ethyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate

Base Information

• Chemical Name: ethyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate
• CAS No.: 6093-71-6
• Molecular Formula: C12H10 O5
• Molecular Weight: 234.208
• Hs Code.: 2932209090
• UNII: X538NC636R
• DSSTox Substance ID: DTXSID30209761
• Nikkaji Number: J1.098.494G
• Wikidata: Q27093678
• Metabolomics Workbench ID: 147292
• ChEMBL ID: CHEMBL155103
• Mol file: 6093-71-6.mol

Synonyms:6093-71-6;ethyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate;ethyl 7-hydroxy-2-oxochromene-3-carboxylate;3-CARBETHOXYUMBELIFERONE;YZ9;7-Hydroxycoumarin-3-carboxylic acid ethyl ester;3-carbethoxy-7-hydroxycoumarin;7-HYDROXY-2-OXO-CHROMENE-3-CARBOXYLIC ACID ETHYL ESTER;2H-1-Benzopyran-3-carboxylic acid, 7-hydroxy-2-oxo-, ethyl ester;7-hydroxy-3-carbethoxycoumarin;CHEMBL155103;X538NC636R;Ethyl 7-hydroxy-2-oxo-2H-1-benzopyran-3-carboxylate;Ethyl umbelliferone-3-carboxylate;1gcz;MFCD00017641;CBMicro_006943;D01HJN;Oprea1_247935;Oprea1_714483;UNII-X538NC636R;SCHEMBL1406240;7-Hydroxy-2-oxo-2H-chromene-3-carboxylic acid ethyl ester;DTXSID30209761;IETDBZQIWIJQJG-UHFFFAOYSA-N;HMS1679D11;HMS3604G20;SMSF0008596;BDBM50095995;STK386371;ethyl 7-hydroxycoumarin-3-carboxylate;AKOS000274468;CB09288;DB02728;DS-8444;NCGC00379249-01;BIM-0006912.P001;HY-110156;Umbelliferone-3-carboxylic Acid Ethyl Ester;CS-0033018;E1017;EU-0000380;FT-0635973;F19857;ethyl7-hydroxy-2-oxo-2H-chromene-3-carboxylate;SR-01000391456;J-512156;SR-01000391456-1;Q27093678;7-Hydroxycoumarin-3-carboxylic acid ethyl ester, ~98%;F1018-0184;2-Oxo-7-hydroxy-2H-1-benzopyran-3-carboxylic acid ethyl ester

Chemical Property of ethyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate

Chemical Property:

• Vapor Pressure: 1.18E-08mmHg at 25°C
• Melting Point: 170.0 to 174.0 °C
• Boiling Point: 448.3ºC at 760 mmHg
• PKA: 7.32±0.20(Predicted)
• Flash Point: 178.7ºC
• PSA: 76.74000
• Density: 1.397g/cm3
• LogP: 1.67530
• Storage Temp.: −20°C
• Solubility.: DMSO: soluble5mg/mL, clear (warmed)
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 234.05282342
• Heavy Atom Count: 17
• Complexity: 360

Purity/Quality:

99% ^*data from raw suppliers

YZ9 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C1=CC2=C(C=C(C=C2)O)OC1=O
• Uses: Z9 is a potent inhibitor of PFKFB3, a member of 6-phosphofructo-2-kinases family. It avidly competes with fructose 6-phosphate (F6P) at PFKFB3. YZ9 is also cell permeable, inhibiting the growth of HeLa cells.

Technology Process of ethyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate

There total 21 articles about ethyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

diethyl malonate (105-53-3) + 2,4-Dihydroxybenzaldehyde (95-01-2) → 7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid ethyl ester (6093-71-6)

Guidance literature:

With pyridine; at 20 ℃; for 1h;

Reference yield: 94.0%

7-acetoxy-3-carbethoxycoumarin (13209-77-3) → 7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid ethyl ester (6093-71-6)

Guidance literature:

With potassium carbonate;

Reference yield: 41.0%

ethyl 4,4,4-trichloroacetoacetate (3702-98-5) + 2,4-Dihydroxybenzaldehyde (95-01-2) → 7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid ethyl ester (6093-71-6)

Guidance literature:

With piperidine; In toluene; for 6h; Reflux;

DOI:10.1016/j.tetlet.2015.01.114

upstream raw materials:

diethyl malonate

2,4-Dihydroxybenzaldehyde

diethyl 2-ethoxymethylenemalonate

recorcinol

Downstream raw materials:

7-methoxycoumarin-3-carboxylic acid ethyl ester

2-oxo-7-(4-pent-4-enyloxy-benzoyloxy)-2H-chromene-3-carboxylic acid ethyl ester

C₂₄H₂₅NO₅

C₂₃H₂₄N₂O₅

Refernces

• 1、 Rastegari, Arezoo,Nadri, Hamid,Mahdavi, Mohammad,Moradi, Alireza,Mirfazli, Seyedeh Sara,Edraki, Najmeh,Moghadam, Farshad Homayouni,Larijani, Bagher,Akbarzadeh, Tahmineh,Saeedi, Mina. "Design, synthesis and anti-Alzheimer's activity of novel 1,2,3-triazole-chromenone carboxamide derivatives". . p. 391 - 401. Retrieved 2019.
• 2、 En, Da,Guo, Yuan,Chen, Bo-Ting,Dong, Biao,Peng, Meng-Jiao. "Coumarin-derived Fe3+-selective fluorescent turn-off chemosensors: Synthesis, properties, and applications in living cells". . p. 248 - 253. Retrieved 2014.
• 3、 Chen, Ping-Feng,Du, Li-Hua,Long, Rui-Jie,Luo, Xi-Ping,Xue, Miao. "A sustainable innovation for the tandem synthesis of sugar-containing coumarin derivatives catalyzed by lipozyme TL im from: Thermomyces lanuginosus in continuous-flow microreactors". . p. 13252 - 13259. Retrieved 2020.
• 4、 Ohta, Yuhei,Wakita, Hiroo,Kawaguchi, Mitsuyasu,Ieda, Naoya,Osada, Shigehiro,Nakagawa, Hidehiko. "Ratiometric assay of CARM1 activity using a FRET-based fluorescent probe". . . Retrieved 2019.
• 5、 Liu, Yunchang,Xiang, Kaiqiang,Guo, Min,Tian, Baozhu,Zhang, Jinlong. "A coumarin-based fluorescent probe for the fast detection of Pd0 with low detection limit". . p. 1451 - 1455. Retrieved 2016.
• 6、 Duan, Chunying,Jiao, Yang,Ma, Chunming,Zuo, Yingying. "A novel fluorescent probe for hydrogen peroxide and its application in bio-imaging". . . Retrieved 2021.
• 7、 Radwan, Eman M.,Elsayed, Elsherbiny H.,El-Moneim, Mohamed Abd,Youssef Moustafa, Amal M.. "Synthesis and Cytotoxicity Against Human Breast Carcinoma Cell Evaluation of Some New 3,4-Disubstituted Coumarin Derivatives". . p. 1040 - 1049. Retrieved 2022/01/11.
• 8、 Wei, Lai,Hou, Tao,Li, Jiaqi,Zhang, Xiuli,Zhou, Han,Wang, Zhenyu,Cheng, Junxiang,Xiang, Kaijing,Wang, Jixia,Zhao, Yaopeng,Liang, Xinmiao. "Structure-Activity Relationship Studies of Coumarin-like Diacid Derivatives as Human G Protein-Coupled Receptor-35 (hGPR35) Agonists and a Consequent New Design Principle". supporting information. p. 2634 - 2647. Retrieved 2021/04/02.