Ethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate
Basic information
- CAS
102-37-4- Standard SMILES
CCOC(=O)C=Cc1ccc(O)c(O)c1- InChIKey
WDKYDMULARNCIS-UHFFFAOYSA-N- Molecular formula
- C11H12O4
- Average molar mass
- 208.21 g/mol
- Monoisotopic mass
- 208.07355886
Overview
ethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate has been reported in Adenocaulon himalaicum, Artemisia minor, and other organisms with data available.
Names & identifiers
- Preferred name
- Ethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate
- IUPAC
- ethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate
- English name
- Ethyl caffeate
- Molecular formula
- C11H12O4
- Molecular weight
- 208.21
Names & synonyms
ethyl 3-(3,4-dihydroxyphenyl)prop-2-enoateMFCD000457543-(3,4-Dihydroxy-phenyl)-acrylic acid ethyl esterSCHEMBL782033orb1221903SCHEMBL30286241WDKYDMULARNCIS-UHFFFAOYSA-NDB-054945S5640ethyl 3-(3',4'-dihydroxyphenyl)-2-propenoateCaffeic acid ethyl esterEthyl 3-(3,4-dihydroxyphenyl)acrylate
Show more names
Ethyl caffeateEthyl caffeoateCaffeoyl acetateETHYL CAFFEATE bCaffeoylEthylEster4-dihydroxyphenyl)acrylateCaffeic acidETHYL CAFFEATECAFFEIC ACID ETHYLESTER(RG)
Database identifiers
- CAS
102-37-4- PubChem CID
- 66883
Properties
Computed structural properties
- XLogP
- 2.6
- Topological polar surface area
- 66.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 237
Physicochemical properties
- Melting point
- 149.5 °C · 149.5 °C
- Boiling point
- 377 · 377.0±32.0 °C(Predicted)
- Density
- 1.271 · 1.271±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- 250 mg/mL · DMSO: 250 mg/mL (1200.71 mM)
- form
- Solid
- pka
- 8.71 · 8.71±0.18(Predicted)
- color
- Light yellow to yellow
- Cosmetics Ingredients Functions
- SKIN CONDITIONING
- LogP
- 2.56 · 2.560
- FDA UNII
- 76 GBB1JU5Y · 76GBB1JU5Y
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H332-H335
- Precautionary statements
- 280 · P280-P305+P351+P338-P310
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H332-H335
- Precautionary statements
- P280-P305+P351+P338-P310
Chemistry & industry
Applications
DescriptionEthyl Caffeate is a natural phenolic compound isolated from Bidens pilosa. It suppresses NF-κB activation and its downstream inflammatory mediators, inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), and prostaglandin E2 (PGE2) in vitro or in mouse skin.
UsesFood antioxidant.
Upstream & downstream products
Upstream raw materials
Additional notes
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.
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