ChemFOnt: Showing chemical card for Caffeic acid ester (CFc000281860)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:33:39 UTC

Chemfont ID

CFc000281860

Molecule Identification

Common Name

Caffeic acid ester

Definition

Caffeic acid ester, also known as caffeic acid phenethyl ester or cape, 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 ester is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Caffeic acid ester can be found in corn, flaxseed, oat, and peach, which makes caffeic acid ester a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Phenylethyl (2E)-3-(3,4-dihydroxyphenyl)acrylate	ChEBI
2-Phenylethyl caffeate	ChEBI
Caffeic acid phenethyl ester	ChEBI
CAPE	ChEBI
2-Phenylethyl (2E)-3-(3,4-dihydroxyphenyl)acrylic acid	Generator
2-Phenylethyl caffeic acid	Generator
Caffeate phenethyl ester	Generator
Phenethyl caffeic acid	Generator
CAPE compound	MeSH
CAPEEE	MeSH
Caffeic acid phenyl ester	MeSH
Phenyl caffeate	MeSH
Caffeate ester	Generator
Phenethyl caffeate	MeSH

Chemical Formula

C₁₇H₁₆O₄

Average Molecular Weight

284.3065

Monoisotopic Molecular Weight

284.104859

IUPAC Name

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

Traditional Name

caffeic acid phenethyl ester

CAS Registry Number

None

SMILES

[H]\C(=C(\[H])C1=CC(O)=C(O)C=C1)C(=O)OCCC1=CC=CC=C1

InChI Identifier

InChI=1S/C17H16O4/c18-15-8-6-14(12-16(15)19)7-9-17(20)21-11-10-13-4-2-1-3-5-13/h1-9,12,18-19H,10-11H2/b9-7+

InChI Key

SWUARLUWKZWEBQ-VQHVLOKHSA-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

alkyl caffeate ester (CHEBI:8062 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302344)

Food

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)
Oat (FooDB: FOOD00022)

Herb and spice

Oilseed crop

Flaxseed (FooDB: FOOD00101)

Fruit

Drupe

Peach (FooDB: FOOD00149)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.063 g/L	ALOGPS
logP	3.65	ALOGPS
logP	3.92	ChemAxon
logS	-3.7	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	6	ChemAxon
Refractivity	81.16 m³·mol⁻¹	ChemAxon
Polarizability	30.74 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon