3967-57-5

Basic information

• Product Name: ETHYL HYDROCAFFEATE
• Synonyms: B-(3,4-DIHYDROXYPHENYL)PROPIONIC ACID ETHYL ESTER;ETHYL B-(3,4-DIHYDROXYPHENYL)PROPIONATE;ETHYL BETA-(3,4-DIHYDROXYPHENYL)PROPIONATE;ETHYL HYDROCAFFEATE;LABOTEST-BB LT00452977;3-(3,4-DIHYDROXY-PHENYL)-PROPIONIC ACID ETHYL ESTER;ethyl 3-(3,4-dihydroxyphenyl)propionate;Ethyl 3,4-dihydroxyhydrocinnamate
• CAS NO: 3967-57-5
• Molecular Formula: C11H14O4
• Molecular Weight: 210.23
• EINECS: 223-585-6
• Product Categories: Aromatic Esters
• Mol File: 3967-57-5.mol

Chemical Properties

• Boiling Point: 360℃
• Flash Point: 139℃
• Appearance: /
• Density: 1.221
• Vapor Pressure: 1.12E-05mmHg at 25°C
• Refractive Index: 1.554
• CAS DataBase Reference: ETHYL HYDROCAFFEATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL HYDROCAFFEATE(3967-57-5)
• EPA Substance Registry System: ETHYL HYDROCAFFEATE(3967-57-5)

Safety Data

• Hazardous Substances Data: 3967-57-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl hydrocaffeate is used as a pharmaceutical compound for its potential role in protecting against oxidative stress, reducing inflammation, and promoting overall health. Its antioxidant and anti-inflammatory properties make it a promising candidate for the development of treatments for various health conditions.
Used in Nutraceutical Industry:
Ethyl hydrocaffeate is used as a nutraceutical ingredient for its potential health benefits, including protection against oxidative stress, reduction of inflammation, and promotion of overall health. Its presence in various plants, such as coffee, makes it a natural and appealing option for incorporation into health supplements and functional foods.
Used in Neuroprotection:
Ethyl hydrocaffeate is used as a neuroprotective agent for its potential role in the prevention and treatment of neurodegenerative diseases. Its antioxidant and anti-inflammatory properties may contribute to the protection of neurons and the maintenance of cognitive function, making it a valuable compound for research and development in this area.

InChI:InChI=1/C11H14O4/c1-2-15-11(14)6-4-8-3-5-9(12)10(13)7-8/h3,5,7,12-13H,2,4,6H2,1H3

Upstream product

• 64-17-5 ethanol 
• 1078-61-1 dihydrocaffeic acid 
• 501-97-3 4-hydroxyphenylpropionic acid 
• 4046-02-0 ethyl 4-hydroxy-3-methoxycinnamate 
• 23795-02-0 3-(4-hydroxy-phenyl)-propionic acid ethyl ester 
• 203571-40-8 3-(3,4-bis-benzyloxy-phenyl)-acrylic acid ethyl ester 
• 2107-70-2 3,4-methoxycinnamic acid 

Downstream Products

• 1075748-12-7 3-(3,4-diethoxyphenyl)propionic acid ethyl ester 
• 1075748-14-9 [3-(3,4-diethoxyphenyl)propyl]methylamine 
• 1075748-13-8 3-(3,4-diethoxyphenyl)-N-methylpropionamide 
• 79622-99-4 3-(3,4-diethoxyphenyl)propionic acid 
• 820215-69-8 ethyl 3-{3,4-bis(2-propynyloxy)phenyl}propionate 
• 7116-48-5 3-benzo[1,3]dioxol-5-yl-propionic acid ethyl ester 

Relevant articles and documents

Chemo- and Regioselective Hydrogenolysis of Diaryl Ether C-O Bonds by a Robust Heterogeneous Ni/C Catalyst: Applications to the Cleavage of Complex Lignin-Related Fragments

We report the chemo- and regioselective hydrogenolysis of the C-O bonds in di-ortho-substituted diaryl ethers under the catalysis of a supported nickel catalyst. The catalyst comprises heterogeneous nickel particles supported on activated carbon and furnishes arenes and phenols in high yields without hydrogenation. The high thermal stability of the embedded metal particles allows C-O bond cleavage to occur in highly substituted diaryl ether units akin to those in lignin. Preliminary mechanistic experiments show that this catalyst undergoes sintering less readily than previously reported catalyst particles that form from a solution of [Ni(cod)2].

