ChemFOnt: Showing chemical card for Isoferulic acid (CFc000000762)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:15 UTC

Chemfont ID

CFc000000762

Molecule Identification

Common Name

Isoferulic acid

Definition

Isoferulic acid (CAS: 537-73-5) is a chlorogenic acid (CGA). CGAs are formed by the esterification of hydroxycinnamic acids (e.g. caffeic acid, ferulic acid, and p-coumaric acid) with quinic acid. CGAs are abundant phenolic compounds in coffee, with caffeoylquinic (CQA), feruloylquinic (FQA), and dicaffeoylquinic (diCQA) acids being the major subclasses, and coffee is the most consumed food product in the world. Isoferulic acid is present in normal human urine in concentrations of 0.05-2.07 umol/mmol creatinine at baseline, and reaches 0.2-9.6 umol/mmol creatinine in four hours after a cup of coffee, with a large inter-individual variation (PMID:17884997 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Hydroxy-4-methoxycinnamic acid	ChEBI
Hesperetic acid	ChEBI
3-Hydroxy-4-methoxycinnamate	Generator
Isoferulate	Generator
3-(3-Hydroxy-4-methoxyphenyl)-2-propenoate	HMDB
3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid	HMDB
3-Hydroxy-4-methoxy-cinnamate	HMDB
3-Hydroxy-4-methoxy-cinnamic acid	HMDB
(2E)-3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid	HMDB
(e)-3-Hydroxy-4-methoxycinnamic acid	HMDB
(e)-4-Methoxycaffeic acid	HMDB
(e)-4-O-Methylcaffeic acid	HMDB
(e)-Hesperetic acid	HMDB
(e)-Isoferulic acid	HMDB
4-Methoxycaffeic acid	HMDB
4-O-Methylcaffeic acid	HMDB
trans-3-Hydroxy-4-methoxycinnamic acid	HMDB
trans-4-Methoxycaffeic acid	HMDB
trans-4-O-Methylcaffeic acid	HMDB
trans-Hesperetic acid	HMDB
trans-Isoferulic acid	HMDB
(2E)-3-(3-Hydroxy-4-methoxyphenyl)prop-2-enoate	HMDB
3'-Hydroxy-4'-methoxycinnamic acid	HMDB
(e)-3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid	HMDB
(2E)-3-(3-Hydroxy-4-methoxyphenyl)prop-2-enoic acid	HMDB

Chemical Formula

C₁₀H₁₀O₄

Average Molecular Weight

194.184

Monoisotopic Molecular Weight

194.057908808

IUPAC Name

(2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid

Traditional Name

isoferulic acid

CAS Registry Number

25522-33-2

SMILES

COC1=C(O)C=C(\C=C\C(O)=O)C=C1

InChI Identifier

InChI=1S/C10H10O4/c1-14-9-4-2-7(6-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+

InChI Key

QURCVMIEKCOAJU-HWKANZROSA-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 or derivatives
Hydroxycinnamic acid
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Ether
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

ferulic acids (CHEBI:27794 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 12592675)

Excreta

Biofluid or Excreta

Urine (PMID: 12592675)
Feces (PMID: 24010549)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000955)

Source

Exogenous

Exogenous (HMDB: HMDB0000955)

Food

Food (HMDB: HMDB0000955)
Legumes (HMDB: HMDB0000955)

Soy

Soy bean (FooDB: FOOD00085)

Fruit

Berry

Bilberry (FooDB: FOOD00193)

Fruits (HMDB: HMDB0000955)

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0000955)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0000955)

Tea

Tea products (HMDB: HMDB0000955)

Fat and oil

Olive oil (HMDB: HMDB0000955)

Vegetable

Vegetables (HMDB: HMDB0000955)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0000955)

Cereal

Common wheat (FooDB: FOOD00187)

Nut

Nuts (HMDB: HMDB0000955)
Peanut (FooDB: FOOD00016)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0000955)

Herb and spice

Oilseed crop

Sunflower (FooDB: FOOD00086)

Herb

German camomile (FooDB: FOOD00107)

Baking good

Seasoning

Vinegar (FooDB: FOOD00628)

Not Available

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000955)

Manufacturing industry

Material processing agent

Solid material processing agent

Protective agent

Antioxidant (HMDB: HMDB0000955)
Antioxidant (HMDB: HMDB0000955)

Biological role

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.87 g/L	ALOGPS
logP	1.56	ALOGPS
logP	1.67	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3.77	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	51.5 m³·mol⁻¹	ChemAxon
Polarizability	19.36 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