Ethyl trans-caffeate

Inquiry

For Research Use Only.

Category

Phenylpropanoids

Cat.No.

NP5399

CAS

66648-50-8

Product Name

Ethyl trans-caffeate

Structure

Product Details

Description

Ethyl trans-caffeate is isolated from the roots of Ferula assafoetida L. It has a role as an anti-inflammatory agent and an antineoplastic agent.

Synonyms

2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, ethyl ester, (2E)-; 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, ethyl ester, (E)-; (E)-Caffeic acid ethyl ester; Ethyl caffeate; Ethyl (E)-3-(3,4-dihydroxyphenyl)acrylate; trans-Caffeic acid ethyl ester; trans-Caffeoyl ethyl ester; (E)-ethyl 3-(3,4-dihydroxyphenyl)acrylate; (E)-Ethyl Dihydroxycinnamate

IUPAC Name

ethyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Molecular Weight

208.21

Molecular Formula

C11H12O4

Canonical SMILES

CCOC(=O)C=CC1=CC(=C(C=C1)O)O

InChI

InChI=1S/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+

InChIKey

WDKYDMULARNCIS-GQCTYLIASA-N

Boiling Point

148-149°C

Melting Point

147-148°C

Purity

98%

Density

1.271±0.06 g/cm3

Solubility

Soluble in Ethanol

Appearance

Powder

Application

anti-inflammatory activity;

Storage

2-8°C

Form

Off-white to brown solid.

Hazard Class

pKa

8.71±0.18(Predicted)

Risk Statements

36/37/38-22

Safety Statements

26-36

Uses

Ethyl 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.

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