Ethyl 3-(3,4-dihydroxyphenyl)propionate

Base Information

• Chemical Name: Ethyl 3-(3,4-dihydroxyphenyl)propionate
• CAS No.: 3967-57-5
• Molecular Formula: C11H14 O4
• Molecular Weight: 210.23
• European Community (EC) Number: 223-585-6
• NSC Number: 619680,158568
• DSSTox Substance ID: DTXSID00192772
• Nikkaji Number: J217.798F
• Wikidata: Q72474411
• ChEMBL ID: CHEMBL3093471
• Mol file: 3967-57-5.mol

Synonyms:Ethyl hydrocaffeate;3967-57-5;ethyl 3-(3,4-dihydroxyphenyl)propanoate;Ethyl dihydrocaffeate;Ethyl 3-(3,4-dihydroxyphenyl)propionate;CHEMBL3093471;EINECS 223-585-6;0XR;SCHEMBL490911;DTXSID00192772;BDBM50062149;NSC158568;NSC619680;AKOS024319689;NSC 158568;NSC-158568;NSC-619680;Ethyl 3,4-dihydroxyhydrocinnamate, 99%;FT-0711706;Hydrocinnamic acid,4-dihydroxy-, ethyl ester;3,4-Dihydroxybenzenepropionic acid ethyl ester;Benzenepropanoic acid,4-dihydroxy-, ethyl ester;Hydrocinnamic acid, 3,4-dihydroxy-, ethyl ester;Benzenepropanoic acid, 3,4-dihydroxy-, ethyl ester

Chemical Property of Ethyl 3-(3,4-dihydroxyphenyl)propionate

Chemical Property:

• Vapor Pressure: 1.12E-05mmHg at 25°C
• Boiling Point: 359.7°Cat760mmHg
• Flash Point: 139.3°C
• PSA: 66.76000
• Density: 1.221g/cm³
• LogP: 2.00940
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 210.08920892
• Heavy Atom Count: 15
• Complexity: 205

Purity/Quality:

99% ^*data from raw suppliers

EthylHydrocaffeate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)CCC1=CC(=C(C=C1)O)O

Technology Process of Ethyl 3-(3,4-dihydroxyphenyl)propionate

There total 8 articles about Ethyl 3-(3,4-dihydroxyphenyl)propionate 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%

3-(4-hydroxy-phenyl)-propionic acid ethyl ester (23795-02-0) → Ethyl dihydrocaffeate (3967-57-5)

Guidance literature:

With Agaricus bisporus; oxygen; In aq. phosphate buffer; dichloromethane; at 25 ℃; for 24h; pH=7; Reagent/catalyst;

DOI:10.1016/j.bmc.2013.10.026

Reference yield: 84.0%

ethanol (64-17-5) + dihydrocaffeic acid (1078-61-1) → Ethyl dihydrocaffeate (3967-57-5)

Guidance literature:

With sulfuric acid; for 24h; Reflux;

DOI:10.1016/j.ejmech.2014.11.055

Reference yield:

ethyl 3-(4-(5-ethyl-2-hydroxy-3-methoxyphenoxy)-3-methoxyphenyl)propanoate → 4-ethylcatechol (1124-39-6) + 4-Ethylguaiacol (2785-89-9) + 5-ethylbenzene-1,2,3-triol (66125-16-4) + 3-(3-methoxyphenyl)propanoic acid ethyl ester (7116-39-4) + ethyl 3-(4-hydroxy-3-methoxyphenyl)propanoate (61292-90-8) + 3-(3-hydroxy-phenyl)propionic acid ethyl ester (34708-60-6) + 5-ethyl-3-methoxybenzene-1,2-diol (7452-04-2) + Ethyl dihydrocaffeate (3967-57-5)

Guidance literature:

ethyl 3-(4-(5-ethyl-2-hydroxy-3-methoxyphenoxy)-3-methoxyphenyl)propanoate; With platinum-nickel nanoclusters on activated carbon; hydrogen; potassium hexamethylsilazane; In m-xylene; at 180 ℃; for 18h; under 775.743 Torr;

With N,O-Bis(trimethylsilyl)trifluoroacetamide; In m-xylene; at 65 ℃; for 1h; Overall yield = 41 %;

DOI:10.1002/anie.201509133

upstream raw materials:

ethanol

dihydrocaffeic acid

3,4-methoxycinnamic acid

3-(3,4-bis-benzyloxy-phenyl)-acrylic acid ethyl ester

Downstream raw materials:

3-(3,4-diethoxyphenyl)propionic acid

3-(3,4-diethoxyphenyl)-N-methylpropionamide

[3-(3,4-diethoxyphenyl)propyl]methylamine

3-(3,4-diethoxyphenyl)propionic acid ethyl ester

Refernces

• 1、 Allegretta, Giuseppe,Weidel, Elisabeth,Empting, Martin,Hartmann, Rolf W.. "Catechol-based substrates of chalcone synthase as a scaffold for novel inhibitors of PqsD". . p. 351 - 359. Retrieved 2015/02/19.
• 2、 Yang, Jian,Yang, Jing Xiang,Zhang, Fang,Chen, Gang,Pan, Wei,Yu, Rui,Wu, Shuwen,Tien, Po. "Design, synthesis and biological evaluation of small molecular polyphenols as entry inhibitors against H5N1". . p. 2680 - 2684. Retrieved 2014/06/09.