99-93-4 | 4'-Hydroxyacetophenone

Packsize	Purity	Availability	Price	Discounted Price
10g	99%	in stock	$5.00	$3.00
25g	99%	in stock	$8.00	$5.00
100g	99%	in stock	$10.00	$7.00
500g	99%	in stock	$28.00	$19.00

Description

• Catalog Number: AB45025
• Chemical Name: 4'-Hydroxyacetophenone
• CAS Number: 99-93-4
• Molecular Formula: C8H8O2
• Molecular Weight: 136.1479
• MDL Number: MFCD00002359
• SMILES: CC(=O)c1ccc(cc1)O
• NSC Number: 3698

Computed Properties

• Complexity: 123
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 10
• Hydrogen Bond Acceptor Count: 2
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 1
• XLogP3: 1.4

Upstream Synthesis Route

4'-Hydroxyacetophenone is a versatile compound widely utilized in chemical synthesis as a key building block for the production of various pharmaceuticals and fine chemicals. This compound is particularly valued for its ability to serve as a precursor in the synthesis of numerous important compounds due to its unique structural features. In organic chemistry, 4'-Hydroxyacetophenone plays a crucial role as a starting material in the preparation of diverse classes of compounds, including but not limited to chiral ligands, heterocyclic compounds, and functionalized aromatics. Its reactivity and functional groups make it a valuable intermediate in the pharmaceutical industry for the synthesis of analgesics, anti-inflammatory agents, antimicrobial agents, and other bioactive compounds. Additionally, 4'-Hydroxyacetophenone is commonly employed in academic research and industrial applications for the development of novel chemical entities with potential therapeutic value. Its significance in chemical synthesis stems from its versatile nature and the wide array of transformations it can undergo to yield structurally diverse and biologically relevant molecules.

Literature

• Aqueous ionic liquid based ultrasonic assisted extraction of four acetophenones from the Chinese medicinal plant Cynanchum bungei Decne.

  Ultrasonics sonochemistry 20130101

• The catalytic mechanism of the hotdog-fold enzyme superfamily 4-hydroxybenzoyl-CoA thioesterase from Arthrobacter sp. strain SU.

  Biochemistry 20120904

• Phenolic constituents of the Chilean herbal tea Fabiana imbricata R. et P.

  Plant foods for human nutrition (Dordrecht, Netherlands) 20120901

• The implication of mediators for enhancement of laccase oxidation of sulfonamide antibiotics.

  Bioresource technology 20120601

• Biodegradation and detoxification of bisphenol A with one newly-isolated strain Bacillus sp. GZB: kinetics, mechanism and estrogenic transition.

  Bioresource technology 20120601

• Polymorphism in 4'-hydroxyacetophenone: a molecular dynamics simulation study.

  The journal of physical chemistry. B 20120503

• Adiabatic triplet state tautomerization of p-hydroxyacetophenone in aqueous solution.

  The journal of physical chemistry. A 20120322

• Bioassay-guided isolation of vasorelaxant compounds from Ziziphora clinopodioides Lam. (Lamiaceae).

  Fitoterapia 20120301

• Applications of p-hydroxyphenacyl (pHP) and coumarin-4-ylmethyl photoremovable protecting groups.

  Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20120301

• Neuroprotective compounds isolated from Cynanchum paniculatum.

  Archives of pharmacal research 20120301

• Pseudomonas putida esterase contains a GGG(A)X-motif confering activity for the kinetic resolution of tertiary alcohols.

  Applied microbiology and biotechnology 20120201

• Inhibited phenol ionization in reverse micelles: confinement effect at the nanometer scale.

  Chemphyschem : a European journal of chemical physics and physical chemistry 20120116

• Aldo-Keto Reductase 1B10 and Its Role in Proliferation Capacity of Drug-Resistant Cancers.

  Frontiers in pharmacology 20120101

• Identification of the para-nitrophenol catabolic pathway, and characterization of three enzymes involved in the hydroquinone pathway, in Peudomonas sp. 1-7.

  BMC microbiology 20120101

• Phenolic compounds from the aerial parts of Diplomorpha canescens.

