2'-hydroxyacetophenone
o-acetylphenol
Identification
| Name | 2'-hydroxyacetophenone |
| IUPAC | 1-(2-hydroxyphenyl)ethanone |
| CAS Number | 118-93-4 |
| EINECS | 204-288-0 |
| FDA UNII | 3E533Z76W0 |
| Molecular Formula | C8 H8 O2 |
| Molecular Weight | 136.15016000 |
| MDL Number | MFCD00002219 |
| Nikkaji Number | J5.308B |
| Beilstein | 0386123 |
| CoE Number | 11784 |
| XlogP3 | 1.90 (est) |
Regulatory
| JECFA Food Flavoring | 727 2'-hydroxyacetophenone |
| DG SANTE Food Flavourings | 07.124 2-hydroxyacetophenone |
| FEMA Number | 3548 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm (SATF) | 118-93-4 ; 2-HYDROXYACETOPHENONE |
Physical Properties
| Appearance | yellow green clear liquid (est) |
| Assay | 98.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 1.13300 to 1.13600 @ 20.00 °C. |
| Pounds per Gallon - (est). | 9.439 to 9.464 |
| Refractive Index | 1.55700 to 1.56100 @ 20.00 °C. |
| Melting Point | 4.00 to 6.00 °C. @ 760.00 mm Hg |
| Boiling Point | 213.00 °C. @ 717.00 mm Hg, 100.00 °C. @ 14.00 mm Hg |
| Vapor Pressure | 0.086000 mmHg @ 25.00 °C. (est) |
| Vapor Density | 4.7 ( Air = 1 ) |
| Flash Point | 223.00 °F. TCC ( 106.11 °C. ) |
| logP (o/w) | 1.920 |
| Soluble in | alcohol |
| Insoluble in | water |
Organoleptic Properties
| Odor Strength | medium , |
| Substantivity | 360 hour(s) at 100.00 % |
| Odor Description |
at 10.00 % in dipropylene glycol. at 2.00 %.
|
| Odor sample from | Sigma-Aldrich |
| Taste Description | at 5.00 ppm. |
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | intraperitoneal-mouse LD50 100 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavor and fragrance agents |
| RIFM Fragrance Material Safety Assessment | Search |
| Recommendation for 2'-hydroxyacetophenone usage levels up to | 3.0000 % in the fragrance concentrate. |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 0.12 (μg/capita/day) |
| Maximised Survey-derived Daily Intakes (MSDI-USA) | 0.01 (μg/capita/day) |
| baked goods | - |
| beverages(nonalcoholic) | - |
| beverages(alcoholic) | - |
| breakfast cereal | - |
| cheese | - |
| chewing gum | - |
| condiments / relishes | - |
| confectionery froastings | - |
| egg products | - |
| fats / oils | - |
| fish products | - |
| frozen dairy | - |
| fruit ices | - |
| gelatins / puddings | - |
| granulated sugar | - |
| gravies | - |
| hard candy | - |
| imitation dairy | - |
| instant coffee / tea | - |
| jams / jellies | - |
| meat products | - |
| milk products | - |
| nut products | - |
| other grains | - |
| poultry | - |
| processed fruits | - |
| processed vegetables | - |
| reconstituted vegetables | - |
| seasonings / flavors | - |
| snack foods | - |
| soft candy | - |
| soups | - |
| sugar substitutes | - |
| sweet sauces | - |
Beijing Lys Chemicals Co, LTD.
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Potential Uses
Natural Occurrence
Synonyms
2-
acetophenol
acetophenone, 2'-hydroxy-
2-
acetyl phenol
ortho-
acetyl phenol
1-
acetyl-2-hydroxybenzene
2-
acetylphenol
o-
acetylphenol
ethanone, 1-(2-hydroxyphenyl)-
o-
hydroxy acetophenone
2-
hydroxyacetophenone
o-
hydroxyacetophenone
ortho-
hydroxyacetophenone
2-
hydroxyphenyl methyl ketone
ortho-
hydroxyphenyl methyl ketone
1-(2-
hydroxyphenyl) ethanone
1-(2-
hydroxyphenyl)ethan-1-one
1-(2-
hydroxyphenyl)ethanone
2-
hydroxyphenylmethyl ketone
o-
hydroxyphenylmethyl ketone
methyl 2-hydroxyphenyl ketone
US Patents:
3,946,080 - Flavouring and perfuming ingredients
PubMed:
Differentiation of Manuka Honey from Kanuka Honey and from Jelly Bush Honey using HS-SPME-GC/MS and UHPLC-PDA-MS/MS.
