Identification

PhytoHub ID
PHUB001047
Name
3-(3'-Hydroxyphenyl)propionic acid
Systematic Name
3-(3'-Hydroxyphenyl)propanoic acid
Synonyms
  • 3-(3-Hydroxyphenyl)propanoic acid
  • 3-(3-hydroxyphenyl)propionic acid
  • 3-hydroxy-dihydrocinnamic acid
  • 3-hydroxyphenylpropionic acid
  • 3'-Hydroxy-dihydrocinnamic acid
  • m-Hydroxy-dihydrocinnamic acid
CAS Number
621-54-5
Average Mass
166.176
Monoisotopic Mass
166.062994182
Chemical Formula
C9H10O3
IUPAC Name
3-(3-hydroxyphenyl)propanoic acid
InChI Key
QVWAEZJXDYOKEH-UHFFFAOYSA-N
InChI Identifier
InChI=1S/C9H10O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-3,6,10H,4-5H2,(H,11,12)
SMILES
OC(=O)CCC1=CC(O)=CC=C1
Structure

Calculated Properties

Solubility (ALOGPS)
2.80e+00 g/l
LogS (ALOGPS)
-1.77
LogP (ALOGPS)
1.14
Hydrogen Acceptors
3
Hydrogen Donors
2
Rotatable Bond Count
3
Polar Surface Area
57.53
Refractivity
43.9475
Polarizability
16.91543079087822
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-5.964060407587342
pKa (strongest acidic)
4.214566239011227
Number of Rings
1
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Metabolite

Family
(Poly)phenol metabolites
Class
Phenolic acid metabolites
Sub-class
Phenylpropanoic acids

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
(-)-EpicatechinPolyphenolsFlavonoidsFlavan-3-olsShow Food Phytochemical
Procyanidin dimer A2PolyphenolsFlavonoidsFlavan-3-olsShow Food Phytochemical
Procyanidin dimer B2PolyphenolsFlavonoidsFlavan-3-olsShow Food Phytochemical
HesperetinPolyphenolsFlavonoidsFlavanonesShow Food Phytochemical
Caffeic acidPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Caftaric acidPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
5-O-Caffeoylquinic acidPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Dihydrocaffeic acidPolyphenolsPhenolic acidsPhenolic acids subclass not specifiedShow Food Phytochemical
Ferulic acidPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Rosmarinic acidPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Orange flavanonesPolyphenolsFlavonoidsFlavanonesShow Food Phytochemical
Cocoa Flavan-3-olsPolyphenolsFlavonoidsFlavan-3-olsShow Food Phytochemical
Coffee Chlorogenic acidsPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Phenylpropanoic acids
Super-class
Phenylpropanoids and polyketides
Sub-class
Not Available
Direct Parent Name
Phenylpropanoic acids
Alternative Parent Names
["1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "Benzene and substituted derivatives", "Carbonyl compounds", "Carboxylic acids", "Hydrocarbon derivatives", "Monocarboxylic acids and derivatives", "Organic oxides"]
External Descriptor Annotations
["monocarboxylic acid"]
Substituent Names
["1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "3-phenylpropanoic-acid", "Aromatic homomonocyclic compound", "Benzenoid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Hydrocarbon derivative", "Monocarboxylic acid or derivatives", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organooxygen compound", "Phenol"]

Spectra from Online Resources

No spectra information available

Food Sources

No food source information available

Food Sources of its Food Phytochemical(s)