Catechol-based substrates of chalcone synthase as a scaffold for novel inhibitors of PqsD

A new strategy for treating Pseudomonas aeruginosa infections could be disrupting the Pseudomonas Quinolone Signal (PQS) quorum sensing (QS) system. The goal is to impair communication among the cells and, hence, reduce the expression of virulence factors and the formation of biofilms. PqsD is an essential enzyme for the synthesis of PQS and shares some features with chalcone synthase (CHS2), an enzyme expressed in Medicago sativa. Both proteins are quite similar concerning the size of the active site, the catalytic residues and the electrostatic surface potential at the entrance of the substrate tunnel. Hence, we evaluated selected substrates of the vegetable enzyme as potential inhibitors of the bacterial protein. This similarity-guided approach led to the identification of a new class of PqsD inhibitors having a catechol structure as an essential feature for activity, a saturated linker with two or more carbons and an ester moiety bearing bulky substituents. The developed compounds showed PqsD inhibition with IC50 values in the single-digit micromolar range. The binding mode of these compounds was investigated by Surface Plasmon Resonance (SPR) experiments revealing that their interaction with the protein is not influenced by the presence of the anthranilic acid bound to active site cysteine. Importantly, some compounds reduced the signal molecule production in cellulo.

Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses

Hydroxytyrosol and dihydrocaffeoyl catechols with lipophilic properties have been synthesized in high yield using tyrosinase immobilized on multi-walled carbon nanotubes by the Layer-by-Layer technique. All synthesized catechols were evaluated against a large panel of DNA and RNA viruses, including Poliovirus type 1, Echovirus type 9, Herpes simplex virus type 1 (HSV-1), Herpes simplex virus type 2 (HSV-2), Coxsackievirus type B3 (Cox B3), Adenovirus type 2 and type 5 and Cytomegalovirus (CMV). A significant antiviral activity was observed in the inhibition of HSV-1, HSV-2, Cox B3 and CMV. The mechanism of action of the most active dihydrocaffeoyl derivative was investigated against a model of HSV-1 infection.

Design, synthesis and biological evaluation of small molecular polyphenols as entry inhibitors against H5N1

To find novel compounds against H5N1, three series of known or novel small molecular polyphenols were synthesized and tested in vitro for anti-H5N1 activity. In addition, the preliminary structure-antiviral activity relationships were elaborated. The results showed that some small molecular polyphenols had better anti-H5N1 activity, and could serve as novel virus entry inhibitors against H 5N1, likely targeting to HA2 protein. Noticeably, compound 4a showed the strongest activity against H5N1 among these compounds, and the molecular modeling analysis also suggested that this compound might target to HA2 protein. Therefore, compound 4a is well qualified to serve as a lead compound or scaffold for the further development of H 5N1 entry inhibitor.

Tyrosinase and Layer-by-Layer supported tyrosinases in the synthesis of lipophilic catechols with antiinfluenza activity

Catechol derivatives with lipophilic properties have been selectively synthesized by tyrosinase in high yield avoiding long and tedious protection/deprotection steps usually required in traditional procedures. The synthesis was effective also with immobilized tyrosinase able to perform for more runs. The novel catechols were evaluated against influenza A virus, that continue to represent a severe threat worldwide. A significant antiviral activity was observed in derivatives characterized by antioxidant activity and long carbon alkyl side-chains, suggesting the possibility of a new inhibition mechanism based on both redox and lipophilic properties.

CATECHOL-BASED DERIVATIVES FOR TREATING OR PREVENTING DIABETICS

The present invention provides a catechol-based derivative and a pharmaceutical acceptable salt therefrom and a solvate therefrom. A pharmaceutical composition for preventing or treating diabetics and ischemics, comprising a catechol-based derivative of formula (I) and at least one selected from the group consisting of a pharmaceutical excipient, a diluent and a carrier.

AMIDES AND METHOD FOR PLANT DISEASE CONTROL WITH THE SAME

N-(α-cyanobenzyl)amide compounds represented by the formula (1): wherein R1 represents a hydrogen atom; a halogen atom; a C1-C6 alkyl group optionally substituted with a halogen atom or the like; or the like, R2 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group or the like, R3 represents a hydrogen atom or the like, R4 represents a C1-C4 alkyl group, a C3-C4 alkenyl group or the like, R5 represents a C1-C4 alkyl group, a C3-C4 alkenyl group, or the like, R6 represents a hydrogen atom or the like, R7 represents a hydrogen atom or the like, R8 represents a hydrogen atom or the like, R9 represents a hydrogen atom or the like, R10 represents a hydrogen atom or the like, R11 represents a hydrogen atom or the like, and R12 represents a hydrogen atom or the like, have excellent control activities against plant diseases.

Mechanism of toxicity of esters of caffeic and dihydrocaffeic acids

Ten esters each of caffeic acid and dihydrocaffeic acid have recently been synthesized. Cytotoxicity evaluations of these esters versus L1210 leukemia and MCF-7 breast cancer cells in culture have led to the delineation of substantially different QSAR for each series. The L1210 QSAR for dihydrocaffeic acid esters resembles the QSAR obtained for simple phenols and estrogenic phenols. However, the QSAR pertaining to the caffeic acid esters differs considerably from its sister QSAR. This difference may be attributed to the presence of the olefinic linkage in the side chain. The octyl ester of caffeic acid is nearly ten times as toxic to the leukemia cells than the widely studied phenethyl ester, CAPE.