ChemFOnt: Showing chemical card for trans-m-Coumaric acid (CFc000333111)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:12:53 UTC

Chemfont ID

CFc000333111

Molecule Identification

Common Name

trans-m-Coumaric acid

Definition

Present in roots of Citrus sinensis (orange), Citrus limon (lemon) and Citrus paradisi (grapefruit) 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-m-Coumaric acid is found in citrus.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2E)-3-(3-Hydroxyphenyl)-2-propenoic acid	ChEBI
(2E)-3-(3-Hydroxyphenyl)acrylic acid	ChEBI
(e)-3-(3-Hydroxyphenyl)-2-propenoic acid	ChEBI
m-Hydroxycinnamic acid	ChEBI
trans-3-Hydroxycinnamate	ChEBI
trans-3-Hydroxycinnamic acid	ChEBI
(2E)-3-(3-Hydroxyphenyl)prop-2-enoate	Kegg
(2E)-3-(3-Hydroxyphenyl)-2-propenoate	Generator
(2E)-3-(3-Hydroxyphenyl)acrylate	Generator
(e)-3-(3-Hydroxyphenyl)-2-propenoate	Generator
3-Coumarate	Generator
m-Hydroxycinnamate	Generator
(2E)-3-(3-Hydroxyphenyl)prop-2-enoic acid	Generator
m-Coumarate	Generator
3'-Hydroxycinnamate	HMDB
3'-Hydroxycinnamic acid	HMDB
3-(3-Hydroxyphenyl)-2-propenoate	HMDB
3-(3-Hydroxyphenyl)-2-propenoic acid	HMDB
3-(3-Hydroxyphenyl)acrylate	HMDB
3-(3-Hydroxyphenyl)acrylsaeure	HMDB
3-(3-Hydroxyphenyl)prop-2-enoate	HMDB
3-(3-Hydroxyphenyl)prop-2-enoic acid	HMDB
3-Hydroxycinnamate	HMDB
3-Hydroxycinnamic acid	HMDB
m-Hydroxy-cinnamate	HMDB
m-Hydroxy-cinnamic acid	HMDB
3-Coumaric acid, (e)-isomer	MeSH, HMDB
Meta-coumaric acid	MeSH, HMDB
(E)-3-(3-Hydroxyphenyl)acrylic acid	HMDB
(E)-3-Hydroxycinnamic acid	HMDB
trans-3-(m-Hydroxyphenyl)-2-propenoic acid	HMDB
trans-m-Coumaric acid	HMDB
trans-m-Hydroxycinnamic acid	HMDB
trans-3-Coumarate	HMDB

Chemical Formula

C₉H₈O₃

Average Molecular Weight

164.158

Monoisotopic Molecular Weight

164.047344122

IUPAC Name

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

Traditional Name

m-coumaric acid

CAS Registry Number

14755-02-3

SMILES

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

InChI Identifier

InChI=1S/C9H8O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6,10H,(H,11,12)/b5-4+

InChI Key

KKSDGJDHHZEWEP-SNAWJCMRSA-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

3-coumaric acid (CHEBI:32357 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0001713)

Food

Vegetable

Cabbage

Broccoli (FooDB: FOOD00034)

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Spinach (FooDB: FOOD00178)

Fruit vegetable

Olive (FooDB: FOOD00121)

Coffee and coffee product

Coffee

Coffee (FooDB: FOOD00058)

Fruit

Berry

Grape (FooDB: FOOD00369)
Blackberry (FooDB: FOOD00906)

Citrus

Citrus (FooDB: FOOD00859)

Beverage

Fermented beverage

Apple cider (FooDB: FOOD00615)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.04 g/L	ALOGPS
logP	1.71	ALOGPS
logP	1.83	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4.01	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	16.37 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