  Chemical & pharmaceutical bulletin 20120101

• Oxidative degradation of 4-hydroxyacetophenone in Arthrobacter sp. TGJ4.

  Bioscience, biotechnology, and biochemistry 20120101

• 1,1'-{[1,4-Phenyl-enebis(methyl-ene)]bis-(-oxy)bis-(4,1-phenyl-ene)}diethanone.

  Acta crystallographica. Section E, Structure reports online 20111201

• Chemical constituents of Cynanchum wilfordii and the chemotaxonomy of two species of the family Asclepiadacease, C. wilfordii and C. auriculatum.

  Archives of pharmacal research 20111201

• (1E,1'E)-4,4'-[1,1'-(Hydrazine-1,2-diyl-idene)bis-(ethan-1-yl-1-yl-idene)]diphenol dihydrate.

  Acta crystallographica. Section E, Structure reports online 20110901

• p-hydroxyacetophenone amides from Cystobacter ferrugineus, strain Cb G35.

  Journal of natural products 20110624

• Wavelength-selective caged surfaces: how many functional levels are possible?

  Journal of the American Chemical Society 20110413

• Gas-phase fragmentation of deprotonated p-hydroxyphenacyl derivatives.

  The Journal of organic chemistry 20110401

• Computational analysis for hepatic safety signals of constituents present in botanical extracts widely used by women in the United States for treatment of menopausal symptoms.

  Regulatory toxicology and pharmacology : RTP 20110201

• Ultrasound-assisted phase-transfer catalysis: benzoylation of sodium 4-acetylphenoxide by dual-site phase-transfer catalyst in a tri-liquid system.

  Ultrasonics sonochemistry 20110101

• Microwave assisted solvent free synthesis of 1,3-diphenylpropenones.

  Chemistry Central journal 20110101

• Synthesis, Antiinflammatory and Antimicrobial Activity of Some New 1-(3-Phenyl-3,4-Dihydro-2H-1,3-Benzoxazin-6-yl)-Ethanone Derivatives.

  Indian journal of pharmaceutical sciences 20110101

• Effects of a fluorescent Myosin light chain phosphatase inhibitor on prostate cancer cells.

  Frontiers in oncology 20110101

• Studies on the chemical constituents of Anabasis aphylla L.

  Yao xue xue bao = Acta pharmaceutica Sinica 20101201

• Investigating the coenzyme specificity of phenylacetone monooxygenase from Thermobifida fusca.

  Applied microbiology and biotechnology 20101101

• Photophysics and photodeprotection reactions of p-methoxyphenacyl phototriggers: an ultrafast and nanosecond time-resolved spectroscopic and density functional theory study.

  The Journal of organic chemistry 20100903

• (E)-1-[4-(Prop-2-yn-1-yl-oxy)phen-yl]-3-(3,4,5-trimeth-oxy-phen-yl)prop-2-en-1-one.

  Acta crystallographica. Section E, Structure reports online 20100901

• Chemical constituents of Saxifraga stolonifera (L.) Meeb.

  Yao xue xue bao = Acta pharmaceutica Sinica 20100601

• Select acetophenones modulate flagellar motility in chlamydomonas.

  Chemical biology & drug design 20100301

• Mast cell-dependent allergic responses are inhibited by ethanolic extract of adlay (Coix lachryma-jobi L. var. ma-yuen Stapf) testa.

  Journal of agricultural and food chemistry 20100224

• Structure-toxicity relationship of phenolic analogs as anti-melanoma agents: an enzyme directed prodrug approach.

  Chemico-biological interactions 20100212

• Divergent chemical cues elicit seed collecting by ants in an obligate multi-species mutualism in lowland Amazonia.

  PloS one 20100101

• General reaction conditions for the palladium-catalyzed vinylation of aryl chlorides with potassium alkenyltrifluoroborates.

  The Journal of organic chemistry 20091106

• Synthesis and antifungal activity of beta-trifluoroalkyl aminovinyl ketone derivatives.

  Journal of agricultural and food chemistry 20090923

• [Phenolic compounds from Galium aparine var. tenerum].

  Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090701

• (E)-3-[4-(Hex-yloxy)phen-yl]-1-(4-hydroxy-phen-yl)prop-2-en-1-one.

  Acta crystallographica. Section E, Structure reports online 20090601

• (E)-3-[4-(Dec-yloxy)phen-yl]-1-(4-hydroxy-phen-yl)prop-2-en-1-one.

  Acta crystallographica. Section E, Structure reports online 20090501

• Palladium-catalyzed cross-coupling reactions of potassium alkenyltrifluoroborates with organic halides in aqueous media.

  The Journal of organic chemistry 20090320

• (E)-N'-[1-(4-Hydroxy-phen-yl)ethyl-idene]-2-(quinolin-8-yl-oxy)acetohydrazide methanol solvate.

  Acta crystallographica. Section E, Structure reports online 20090301

• Controlling accumulation of fermentation inhibitors in biorefinery recycle water using microbial fuel cells.

  Biotechnology for biofuels 20090101

• [Determination of four acetophenones in Radix Cynanchi bungei by high performance liquid chromatography-photodiode array detection].

  Se pu = Chinese journal of chromatography 20090101

• Analysis of proteins with the 'hot dog' fold: prediction of function and identification of catalytic residues of hypothetical proteins.

  BMC structural biology 20090101

• [Studies on chemical constituents of aerial parts of Ammopiptanthus mongolicus].

  Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20081001

• Simultaneous determination of 13 bioactive compounds in Herba Artemisiae Scopariae (Yin Chen) from different harvest seasons by HPLC-DAD.

  Journal of pharmaceutical and biomedical analysis 20080805

• Anaerobic degradation of p-ethylphenol by 'Aromatoleum aromaticum' strain EbN1: pathway, regulation, and involved proteins.

  Journal of bacteriology 20080801

• Cytotoxic constituents from the bark of Salix hulteni.

  Archives of pharmacal research 20080801

• Fluorinated photoremovable protecting groups: the influence of fluoro substituents on the photo-Favorskii rearrangement.

  Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20080501

• [Studies on chemical constituents of Saussurea laniceps].

  Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20080501

• Ultrasonic cavitation applied to the treatment of bisphenol A. Effect of sonochemical parameters and analysis of BPA by-products.

  Ultrasonics sonochemistry 20080401

• The photo-Favorskii reaction of p-hydroxyphenacyl compounds is initiated by water-assisted, adiabatic extrusion of a triplet biradical.

  Journal of the American Chemical Society 20080319

• (4-Formyl-2-methoxy-phenolato)tris-(2-methyl-2-phenyl-prop-yl)tin(IV).

  Acta crystallographica. Section E, Structure reports online 20080301

• Efficient microbial degradation of bisphenol A in the presence of activated carbon.

  Journal of bioscience and bioengineering 20080201

• Structures of dimeric dihydrodiol dehydrogenase apoenzyme and inhibitor complex: probing the subunit interface with site-directed mutagenesis.

  Proteins 20080101

• Synthesis of 1-Aryl-3-phenethylamino-1-propanone hydrochlorides as possible potent cytotoxic agents.

  Molecules (Basel, Switzerland) 20071212

• Interference by Mes [2-(4-morpholino)ethanesulfonic acid] and related buffers with phenolic oxidation by peroxidase.

  Free radical biology & medicine 20071101

• A theoretical investigation of P-hydroxyphenacyl caged phototrigger compounds: how water induces the photodeprotection and subsequent rearrangement reactions.

  The journal of physical chemistry. B 20071011

• Exudation of allelopathic substances in buckwheat (Fagopyrum esculentum Moench).

  Journal of agricultural and food chemistry 20070808

• Anaerobic co-metabolic oxidation of 4-alkylphenols with medium-length or long alkyl chains by Thauera sp., strain R5.

  Applied microbiology and biotechnology 20070701

• Optimization of phenolic compounds analysis by capillary electrophoresis.

  Talanta 20070615

• Simultaneous determination of p-hydroxyacetophenone, chlorogenic acid, and caffeic acid in Herba Artemisiae Scopariae by capillary electrophoresis with electrochemical detection.

