acids to Alkyl Nitriles for Synthesis of Aryl Ketones in Fluorinated Solvent

A mild and efficient nickel-catalyzed addition of arylboronic acids to alkyl nitriles in a fluorinated solvent for the synthesis of various aryl ketones is described. A broad range of arylboronic acids and alkyl nitriles were investigated, and the desired products were obtained with good to excellent yields under the optimized conditions. This method provides an opportunity for the synthesis of aryl ketones from alkyl nitriles, especially acetonitrile, with a non-noble metal catalyst in one pot.

Visible Light Copper Photoredox-Catalyzed Aerobic Oxidative Coupling of Phenols and Terminal Alkynes: Regioselective Synthesis of Functionalized Ketones via C C Triple Bond Cleavage

Direct oxidative coupling of phenols and terminal alkynes was achieved at room temperature by a visible-light-mediated copper-catalyzed photoredox process. This method allows regioselective synthesis of hydroxyl-functionalized aryl and alkyl ketones from simple phenols and phenylacetylene via C C triple bond cleavage. 47 examples were presented. From a synthetic perspective, this protocol offers an efficient synthetic route for the preparation of pharmaceutical drugs, such as pitofenone and fenofibrate.

THIOSEMICARBAZONES INHIBITORS OF LYSOPHOSPHATIDIC ACID ACYLTRANSFERASE AND USES THEREOF

Lysophosphatidic acid acyltransferase-beta (LPAAT-β) catalyzes the production of phosphatidic acid (PA) from lysophosphatidic acid (LPA). The lipid cofactor PA contributes to the activation of c-Raf, BRAF, mTOR and PKC-ζ. LPAAT-β expression is a prognostic factor in gynecologic malignancies and is being investigated as a therapeutic target in a variety of tumor types. A class of thiosemicarbazones was identified as inhibitors of LPAAT-β from a screen of a library of small molecules. A focused library of thiosemicarbazones derivatives was prepared and led to the development of compounds which potently inhibit LPAAT-β and inhibit the growth of MiaPaCa2 human pancreatic cancer cells.

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.

Comparisons of O-acylation and Friedel-Crafts acylation of phenols and acyl chlorides and Fries rearrangement of phenyl esters in trifluoromethanesulfonic acid: Effective synthesis of optically active homotyrosines

Reactions involving phenol derivatives and acyl chlorides have to be controlled for competitive O-acylations and C-acylations (Friedel-Crafts acylations and Fries rearrangements) in acidic condition. The extent for these reactions in trifluoromethanesulfonic acid (TfOH), which is used as catalyst and solvent, is examined. Although diluted TfOH was needed for effective O-acylation, concentrated TfOH was required for effective C-acylations in mild condition. These results have been applied to the novel synthesis of homotyrosine derivatives. Both Fries rearrangement of N-TFA-Asp(OBn)-OMe and Friedel-Crafts acylation of phenol with N-TFA-Asp(Cl)-OMe in TfOH afforded the homotyrosine skeleton, followed by reduction and deprotection afforded homotyrosines maintaining stereochemistry of Asp as an optically pure form.

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.

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.