1878-81-5

Basic information

• Product Name: 4-ACETYLPHENOXYACETIC ACID
• Synonyms: AKOS BB-9444;4-ACETYLPHENOXYACETIC ACID;2-(4-ACETYLPHENOXY)ACETIC ACID;(p-acetylphenoxy)acetic acid;4-ACETYLPHENOXYACETIC ACID, 98+%
• CAS NO: 1878-81-5
• Molecular Formula: C₁₀H₁₀O₄
• Molecular Weight: 194.18
• EINECS: 217-524-2
• Product Categories: Phenoxyacetic Acids and Alcohols (substituted);C10;Carbonyl Compounds;Carboxylic Acids
• Mol File: 1878-81-5.mol

Chemical Properties

• Melting Point: 175-177 °C (dec.)(lit.)
• Boiling Point: 380.5°Cat760mmHg
• Flash Point: 154.2°C
• Appearance: /
• Density: 1.243g/cm³
• Vapor Pressure: 1.81E-06mmHg at 25°C
• Solubility: methanol: soluble25mg/mL, clear, colorless to faintly yellow
• BRN: 1956136
• CAS DataBase Reference: 4-ACETYLPHENOXYACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ACETYLPHENOXYACETIC ACID(1878-81-5)
• EPA Substance Registry System: 4-ACETYLPHENOXYACETIC ACID(1878-81-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 1878-81-5(Hazardous Substances Data)

Usage

Uses

Used in Research and Development:
4-Acetylphenoxyacetic acid is used as a test compound for studying the phenylacetic acid transport system (PATS) of Pseudomonas putida U. It is employed in the aerobic catabolism of phenylacetic acid derivatives, which serve as the sole carbon source for the bacteria. This application aids in understanding the metabolic pathways and transport mechanisms of these bacteria, contributing to the broader field of microbiology and biochemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Acetylphenoxyacetic acid may be utilized as an intermediate or building block for the synthesis of various pharmaceutical compounds. Its unique chemical structure allows for further modification and functionalization, making it a versatile component in the development of new drugs and therapeutic agents.
Used in Chemical Synthesis:
4-Acetylphenoxyacetic acid can be used as a key component in the synthesis of various organic compounds, such as dyes, agrochemicals, and other specialty chemicals. Its reactivity and functional groups enable it to participate in a range of chemical reactions, making it a valuable starting material for the production of diverse chemical products.
Used in Analytical Chemistry:
As an off-white crystalline powder, 4-Acetylphenoxyacetic acid can be employed as a reference material or standard in analytical chemistry. It can be used to calibrate instruments, validate analytical methods, and ensure the accuracy and precision of chemical measurements.

InChI:InChI=1/C10H10O4/c1-7(11)8-2-4-9(5-3-8)14-6-10(12)13/h2-5H,6H2,1H3,(H,12,13)/p-1

Upstream product

• 79-11-8 chloroacetic acid 
• 99-93-4 4-Hydroxyacetophenone 
• 105-36-2 ethyl bromoacetate 
• 79-08-3 bromoacetic acid 
• 51828-69-4 ethyl (4-acetylphenoxy)-acetate 
• 6296-28-2 methyl-[4-(1-oxoethyl)phenoxy] Acetate 
• 79-14-1 glycolic Acid 
• 13329-40-3 4-Iodoacetophenone 
• 3926-62-3 sodium monochloroacetic acid 

Downstream Products

• 52299-08-8 4-carboxy methoxy phenyl acetic acid 
• 63787-21-3 n-hexyl 4-acetylphenoxyacetate 
• 6296-28-2 methyl-[4-(1-oxoethyl)phenoxy] Acetate 
• 50-00-0 formaldehyd 
• 201230-82-2 carbon monoxide 
• 99-93-4 4-Hydroxyacetophenone 
• 245555-36-6 {4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-phenoxy}-acetic acid 
• 923785-97-1 3-[2-(4-acetylphenoxy)acetylamino]benzoic acid methyl ester 
• 113787-98-7 (p-acetylphenoxy)acetyl-L-cysteinyl-D-valine 
• 36213-82-8 (2S,5R,6R)-6-[2-(4-Acetyl-phenoxy)-acetylamino]-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 
• 63787-05-3 [4-(2-Azido-acetyl)-phenoxy]-acetic acid hexyl ester 
• 63787-08-6 n-hexyl 4-(bromoacetyl)phenoxyacetate 
• 474970-07-5 (4-acetylphenyloxy)-N-[1-(3,4-dichlorobenzyl)piperidin-4-yl]acetamide 
• 168127-34-2 2-(4-(2-aminothiazol-4-yl)phenoxy)acetic acid 

