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(E)-ETHYL 4-(4-METHOXYPHENYL)-4-OXOBUT-2-ENOATE, also known as ethyl 4-(4-methoxyphenyl)-2-oxobut-3-enoate, is an organic compound with the molecular formula C13H14O4. It is a derivative of 4-methoxycinnamic acid and is characterized by its yellowish liquid appearance, fruity odor, and solubility in organic solvents. (E)-ETHYL 4-(4-METHOXYPHENYL)-4-OXOBUT-2-ENOATE is widely utilized in various fields due to its unique properties and potential pharmacological effects.

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  • 127427-28-5 Structure
  • Basic information

    1. Product Name: (E)-ETHYL 4-(4-METHOXYPHENYL)-4-OXOBUT-2-ENOATE
    2. Synonyms: (E)-ETHYL 4-(4-METHOXYPHENYL)-4-OXOBUT-2-ENOATE
    3. CAS NO:127427-28-5
    4. Molecular Formula: C13H14O4
    5. Molecular Weight: 234.25
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 127427-28-5.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 358.2°C at 760 mmHg
    3. Flash Point: 158.1°C
    4. Appearance: /
    5. Density: 1.125g/cm3
    6. Vapor Pressure: 2.6E-05mmHg at 25°C
    7. Refractive Index: 1.52
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: (E)-ETHYL 4-(4-METHOXYPHENYL)-4-OXOBUT-2-ENOATE(CAS DataBase Reference)
    11. NIST Chemistry Reference: (E)-ETHYL 4-(4-METHOXYPHENYL)-4-OXOBUT-2-ENOATE(127427-28-5)
    12. EPA Substance Registry System: (E)-ETHYL 4-(4-METHOXYPHENYL)-4-OXOBUT-2-ENOATE(127427-28-5)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 127427-28-5(Hazardous Substances Data)

127427-28-5 Usage

Uses

Used in Pharmaceutical Industry:
(E)-ETHYL 4-(4-METHOXYPHENYL)-4-OXOBUT-2-ENOATE is used as an intermediate in the synthesis of various pharmaceutical compounds. Its versatile chemical structure allows for the development of new drugs with potential therapeutic applications.
Used in Fragrance Industry:
In the fragrance industry, (E)-ETHYL 4-(4-METHOXYPHENYL)-4-OXOBUT-2-ENOATE is used as a key component in the creation of various scent profiles. Its fruity odor contributes to the development of unique and appealing fragrances.
Used in Flavorings Industry:
(E)-ETHYL 4-(4-METHOXYPHENYL)-4-OXOBUT-2-ENOATE is also utilized in the flavorings industry to enhance the taste and aroma of various food and beverage products. Its fruity characteristics make it a valuable addition to the flavorist's toolbox.
Used in Medicinal Chemistry:
(E)-ETHYL 4-(4-METHOXYPHENYL)-4-OXOBUT-2-ENOATE is used as a starting material in the development of new medicinal compounds. Its potential anti-inflammatory properties make it a promising candidate for the treatment of various inflammatory conditions.

Check Digit Verification of cas no

The CAS Registry Mumber 127427-28-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,7,4,2 and 7 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 127427-28:
(8*1)+(7*2)+(6*7)+(5*4)+(4*2)+(3*7)+(2*2)+(1*8)=125
125 % 10 = 5
So 127427-28-5 is a valid CAS Registry Number.
InChI:InChI=1/C13H14O4/c1-3-17-13(15)9-8-12(14)10-4-6-11(16-2)7-5-10/h4-9H,3H2,1-2H3/b9-8+

127427-28-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name ethyl 4-(4-methoxyphenyl)-4-oxobut-2-enoate

1.2 Other means of identification

Product number -
Other names 2-Butenoic acid,4-(4-methoxyphenyl)-4-oxo-,ethyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:127427-28-5 SDS

127427-28-5Relevant articles and documents

An efficient synthesis of β-Aroylacrylic acid ethyl ester by the Friedel-Crafts reaction in the presence of diethyl sulfate

Onoue, Ken-Ichi,Shintou, Taichi,Zhang, Chang Shan,Itoh, Isamu

, p. 22 - 23 (2006)

An β-Aroylacrylic acid ethyl ester such as ethyl (E)-4-(3,4- dimethoxyphenyl)-4-oxo-2-butenoate (1) can be obtained in good yield and with excellent purity by way of the Friedel-Crafts reaction in which 1,2-dimethoxybenzene (2) is treated with maleic anhydride (3) and aluminum chloride in the presence of diethyl sulfate (4) under mild conditions. Copyright

