ChemFOnt: Showing chemical card for Caffeic acid ethyl ester (CFc000281228)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:24 UTC

Chemfont ID

CFc000281228

Molecule Identification

Common Name

Caffeic acid ethyl ester

Definition

Caffeic acid ethyl ester, also known as (E)-ethyl 3,4-dihydroxycinnamate or (E)-ethyl caffeate, belongs to coumaric acids and derivatives class of compounds. Those are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Caffeic acid ethyl ester is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Caffeic acid ethyl ester can be found in eggplant and vinegar, which makes caffeic acid ethyl ester a potential biomarker for the consumption of these food products. Ethyl caffeate is an ester of an hydroxycinnamic acid, a naturally occurring organic compound .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(e)-Ethyl 3,4-dihydroxycinnamate	ChEBI
(e)-Ethyl 3-(3,4-dihydroxyphenyl)acrylate	ChEBI
(e)-Ethyl caffeate	ChEBI
Ethyl (2E)-3-(3,4-dihydroxyphenyl)acrylate	ChEBI
Ethyl 3,4-dihydroxycinnamate	ChEBI
Ethyl caffeate	ChEBI
(e)-Ethyl 3,4-dihydroxycinnamic acid	Generator
(e)-Ethyl 3-(3,4-dihydroxyphenyl)acrylic acid	Generator
(e)-Ethyl caffeic acid	Generator
Ethyl (2E)-3-(3,4-dihydroxyphenyl)acrylic acid	Generator
Ethyl 3,4-dihydroxycinnamic acid	Generator
Ethyl caffeic acid	Generator
Ethyl trans-caffeic acid	Generator
Ethyl 1-(3'4'-dihydroxyphenyl)propenate	ChEMBL
Ethyl 1-(3'4'-dihydroxyphenyl)propenic acid	Generator
Ethyl cinnamic acid,3,4-dihydroxy	Generator
Caffeate ethyl ester	Generator
Ethyl trans-caffeate	MeSH

Chemical Formula

C₁₁H₁₂O₄

Average Molecular Weight

208.2106

Monoisotopic Molecular Weight

208.073558872

IUPAC Name

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

Traditional Name

ethyl cinnamate,3,4-dihydroxy

CAS Registry Number

102-37-4

SMILES

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

InChI Identifier

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+

InChI Key

WDKYDMULARNCIS-GQCTYLIASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

hydroxycinnamic acid (CHEBI:69656 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301712)

Food

Vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)

Baking good

Seasoning

Vinegar (FooDB: FOOD00628)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.81 g/L	ALOGPS
logP	2.6	ALOGPS
logP	2.26	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	56.54 m³·mol⁻¹	ChemAxon
Polarizability	21.58 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0301712

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000243

KNApSAcK ID

C00030221

Chemspider ID

4476132

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ethyl_caffeate

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

132714

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Caffeic acid ethyl ester (CFc000281228)

MOL for CFc000281228 (Caffeic acid ethyl ester)

3D MOL for CFc000281228 (Caffeic acid ethyl ester)

3D SDF for CFc000281228 (Caffeic acid ethyl ester)

3D-SDF for CFc000281228 (Caffeic acid ethyl ester)

PDB for CFc000281228 (Caffeic acid ethyl ester)

3D PDB for CFc000281228 (Caffeic acid ethyl ester)

SMILES for CFc000281228 (Caffeic acid ethyl ester)

INCHI for CFc000281228 (Caffeic acid ethyl ester)

Structure for CFc000281228 (Caffeic acid ethyl ester)

3D Structure for CFc000281228 (Caffeic acid ethyl ester)