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Cas Database

2051-95-8

2051-95-8

Identification

  • Product Name:3-Benzoylpropionic Acid

  • CAS Number: 2051-95-8

  • EINECS:218-135-0

  • Molecular Weight:178.188

  • Molecular Formula: C10H10O3

  • HS Code:29183000

  • Mol File:2051-95-8.mol

Synonyms:Propionicacid, 3-benzoyl- (6CI,7CI,8CI);3-Benzoylpropanoic acid;4-Oxo-4-phenylbutanoic acid;4-Oxo-4-phenylbutyric acid;4-Phenyl-4-oxobutanoic acid;NSC 2092;NSC 229040;NSC 51010;Propanoic acid,3-benzoyl-;b-Benzoylpropionicacid;g-Oxobenzenebutanoic acid;

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Safety information and MSDS

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi,Xn

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  • Manufacture/Brand:TRC
  • Product Description:3-BenzoylpropanoicAcid
  • Packaging:25g
  • Price:$ 75
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  • Manufacture/Brand:TRC
  • Product Description:3-BenzoylpropanoicAcid
  • Packaging:50g
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  • Manufacture/Brand:TCI Chemical
  • Product Description:3-Benzoylpropionic Acid >98.0%(GC)(T)
  • Packaging:100g
  • Price:$ 124
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  • Manufacture/Brand:TCI Chemical
  • Product Description:3-Benzoylpropionic Acid >98.0%(GC)(T)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:3-Benzoylpropionic Acid >98.0%(GC)(T)
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:4-Oxo-4-phenylbutanoic acid
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  • Product Description:4-Oxo-4-phenylbutanoic acid
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  • Product Description:4-Oxo-4-phenylbutanoic acid
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  • Product Description:Phenylbutyrate Related Compound A United States Pharmacopeia (USP) Reference Standard
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Relevant articles and documentsAll total 124 Articles be found

The lesser burden borne by o-succinylbenzoate synthase: An easy reaction involving a carboxylate carbon acid [1]

Taylor,Palmer,Gerlt

, p. 5824 - 5825 (2001)

-

-

Yoshisato et al.

, p. 1500 (1969)

-

Novel pyrrol-2(3H)-ones and pyridazin-3(2H)-ones carrying quinoline scaffold as anti-proliferative tubulin polymerization inhibitors

Abdelbaset, Mahmoud S.,Abuo-Rahma, Gamal El-Din A.,Abdelrahman, Mostafa H.,Ramadan, Mohamed,Youssif, Bahaa G.M.,Bukhari, Syed Nasir Abbas,Mohamed, Mamdouh F.A.,Abdel-Aziz, Mohamed

, p. 151 - 163 (2018)

A novel quinolinyl pyrrolone and quinolinyl pyridazinone derivatives has been synthesized and characterized using different spectroscopic and elemental analysis techniques. Most of the target compounds displayed promising antiproliferative activity; In general, the pyrrolone derivatives 4a-f exhibited higher antiproliferative activity than their corresponding pyridazinone. The pyrrolone 4f showed outstanding antiproliferative activity with moderate selectivity against CNS and renal cancer with selectivity ratio of 3.49 and 3.56, respectively. Compound 4e and 5d experienced tubulin polymerization inhibitory activity comparable to that of vincristine while 4c, 4e and 4d showed good BRAF kinase inhibition compared to Erlotinib. Docking of compound 4e into colchicine binding site and biological assay results revealed that these compounds act mainly through tubulin polymerization inhibitory mechanism and can exhibit pre G1 apoptosis and cell cycle arrest at G2/M phase.

Design and synthesis of butenolide-based amide derivatives as anti-inflammatory agents

Ali, Yakub,Alam, Mohammad Sarwar,Hamid, Hinna,Husain, Asif,Dhulap, Abhijeet,Bano, Sameena,Kharbanda, Chetna,Nazreen, Syed,Haider, Saqlain

, p. 3775 - 3784 (2015)

Butenolide-based eighteen new amide derivatives (1-18) have been synthesized and evaluated for anti-inflammatory activity. The compounds 9, 17 and 4 exhibited significant in vivo inhibition of 84.69, 76.52 and 76.22 % inflammation, respectively, after 5 h without causing any damage to stomach and liver in comparison with the standard drug indomethacin which showed 79.04 % inhibition. The compounds showing potent anti-inflammatory activity were further evaluated for ex vivo TNF-α suppression. Compounds 9, 17 and 4 significantly suppressed TNF-α concentration to 74.83, 71.74 and 67.11 % as compared to indomethacin which exhibited a suppression of 69.01 %. Compounds 9 and 17 were also found to suppress the expression of COX-2 and NF-κB in the paw tissue. Moreover, compound 9 showed significant analgesic activity (57.03 %) which was comparable to indomethacin (61.03 %).

