16636-62-7

Basic information

• Product Name: O-HYDROXYBENZOYLACETONE
• Synonyms: 1-(2-HYDROXYPHENYL)-1,3-BUTANEDIONE;2-(ACETOACETYL)PHENOL;O-HYDROXYBENZOYLACETONE;SALICYLOYLACETONE;TIMTEC-BB SBB007835;2-Acetyl-2'-hydroxyacetophenone;2-Hydroxybenzoylacetone;o-Acetoacetylphenol
• CAS NO: 16636-62-7
• Molecular Formula: C₁₀H₁₀O₃
• Molecular Weight: 178.18
• Mol File: 16636-62-7.mol

Chemical Properties

• Melting Point: 102℃ (ligroine ethanol )
• Boiling Point: 295.1 °C at 760 mmHg
• Flash Point: 146.5 °C
• Appearance: /
• Density: 1.191 g/cm³
• Vapor Pressure: 0.000884mmHg at 25°C
• Refractive Index: 1.547
• PKA: 7.81±0.30(Predicted)
• CAS DataBase Reference: O-HYDROXYBENZOYLACETONE(CAS DataBase Reference)
• NIST Chemistry Reference: O-HYDROXYBENZOYLACETONE(16636-62-7)
• EPA Substance Registry System: O-HYDROXYBENZOYLACETONE(16636-62-7)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 16636-62-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
O-HYDROXYBENZOYLACETONE is used as a precursor in the synthesis of various pharmaceuticals for its ability to contribute to the formation of complex organic molecules that are essential in medicinal chemistry.
Used in Dye Industry:
In the dye industry, O-HYDROXYBENZOYLACETONE is utilized as a precursor for the production of dyes, where its chemical structure allows for the creation of diverse colorants.
Used in Perfume Industry:
O-HYDROXYBENZOYLACETONE is used as a precursor in the synthesis of perfumes, contributing to the development of aromatic compounds that provide distinctive scents.
Used in Organic Chemistry:
O-HYDROXYBENZOYLACETONE serves as a ligand in coordination chemistry, playing a crucial role in the formation of coordination compounds that have various applications in chemical research and industry.
Used as a Reagent in Organic Synthesis:
In organic synthesis, O-HYDROXYBENZOYLACETONE is employed as a reagent, facilitating various chemical reactions and contributing to the synthesis of a wide range of organic compounds.

InChI:InChI=1/C10H10O3/c1-7(11)6-10(13)8-4-2-3-5-9(8)12/h2-5,12H,6H2,1H3

Upstream product

• 10037-20-4 3-acetyl-2-methyl-4-oxo-4H-<1>benzopyran 
• 141-52-6 sodium ethanolate 
• 60-29-7 diethyl ether 
• 7250-94-4 o-acetoxyacetophenone 
• 4303-71-3 triphenylmethyl sodium 
• 90-02-8 salicylaldehyde 
• 67-64-1 acetone 
• 141-78-6 ethyl acetate 
• 118-93-4 o-hydroxyacetophenone 
• 35115-15-2 2-(propionylacetyl)phenol 
• 51751-37-2 2-Methyl-4-oxo-4H-<1>benzopyran-3-carboxylic acid 

Downstream Products

• 51138-49-9 5-(2-hydroxyphenyl)-3-methylisoxazole 
• 51138-46-6 3⁽⁵⁾-methyl-5⁽³⁾-(2-hydroxyphenyl)pyrazole 
• 98603-71-5 (Z)-1-(2-Hydroxy-phenyl)-3-(2-pyridin-2-yl-ethylamino)-but-2-en-1-one 
• 79709-81-2 (Z)-3-(2-Amino-2-methyl-propylamino)-1-(2-hydroxy-phenyl)-but-2-en-1-one 
• 5751-48-4 2-methylchromone 
• 69932-31-6 3-bromo-2-methyl-4H-chromen-4-one 
• 51138-45-5 1-phenyl-3-methyl-5-(2'-hydroxyphenyl)pyrazole 
• 79709-80-1 6-amino-1-(2'-hydroxyphenyl)-3-methyl-4-azahept-2-en-1-one 

