ChemFOnt: Showing chemical card for Dihydroferulic acid (CFc000042533)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:45:06 UTC

Chemfont ID

CFc000042533

Molecule Identification

Common Name

Dihydroferulic acid

Definition

Dihydroferulic acid, also known as 3-(4-hydroxy-3-methoxyphenyl)propionic acid or dihydroconiferylate, is classified as a member of the phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. Dihydroferulic acid is considered to be slightly soluble (in water) and acidic. Dihydroferulic acid is a phenolic acid metabolite and was found to be significantly elevated in serum after whole grain consumption which makes this compound a potential serum biomarker of whole grain intake (PMID: 25646321 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Dihydroconiferylic acid	ChEBI
3-(4-Hydroxy-3-methoxyphenyl)propionate	Generator
Dihydroconiferylate	Generator
Dihydroferulate	Generator
Hydroferulate	HMDB
(4-Hydroxy-3-methoxyphenyl)propionic acid	HMDB
3-(3'-Methoxy-4'-hydroxyphenyl)propionic acid	HMDB
3-(3-Methoxy-4-hydroxyphenyl)propanoic acid	HMDB
3-(3-Methoxy-4-hydroxyphenyl)propionic acid	HMDB
3-(3’-methoxy-4’-hydroxyphenyl)propionic acid	HMDB
3-(4-Hydroxy-3-methoxyphenyl)propanoic acid	HMDB
3-Methoxy-4-hydroxyphenylpropionic acid	HMDB
3-Methoxyphloretic acid	HMDB
4-Hydroxy-3-methoxybenzenepropanoic acid	HMDB
DHFA	HMDB
Shorbic acid	HMDB
beta-(4-Hydroxy-3-methoxyphenyl)propionic acid	HMDB
beta-3-Methoxy-4-hydroxyphenylpropionic acid	HMDB
Β-(4-hydroxy-3-methoxyphenyl)propionic acid	HMDB
Β-3-methoxy-4-hydroxyphenylpropionic acid	HMDB
3-(4'-Hydroxy-3'-methoxyphenyl)propanoic acid	HMDB
4-Hydroxy-3-methoxyhydrocinnamic acid	PhytoBank
4-Hydroxy-3-methoxybenzenepropionic acid	PhytoBank
(4-Hydroxy-3-methoxyphenyl)propanoic acid	PhytoBank
3-(3'-Methoxy-4'-hydroxyphenyl)propanoic acid	PhytoBank
3-(3’-Methoxy-4’-hydroxyphenyl)propanoic acid	PhytoBank
3-Methoxy-4-hydroxyphenylpropanoic acid	PhytoBank
alpha,beta-Dihydroferulic acid	PhytoBank
α,β-Dihydroferulic acid	PhytoBank
beta-(4-Hydroxy-3-methoxyphenyl)propanoic acid	PhytoBank
β-(4-Hydroxy-3-methoxyphenyl)propanoic acid	PhytoBank
beta-3-Methoxy-4-hydroxyphenylpropanoic acid	PhytoBank
β-3-Methoxy-4-hydroxyphenylpropanoic acid	PhytoBank
3-(4-Hydroxy-3-methoxyphenyl) propanoic acid	HMDB

Chemical Formula

C₁₀H₁₂O₄

Average Molecular Weight

196.1999

Monoisotopic Molecular Weight

196.073558872

IUPAC Name

3-(4-hydroxy-3-methoxyphenyl)propanoic acid

Traditional Name

homovanillinic acid

CAS Registry Number

1135-23-5

SMILES

COC1=CC(CCC(O)=O)=CC=C1O

InChI Identifier

InChI=1S/C10H12O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2,4,6,11H,3,5H2,1H3,(H,12,13)

InChI Key

BOLQJTPHPSDZHR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:86612 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 25646321)

Excreta

Biofluid or Excreta

Feces (PMID: 27015276)
Urine (PMID: 28157703)

Source

Exogenous

Exogenous (HMDB: HMDB0062121)

Food

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0062121)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0062121)

Tea

Tea products (HMDB: HMDB0062121)

Fat and oil

Olive oil (HMDB: HMDB0062121)

Fruit

Fruits (HMDB: HMDB0062121)

Vegetable

Vegetables (HMDB: HMDB0062121)

Legumes (HMDB: HMDB0062121)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0062121)

Nut

Nuts (HMDB: HMDB0062121)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0062121)

Endogenous

Plant

Plant (HMDB: HMDB0062121)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.3 g/L	ALOGPS
logP	1.03	ALOGPS
logP	1.59	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	3.95	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	4	ChemAxon
Refractivity	50.41 m³·mol⁻¹	ChemAxon
Polarizability	19.8 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

HMDB0062121

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029987

KNApSAcK ID

C00040946

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14340

PDB ID

Not Available

ChEBI ID

86612

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Dihydroferulic acid (CFc000042533)

MOL for CFc000042533 (Dihydroferulic acid)

3D MOL for CFc000042533 (Dihydroferulic acid)

3D SDF for CFc000042533 (Dihydroferulic acid)

3D-SDF for CFc000042533 (Dihydroferulic acid)

PDB for CFc000042533 (Dihydroferulic acid)

3D PDB for CFc000042533 (Dihydroferulic acid)

SMILES for CFc000042533 (Dihydroferulic acid)

INCHI for CFc000042533 (Dihydroferulic acid)

Structure for CFc000042533 (Dihydroferulic acid)

3D Structure for CFc000042533 (Dihydroferulic acid)