49594-75-4

Basic information

• Product Name: 3-(4-ETHYLBENZOYL)PROPIONIC ACID
• Synonyms: 4-(4-ETHYLPHENYL)-4-OXOBUTANOIC ACID;4-(4-ETHYLPHENYL)-4-OXOBUTYRIC ACID;3-(4-ETHYLBENZOYL)PROPIONIC ACID;4-(4-ETHYLPHENYL)-4-OXOBUTYRIC ACID 95%;4-(4-ethylphenyl)-4-keto-butyric acid;Benzenebutanoic acid, 4-ethyl-.gamma.-oxo-;Maybridge1_002070;NSC246068
• CAS NO: 49594-75-4
• Molecular Formula: C₁₂H₁₄O₃
• Molecular Weight: 206.24
• Mol File: 49594-75-4.mol

Chemical Properties

• Melting Point: 92-94°C
• Boiling Point: 398.6°Cat760mmHg
• Flash Point: 209°C
• Appearance: /
• Density: 1.136g/cm³
• Vapor Pressure: 4.56E-07mmHg at 25°C
• CAS DataBase Reference: 3-(4-ETHYLBENZOYL)PROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-ETHYLBENZOYL)PROPIONIC ACID(49594-75-4)
• EPA Substance Registry System: 3-(4-ETHYLBENZOYL)PROPIONIC ACID(49594-75-4)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 49594-75-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-(4-ETHYLBENZOYL)PROPIONIC ACID is used as a key intermediate in the synthesis of various pharmaceutical compounds, particularly in the preparation of 1,8-naphthyridinyl-3(2H)-pyridazinones. These pyridazinones are known for their potential therapeutic applications, including antimicrobial and anticancer properties.
Used in Organic Synthesis:
In the field of organic synthesis, 3-(4-ETHYLBENZOYL)PROPIONIC ACID serves as a valuable reagent for the preparation of a wide range of organic compounds. Its unique structure allows for various chemical reactions, such as esterification, amidation, and condensation, which can lead to the formation of complex molecules with diverse applications.
Used in Catalyst Preparation:
3-(4-ETHYLBENZOYL)PROPIONIC ACID is also utilized in the preparation of catalysts for various chemical reactions. For instance, it can be used in the synthesis of zeolite-HY supported on silica gel catalysts, which are employed in dry media under microwave irradiation for efficient and eco-friendly organic transformations.
Overall, 3-(4-ETHYLBENZOYL)PROPIONIC ACID is a versatile and valuable compound with applications in various industries, particularly in pharmaceuticals, organic synthesis, and catalyst preparation. Its unique structure and reactivity make it an essential component in the development of new and innovative chemical processes.

InChI:InChI=1/C12H14O3/c1-2-9-3-5-10(6-4-9)11(13)7-8-12(14)15/h3-6H,2,7-8H2,1H3,(H,14,15)/p-1

Upstream product

• 108-30-5 succinic acid anhydride 
• 100-41-4 ethylbenzene 
• 100-42-5 styrene 
• 543-20-4 succinoyl dichloride 
• 103-73-1 Phenetole 

Downstream Products

• 5467-53-8 γ-(p-ethylphenyl)butyric acid 
• 56705-44-3 methyl 4-(4-ethylphenyl)-4-oxobutanoate 
• 854676-64-5 4-(4-ethyl-phenyl)-3-bromo-4-oxo-butyric acid 
• 132659-70-2 3-[5-(4-ethyl-phenyl)-2-oxo-furan-3-ylidene]-2,3-dihydro-isoindol-1-one 
• 64637-12-3 3-[1-Benzo[1,3]dioxol-5-yl-meth-(E)-ylidene]-5-(4-ethyl-phenyl)-3H-furan-2-one 
• 124-38-9 carbon dioxide 
• 619-64-7 p-ethylbenzoic acid 
• 49594-80-1 1-(4-ethylphenyl)prop-2-en-1-one 
• 511311-09-4 5-(4-Ethyl-phenyl)-3-[1-thiophen-2-yl-meth-(E)-ylidene]-3H-furan-2-one 
• 106165-84-8 4-(4-ethyl-phenyl)-pent-3-enoic acid 
• 1627186-25-7 4-(4-methoxybenzyl)-3a-(4-ethylphenyl)-2,3,3a,4-tetrahydropyrrolo[1,2-a]quinazoline-1,5-dione 
• 1627186-20-2 4-benzyl-3a-(4-ethylphenyl)-2,3,3a,4-tetrahydropyrrolo[1,2-a]quinazoline-1,5-dione 
• 1427435-41-3 7-(4-ethylphenyl)-3,4,8,9-tetrahydro-2H-pyridazino[1,6-a][1,3,5]triazin-2-one 
• 1427435-42-4 7-(4-ethylphenyl)-3,4,8,9-tetrahydro-2H-pyridazino[1,6-a][1,3,5]triazin-2-thione 