Relevant articles and documents

3-Hydroxy-(4H)-benzopyran-4-ones as potential iron chelating agents in vivo

Increasing evidence suggests that iron plays an important role in tissue damage both during chronic iron overload diseases (i.e., hemochromatosis) and when, in the absence of actual tissue iron overload, iron is delocalised from specific carriers or intracellular sites (inflammation, eurodegenerative diseases, post-ischaemic reperfusion, etc.). In order to be used for therapeutical purposes in vivo, a reliable iron chelator should be capable of preventing the undesired effects that follow the electrochemical activation of iron (see below). Bearing in mind the molecular structure of some flavonols that are able to chelate iron, we synthesised a new oral iron-chelator, 2-methyl-3-hydroxy-4H-benzopyran-4-one (MCOH). We demonstrate that MCOH chelates iron in a 2:1 ratio showing a stability constant of ～1010. MCOH is able to cross cell membranes (erythrocytes, ascite tumour cells) in both directions. Following intraperitoneal administratio to rats, it is quickly taken up by the liver and excreted in the urine withi 24 h. A similar behaviour has bee documented after oral administration. We propose that MCOH may represent the prototype of a new class of iron chelating agents to be developed for iron-removal therapy in vivo with the goal of preventing tissue damage caused by the iron redox cycle. Copyright

A novel near-infrared fluorescent probe for detection of early-stage Aβ protofibrils in Alzheimer's disease

Detection of Aβ protofibrils at the early stage of Alzheimer's disease was realized by a novel near-infrared probe (DCM-AN) based on dicyanomethylene-4H-pyran. This probe exhibits high affinity towards Aβ protofibrils in vitro and in brain sections of tra

A “turn-on” fluorescent probe with high selectivity and large stokes shift for the detection of hydrogen peroxide and its bioimaging applications

Hydrogen peroxide (H2O2) plays pivotal roles in various biological functions and pharmacological activities. High selectivity and sensitivity remain challenges for fluorescent probes to detection of H2O2 with a large stokes shift. Herein, a new “turn-on” fluorescent probe (DCM-C) was designed based on the mechanism of intramolecular charge transfer (ICT). In PBS buffer (10 mM, pH 7.4, with 20% DMSO, v/v), DCM-C exhibited high selectivity and sensitivity for H2O2 over other interfering analytes with a large stokes shift (187 nm), and the detection limit was as low as 35.5 nM. In addition, the probe was effective for detecting exogenous and endogenous H2O2 in living cells, and identifying stained in cytoplasm. Moreover, the probe has been used successfully for determining H2O2 in zebrafish by fluorescence imaging.

Near-infrared hydrazine fluorescence sensor as well as preparation method and application thereof

The invention discloses a near-infrared hydrazine fluorescence sensor as well as a preparation method and application thereof. According to the method, a target product (E) 4-(2-(4-(dicyanomethylene) chroman-2-yl) vinyl) phenyl 4-bromobutyric acid is synthesized. An ultraviolet-visible spectrophotometer and a fluorescence spectrophotometer are adopted to determine the intensity change of a characteristic peak of a probe in a water phase, so as to determine the existence of hydrazine. The invention provides application of the hydrazine fluorescence sensor in hydrazine detection, and the hydrazine fluorescence sensor can be used for high-selectivity and high-sensitivity detection of hydrazine in a water phase. It is found that thehydrazine fluorescence sensor has a good hydrazine detection effect. Compared with the prior art, the hydrazine fluorescence sensor has the advantages of easily available raw materials, simple synthesis steps, convenient post-treatment, easy realization of large-scale production, and great application prospect in hydrazine detection.

Design, synthesis, and evaluation of near-infrared fluorescent molecules based on 4h-1-benzopyran core

A series of novel fluorescent 4H-1-benzopyrans was designed and developed as near-infrared fluorescent molecules with a compact donor–acceptor-donor architecture. Spectral intensity of the fluorescent molecules M-1, M-2, M-3 varied significantly with the increasing polarities of solvents, where M-3 showed high viscosity sensitivity in glycerol-ethanol system with a 3-fold increase in emission intensity. Increasing concentrations of compound M-3 to 5% BSA in PBS elicited a 4-fold increase in fluorescence intensity, exhibiting a superior environmental sensitivity. Furthermore, the in vitro cellular uptake behavior and CLSM assay of cancer cell lines demonstrated that M-3 could easily enter the cell nucleus and bind to proteins with low toxicity. Therefore, the synthesized near-infrared fluorescent molecules could provide a new direction for the development of optical imaging probes and potential further drugs.

A matrix targeted fluorescent probe to monitor mitochondrial dynamics

Mitochondria are an indispensable organelle for energy production and regulation of cellular metabolism. The structural and functional alterations to mitochondria instigate pathological conditions of cancer, and aging-associated and neurodegenerative disorders. The normal functioning of mitochondria is maintained by quality control mechanisms involving dynamic fission, fusion, biogenesis and mitophagy. Under conditions of mitophagy and neurodegenerative diseases, mitochondria are exposed to different acidic environments and high levels of reactive oxygen species (ROS). Therefore stable molecular tools and methods are required to monitor the pathways linked to mitochondrial dysfunction and disease conditions. Herein, we report a far-red fluorescent probe (Mito-TG) with excellent biocompatibility, biostability, photostability, chemical stability and turn on emission for selective targeting of the mitochondrial matrix in different live cells. The probe was successfully employed for monitoring dynamic processes of mitophagy and amyloid beta (Aβ) induced mitochondrial structural changes.

