ChemFOnt: Showing chemical card for 2-Hydroxycinnamic acid (CFc000001667)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:21 UTC

Chemfont ID

CFc000001667

Molecule Identification

Common Name

2-Hydroxycinnamic acid

Definition

2-coumaric acid, also known as o-coumaric acid, is a monohydroxycinnamic acid in which the hydroxy substituent is located at C-2 of the phenyl ring. It has a role as a plant metabolite. It is a conjugate acid of a 2-coumarate. It is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers of coumaric acids: o-coumaric acid, m-coumaric acid, and p-coumaric acid, that differ by the position of the hydroxy substitution of the phenyl group. 2-Hydroxycinnamic acid 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. 2-Hydroxycinnamic acid exists in all living organisms, ranging from bacteria to humans. 2-Hydroxycinnamic acid has been found in a few different foods, such as corns, hard wheats, and olives and in a lower concentration in pomegranates, american cranberries, and peanuts. 2-Hydroxycinnamic acid has also been detected, but not quantified in several different foods, such as carrots, soy beans, ryes, rye bread, and turmerics.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2E)-3-(2-Hydroxyphenyl)-2-propenoic acid	ChEBI
(2E)-3-(2-HYDROXYPHENYL)acrylIC ACID	ChEBI
(e)-2-Hydroxycinnamic acid	ChEBI
(e)-3-(2-Hydroxy-phenyl)-acrylic acid	ChEBI
(e)-3-(2-Hydroxyphenyl)-2-propenoic acid	ChEBI
(e)-O-Hydroxycinnamic acid	ChEBI
2-Coumarate	ChEBI
2-Coumaric acid	ChEBI
2-Hydroxycinnamate	ChEBI
O-Coumaric acid	ChEBI
O-Hydroxy-trans-cinnamic acid	ChEBI
trans-2-Hydroxycinnamate	ChEBI
trans-2-Hydroxycinnamic acid	ChEBI
trans-O-Hydroxycinnamic acid	ChEBI
(2E)-3-(2-Hydroxyphenyl)-2-propenoate	Generator
(2E)-3-(2-HYDROXYPHENYL)acrylate	Generator
(e)-2-Hydroxycinnamate	Generator
(e)-3-(2-Hydroxy-phenyl)-acrylate	Generator
(e)-3-(2-Hydroxyphenyl)-2-propenoate	Generator
(e)-O-Hydroxycinnamate	Generator
O-Coumarate	Generator
O-Hydroxy-trans-cinnamate	Generator
trans-O-Hydroxycinnamate	Generator
2-Hydroxycinnamic acid, (e)-isomer	MeSH
Ortho-hydroxycinnamic acid	MeSH
2-Hydroxycinnamic acid, (Z)-isomer	MeSH
3-(2-Hydroxyphenyl)prop-2-enoate	HMDB
3-(2-Hydroxyphenyl)prop-2-enoic acid	HMDB
O-Hydroxycinnamate	HMDB
O-Hydroxycinnamic acid	HMDB
ortho-Hydroxycinnamate	HMDB
trans-O-Coumarate	HMDB
trans-O-Coumaric acid	HMDB
2-Hydroxycinnamic acid	Generator
trans-2-Coumarate	Generator, HMDB
(E)-3-(2-Hydroxyphenyl)acrylic acid	HMDB
3-(2-Hydroxyphenyl)-2-propenoic acid	HMDB
o-Hydroxycinnamic acid	HMDB
trans-o-Coumaric acid	HMDB
3-(2-Hydroxyphenyl)acrylic acid	HMDB
trans-2-Coumaric acid	HMDB
(2E)-3-(2-Hydroxyphenyl)prop-2-enoic acid	HMDB
2'-Hydroxycinnamic acid	HMDB

Chemical Formula

C₉H₈O₃

Average Molecular Weight

164.158

Monoisotopic Molecular Weight

164.047344122

IUPAC Name

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

Traditional Name

O-coumaric acid

CAS Registry Number

614-60-8

SMILES

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

InChI Identifier

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

InChI Key

PMOWTIHVNWZYFI-AATRIKPKSA-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-4-unsubstituted benzenoid
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

phenols (CHEBI:18125 )
2-coumaric acid (CHEBI:18125 )
Monolignols (C01772 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 19812218)

Excreta

Biofluid or Excreta

Urine (PMID: 19812218)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002641)

Source

Exogenous

Exogenous (HMDB: HMDB0002641)

Food

Food (HMDB: HMDB0002641)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)
Grape wine (FooDB: FOOD00612)

Fruit

Pome

Apple (FooDB: FOOD00105)
Pear (FooDB: FOOD00152)

Berry

Other fruit

Date (FooDB: FOOD00135)

Tropical fruit

Pomegranate (FooDB: FOOD00151)

Drupe

Sweet cherry (FooDB: FOOD00145)

Cereal and cereal product

Cereal

Barley (FooDB: FOOD00088)
Corn (FooDB: FOOD00205)
Rye (FooDB: FOOD00169)
Common wheat (FooDB: FOOD00187)
Hard wheat (FooDB: FOOD00242)

Leavened bread

Rye bread (FooDB: FOOD00809)

Soy

Soy bean (FooDB: FOOD00085)

Vegetable

Root vegetable

Carrot (FooDB: FOOD00245)

Fruit vegetable

Olive (FooDB: FOOD00121)
Garden tomato (var.) (FooDB: FOOD00173)

Herb and spice

Herb

Oilseed crop

Sesame (FooDB: FOOD00170)
Evening primrose (FooDB: FOOD00120)

Spice

Turmeric (FooDB: FOOD00068)

Nut

Peanut (FooDB: FOOD00016)

Pulse

Pea

Common pea (FooDB: FOOD00141)

Endogenous

Endogenous (HMDB: HMDB0002641)

Plant

Process

Not Available

Role

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.15 g/L	ALOGPS
logP	1.9	ALOGPS
logP	1.83	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4.04	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	16.11 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

HMDB0002641

DrugBank ID

DB01650

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

O-Coumaric_acid

METLIN ID

6727

PubChem Compound

637540

PDB ID

Not Available

ChEBI ID

18125

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Adams, Roger; Bockstahler, Theodore E. Preparation and reactions of o-hydroxycinnamic acids and esters. Journal of the American Chemical Society (1952), 74 5346-8.

Showing chemical card for 2-Hydroxycinnamic acid (CFc000001667)

MOL for CFc000001667 (2-Hydroxycinnamic acid)

3D MOL for CFc000001667 (2-Hydroxycinnamic acid)

3D SDF for CFc000001667 (2-Hydroxycinnamic acid)

3D-SDF for CFc000001667 (2-Hydroxycinnamic acid)

PDB for CFc000001667 (2-Hydroxycinnamic acid)

3D PDB for CFc000001667 (2-Hydroxycinnamic acid)

SMILES for CFc000001667 (2-Hydroxycinnamic acid)

INCHI for CFc000001667 (2-Hydroxycinnamic acid)

Structure for CFc000001667 (2-Hydroxycinnamic acid)

3D Structure for CFc000001667 (2-Hydroxycinnamic acid)