US Patents:
3,952,024 - Furfurylthioacetone
PubMed:
Crystallization and preliminary X-ray diffraction analysis of (R)-carbonyl reductase from Candida parapsilosis.
PubMed:
Particle size and shape modification of hydroxyapatite nanostructures synthesized via a complexing agent-assisted route.
PubMed:
Bis(4-hydroxy-2H-chromen-2-one): synthesis and effects on leukemic cell lines proliferation and NF-κB regulation.
PubMed:
New ruthenium(II) carbonyl complexes bearing disulfide Schiff base ligands and their applications as catalyst for some organic transformations.
PubMed:
Combined experimental and theoretical studies on the X-ray crystal structure, FT-IR, 1H NMR, 13C NMR, UV-Vis spectra, NLO behavior and antimicrobial activity of 2-hydroxyacetophenone benzoylhydrazone.
PubMed:
Synthesis of isoflavones by room-temperature nickel-catalyzed cross-couplings of 3-iodo(bromo)chromones with arylzincs.
PubMed:
2,2,6,6-Tetramethylpiperidine-catalyzed, ortho-selective chlorination of phenols by sulfuryl chloride.
PubMed:
Photochromic cycle of 2'-hydroxyacetophenone azine studied by absorption and emission spectroscopy in different solvents.
PubMed:
The role of a Schiff base scaffold, N-(2-hydroxy acetophenone) glycinate-in overcoming multidrug resistance in cancer.
PubMed:
Preparation of crystal-like periodic mesoporous phenylene-silica derivatized with ferrocene and its use as a catalyst for the oxidation of styrene.
PubMed:
Synthesis, docking study and relaxant effect of 2-alkyl and 2-naphthylchromones on rat aorta and guinea-pig trachea through phosphodiesterase inhibition.
PubMed:
Optimized expression of (S)-carbonyl reductase in Pichia pastoris for efficient production of (S)-1-phenyl-1, 2-ethanediol.
PubMed:
Acaricidal potentials of active properties isolated from Cynanchum paniculatum and acaricidal changes by introducing functional radicals.
PubMed:
New nickel(II) and copper(II) complexes with unsymmetrical Schiff bases derived from (1R,2R)(-)cyclohexanediamine and the application of Cu(II) complexes for hybrid thin layers deposition.
PubMed:
Synthesis, spectral and antimicrobial activity of Zn(II) complexes with Schiff bases derived from 2-hydrazino-5-[substituted phenyl]-1,3,4-thiadiazole and benzaldehyde/2-hydroxyacetophenone/indoline-2,3-dione.
PubMed:
1, 5-Bis (2-hydroxyacetophenone)thiocarbohydrazone: a novel colorimetric and fluorescent dual-mode chemosensor for the recognition of fluoride.
PubMed:
Flame atomic absorption spectrometric (FAAS) determination of copper, iron and zinc in food samples after solid-phase extraction on Schiff base-modified duolite XAD 761.
PubMed:
Efficient one-step production of (S)-1-phenyl-1,2-ethanediol from (R)-enantiomer plus NAD(+)-NADPH in-situ regeneration using engineered Escherichia coli.
PubMed:
A simple route to synthesize mesoporous ZSM-5 templated by ammonium-modified chitosan.
PubMed:
Palladium-catalyzed carbonylation reaction of aryl bromides with 2-hydroxyacetophenones to form flavones.
PubMed:
Co(II), Cd(II), Hg(II) and U(VI)Oâ complexes of o-hydroxyacetophenone[N-(3-hydroxy-2-naphthoyl)] hydrazone: physicochemical study, thermal studies and antimicrobial activity.
PubMed:
Accessibility and selective stabilization of the principal spin states of iron by pyridyl versus phenolic ketimines: modulation of the 6A1 â 2T2 ground-state transformation of the [FeN4O2]+ chromophore.
PubMed:
Isolation and identification of the metabolites of paeonol in human urine.
PubMed:
Synthesis, Characterization and In Vitro Antibacterial Studies of Organotin(IV) Complexes with 2-Hydroxyacetophenone-2-methylphenylthiosemicarbazone (H(2)dampt).
PubMed:
Organocatalytic Dakin oxidation by nucleophilic flavin catalysts.
PubMed:
Template synthesis, spectroscopic characterization and preliminary insulin-mimetic activity of oxovanadium(IV) complexes with NâOâ diazadioxa macrocycles.
PubMed:
Molecular and catalytic properties of 2,4'-dihydroxyacetophenone dioxygenase from Burkholderia sp. AZ11.