Relevant articles and documents

4, 5-Dihydrooxazole-pyrazoline hybrids: Synthesis and their evaluation as potential antimalarial agents

A new series of oxazoline-pyrazoline hybrids (4a-p) were synthesized by condensation reaction of substituted oxazoline based chalcones (3a-m) and substituted hydrazines in methanol. Some of the compounds exhibited promising in?vitro antimalarial activity for chloroquine sensitive CQS(3D7) strain and chloroquine resistant CQR(RKL9) strain. The most potent analogue 4i (IC500.322?μg/ml) exhibited significant in vivo antimalarial potential against Plasmodium berghei mouse model. The stable complex of 4i with hematin (1:1 stoichiometry) suggests that heme may be one possible target for these hybrid compounds. The study has revealed potential of title compounds as lead for the development of antimalarial agents.

Non-natural amino acid and application thereof Recombinant protein and recombinant protein conjugate comprising same

The invention provides a non-natural amino acid. A compound represented by formula (I) or an enantiomer thereof. The invention also provides application of the non-natural amino acid. Further, the present invention also provides a protein conjugate comprising the recombinant protein and of the non-natural amino acid prepared from the recombinant protein. The non-natural amino acid provided by the invention is simple and convenient to prepare, good in safety, not prone to inactivation during protein insertion, high in conjugate rate with a coupling part, and higher in stability of the obtained conjugate.

P-hydroxyacetophenone hapten and p-hydroxyacetophenone artificial antigen, and synthesis methods and application of p-hydroxyacetophenone hapten and p-hydroxyacetophenone artificial antigen

The invention discloses a p-hydroxyacetophenone hapten and a p-hydroxyacetophenone artificial antigen, and synthesis methods and application of the p-hydroxyacetophenone hapten and the p-hydroxyacetophenone artificial antigen According to the invention, p-hydroxyacetophenone is used as a raw material and reacts with halogenated acid salt to generate the p-hydroxyacetophenone hapten containing -COOH active groups; and the p-hydroxyacetophenone hapten is coupled with carrier protein through an active ester method or a mixed anhydride method to synthesize the p-hydroxyacetophenone artificial antigen. The p-hydroxyacetophenone artificial antigen prepared by the invention can be applied to preparation of a p-hydroxyacetophenone polyclonal antibody or a monoclonal antibody. An immunodetection method using the p-hydroxyacetophenone artificial antigen is very low in detection cost, simple to use and suitable for screening and detection of a large number of samples.

Albumin-binding prodrugs via reversible iminoboronate forming nanoparticles for cancer drug delivery

Albumin-based nanomedicines are important nanoplatforms for cancer drug delivery. The drugs are either physically encapsulated or covalently conjugated to albumin or albumin-based nanosystems. Physical encapsulation is advantageous due to requiring no chemical modification of drug molecules, but many drugs, for instance, camptothecin (CPT) and curcumin (CCM), though very hydrophobic, can't be loaded in or form nanoformulations with albumin. Herein, we demonstrate prodrugs readily binding to proteins via iminoboronates and forming nanoparticles for cancer drug delivery. CPT and CCM were functionalized with 2-acetylphenylboronic acid (2-APBA) to produce prodrugs CPT-SS-APBA and CCM- APBA. The prodrugs bound to bovine serum albumin (BSA) via formation of iminoboronates and the produced BSA/prodrug readily self-assembled into well-defined nanoparticles with high loading efficiency, improved colloidal stability, and much-improved pharmacokinetics. The nanoparticles effectively released drugs in the intracellular acidic environment or the cytosol rich in glutathione (GSH). In vivo, the nanoparticles showed enhanced anticancer efficacy compared with clinically used irinotecan or sorafenib in subcutaneous 4 T1 or HepG2 tumor models. This work demonstrates a versatile protein-binding prodrug platform applicable to protein-based drug formulations and even antibody-drug conjugates.