Insight into the mechanism and stereochemistry of the transformations of alkyltitanium Ate-Complexes. An enhanced enantioselectivity in the cyclopropanation of the carboxylic esters with titanacyclopropane reagents

Kulinkovich, Oleg G.,Kananovich, Dzmitry G.,Lopp, Margus,Snieckus, Victor

, p. 3615 - 3626 (2014)

The dependence of the stereoselectivity of the cyclopropanation reaction of g,g-diphenyl-g-butyrolactone and carboxylic esters with alkylmagnesium bromides in the presence of titanium(IV) TADDOLates on the structure of the reactants has been examined in d

A simple procedure for the isolation of γ-oxobenzenebutanoic acid derivatives: Application to the synthesis of fenbufen

Srinivas,Haricharan Raju,Acharyulu, Palle V. R.

, p. 291 - 292 (2004)

A simple, convenient, and industrially viable process for the isolation of 4-oxobutanoic acid derivatives resulting from Friedel-Crafts acylation products of aromatic hydrocarbons with succinic anhydride is reported. The isolation procedure involves simple quenching of the reaction mixture followed by filtration of the product in good yield and with excellent purity. The generality of the procedure has been demonstrated with representative examples of aromatic hydrocarbon precursors and has also been applied to the isolation of fenbufen. The quantity of aluminum chloride used in the reaction has also been optimized to reduce the load on effluent.

Design, synthesis, and bioactive screen in vitro of cyclohexyl (E)-4-(Hydroxyimino)-4-phenylbutanoates and their ethers for anti-Hepatitis B Virus agents

Cui, Xinhua,Zhou, Min,Tan, Jie,Wei, Zhuocai,Wei, Wanxing,Luo, Peng,Lin, Cuiwu

, (2019)

A series of oxime Cyclohexyl (E)-4-(hydroxyimino)-4-phenylbutanoates and their ethers were designed, synthesized, and evaluated for anti-hepatitis B virus (HBV) activities with HepG 2.2.15 cell line in vitro. Most of these compounds possessed anti-HBV activities, and among them, compound 4B-2 showed significant inhibiting effects on the secretion of HBsAg (IC50 = 63.85 ± 6.26 μM, SI = 13.41) and HBeAg (IC50 = 49.39 ± 4.17 μM, SI = 17.34) comparing to lamivudine (3TC) in HBsAg (IC50 = 234.2 ± 17.17 μM, SI = 2.2) and HBeAg (IC50 = 249.9 ± 21.51 μM, SI = 2.07). Docking study of these compounds binding to a protein residue (PDB ID: 3OX8) from HLA-A2 that with the immunodominant HBcAg18-27 epitope (HLA-A2.1- restricted CTL epitope) active site was carried out by using molecular operation environment (MOE) software. Docking results showed that behaviors of these compounds binding to the active site in HLA-A protein residue partly coincided with their behaviors in vitro anti-HBV active screening.

Kinetic and thermodynamic study for the oxidation of 4-oxo-4-phenyl butanoic acid by tripropylammonium fluorochromate in aqueous acetic acid medium

Yogananth,Mansoor, S. Sheik

, p. 17 - 23 (2015)

Tripropylammonium fluorochromate (TriPAFC) in acetic acid-water medium oxidizes 4-oxo-4-phenyl butanoic acid (4-Oxo acid) in the presence of perchloric acid. The reaction is first order each in [TriPAFC], [4-Oxo acid] and [H+]. From the observed kinetic results a suitable mechanism has been proposed.

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

Kharbanda, Chetna,Alam, Mohammad Sarwar,Hamid, Hinna,Ali, Yakub,Nazreen, Syed,Dhulap, Abhijeet,Alam, Perwez,Pasha

, (2020/11/27)

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.

Design, synthesis, and biological evaluation of new series of pyrrol-2(3H)-one and pyridazin-3(2H)-one derivatives as tubulin polymerization inhibitors

Abdelbaset, Mahmoud S.,Abdelrahman, Mostafa H.,Bukhari, Syed Nasir Abbas,Gouda, Ahmed M.,Youssif, Bahaa G.M.,Abdel-Aziz, Mohamed,Abuo-Rahma, Gamal El-Din A.