PubMed:
The molecular interaction of a copper chelate with human P-glycoprotein.
PubMed:
Synthesis of the first heterometalic star-shaped oxido-bridged MnCu3 complex and its conversion into trinuclear species modulated by pseudohalides (N3(-), NCS- and NCO-): structural analyses and magnetic properties.
PubMed:
Synthesis, spectral characterization and biological activity of zinc(II) complexes with 3-substituted phenyl-4-amino-5-hydrazino-1, 2, 4-triazole Schiff bases.
PubMed:
Synthesis, characterization and biological activities of Cu(II), Co(II), Mn(II), Fe(II), and UO2(VI) complexes with a new Schiff Base hydrazone: O-hydroxyacetophenone-7-chloro-4-quinoline hydrazone.
PubMed:
[Expression and subcellular localization of (R)- and (S)-specific carbonyl reductases from Candida parapsilosis in Saccharomyces cerevisia].
PubMed:
[Broader substrate specifity of Candida parapsilosis SCR II for catalyzing acetophenone derivatives by site-directed mutagenesis].
PubMed:
Weak interactions modulating the dimensionality in supramolecular architectures in three new nickel(II)-hydrazone complexes, magnetostructural correlation, and catalytic potential for epoxidation of alkenes under phase transfer conditions.
PubMed:
Bivalent transition metal complexes of o-hydroxyacetophenone [N-(3-hydroxy-2-naphthoyl)] hydrazone: spectroscopic, antibacterial, antifungal activity and thermogravimetric studies.
PubMed:
An in vitro and in vivo study of a novel zinc complex, zinc N-(2-hydroxyacetophenone)glycinate to overcome multidrug resistance in cancer.
PubMed:
Novel anti-Prelog stereospecific carbonyl reductases from Candida parapsilosis for asymmetric reduction of prochiral ketones.
PubMed:
Exploration on asymmetric synthesis of flavanone catalyzed by (S)-pyrrolidinyl tetrazole.
PubMed:
Redox active copper chelate overcomes multidrug resistance in T-lymphoblastic leukemia cell by triggering apoptosis.
PubMed:
Synthesis and biological evaluation of 4-styrylcoumarin derivatives as inhibitors of TNF-α and IL-6 with anti-tubercular activity.
PubMed:
Isolation of four new CoII/CoIII and NiII complexes with a pentadentate Schiff base ligand: syntheses, structural descriptions and magnetic studies.
PubMed:
Pharmacological activity of novel 2-hydroxyacetophenone isatin derivatives on cardiac and vascular smooth muscles in rats.
PubMed:
Dithiocarbazate complexes with the [M(PPh3)]2+ (M = Pd or Pt) moiety: synthesis, characterization and anti-Trypanosoma cruzi activity.
PubMed:
Carbonyl reductase SCRII from Candida parapsilosis catalyzes anti-Prelog reaction to (S)-1-phenyl-1,2-ethanediol with absolute stereochemical selectivity.
PubMed:
A unique example of structural and magnetic diversity in four interconvertible copper(II)-azide complexes with the same schiff base ligand: a monomer, a dimer, a chain, and a layer.
PubMed:
HPLC method for simultaneous determination of impurities and degradation products in zonisamide.
PubMed:
Synthesis and preliminary biological evaluation of chrysin derivatives as potential anticancer drugs.
PubMed:
Complexes of 2-hydroxyacetophenone semicarbazones: A novel series of superoxide dismutase mimetics.
PubMed:
[Improved expression and catalytic efficiency of (R)-carbonyl reductase in Escherichia coli by secondary structure optimization of mRNA translation initiation region].
PubMed:
[Gene cloning and expression of a novel (S)-specific carbonyl reductase].
PubMed:
Silica gel-catalyzed one-pot syntheses in water and fluorescence properties studies of 5-amino-2-aryl-3H-chromeno[4,3,2-de][1,6]naphthyridine-4-carbonitriles and 5-amino-2-aryl-3H-quinolino[4,3,2-de][1,6]naphthyridine-4-carbonitriles.
PubMed:
A preconcentration procedure for copper, nickel and chromium ions in some food and environmental samples on modified Diaion SP-850.
PubMed:
Na(I)/Cu(I-II) heterometallic cages interconnected by unusual linear 2-coordinate OCN-Cu(I)-NCO links: synthesis, structural, magnetostructural correlation and computational studies.
PubMed:
Detection and characterization of a glutathione conjugate of a novel copper complex.
PubMed:
Antibacterial compounds from the root of the indigenous Australian medicinal plant Carissa lanceolata R.Br.