Relevant articles and documents

In silico designing, in vitro and in vivo evaluation of potential PPAR-γ agonists derived from aryl propionic acid scaffold

Attributed to several side effects, especially on hepatic tissues and body weight, there is always an urge of innovation and upgrading in already existing medication being used in maintaining diabetic condition. Therefore, in the present work, forty-eight molecules derived from arylpropionic acid scaffold were synthesized and their evaluation against diabetes was carried out. The synthesis of these molecules attributed to excellent dock score displayed by all the structures performed against PPAR-γ receptor site. Subsequently, all the derivatives were primarily deduced for their antidiabetic potential by OGTT. The compounds that showed significant antidiabetic activity in OGT Test and also exhibited high dock scores were assessed further by in vitro PPAR transactivation assay to assure analogy between in vivo and in vitro studies. The antidiabetic activity of these active compounds was then evaluated on STZ induced diabetic model in vivo. The most active compounds were scrutinized for its effect on PPAR-γ gene expression and hepatotoxic effect. Finally, it was recapitulated that these derivatives can provide a new prospect towards the development of antidiabetic agents with fewer side effects.

Synthesis, anti-convulsant activity and molecular docking study of novel thiazole pyridazinone hybrid analogues

Pyridazinone analogues have been known to be potential candidates for anticonvulsant agents. We have identified several pyridazinone-based anticonvulsant agents. As a continuation to our previous research, a series of hybrid pyridazinone-thiazole connected through amide linkage were designed and synthesized. Among these, compound SP-5F demonstrated significant anticonvulsant activity with median effective dose of 24.38 mg/kg (MES) and 88.23 mg/kg (scPTz). Results of GABA estimation showed a marked increase in the GABA level when compared with control. Molecular docking studies at the active site of GABA receptor, further confirmed the GABA modulatory effects of SP-5F.

Design, Synthesis, and Pharmacological Screening of Pyridazinone Hybrids as Anticonvulsant Agents

A series of new hybrid benzimidazole containing pyridazinones derivatives were designed and synthesized in accordance with the pharmacophoric requirements essential for the anticonvulsant activity. The synthesized compounds were evaluated for anticonvulsant activity on mice by the gold standard maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ)-induced seizure models. Among the compounds tested, SS-4F showed significant anticonvulsant activity in both the screens with ED50 values of 25.10 and 85.33 mg/kg in the MES and scPTZ screens, respectively. Compound SS-4F emerged as safer and effective anticonvulsant due to its several-fold higher protective indices. Further, the gamma-aminobutyric acid (GABA) estimation result showed a marked increase in the GABA level (1.7-fold) as compared to the control, which was further confirmed by good binding properties with the GABAA receptor.

Efficient synthesis, anticonvulsant and muscle relaxant activities of new 2-((5-amino-1,3,4-thiadiazol-2-yl)methyl)-6-phenyl-4,5-dihydropyridazin-3(2H) -one derivatives

A series of 2-(2-(3-(4-chlorophenyl)-6-oxo-5,6-dihydropyridazin-1(4H)yl) acetyl)hydrazine carbothioamide and 2-((5-amino-1,3,4-thiadiazol-2-yl)methyl)-6- (4-chlorophenyl)-4,5-dihydropyridazin-3(2H)-one derivatives were synthesized, characterized, and evaluated for anticonvulsant activity and muscle relaxant activity. The synthesized compounds 5d (82.75 %) and 5e (85.44 %) showed promising anticonvulsant activity by protection against tonic hind limb extensor phase in maximal electroshock model (MES) at (50 mg/kg) compared to standard drug phenytoin and also compounds 5d (82.75 %), and 5e (85.44 %) showed significant anticonvulsant activity by protection against pentylenetetrazole- induced generalized convulsions in pentylenetetrazole model (PTZ) at (100 mg/kg) compared to standard drug diazepam. On the other hand, compound 5e showed significant muscle relaxant activity (84.57 %) by rotarod and traction test model comparing with diazepam as a standard drug.