, (2020/12/21)

A potential microtubule destabilizing series of new thirty-five Pyrrol-2-one, Pyridazin-3(2H)-one and Pyridazin-3(2H)-one/oxime derivatives has been synthesized and tested for their antiproliferative activity against a panel of 60 human cancer cell lines. Compounds IVc, IVg and IVf showed a broad spectrum of growth inhibitory activity against cancer cell lines representing renal, cancer of lung, colon, central nervous system, ovary, and kidney. Among them, compound IVg was found to have broad spectrum anti-tumor activity against the tested nine tumor subpanels with selectivity ratios ranging between 0.21 and 3.77 at the GI50 level. In vitro assaying revealed tubulin polymerization inhibition by all active compounds IVc, IVg and IVf. The results of the docking study revealed nice fitting of compounds IVc, IVf, and IVg into CA-4 binding site in tubulin. The three compounds exhibited high binding affinities (ΔGb = ?12.49 to ?12.99 kcal/mol) toward tubulin compared to CA-4 (?8.87 kcal/mol). Investigation of the binding modes of the three compounds IVc, IVf, and IVg revealed that they interacted mainly hydrophobically with tubulin and similar binding orientations to that of CA-4. These observations suggest that tubulin is a possible target for these compounds.

Brine Shrimp (Artemia salina) Lethality Bioassay of Some 2-(Alkyl/Aryl)-6-Phenyl-4,5-Dihydropyridazin-3(2H)-one Derivatives

Acharya, Mrityunjoy,Asif, Mohammad,Imran, Mohd,Kamal, Mehnaz

, p. 57 - 61 (2021/08/12)

A series of pyridazinone derivatives, 2-(alkyl/aryl)-6-phenyl-4,5-dihydropyridazin-3(2H)-ones (3a-h), was synthesized from 6-phenyl-4,5-dihydropyridazin-3(2H)-one (2). Compound 2 was synthesized from benzoylpropionic acid (1). The synthesized compounds were characterized on the basis of their spectral (infrared, proton nuclear magnetic resonance, carbon-13 nuclear magnetic resonance, and mass spectra) and elemental analytical data. The compounds 2 and 3a-h and potassium dichromate (as reference drug) were tested at the dose level of 10, 20, and 30 μg/mL. Compounds 3d and 3b exhibited potent brine shrimp lethality with LC50values of 4.023 μg and 4.20 μg. Other compounds 3g, 3f, 3c, 3h, 2, 3a, and 3e also showed significant cytotoxic activity with LC50values of 13.91, 12.58, 11.91, 11.76, 10.58, 9.76, and 7.46 μg, respectively. The present study supports that brine shrimp bioassay is a simple, reliable, and suitable method for estimation of bioactivity of synthesized compounds and provides support for their use in medicine.

Nickel-Mediated Photoreductive Cross Coupling of Carboxylic Acid Derivatives for Ketone Synthesis**

Brauer, Jan,Quraishi, Elisabeth,Kammer, Lisa Marie,Opatz, Till

, p. 18168 - 18174 (2021/11/30)

A simple visible light photochemical, nickel-catalyzed synthesis of ketones from carboxylic acid-derived precursors is presented. Hantzsch ester (HE) functions as a cheap, green and strong photoreductant to facilitate radical generation and also engages in the Ni-catalytic cycle to restore the reactive species. With this dual role, HE allows for the coupling of a large variety of radicals (1°,2°, benzylic, α-oxy & α-amino) with aroyl and alkanoyl moieties, a new feature in reactions of this type. With both precursors deriving from abundant carboxylic acids, this protocol is a welcome addition to the organic chemistry toolbox. The reaction proceeds under mild conditions without the need for toxic metal reagents or bases and shows a wide scope, including pharmaceuticals and complex molecular architectures.

Tunable Trifunctionalization of Tertiary Enaminones for the Regioselective and Metal-Free Synthesis of Discrete and Proximal Phosphoryl Nitriles

Xu, Zhongrong,Fu, Leiqing,Fang, Xia,Huang, Bin,Zhou, Liyun,Wan, Jie-Ping

, p. 5049 - 5053 (2021/07/19)

This paper reports an unprecedented trifunctionalization of tertiary enaminones for the synthesis phosphoryl nitriles by the reactions of enaminones with diarylphosphine oxides and trimethylsilyl cyanide (TMSCN) without the use of any metal reagent. Emplo

