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Ethyl 3,4-dihydroxycinnamate

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Ethyl 3,4-dihydroxycinnamate Basic information
Product Name:Ethyl 3,4-dihydroxycinnamate
Synonyms:2-Propenoicacid,3-(3,4-dihydroxyphenyl)-,ethylester,(2E)-(9CI);E-Caffeic acid ethyl ester;Zinc01614326;Ethyl-3,4-dihydroxycinnamte;2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, ethyl ester, (2E)-;ethyl (E)-caffeate;Ethyl 3,4-dihydroxycinnamate,97%;Ethyl transcaffeate,Ethyl trans caffeate
CAS:66648-50-8
MF:C11H12O4
MW:208.21
EINECS:
Product Categories:ALCOHOL;Aromatic Esters
Mol File:66648-50-8.mol
Ethyl 3,4-dihydroxycinnamate Structure
Ethyl 3,4-dihydroxycinnamate Chemical Properties
Melting point 147~151℃
Boiling point 148-149 °C
density 1.271±0.06 g/cm3(Predicted)
storage temp. 2-8°C
pka8.71±0.18(Predicted)
form Off-white to brown solid.
color White to off-white
biological sourceplant
Major Applicationmetabolomics
vitamins, nutraceuticals, and natural products
InChI1S/C11H12O4/c1-2-15-11(14)6-4-8-3-5-9(12)10(13)7-8/h3-7,12-13H,2H2,1H3/b6-4+
InChIKeyWDKYDMULARNCIS-GQCTYLIASA-N
SMILESO(CC)C(=O)\C=C\c1cc(c(cc1)O)O
LogP2.418 (est)
Safety Information
Hazard Codes Xn
Risk Statements 36/37/38-22
Safety Statements 26-36
WGK Germany WGK 3
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
MSDS Information
ProviderLanguage
ALFA English
Ethyl 3,4-dihydroxycinnamate Usage And Synthesis
UsesEthyl 3,4-dihydroxycinnamate shows anti-inflammatory, immunomodulatory, and anti-carcinogenic properties. It is a potent and specific inhibitor of NF-κB and its downstream inflammatory mediators: NOS2 (inducible nitric oxide synthase; NOS; NOS II), Cox-2 (cyclooxygenase-2), and prostaglandin E2 (PGE2). Ethyl 3,4-Dihydroxycinnamate prevents DNA single-strand breaks caused by H2O2.
DefinitionChEBI: Ethyl trans-caffeate is an ethyl ester resulting from the formal condensation of the carboxy group of trans-caffeic acid with ethanol. It has a role as an anti-inflammatory agent and an antineoplastic agent. It is an alkyl caffeate ester and an ethyl ester. It is functionally related to a trans-caffeic acid.
General DescriptionThis substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG
Biological ActivityEthyl dihydroxycinnamate exhibits potent cytotoxicity, inhibits COX-2 and P-hydroxybenzoic acid, both involved in inflammation and cytokine synthesis. It demonstrates antibacterial efficacy against MRSA and Bacillus subtilis and inhibits cancer cell growth, countering tumor formation.
Ethyl 3,4-dihydroxycinnamate Preparation Products And Raw materials
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