ChemFOnt: Showing chemical card for trans-o-Coumaric acid (CFc000333110)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:12:53 UTC

Chemfont ID

CFc000333110

Molecule Identification

Common Name

trans-o-Coumaric acid

Definition

Occurs in many plants e.g. Melilotus officinalis (sweet clover) Coumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers, o-coumaric acid, m-coumaric acid, and p-coumaric acid, that differ by the position of the hydroxy substitution of the phenyl group. p-Coumaric acid is the most abundant isomer of the three in nature. trans-o-Coumaric acid is found in green vegetables.

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

Not Available

Exogenous (HMDB: HMDB0002641)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Fruit

Pome

Apple (FooDB: FOOD00105)

Fruits (HMDB: HMDB0002641)

Berry

American cranberry (FooDB: FOOD00192)

Beverage

Other beverage

Fruit juice (FooDB: FOOD00763)

Alcoholic beverage

Red wine (HMDB: HMDB0002641)

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0002641)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0002641)

Tea

Tea products (HMDB: HMDB0002641)

Fat and oil

Olive oil (HMDB: HMDB0002641)

Vegetable

Vegetables (HMDB: HMDB0002641)

Fruit vegetable

Olive (FooDB: FOOD00121)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Legumes (HMDB: HMDB0002641)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0002641)

Nut

Nuts (HMDB: HMDB0002641)

Process

Not Available

Role

Not Available

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