ChemFOnt: Showing chemical card for Hydroxycinnamic acid (CFc000333416)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:13:29 UTC

Chemfont ID

CFc000333416

Molecule Identification

Common Name

Hydroxycinnamic acid

Definition

Trans-4-coumaric acid, also known as 4-hydroxycinnamic acid or trans-P-hydroxycinnamate, is a member of the class of compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. Trans-4-coumaric acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Trans-4-coumaric acid can be found in a number of food items such as garden onion, lowbush blueberry, german camomile, and garden rhubarb, which makes trans-4-coumaric acid a potential biomarker for the consumption of these food products. Trans-4-coumaric acid can be found primarily in blood, feces, and urine, as well as in human fibroblasts tissue. Trans-4-coumaric acid exists in all eukaryotes, ranging from yeast to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2E)-3-(4-Hydroxyphenyl)acrylic acid	ChEBI
(e)-3-(4-Hydroxyphenyl)-2-propenoic acid	ChEBI
(e)-p-Coumaric acid	ChEBI
(e)-p-Hydroxycinnamic acid	ChEBI
4'-HYDROXYCINNAMIC ACID	ChEBI
Naringeninic acid	ChEBI
p-Coumaric acid	ChEBI
trans-p-Coumaric acid	ChEBI
trans-p-Coumarinic acid	ChEBI
trans-p-Hydroxycinnamate	ChEBI
trans-p-Hydroxycinnamic acid	ChEBI
trans-4-Hydroxycinnamate	Kegg
4-Hydroxycinnamate	Kegg
(2E)-3-(4-Hydroxyphenyl)acrylate	Generator
(e)-3-(4-Hydroxyphenyl)-2-propenoate	Generator
(e)-p-Coumarate	Generator
(e)-p-Hydroxycinnamate	Generator
4'-HYDROXYCINNAMate	Generator
Naringeninate	Generator
p-Coumarate	Generator
trans-p-Coumarate	Generator
trans-p-Coumarinate	Generator
4-Coumaric acid, (e)-isomer	MeSH
4-Coumaric acid, (Z)-isomer	MeSH
4-Coumaric acid, disodium salt	MeSH
p-Coumaryl alcohol	MeSH
p-Hydroxycinnamic acid	MeSH
Para-coumaric acid	MeSH
trans-3-(4'-Hydroxyphenyl)-2-propenoic acid	MeSH
trans-HPPA	MeSH
3-(4-Hydroxyphenyl)-2-propenoate	HMDB
3-(4-Hydroxyphenyl)-2-propenoic acid	HMDB
3-(4-Hydroxyphenyl)acrylate	HMDB
3-(4-Hydroxyphenyl)acrylic acid	HMDB
4-Coumarate	HMDB
4-Hydroxy cinnamate	HMDB
4-Hydroxy cinnamic acid	HMDB
4-Hydroxyphenylpropenoate	HMDB
4-Hydroxyphenylpropenoic acid	HMDB
b-[4-Hydroxyphenyl]acrylate	HMDB
b-[4-Hydroxyphenyl]acrylic acid	HMDB
beta-[4-Hydroxyphenyl]acrylate	HMDB
beta-[4-Hydroxyphenyl]acrylic acid	HMDB
cis-P-Coumarate	HMDB
Hydroxycinnamate	HMDB
Hydroxycinnamic acid	HMDB
P-Cumarate	HMDB
P-Cumaric acid	HMDB
P-Hydroxycinnamate	HMDB
P-Hydroxyphenylacrylate	HMDB
P-Hydroxyphenylacrylic acid	HMDB
Para coumarate	HMDB
Para coumaric acid	HMDB
Para-coumarate	HMDB
4-Hydroxycinnamic acid	ChEBI
trans-4-Coumarate	Generator, HMDB
(2E)-3-(4-Hydroxyphenyl)-2-propenoic acid	HMDB
(2E)-3-(4-Hydroxyphenyl)prop-2-enoic acid	HMDB
(E)-3-(4-Hydroxyphenyl)acrylic acid	HMDB
(E)-4-Hydroxycinnamic acid	HMDB
4’-Hydroxycinnamic acid	HMDB
p-Cumaric acid	HMDB
p-Hydroxy-trans-cinnamic acid	HMDB
p-Hydroxyphenylacrylic acid	HMDB
p-trans-Coumaric acid	HMDB
trans-3-(4-Hydroxyphenyl)-2-propenoic acid	HMDB
trans-4-Coumaric acid	HMDB
β-[4-Hydroxyphenyl]acrylic acid	HMDB

Chemical Formula

C₉H₈O₃

Average Molecular Weight

164.158

Monoisotopic Molecular Weight

164.047344122

IUPAC Name

(2E)-3-(4-hydroxyphenyl)prop-2-enoic acid

Traditional Name

coumaric acid

CAS Registry Number

7400-08-0 501-98-4

SMILES

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

InChI Identifier

InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+

InChI Key

NGSWKAQJJWESNS-ZZXKWVIFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids

Alternative Parents

Substituents

Cinnamic acid
Coumaric acid
Coumaric acid or derivatives
Hydroxycinnamic acid
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

4-coumaric acid (CHEBI:32374 )
Paracoumaryl alcohol derivatives (C00811 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0002035)

Food

Fruit

Pome

Apple (FooDB: FOOD00105)

Berry

Cereal and cereal product

Leavened bread

Wheat bread (FooDB: FOOD00808)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)
Apple cider (FooDB: FOOD00615)

Other beverage

Fruit juice (FooDB: FOOD00763)

Coffee and coffee product

Coffee

Coffee (FooDB: FOOD00058)

Vegetable

Leaf vegetable

Endive (FooDB: FOOD00048)

Fruit vegetable

Olive (FooDB: FOOD00121)
Garden tomato (FooDB: FOOD00171)

Herb and spice

Spice

Horseradish (FooDB: FOOD00018)

Nut

Peanut (FooDB: FOOD00016)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.02 g/L	ALOGPS
logP	1.74	ALOGPS
logP	1.83	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	45.04 m³·mol⁻¹	ChemAxon
Polarizability	16.43 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