Food PhytochemicalFood SourceFood Source Group
(-)-EpicatechinAlmondNuts PublicationsShow
Procyanidin dimer A2American cranberryFruit, Berries PublicationsShow
Caffeic acidAmerican cranberryFruit, Berries PublicationsShow
Ferulic acidAmerican cranberryFruit, Berries PublicationsShow
(-)-EpicatechinAppleFruit, Pomes PublicationsShow
Procyanidin dimer B2AppleFruit, Pomes PublicationsShow
Caffeic acidAppleFruit, Pomes PublicationsShow
5-O-Caffeoylquinic acidAppleFruit, Pomes PublicationsShow
(-)-EpicatechinApple ciderBeverages, Alcoholic PublicationsShow
Procyanidin dimer B2Apple ciderBeverages, Alcoholic PublicationsShow
5-O-Caffeoylquinic acidApple ciderBeverages, Alcoholic PublicationsShow
(-)-EpicatechinApple juiceBeverages, Non-alcoholic PublicationsShow
Procyanidin dimer B2Apple juiceBeverages, Non-alcoholic PublicationsShow
Caffeic acidApple juiceBeverages, Non-alcoholic PublicationsShow
5-O-Caffeoylquinic acidApple juiceBeverages, Non-alcoholic PublicationsShow
Ferulic acidApple juiceBeverages, Non-alcoholic PublicationsShow
(-)-EpicatechinApricotFruit, Drupes PublicationsShow
Procyanidin dimer B2ApricotFruit, Drupes PublicationsShow
5-O-Caffeoylquinic acidApricotFruit, Drupes PublicationsShow
(-)-EpicatechinBeerBeverages, Alcoholic PublicationsShow
Caffeic acidBeerBeverages, Alcoholic PublicationsShow
Ferulic acidBeerBeverages, Alcoholic PublicationsShow
Ferulic acidBilberryFruit, Berries PublicationsShow
Ferulic acidBlack mulberryFruit, Berries PublicationsShow
(-)-EpicatechinBlack teaTeas and herbal teas PublicationsShow
Procyanidin dimer B2Black teaTeas and herbal teas PublicationsShow
(-)-EpicatechinBlackberryFruit, Berries PublicationsShow
Procyanidin dimer B2BlackberryFruit, Berries PublicationsShow
Caffeic acidBlackberryFruit, Berries PublicationsShow
5-O-Caffeoylquinic acidBlackberryFruit, Berries PublicationsShow
Ferulic acidBlackberryFruit, Berries PublicationsShow
5-O-Caffeoylquinic acidBlackcurrantFruit, Berries PublicationsShow
Caffeic acidBlueberryFruit, Berries PublicationsShow
5-O-Caffeoylquinic acidBlueberryFruit, Berries PublicationsShow
Dihydrocaffeic acidBlueberryFruit, BerriesShow
Ferulic acidBlueberryFruit, Berries PublicationsShow
(-)-EpicatechinBroad beanPulses and beans PublicationsShow
Caffeic acidBroccoliVegetables, Cabbages PublicationsShow
5-O-Caffeoylquinic acidBroccoliVegetables, Cabbages PublicationsShow
Dihydrocaffeic acidBroccoliVegetables, CabbagesShow
Ferulic acidBroccoliVegetables, Cabbages PublicationsShow
Caffeic acidCarrotVegetables, Root vegetables PublicationsShow
5-O-Caffeoylquinic acidCarrotVegetables, Root vegetables PublicationsShow
5-O-Caffeoylquinic acidCherry tomatoVegetables, Fruit vegetables PublicationsShow
(-)-EpicatechinChocolateCocoa and cocoa products PublicationsShow
(-)-EpicatechinCiderBeverages, Alcoholic PublicationsShow
Caffeic acidCiderBeverages, Alcoholic PublicationsShow
5-O-Caffeoylquinic acidCiderBeverages, Alcoholic PublicationsShow
Dihydrocaffeic acidCiderBeverages, AlcoholicShow
(-)-EpicatechinCocoaCocoa and cocoa products PublicationsShow
Procyanidin dimer B2CocoaCocoa and cocoa products PublicationsShow
(-)-EpicatechinCocoa beanCocoa and cocoa products PublicationsShow
Procyanidin dimer B2Cocoa beanCocoa and cocoa products PublicationsShow
Ferulic acidCocoa beanCocoa and cocoa products PublicationsShow
(-)-EpicatechinCocoa powderCocoa and cocoa products PublicationsShow
Caffeic acidCoffeeCoffee and coffee products PublicationsShow
5-O-Caffeoylquinic acidCoffeeCoffee and coffee products PublicationsShow
Dihydrocaffeic acidCoffeeCoffee and coffee productsShow
Ferulic acidCoffeeCoffee and coffee products PublicationsShow
Ferulic acidCommon beanPulses and beans PublicationsShow
(-)-EpicatechinCommon chokecherryFruit, Drupes PublicationsShow
Rosmarinic acidCommon oreganoHerbs and Spices PublicationsShow
Rosmarinic acidCommon sageHerbs and Spices PublicationsShow
Rosmarinic acidCommon thymeHerbs and Spices PublicationsShow
(-)-EpicatechinCommon walnutNuts PublicationsShow
Ferulic acidCommon walnutNuts PublicationsShow
Caffeic acidCommon wheatCereals and cereal products PublicationsShow
Dihydrocaffeic acidCommon wheatCereals and cereal productsShow
Ferulic acidCommon wheatCereals and cereal products PublicationsShow
Dihydrocaffeic acidCornCereals and cereal productsShow
Ferulic acidCornCereals and cereal products PublicationsShow
Ferulic acidDateFruit, Other fruits PublicationsShow