Copper-Catalyzed N-O Cleavage of α,β-Unsaturated Ketoxime Acetates toward Structurally Diverse Pyridines

Ding, Xiaojuan,Duan, Jindian,Fang, Zheng,Guo, Kai,Li, Zhenjiang,Mao, Yiyang,Rong, Binsen,Xu, Gaochen,Zhang, Lei,Zhu, Ning

, p. 2532 - 2542 (2020/03/13)

The copper-catalyzed [4 + 2] annulation of α,β-unsaturated ketoxime acetates with 1,3-dicarbonyl compounds for the synthesis of three classes of structurally diverse pyridines has been developed. This method employs 1,3-dicarbonyl compounds as C2 synthons and enables the synthesis of multifunctionalized pyridines with diverse electron-withdrawing groups in moderate to good yields. The mechanistic investigation suggests that the reactions proceed through an ionic pathway.

Design, synthesis, and bioevaluation of a novel class of (E)-4-oxo-crotonamide derivatives as potent antituberculosis agents

Ren, Jinfeng,Xu, Jian,Zhang, Guoning,Xu, Changliang,Zhao, LiLi,You, XueFu,Wang, Yucheng,Lu, Yu,Yu, Liyan,Wang, Juxian

, p. 539 - 543 (2019/01/09)

A series of novel (E)-4-oxo-2-crotonamide derivatives were designed and synthesized to find potent antituberculosis agents. All the target compounds were evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv(MTB). Results reveal that 4-phenyl moiety at part A and short methyl group at part C were found to be favorable. Most of the derivatives displayed promising activity against MTB with MIC ranging from 0.125 to 4 μg/mL. Especially, compound IIIa16 was found to have the best activity with MIC of 0.125 μg/mL against MTB and with MIC in the range of 0.05–0.48 μg/mL against drug-resistant clinical MTB isolates.

Potassium 2-oxo-3-enoates as Effective and Versatile Surrogates for α, β-Unsaturated Aldehydes in NHC-Catalyzed Asymmetric Reactions

Gao, Yaru,Ma, Yafei,Xu, Chen,Li, Lin,Yang, Tianjian,Sima, Guoqing,Fu, Zhenqian,Huang, Wei

supporting information, p. 479 - 484 (2017/12/26)

Potassium 2-oxo-3-enoates, which are readily prepared at scale and easily stored, have been found to be effective and versatile surrogates for α,β-unsaturated aldehydes in NHC-catalyzed asymmetric reactions. Promoted by chiral N-heterocyclic carbenes combined with LiCl, these easy-to-handle solid salts could release of CO2 and then undergo asymmetric reactions via homoenolate and α, β-unsaturated acyl azolium intermediate. The reactions have broad substrate scopes with high enantioselectivities. (Figure presented.).

Enantioselective NHC-catalysed redox [4+2]-hetero-Diels-Alder reactions using α-aroyloxyaldehydes and unsaturated ketoesters

Taylor, James E.,Davies, Alyn T.,Douglas, James J.,Churchill, Gwydion,Smith, Andrew D.

, p. 355 - 366 (2017/02/15)

N-Heterocyclic carbene (NHC)-catalysed redox [4+2]-hetero-Diels-Alder reactions of α-aroyloxyaldehydes with either β,γ-unsaturated α-ketoesters or α,β-unsaturated γ-ketoesters generates substituted syn-dihydropyranones in good yield with excellent enantioselectivity (up to >99:1 er). The product diastereoselectivity is markedly dependent upon the nature of the unsaturated enone substituent. The presence of either electron-neutral or electron-rich aryl substituents gives excellent diastereoselectivity (up to >99:5 dr), while electron-deficient aryl substituents give reduced diastereoselectivity. In these cases, the syn-dihydropyranone products are more susceptible to base-promoted epimerisation at the C(4)-position under the reaction conditions, accounting for the lower diastereoselectivity obtained.

Substituted 4-oxo-crotonic acid derivatives as a new class of protein kinase B (PknB) inhibitors: synthesis and SAR study

Xu, Changliang,Bai, Xiaoguang,Xu, Jian,Ren, Jinfeng,Xing, Yun,Li, Ziqiang,Wang, Juxian,Shi, Jingjing,Yu, Liyan,Wang, Yucheng

, p. 4763 - 4775 (2017/02/05)

Protein kinase B (PknB) is an essential serine/threonine protein kinase required for Mycobacterium tuberculosis (M. tb) cell division and cell-wall biosynthesis. A high throughput screen using PknB identified a (E)-4-oxo-crotonic acid inhibitor, named YH-8, which was used as a scaffold for SAR investigations. A significant improvement in enzyme affinity was achieved. The results indicated that the α,β-unsaturated ketone scaffold and “trans-” configuration are essential for the activity against PknB. And compounds with an aryl group, especially with electron-withdrawing substituents on benzene ring, exhibited four fold potency than that of YH-8.