PubMed:
Cloud point extraction and flame atomic absorption spectrometry determination of trace amounts of copper(II) ions in water samples.
PubMed:
Design of conformationally constrained azole antifungals: efficient synthesis and antifungal activity of trans-3-imidazolylflavanones.
PubMed:
[Co-expression of formate dehydrogenase from Candida boidinii and (R)-specific carbonyl reductase from Candida parapsilosis CCTCC M203011 in Escherichia coli].
PubMed:
Improved production of (R)-1-phenyl-1,2-ethanediol by a codon-optimized R-specific carbonyl reductase from Candida parapsilosis in Escherichia coli.
PubMed:
Ser67Asp and His68Asp substitutions in candida parapsilosis carbonyl reductase alter the coenzyme specificity and enantioselectivity of ketone reduction.
PubMed:
Flame atomic absorption spectrometric determination of zinc, nickel, iron and lead in different matrixes after solid phase extraction on sodium dodecyl sulfate (SDS)-coated alumina as their bis (2-hydroxyacetophenone)-1, 3-propanediimine chelates.
PubMed:
Sodium dodecyl sulfate coated poly (vinyl) chloride: an alternative support for solid phase extraction of some transition and heavy metals.
PubMed:
Synthesis and spectral investigations of vanadium(IV/V) complexes derived from an ONS donor thiosemicarbazone ligand.
PubMed:
Energetics of the O-H bond and of intramolecular hydrogen bonding in HOC6H4C(O)Y (Y = H, CH3, CH2CH=CH2, C[triple bond]CH, CH2F, NH2, NHCH3, NO2, OH, OCH3, OCN, CN, F, Cl, SH, and SCH3) compounds.
PubMed:
Synthesis of two new linear trinuclear Cu(II) complexes: mechanism of magnetic coupling through hybrid B3LYP functional and CShM studies.
PubMed:
Crystal structure of a carbonyl reductase from Candida parapsilosis with anti-Prelog stereospecificity.
PubMed:
Polymetallic clusters of iron(III) with derivatised salicylaldoximes.
PubMed:
Synthesis, spectral and antimicrobial studies of bis(cyclopentadienyl)titanium(IV) derivatives with Schiff bases derived from 2-amino-5-phenyl-1,3,4-thiadiazole.
PubMed:
Design and synthesis of propeller-shaped dispiroisoxazolinopiperidinochromanones.
PubMed:
On the inoperativeness of the ESIPT process in the emission of 1-hydroxy-2-acetonaphthone: a reappraisal.
PubMed:
Resonance Raman intensity analysis of the excited-state proton-transfer dynamics of 2-hydroxybenzaldehyde in the charge-transfer/proton-transfer absorption band.
PubMed:
Highly selective and sensitive copper membrane electrode based on a new synthesized Schiff base.
PubMed:
Synthesis and photoluminescence properties of novel europium complexes of 2'-hydroxyacetophenone and 4,6-diacetylresorcinol.
PubMed:
Purification, characterization, gene cloning, and expression of a novel alcohol dehydrogenase with anti-prelog stereospecificity from Candida parapsilosis.
PubMed:
Resonance Raman intensity analysis of the excited state proton transfer dynamics of 2-nitrophenol in the charge-transfer band absorption.
PubMed:
A novel copper complex induces ROS generation in doxorubicin resistant Ehrlich ascitis carcinoma cells and increases activity of antioxidant enzymes in vital organs in vivo.
PubMed:
2-Hydroxyacetophenone 4-phenylthiosemicarbazone.
PubMed:
Bis(2-hydroxyacetophenone)ethylenediimine as a neutral carrier in a coated-wire membrane electrode for lead(II).
PubMed:
Reaction coordinate analysis for beta-diketone cleavage by the non-heme Fe2+-dependent dioxygenase Dke1.
PubMed:
Dinuclear triple helicates with diazine ligands: X-ray structural, electrochemical, and magnetic studies.
PubMed:
Preparation of ordered large pore SBA-15 silica functionalized with aminopropyl groups through one-pot synthesis.
PubMed:
Novel salicylaldehyde-based mineral-supported expeditious synthesis of benzoxazin-2-ones.
PubMed:
Design and synthesis of two pyrazole libraries based on o-hydroxyacetophenones.
PubMed:
Estimations of excited state dipole moments of conformers in some o-substituted acetophenones by solvato-chromic shifts.
PubMed:
Using model complexes to augment and advance metalloproteinase inhibitor design.