  Analytical and bioanalytical chemistry 20070501

• Chemical constituents of cape aloe and their synergistic growth-inhibiting effect on Ehrlich ascites tumor cells.

  Bioscience, biotechnology, and biochemistry 20070501

• Biodegradation of bisphenol A and related compounds by Sphingomonas sp. strain BP-7 isolated from seawater.

  Bioscience, biotechnology, and biochemistry 20070101

• Degradation of bisphenol A by Bacillus pumilus isolated from kimchi, a traditionally fermented food.

  Applied biochemistry and biotechnology 20070101

• Resolution of chiral phosphate, phosphonate, and phosphinate esters by an enantioselective enzyme library.

  Journal of the American Chemical Society 20061213

• A theoretical investigation of p-hydroxyphenacyl caged phototrigger compounds: an examination of the excited state photochemistry of p-hydroxyphenacyl acetate.

  The journal of physical chemistry. A 20061116

• Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.

  Journal of molecular graphics & modelling 20061101

• 4-Hydroxyacetophenone-induced choleresis in rats is mediated by the Mrp2-dependent biliary secretion of its glucuronide conjugate.

  Pharmaceutical research 20061101

• Differential effects of hydroxyacetophenone analogues on the transcytotic vesicular pathway in rat liver.

  European journal of pharmacology 20061010

• Separation and determination of trace amounts of zinc, lead, cadmium and mercury in tap and Qaroun lake water using polyurethane foam functionalized with 4-hydroxytoluene and 4-hydroxyacetophenone.

  Analytica chimica acta 20061010

• Inhibition of respiratory burst in human neutrophils and lipoxygenase enzyme by compounds from Haloxylon griffithii.

  Phytotherapy research : PTR 20061001

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

  Bioorganic & medicinal chemistry letters 20060901

• Chemical composition of propolis from Canada, its antiradical activity and plant origin.

  Natural product research 20060520

• Ultrafast time-resolved transient absorption and resonance raman spectroscopy study of the photodeprotection and rearrangement reactions of p-hydroxyphenacyl caged phosphates.

  Journal of the American Chemical Society 20060301

• Inhibition of GABA shunt enzymes' activity by 4-hydroxybenzaldehyde derivatives.

  Bioorganic & medicinal chemistry letters 20060201

• Ethnopharmacological evaluation of radal (leaves of Lomatia hirsuta) and isolation of 2-methoxyjuglone.

  BMC complementary and alternative medicine 20060101

• Interactions of alcohol dehydrogenase to p-hydroxyacetophenone-sepharose and p-acetamidophenol-sepharose.

  Alcoholism, clinical and experimental research 20051201

• Enhancement of alcohol dehydrogenase activity in vitro by acetylsalicylic acid.

  European journal of pharmacology 20051031

• Time-resolved resonance Raman and density functional theory study of the deprotonation reaction of the triplet state of p-hydroxyacetophenone in water solution.

  The Journal of organic chemistry 20051028

• Chemical composition of propolis from Canada, its antiradical activity and plant origin.

  Natural product research 20051001

• New multi-1,2,3-selenadiazole aromatic derivatives.

  Molecules (Basel, Switzerland) 20050930

• Extraction of p-hydroxyacetophenone and catechin from Norway spruce needles. Comparison of different extraction solvents.

  Analytical and bioanalytical chemistry 20050601

• Mono- and beta,beta-double-Heck reactions of alpha,beta-unsaturated carbonyl compounds in aqueous media.

  The Journal of organic chemistry 20050527

• Biosynthesis of benzofuran derivatives in root cultures of Tagetes patula via phenylalanine and 1-deoxy-D-xylulose 5-phosphate.

  Phytochemistry 20050401

• Theoretical study of the o-OH participation in catechol ester ammonolysis.

  Organic & biomolecular chemistry 20050307

• Ultrafast time-resolved study of photophysical processes involved in the photodeprotection of p-hydroxyphenacyl caged phototrigger compounds.