Process route upstream and downstream products

Process route

water
7732-18-5

water

4-bromo-5-phenyl-dihydro-furan-2-one
87629-98-9

4-bromo-5-phenyl-dihydro-furan-2-one

hydrogen bromide
10035-10-6,12258-64-9

hydrogen bromide

succinylbenzene
2051-95-8

succinylbenzene

Conditions
Conditions Yield
lower-melting form;
4-phenyl-butan-1-ol
3360-41-6

4-phenyl-butan-1-ol

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

succinylbenzene
2051-95-8

succinylbenzene

Conditions
Conditions Yield
With oxone; manganese(II) chloride tetrahydrate; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine; In acetone; at 0 - 20 ℃; for 4h; chemoselective reaction;
58%
3.4%
(3-oxo-1,3-diphenyl-propyl)-succinic acid

(3-oxo-1,3-diphenyl-propyl)-succinic acid

Benzoylformic acid
611-73-4

Benzoylformic acid

succinylbenzene
2051-95-8

succinylbenzene

Conditions
Conditions Yield
at 13 - 15 ℃;
(1-benzoyl-2-hydroxy-2-phenyl-ethyl)-malonic acid
861356-98-1

(1-benzoyl-2-hydroxy-2-phenyl-ethyl)-malonic acid

benzaldehyde
100-52-7

benzaldehyde

succinylbenzene
2051-95-8

succinylbenzene

Conditions
Conditions Yield
stilben-α-yl-succinic acid
54432-64-3,67131-64-0

stilben-α-yl-succinic acid

2-benzoyl-5-oxo-2-phenyl-tetrahydro-furan-3-carboxylic acid

2-benzoyl-5-oxo-2-phenyl-tetrahydro-furan-3-carboxylic acid

benzaldehyde
100-52-7

benzaldehyde

benzoic acid
65-85-0,8013-63-6

benzoic acid

succinylbenzene
2051-95-8

succinylbenzene

Conditions
Conditions Yield
4-oxo-4-phenyl-butyraldehyde
56139-59-4

4-oxo-4-phenyl-butyraldehyde

succinylbenzene
2051-95-8

succinylbenzene

Conditions
Conditions Yield
With N-hydroxyphthalimide; oxygen; In acetonitrile; at 30 ℃; for 3h; Schlenk technique;
91%
With N-hydroxyphthalimide; oxygen; In acetonitrile; at 30 ℃; for 3h; under 760.051 Torr; Schlenk technique;
91%
With silver(l) oxide; In ethanol;
succinic acid anhydride
108-30-5