PubMed:
Synthesis and inhibitory activity against COX-2 catalyzed prostaglandin production of chrysin derivatives.
PubMed:
Unexpected migration and oxidative cyclization of substituted 2-acetophenone triflates under basic conditions: synthetic and mechanistic insights.
PubMed:
Construction of Escherichia coli strains for conversion of nitroacetophenones to ortho-aminophenols.
PubMed:
Unprecedented chemical transformation of semicarbazones mediated by Wilkinson's catalyst.
PubMed:
6-(2-Hydroxybenzoyl)-5-(pyrrol-2-yl)-3H-pyrrolizine.
PubMed:
Spectral studies and structure of a 2-hydroxyacetophenone 3-hexamethyleneiminyl thiosemicarbazonate(-2) copper(II) complex containing 1,10-phenanthroline.
PubMed:
Recent progress in asymmetric two-center catalysis.
PubMed:
Efficient liquid-phase synthesis of 2'-hydroxychalcones.
PubMed:
Effects of 4,4-dimethyl-5,8-dihydroxynaphtalene-1-one and 4,4-dimethyl-5,8-dihydroxytetralone derivatives on tumor cell respiration.
PubMed:
A comparative photomechanistic study (spin trapping, EPR spectroscopy, transient kinetics, photoproducts) of nucleoside oxidation (dG and 8-oxodG) by triplet-excited acetophenones and by the radicals generated from alpha-oxy-substituted derivatives through Norrish-type I cleavage.
PubMed:
19F NMR study on the biological Baeyer-Villiger oxidation of acetophenones.
PubMed:
Multifunctional asymmetric catalysis.
PubMed:
19F NMR study on the biological Baeyer-Villiger oxidation of acetophenones.
PubMed:
Pyriform cortex beta-waves: odor-specific sensitization following repeated olfactory stimulation.
PubMed:
Bis(4,7-dimethyl-1,10-phenanthroline) sulfatooxovanadium(IV) as a novel apoptosis-inducing anticancer agent.
PubMed:
Spermicidal activity of oxovanadium(IV) complexes of 1, 10-phenanthroline, 2,2'-bipyridyl, 5'-bromo-2'-hydroxyacetophenone and derivatives in humans.
PubMed:
Enzymatic resolution of 1-phenyl-1,2-ethanediol by enantioselective oxidation: overcoming product inhibition by continuous extraction.
PubMed:
Toluene and ethylbenzene oxidation by purified naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816-4.
PubMed:
Synthetic and structure/activity studies on acid-substituted 2-arylphenols: discovery of 2-[2-propyl-3-[3-[2-ethyl-4-(4-fluorophenyl)-5- hydroxyphenoxy]-propoxy]phenoxy]benzoic acid, a high-affinity leukotriene B4 receptor antagonist.
PubMed:
Spectral Studies and Bactericidal, Fungicidal, Insecticidal and Parasitological Activities of Organotin(IV) Complexes of Thio Schiff Bases Having no Donor Atoms.
PubMed:
Synthesis and pharmacological evaluation of some potential beta-adrenolytics derivated from o-hydroxyacetophenone.
PubMed:
Further isolation of glycosides from Cynanchum hancockianum.
PubMed:
Synthesis and evaluation of technetium-99m monocationic mixed ligand complexes of phenyl substituted/condensed tetradentate Schiff's bases and trimethylphosphine.
PubMed:
Metabolism of Dibenzofuran by Pseudomonas sp. Strain HH69 and the Mixed Culture HH27.
PubMed:
3,4-Dihydro-2H-1-benzopyran-2-carboxylic acids and related compounds as leukotriene antagonists.
PubMed:
Initial reactions of xanthone biodegradation by an Arthrobacter sp.
PubMed:
2-Hydroxyacetophenone: principal root volatile of the East African medicinal plant, Carissa edulis.
PubMed:
Derivatization of carboxylic acids by reaction with 4'-bromophenacyl trifluoromethanesulfonate prior to determination by high-performance liquid chromatography.
PubMed:
Extraction and spectrophotometric determination of nickel with 2-hydroxyacetophenone oxime and simultaneous determination of copper and nickel.
PubMed:
Inhibitors of hepatic mixed function oxidase. 3. Inhibition of hepatic microsomal aniline hydroxylase and aminopyrine demethylase by 2,6- and 2,4-dihydroxyphenyl alkyl ketones and related compounds.
PubMed:
[Condensation of 2-hydroxyacetophenone derivatives to Mannich bases with 4-chromanones].
PubMed:
[Some esters of 2-hydroxyacetophenone with vascular effects and anti-permeability effects].