Substrate-Controlled, One-Pot Synthesis: Access to Chiral Chroman-2-one and Polycyclic Derivatives

Sun, Xue-Li,Chen, Ying-Han,Zhu, Dan-Yang,Zhang, Yan,Liu, Yan-Kai

supporting information, p. 864 - 867 (2016/03/04)

Based on the appropriate choice of electrophiles, one-pot, multicomponent, enantioselective domino reactions have been realized which contain a five-step sequence and provide highly efficient access to potentially bioactive chroman-2-one derivatives as a single diastereoisomer with excellent enantioselectivities and in high yields. This new strategy could significantly improve the previous protocol by directly starting from commercial 2-hydroxybenzaldehydes rather than preformed lactols, which have to be synthesized in several additional steps. (Chemical Equation Presented).

Enantioselective conjugate addition of aliphatic thiols to divergently activated electron poor alkenes and dienes

Kowalczyk, Rafa?,Wierzba, Aleksandra J.,Boratyński, Przemys?aw J.,Ba?kowicz, Julia

supporting information, p. 5834 - 5842 (2015/03/30)

Divergently activated double bonds in electron poor 4-oxo-butenoates and (2E,4E)-6-oxo-2,4-dienoates underwent stereoselective and regioselective addition of mercaptans catalyzed by simple Cinchona alkaloids. Application of quinine and quinidine afforded both enantiomers of the 1,4-adducts with respect to the ketone carbonyl group in ees of up to 80%. Single recrystallization of some adducts resulted in further enrichment of up to 99%ee.

Structure-activity relationship, cytotoxicity and mode of action of 2-ester-substituted 1,5-benzothiazepines as potent antifungal agents

Kang, Wang,Du, Xingqiong,Wang, Lanzhi,Hu, Lijuan,Dong, Yuhuan,Bian, Yanqing,Li, Yuan

, p. 1305 - 1314 (2013/11/06)

Our studies examined the structural features responsible for the antifungal activity of 2-ethoxycarbonyl-1,5-benzothiazepine (7a). Three series of 1,5-benzothiazepine derivatives were synthesized and screened for their antifungal activity. The results suggested that the ethoxycarbonyl group at the 2 position and the imine moiety on the seven-membered ring are essential for activity. The most potent of the synthesized analogues (7a, 7b) were further studied by evaluating their cytotoxicity and mode of action (for 7a). The results showed that compounds 7a and 7b were relatively safe for BV2 cells, but compound 7a interfered with Cryptococcus neoformans cell wall integrity by increasing the chitinase activity. Therefore, compound 7a was considered safe as an antifungal agent for animal cells. Three series of 1,5-benzothiazepine derivatives were synthesized and their antifungal activities were evaluated to determine the structure-activity relationships with respect to the antifungal activity of 2-ester-substituted 1,5-benzothiazepines. The effective antifungal compounds 7a and 7b were further studied for their antifungal activity, cytotoxicity and mechanism of action (for compound 7a). The results provided important information about this class of benzothiazepines. Copyright

Design, synthesis and conformational analysis of turn inducer cyclopropane scaffolds: microwave assisted amidation of unactivated esters on catalytic solid support to obtain γ-turn mimic scaffolds

Bhella, Surinderjit Singh,Elango, Munusamy,Ishar, Mohan Paul S.

experimental part, p. 240 - 246 (2009/04/06)

Novel constrained 1-aroyl-cyclopropane-2,3-cis-dicarboxylic acid bis-[(2-hydroxy-ethyl)-amides] (17a-e) with varied torsional angles have been synthesized in high yield from unactivated esters of 1-aroyl-2,3-cis-diethoxycarbonylcyclopropanes (15a-e) on a catalytic solid support with reduced reaction times by using the monomode-microwave irradiation; 15a-e were obtained by diastereoselective ethoxycarbonylmethylene transfer from a sulfur ylide to ethyl β-aroylacrylates (10a-e). Torsional angles and interatomic distance measurements on the energy minimized structures of the obtained molecules (17a-e, DFT, B3LYP/6-31G* level) have established these molecules as valuable γ-turn mimic scaffolds.

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