succinic acid anhydride

succinylbenzene
2051-95-8

succinylbenzene

Conditions
Conditions Yield
With aluminum (III) chloride; at 35 - 80 ℃; for 3h; Reagent/catalyst;
99.6%
succinic acid anhydride; With sulfuryl dichloride; for 3h; Inert atmosphere; Reflux;
benzene; With aluminum (III) chloride; In 1,1,2,2-tetrachloroethane; at 0 ℃; for 16h; Inert atmosphere;
96%
With aluminium trichloride; for 0.5h; Heating;
90%
With [bmim]Cl*AlCl3; at 50 ℃; for 3h;
87%
With aluminum (III) chloride; at 60 ℃; Ionic liquid; Irradiation;
85%
With aluminum (III) chloride; at 0 ℃; for 1h; Reflux;
85%
With aluminum (III) chloride; In benzene; for 0.75h; Reflux;
84%
With aluminum (III) chloride;
83%
With aluminium trichloride; at 20 ℃; for 0.333333h;
80%
With aluminium trichloride; In 1,2-dichloro-ethane; 1) 20 deg C, 3 h, 2) 45 deg C, 1 h;
79%
With aluminum (III) chloride; at 20 - 80 ℃; for 1.5h;
78%
With aluminum (III) chloride; for 6h;
77%
With aluminum (III) chloride; for 4h; Reflux;
75%
With aluminium trichloride; for 6h; Heating;
73%
With aluminum (III) chloride; In benzene; Heating;
73%
benzene; With aluminum (III) chloride; Reflux;
succinic acid anhydride; Heating;
73%
With aluminum (III) chloride; Reflux;
73%
With aluminum (III) chloride; at 80 ℃; for 4h; Reflux;
72%
With aluminum (III) chloride; for 4h; Reflux;
70%
With aluminum (III) chloride;
66%
succinic acid anhydride; benzene; With aluminum (III) chloride; at 65 ℃; for 3h;
With hydrogenchloride; In water; at 80 ℃; for 0.333333h;
65%
succinic acid anhydride; benzene; With aluminum (III) chloride; at 50 ℃; for 6h;
With hydrogenchloride; In water; at 20 ℃;
63%
With aluminum (III) chloride; for 4h; Reflux;
62%
With aluminum (III) chloride; In 1,2-dichloro-ethane; at 15 - 20 ℃; Cooling;
60%
With aluminium trichloride; for 5h; Heating;
58%
Reaktion ueber mehrere Stufen;
With aluminium trichloride;
With aluminium trichloride;
With aluminium trichloride; In 1,2-dichloro-ethane; for 4h;
With aluminium trichloride; In nitrobenzene;
With aluminum (III) chloride; Reflux;
With aluminum (III) chloride; Reflux;
With aluminum (III) chloride; at -10 - 20 ℃;
With aluminum (III) chloride;
With aluminum (III) chloride;
With aluminum (III) chloride;
With aluminum (III) chloride;
With aluminum (III) chloride; In 1,1,2,2-tetrachloroethane;
With HY-Zeolite; In 1,2-dichloro-ethane; Reflux;
With aluminum (III) chloride;
benzene; With aluminum (III) chloride; at 20 ℃; for 0.5h;
succinic acid anhydride; at 20 ℃; for 6h;
With aluminum (III) chloride;
With aluminum (III) chloride;
With aluminum (III) chloride; Reflux;
With aluminum (III) chloride;
benzene; With aluminum (III) chloride; at 20 ℃; for 0.5h;
succinic acid anhydride; at 20 ℃; for 6h;
With aluminum (III) chloride; In dichloromethane; at 20 ℃; Inert atmosphere;
With aluminum (III) chloride;
With aluminum (III) chloride; for 1h; Reflux;
With aluminum (III) chloride; for 6h;
succinic acid anhydride; benzene; With aluminum (III) chloride; for 6h; Reflux;
at 20 ℃;
With aluminum (III) chloride; In dichloromethane; Inert atmosphere;
With aluminum (III) chloride; In dichloromethane; at 20 ℃; for 6.5h; Cooling with ice;
With aluminum (III) chloride;
With aluminum (III) chloride;
With aluminum (III) chloride;
With aluminum (III) chloride; In dichloromethane; at 0 - 5 ℃; for 2h; Schlenk technique; Inert atmosphere;
With aluminum (III) chloride; In dichloromethane; at 20 ℃; for 16h; Inert atmosphere;
succinic acid anhydride; benzene; In dichloromethane; at 0 ℃; for 0.5h;
With aluminum (III) chloride; In dichloromethane; at 0 - 20 ℃; for 6h;
With aluminum (III) chloride; for 4h; Reflux;
With aluminum (III) chloride; at 90 ℃; Inert atmosphere;
With aluminum (III) chloride;
With aluminum (III) chloride; for 6h; Reflux;
With aluminum (III) chloride; for 0.5h; Reflux;
With aluminum (III) chloride; Reflux;
Benzoylacrylic acid
17812-07-6

Benzoylacrylic acid

succinylbenzene
2051-95-8

succinylbenzene

Conditions
Conditions Yield
With hydrogen; palladium; In methanol; at 20 ℃; for 2h;
100%
With formic acid; Noyori's catalyst; triethylamine; In neat (no solvent); at 20 ℃; for 12h; chemoselective reaction; Sealed tube;
82%
5-hydroxy-1-phenylpentane-1,4-dione
70107-41-4

5-hydroxy-1-phenylpentane-1,4-dione

2-hydroxy-3-phenylcyclopent-2-en-1-one
51307-01-8

2-hydroxy-3-phenylcyclopent-2-en-1-one

benzoic acid
65-85-0,8013-63-6

benzoic acid

succinylbenzene
2051-95-8

succinylbenzene

Conditions
Conditions Yield
With sodium hydroxide; In diethyl ether; water; at 20 ℃; for 0.5h; Inert atmosphere; Schlenk technique;
75%
ethyl 3-benzoylpropanoate
6270-17-3

ethyl 3-benzoylpropanoate

(-)-(S)-5-phenyl-4,5-dihydrofuran-2(3H)-one
111138-02-4

(-)-(S)-5-phenyl-4,5-dihydrofuran-2(3H)-one

(R)-4-phenylbutyrolactone
111138-03-5

(R)-4-phenylbutyrolactone

succinylbenzene
2051-95-8

succinylbenzene

Conditions
Conditions Yield
With D-glucose; In aq. phosphate buffer; at 28 ℃; for 12h; pH=7; enantioselective reaction; Microbiological reaction;
55%

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