Design, synthesis and antihypertensive screening of novel pyridazine substituted s-triazin-2-imine/one/thione derivatives

Some new 7-substituted-phenyl-3,4,8,9-tetrahydro-2H-pyridazino[1,6-a][1,3,5]triazin-2-imine/one/thione derivatives were synthesized by a sequence of reactions starting from appropriate aryl hydrocarbons. The final compounds were screened for antihypertensive activities by non-invasive method using Tail Cuff method. All the test compounds showed significant antihypertensive activity; 7-(biphenyl-4-yl)-3,4,8,9-tetrahydro-2H-pyridazino[1,6-a][1,3,5]triazin-2-imine (4p) exhibited antihypertensive activity more than the reference standard drugs.

Synthesis, antiproliferative and anti-inflammatory activities of some novel 6-aryl-2-(p-(methanesulfonyl)phenyl)-4,5-dihydropyridazi-3(2H)-ones

Sixteen new 6-aryl-2-(p-(methanesulfonyl)phenyl)-4,5-dihydropyridazi-3(2 H)-ones (2a-p) were synthesized and tested for in vitro anticancer and in vivo anti-inflammatory activities. Eleven (2b, 2d , 2-ej and 2m-p) of the obtained compounds were screened for their antiproliferative activity towards 60 human cancer cell lines by the National Cancer Institute (USA). Compound 2f showed remarkable activity with GI50 less than 1 μM on 36 human tumor cell lines and has been referred to Biological Evaluation Committee (NCI) for advance study. Compound 2g also displayed promising antiproliferative activity against 20 different cell lines with GI50 less than 1 μM. Compounds 2k and 2n were found to have a comparable anti-inflammatory activity to that of standard drug etoricoxib in carrageenan-induced rat hind paw edema model at 5 h.

Design and synthesis of 2(3H)-furanone derivatives as γ-Aminobutyric acid receptor modulator

Eleven new 3-(substituted-arylidene)-5-(4-chloro-3-methyl-phenyl)-)-3H- furan-2-one were synthesized from appropriate 4-(substituted -phenyl)-4-oxo-butyric acid and isatin derivatives. Molecular docking calculations experiments were performed using EXHZ version 1.4 and Auto Dock 4.0 to identify potential g-aminobutyric acid receptor modulator among all synthesized furanones. The anticonvulsant activities of selected compounds were evaluated in mice by PTZ induced seizure method. Result indicate that all tested compounds possess anti-convulsant activity after oral administration and that the compounds 1-acetyl-3-[5-(4-bromo-phenyl) -2-oxo -furan-3-ylidene]- 1,3-dihydro-indol-2-one (C-6) and 1-acetyl-3-[5-(4-ethyl-phenyl)-2-oxo- furan-3-ylidene]-5-ethyl-1,3-dihydro-indol-2-one (C-8) possess significant anticonvulsant activity could be comparable to that of diazepam a standard.

Triazole incorporated pyridazinones as a new class of antihypertensive agents: Design, synthesis and in vivo screening

A number of 6-(substituted phenyl)-2-(4-substituted phenyl-5-thioxo-4,5- dihydro-1H-1,2,4-triazol-3-yl)-4,5-dihydropyridazin-3(2H)-one derivatives were designed and synthesized by a sequence of reactions starting from respective aryl hydrocarbons. The final compounds (4a-4u) were evaluated for antihypertensive activities by non-invasive method using Tail Cuff method. The compounds 4e, 4i and 4k showed appreciable antihypertensive activity comparable with that of standard hydralazine and propranolol.

New amides of sulphonamides: Synthesis and biological evaluation

A series of amide-derivatives has been synthesized by establishing an amide linkage (-CONH-) between appropriate sulphonamide moiety and different 3-(4-substituted-benzoyl) propionic acids through one-pot reaction. The structures of the newly synthesized compounds were established on the basis of modern analytical techniques. These amides were evaluated for their antiinflammatory, ulcerogenic and antibacterial activities. Some of the compounds showed good antiinflammatory activity. Additionally, these derivatives were very low in their ulcerogenic action.

Novel selective thiazoleacetic acids as CRTH2 antagonists developed from in silico derived hits. Part 1

Structure-activity relationships of three related series of 4-phenylthiazol-5-ylacetic acids, derived from two hits emanating from a focused library obtained by in silico screening, have been explored as CRTH2 (chemoattractant receptor-homologous molecule expressed on Th2 cells) antagonists. Several compounds with double digit nanomolar binding affinity and full antagonistic efficacy for human CRTH2 receptor were obtained in all subclasses. The most potent compound was [2-(4-chloro-benzyl)-4-(4-phenoxy-phenyl)-thiazol-5-yl]acetic acid having an binding affinity of 3.7 nM and functional antagonistic effect of 66 nM in a BRET and 12 nM in a cAMP assay with no functional activity for the other PGD2 DP receptor (27 μM in cAMP).