Near-infrared compound with aggregation-induced emission property as well as preparation method and application thereof

The invention discloses a near-infrared compound with an aggregation-induced emission property as well as a preparation method and application of the near-infrared compound. The near-infrared compoundhas high-brightness far-infrared and near-infrared fluorescence emission characteristics, has aggregation-induced emission and crystallization-induced emission characteristics in a near-infrared region, and has the characteristic of aggregation-induced nonlinear optical effect. The nanocrystal can be used for biological imaging and can be prepared into nanocrystals for living body deep high-resolution multi-photon fluorescence and third harmonic imaging. The material synthesized by the method shows the properties of aggregation-induced emission and crystallization-induced emission, while thetraditional fluorescent dye has the phenomenon of aggregation-induced fluorescence quenching under the condition of high concentration, so that the defects of the traditional fluorescent dye are effectively overcome.

Rational Design of a Highly Selective Near-Infrared Two-Photon Fluorogenic Probe for Imaging Orthotopic Hepatocellular Carcinoma Chemotherapy

Selective fluorescence imaging of biomarkers in vivo and in situ for evaluating orthotopic hepatocellular carcinoma (HCC) chemotherapy remains a great challenge due to current imaging agents suffering from the potential interferences of other hydrolases. Herein, we observed that carbamate unit showed a high selectivity toward the HCC-related biomarker carboxylesterase (CE) for evaluation of treatment. A near-infrared two-photon fluorescent probe was developed to not only specially image CE activity in vivo and in situ but also target orthotopic liver tumor after systemic administration. The in vivo signals of the probe correlate well with tumor apoptosis, making it possible to evaluate the status of treatment. The probe enables the imaging of CE activity in situ with a high-resolution three-dimensional view for the first time. This study may promote advances in optical imaging approaches for precise imaging-guided diagnosis of HCC in situ and its evaluation of treatment.

Molecular Aggregation of Naphthalene Diimide(NDI) Derivatives in Electron Transport Layers of Inverted Perovskite Solar Cells and Their Influence on the Device Performance

One of key factors to design applicable electron transport layers (ETLs) for perovskite solar cells is the morphology of ETLs since a good morphology would help to facilitate the carrier transport at two interfaces (perovskiteETL and ETLcathode). However, one drawback of most organic ETL small molecules is the internal undesired accumulation, which would cause the formation of inappropriate morphology and rough ETL surface. Here, by elaborately designing the side chains of NDI derivatives, the molecular interaction could be modified to achieve the aggregation in different degrees, which would eventually affect the accumulation of molecules and surface qualities of ETLs. By speculating from the comparison between the absorption spectra of solutions and films, the sequence of extent of molecule interaction and aggregation was built among three NDI derivatives, which is further confirmed by direct evidence of atomic force microscopy (AFM) images. Then, carrier exaction abilities are simply studied by steady-state photoluminescence spectroscopy. The carrier transport process is also discussed based on cyclic voltammetry, time-resolved photoluminescence spectroscopy and mobility. NDIF1 are proven to have the appropriate internal aggregation to smooth the contact with cathode and low series resistance, and a device performance of 15.6 % is achieved. With the ability of preventing the thermal diffusion of Ag towards the perovskite surface due to the strong interaction between molecules, NDIF2 at high concentration shows the highest fill factor (80 %).

Preparation method and application of novel photosensitizer

The invention relates to a preparation method and application of a novel photosensitizer. The photosensitizer is synthesized for the first time. A general formula compound represented by an intermediate formula (I) is used as a mother core, and is subjected to a Knoevenagel reaction with 4-hydroxybenzaldehyde, 3,5-dibromo-4-hydroxybenzaldehyde and 3,5-diiodo-4-hydroxybenzaldehyde to obtain the general formula photosensitizer represented by a formula (II). The method creatively reserves functional groups (R1, R2) on the intermediate formula (I) and the photosensitizer formula (II), and synthesizes the intermediate and the photosensitizer with S and Se as central atoms (Q) for the first time. The novel photosensitizer provided by the invention solves the technical problems that an existing photosensitizer has a narrow absorption range, a poor therapeutic effect in the visible light range, excessive power of a used light source, and inability to introduce functional groups.