ChemFOnt: Showing chemical card for 3,4-Dihydroxyhydrocinnamic acid (CFc000000321)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:41 UTC

Chemfont ID

CFc000000321

Molecule Identification

Common Name

3,4-Dihydroxyhydrocinnamic acid

Definition

3,4-Dihydroxyhydrocinnamic acid, also known as dihydrocaffeic acid (DHCA), is a metabolite product of the hydrogenation of caffeoylquinic acids, occurring in normal human biofluids, with potent antioxidant properties. DHCA has been detected in human plasma following coffee ingestion (PMID: 15607645 ) and is increased with some dietary sources, such as after ingestion of phenolic constituents of artichoke leaf extract (PMID: 15693705 ). Polyphenol-rich foods such as vegetables and fruits have been shown to significantly improve platelet function in ex vivo studies in humans (PMID: 16038718 ). Its antioxidant activity has been tested to reduce ferric iron in the ferric reducing antioxidant power (FRAP) assay, and it has been suggested that its catechol structure conveys the antioxidant effect in plasma and in erythrocytes (PMID: 11768243 ). 3,4-Dihydroxyhydrocinnamic acid is a microbial metabolite found in Bifidobacterium, Escherichia, Lactobacillus, and Clostridium (PMID: 28393285 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,4-Dihydroxy-beta-phenylpropionic acid	ChEBI
3,4-Dihydroxybenzenepropionic acid	ChEBI
3,4-Dihydroxydihydrocinnamic acid	ChEBI
3,4-Dihydroxyphenylpropionic acid	ChEBI
3-(3,4-Dihydroxyphenyl)propanoate	Kegg
3,4-Dihydroxy-b-phenylpropionate	Generator
3,4-Dihydroxy-b-phenylpropionic acid	Generator
3,4-Dihydroxy-beta-phenylpropionate	Generator
3,4-Dihydroxy-β-phenylpropionate	Generator
3,4-Dihydroxy-β-phenylpropionic acid	Generator
3,4-Dihydroxybenzenepropanoate	Generator
3,4-Dihydroxybenzenepropionate	Generator
3,4-Dihydroxydihydrocinnamate	Generator
3,4-Dihydroxyphenylpropionate	Generator
3-(3,4-Dihydroxyphenyl)propionate	Generator
Dihydrocaffeate	Generator
Hydrocaffeate	Generator
3-(3,4-Dihydroxyphenyl)propanoic acid	Generator
3,4-Dihydroxyhydrocinnamate	Generator
3,4-Dihydroxy-(6ci,7ci,8ci)hydrocinnamate	HMDB
3,4-Dihydroxy-(6ci,7ci,8ci)hydrocinnamic acid	HMDB
3,4-Dihydroxyphenylpropionic acid, potassium salt	HMDB
DHC	HMDB
3,4-Dihydroxyhydrocinnamic acid	HMDB
3-(3',4'-Dihydroxyphenyl)propanoic acid	HMDB

Chemical Formula

C₉H₁₀O₄

Average Molecular Weight

182.1733

Monoisotopic Molecular Weight

182.057908808

IUPAC Name

3-(3,4-dihydroxyphenyl)propanoic acid

Traditional Name

dihydrocaffeic acid

CAS Registry Number

1078-61-1

SMILES

OC(=O)CCC1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13)

InChI Key

DZAUWHJDUNRCTF-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
Catechol
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
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:48400 )
catechols (CHEBI:48400 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 17408528)

Excreta

Biofluid or Excreta

Urine (PMID: 12663291)
Feces (PMID: 24010549)

Cellular substructure

Cytoplasm (HMDB: HMDB0000423)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000423)

Source

Exogenous

Exogenous (HMDB: HMDB0000423)

Food

Food (HMDB: HMDB0000423)
Legumes (HMDB: HMDB0000423)

Cereal and cereal product

Leavened bread

Wheat bread (FooDB: FOOD00808)

Cereal product

Whole grain cereal products (HMDB: HMDB0000423)

Cereal

Corn (FooDB: FOOD00205)
Common wheat (FooDB: FOOD00187)

Vegetable

Root vegetable

Red beetroot (FooDB: FOOD00264)

Vegetables (HMDB: HMDB0000423)

Cabbage

Broccoli (FooDB: FOOD00034)

Leaf vegetable

Fruit vegetable

Olive (FooDB: FOOD00121)

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0000423)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0000423)

Coffee

Tea

Tea products (HMDB: HMDB0000423)

Fat and oil

Olive oil (HMDB: HMDB0000423)

Fruit

Fruits (HMDB: HMDB0000423)

Berry

Grape (FooDB: FOOD00369)

Citrus

Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)

Nut

Nuts (HMDB: HMDB0000423)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0000423)

Fermented beverage

Apple cider (FooDB: FOOD00615)

Endogenous

Plant

Plant (HMDB: HMDB0000423)

Microbe

Microbe (HMDB: HMDB0000423)
Escherichia coli (HMDB: HMDB0000423)
Clostridium (HMDB: HMDB0000423)
Bifidobacterium lactis (HMDB: HMDB0000423)
Lactobacillus gasseri (HMDB: HMDB0000423)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Solid material processing agent

Protective agent

Antioxidant (HMDB: HMDB0000423)
Antioxidant (HMDB: HMDB0000423)

Pharmaceutical industry

Biomarker

Eosinophilic esophagitis (MarkerDB: MDB00029981)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.62 g/L	ALOGPS
logP	1.04	ALOGPS
logP	1.45	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.84	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	45.93 m³·mol⁻¹	ChemAxon
Polarizability	17.85 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

HMDB0000423

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5412

PubChem Compound

348154

PDB ID

Not Available

ChEBI ID

48400

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Sabally Kebba; Karboune Salwa; St-Louis Richard; Kermasha Selim Lipase-catalyzed transesterification of dihydrocaffeic acid with flaxseed oil for the synthesis of phenolic lipids. Journal of biotechnology (2006), 127(1), 167-76.

Showing chemical card for 3,4-Dihydroxyhydrocinnamic acid (CFc000000321)

MOL for CFc000000321 (3,4-Dihydroxyhydrocinnamic acid)

3D MOL for CFc000000321 (3,4-Dihydroxyhydrocinnamic acid)

3D SDF for CFc000000321 (3,4-Dihydroxyhydrocinnamic acid)

3D-SDF for CFc000000321 (3,4-Dihydroxyhydrocinnamic acid)

PDB for CFc000000321 (3,4-Dihydroxyhydrocinnamic acid)

3D PDB for CFc000000321 (3,4-Dihydroxyhydrocinnamic acid)

SMILES for CFc000000321 (3,4-Dihydroxyhydrocinnamic acid)

INCHI for CFc000000321 (3,4-Dihydroxyhydrocinnamic acid)

Structure for CFc000000321 (3,4-Dihydroxyhydrocinnamic acid)

3D Structure for CFc000000321 (3,4-Dihydroxyhydrocinnamic acid)