A novel chalcone derivative as Nrf2 activator attenuates learning and memory impairment in a scopolamine-induced mouse model

Alzheimer's disease is a common neurodegenerative disease characterized by progressive degeneration and neuronal cell death, resulting in neural network dysfunction. As the underlying mechanisms, oxidative damage and neuroinflammation have been reported to contribute to the onset and deterioration of Alzheimer's disease. The nuclear factor E2-related factor 2-antioxidant responsive element signaling pathway is a pivotal cellular defense mechanism against oxidative stress. Nrf2, a transcription factor, regulates the cellular redox balance and is primarily involved in anti-inflammatory responses. In this study, we synthesized novel chalcone derivatives and found a highly potent Nrf2 activator, compound 20a. Compound 20a confirmed to activate Nrf2 and induce expression of the Nrf2-dependent enzymes HO-1 and GCLC at both mRNA and protein levels. It also suppressed the production of nitric oxide and downregulated inflammatory mediators in BV-2 microglial cells. We found that compound 20a effectively increased the expression level and the activity of superoxide dismutase in both BV-2 microglial cells and brain hippocampus region of the scopolamine-induced mouse model. In addition, compound 20a effectively recovered the learning and memory impairment in a scopolamine-induced mouse model.

Design, synthesis, biological evaluation and inhibition mechanism of 3-/4-alkoxy phenylethylidenethiosemicarbazides as new, potent and safe tyrosinase inhibitors

Tyrosinase plays important roles in many different disease related processes, and the development of its inhibitors is particularly important in biotechnology. In this study, thirty-nine 3-/4-alkoxyphenylethyli-denethiosemicarbazides were synthesized as novel tyrosinase inhibitors based on structure-based molecular design. Our experimental results demonstrated that thirty-one of them possess remarkable tyrosinase inhibitory activities with IC50 value below 1μM, and 5a, 6e, 6g and 6t did not display any toxicity to 293T cell line at the concentration of 1000μmol/L. According to the inhibitory activities, several compounds were selected for detail investigation on the structure–activity relationships (SARs), mechanisms of enzyme inhibition, inhibitory kinetics and cytotoxicity. In particular, the interaction between the selected inhibitors and the active center of tyrosinase was considered and discussed in detail based on their structural characteristics. Taken together, the results presented here demonstrated that the newly designed compounds are promising candidates for the treatment of tyrosinase-related disorders and further development of them may have significant contribution in biomedical science.

Chalcone aryloxyacetamide compound as well as preparation method and application thereof

The invention relates to the field of pharmaceutical chemistry, in particular to a chalcone aryloxyacetamide compound (I) or (II) and a preparation method thereof. As proved by a pharmacodynamic test,the compound has the effects of reducing blood glucose, reducing triglyceride and reducing cholesterol, and can be used for treating abnormal glucolipid metabolism and obesity. A general formula of the compound is shown in the description.

Design, synthesis chalcone derivatives as AdipoR agonist for type 2 diabetes

Two structurally novel series of chalcone derivatives were designed and synthesized as potential agents against type 2 diabetes. As a result of the antidiabetic biological evaluation in streptozotocin (STZ)-induced type 2 diabetes animal model, 13e, 13g, and 19f showed more significant reduction in serum Glu, TG, TC levels by contrast to the positive control AdipoRon. In addition to upregulating the expression of AdipoR1 and AdipoR2, 13e and 19f treatment also increased expression of AMPK and PPAR-α. Taken together, these results suggested that 13e and 19f might be a promising compound for type 2 diabetes treatment.

Synthesis and in vitro antiplasmodial evaluation of 7-chloroquinoline-chalcone and 7-chloroquinoline-ferrocenylchalcone conjugates

Abstract The manuscript describes the synthesis of novel amide tethered 7-chloroquinoline-chalcone and 7-chloroquinoline-ferrocenylchalcone bifunctional hybrids and their evaluation as antimalarial agents against W2 resistant strain of Plasmodium falciparum. The antiplasmodial activity of 7-chloroquinoline-ferrocenylchalcones was found to be less than their corresponding simple chalcone conjugates. The presence of a methoxy substituent at para position of ring B on chalcones and longer alkyl chain length markedly improved the antiplasmodial profiles of the synthesized scaffolds with the most potent of the test compound exhibiting an IC50 value of 17.8 nM. Synthesis of 7-chloroquinoline-chalcone and 7-chloroquinoline-ferrocenylchalcone conjugates.Antimalarial potency of synthesized conjugates was evaluated against W2 strain.Most potent and non-cytotoxic conjugate exhibited IC50 of 17.8 nM.

Copper(II)-catalyzed hydroxylation of aryl halides using glycolic acid as a ligand

Copper(II)-catalyzed hydroxylation of aryl halides has been developed to afford functionalized phenols. The protocol utilizes the reagent combination of Cu(OH)2, glycolic acid, and NaOH in aqueous DMSO, all of which are cheap, readily available, and easily removable after the reaction. A broad range of aryl iodides and activated aryl bromides were transformed into the corresponding phenols in excellent yields. Moreover, it has been shown that C-O(alkyl)-coupled product, instead of phenol, can be predominantly formed under similar reaction conditions.