  Journal of the American Chemical Society 20050209

• Volatile compounds in shoulder gland secretions of male flying foxes, genus Pteropus (Pteropodidae, Chiroptera).

  Zeitschrift fur Naturforschung. C, Journal of biosciences 20050101

• Anti-oxidative compounds in barley tea.

  Bioscience, biotechnology, and biochemistry 20041201

• Time-resolved resonance Raman study of the triplet states of p-hydroxyacetophenone and the p-hydroxyphenacyl diethyl phosphate phototrigger compound.

  The Journal of organic chemistry 20041001

• Variability of catechin and 4-hydroxyacetophenone distribution in Norway spruce needles in relation to their position, age, and growing conditions.

  Environmental pollution (Barking, Essex : 1987) 20040901

• Constituents of Senecio chionophilus with potential antitubercular activity.

  Journal of natural products 20040901

• Inhibiting activities of the secondary metabolites of Phlomis brunneogaleata against parasitic protozoa and plasmodial enoyl-ACP Reductase, a crucial enzyme in fatty acid biosynthesis.

  Planta medica 20040801

• Constituents of two Flourensia species.

  Phytochemistry 20040701

• Determination of the liver cytosolic proteins that bind to p-hydroxyacetophenone.

  Biomedical chromatography : BMC 20040601

• Trypanocidal and antifungal activities of p-hydroxyacetophenone derivatives from Calea uniflora (Heliantheae, Asteraceae).

  The Journal of pharmacy and pharmacology 20040501

• The use of novel water-in-oil microemulsions in microemulsion electrokinetic chromatography.

  Electrophoresis 20040201

• A validated, sensitive HPLC method for the determination of trace impurities in acetaminophen drug substance.

  Journal of pharmaceutical and biomedical analysis 20040127

• New simple method for purification of class I alcohol dehydrogenase.

  Alcohol and alcoholism (Oxford, Oxfordshire) 20040101

• The Hotdog fold: wrapping up a superfamily of thioesterases and dehydratases.

  BMC bioinformatics 20040101

• Free radical scavengers and antioxidants from Tagetes mendocina.

  Zeitschrift fur Naturforschung. C, Journal of biosciences 20040101

• Potential inhibitors from wet oxidation of wheat straw and their effect on ethanol production of Saccharomyces cerevisiae: wet oxidation and fermentation by yeast.

  Biotechnology and bioengineering 20030320

• Xenoestrogens in the River Elbe and its tributaries.

  Environmental pollution (Barking, Essex : 1987) 20030101

• Protein tyrosine phosphatases in Chaetopterus egg activation.

  Development, growth & differentiation 20030101

• Acute toxicity, mutagenicity, and estrogenicity of biodegradation products of bisphenol-A.

  Environmental toxicology 20021001

• Effects of 4,4-dimethyl-5,8-dihydroxynaphtalene-1-one and 4,4-dimethyl-5,8-dihydroxytetralone derivatives on tumor cell respiration.

  Bioorganic & medicinal chemistry 20020901

• Plant growth inhibitory activity of p-hydroxyacetophenones and tremetones from Chilean endemic Baccharis species and some analogous: a comparative study.

  Journal of agricultural and food chemistry 20020410

• [Constituents of Liguliria vellerea (Franch.) Hand-Mazz].

  Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20011201

• Selective and quantitative analysis of 4-hydroxybenzoate preservatives by microemulsion electrokinetic chromatography.

  Journal of chromatography. A 20010727

• Phytochemical constituents of Artemisia japonica ssp. littoricola.

  Archives of pharmacal research 20010601

• 4-Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB. A novel flavoprotein catalyzing Baeyer-Villiger oxidation of aromatic compounds.

  European journal of biochemistry 20010501

• Conversion of 4-hydroxyacetophenone into 4-phenyl acetate by a flavin adenine dinucleotide-containing Baeyer-Villiger-type monooxygenase.

  Journal of bacteriology 20001201

• Novel pathway for bacterial metabolism of bisphenol A. Rearrangements and stilbene cleavage in bisphenol A metabolism.

  The Journal of biological chemistry 19940311