Caffeic acidEggplantVegetables, Fruit vegetables PublicationsShow
5-O-Caffeoylquinic acidEggplantVegetables, Fruit vegetables PublicationsShow
Ferulic acidEggplantVegetables, Fruit vegetables PublicationsShow
(-)-EpicatechinEuropean cranberryFruit, Berries PublicationsShow
Caffeic acidEuropean cranberryFruit, Berries PublicationsShow
5-O-Caffeoylquinic acidEuropean cranberryFruit, Berries PublicationsShow
Ferulic acidEuropean cranberryFruit, Berries PublicationsShow
(-)-EpicatechinEuropean plumFruit, Drupes PublicationsShow
Caffeic acidEuropean plumFruit, Drupes PublicationsShow
5-O-Caffeoylquinic acidEuropean plumFruit, Drupes PublicationsShow
Ferulic acidFennelHerbs and Spices PublicationsShow
5-O-Caffeoylquinic acidGlobe artichokeVegetables, Other vegetables PublicationsShow
(-)-EpicatechinGrapeFruit, Berries PublicationsShow
Caftaric acidGrapeFruit, Berries PublicationsShow
Caftaric acidGrape juiceBeverages, Non-alcoholic PublicationsShow
Caftaric acidGrape wineBeverages, Alcoholic PublicationsShow
Ferulic acidGrapefruitFruit, Citrus PublicationsShow
Dihydrocaffeic acidGrapesFruit, BerriesShow
(-)-EpicatechinGreen teaTeas and herbal teasShow
Procyanidin dimer B2Green teaTeas and herbal teas PublicationsShow
5-O-Caffeoylquinic acidGreen teaTeas and herbal teas PublicationsShow
Ferulic acidHard wheatCereals and cereal products PublicationsShow
HesperetinLemonFruit, CitrusShow
Dihydrocaffeic acidLemonFruit, CitrusShow
Caftaric acidLettuceVegetables, Leaf vegetables PublicationsShow
5-O-Caffeoylquinic acidLettuceVegetables, Leaf vegetables PublicationsShow
Dihydrocaffeic acidLettuceVegetables, Leaf vegetablesShow
HesperetinLimeFruit, CitrusShow
Dihydrocaffeic acidLimeFruit, CitrusShow
Procyanidin dimer A2LingonberryFruit, Berries PublicationsShow
Caffeic acidMateTeas and herbal teas PublicationsShow
5-O-Caffeoylquinic acidMateTeas and herbal teas PublicationsShow
Rosmarinic acidMintHerbs and Spices PublicationsShow
Caffeic acidOlive, blackFruit, Drupes PublicationsShow
5-O-Caffeoylquinic acidOlive, blackFruit, Drupes PublicationsShow
Dihydrocaffeic acidOlive, blackFruit, Drupes PublicationsShow
Ferulic acidOlive, blackFruit, Drupes PublicationsShow
Caffeic acidOlive, greenFruit, Drupes PublicationsShow
Dihydrocaffeic acidOlive, greenFruit, Drupes PublicationsShow
Ferulic acidOlive, greenFruit, Drupes PublicationsShow
HesperetinOrange juiceBeverages, Non-alcoholicShow
Ferulic acidOrange juiceBeverages, Non-alcoholic PublicationsShow
(-)-EpicatechinPeachFruit, Drupes PublicationsShow
5-O-Caffeoylquinic acidPeachFruit, Drupes PublicationsShow
(-)-EpicatechinPearFruit, Pomes PublicationsShow
Caffeic acidPearFruit, Pomes PublicationsShow
5-O-Caffeoylquinic acidPearFruit, Pomes PublicationsShow
Rosmarinic acidPeppermintHerbs and Spices PublicationsShow
(-)-EpicatechinPomegranateFruit, Tropical fruits PublicationsShow
5-O-Caffeoylquinic acidPotatoVegetables, Tubers PublicationsShow
Ferulic acidRapeseedOilseed crops PublicationsShow
Ferulic acidRed raspberryFruit, Berries PublicationsShow
Caftaric acidRed wineBeverages, Alcoholic PublicationsShow
Ferulic acidRiceCereals and cereal products PublicationsShow
5-O-Caffeoylquinic acidRoasted coffeeCoffee and coffee products PublicationsShow
Ferulic acidRosemaryHerbs and Spices PublicationsShow
Rosmarinic acidRosemaryHerbs and Spices PublicationsShow
Ferulic acidRye breadCereals and cereal products PublicationsShow
Caftaric acidSpinachVegetables, Leaf vegetables PublicationsShow
Dihydrocaffeic acidSpinachVegetables, Leaf vegetablesShow
Ferulic acidSpinachVegetables, Leaf vegetables PublicationsShow
(-)-EpicatechinStrawberryFruit, Berries PublicationsShow
Caffeic acidStrawberryFruit, Berries PublicationsShow
5-O-Caffeoylquinic acidStrawberryFruit, Berries PublicationsShow
Ferulic acidStrawberryFruit, Berries PublicationsShow
Rosmarinic acidSweet basilHerbs and Spices PublicationsShow
(-)-EpicatechinSweet cherryFruit, Drupes PublicationsShow
Caffeic acidSweet cherryFruit, Drupes PublicationsShow
5-O-Caffeoylquinic acidSweet cherryFruit, Drupes PublicationsShow
HesperetinSweet orangeFruit, CitrusShow
Ferulic acidSweet orangeFruit, Citrus PublicationsShow
Ferulic acidTarragonHerbs and Spices PublicationsShow
(-)-EpicatechinTeaTeas and herbal teas PublicationsShow
Caffeic acidTomatoVegetables, Fruit vegetables PublicationsShow
5-O-Caffeoylquinic acidTomatoVegetables, Fruit vegetables PublicationsShow
Ferulic acidTomatoVegetables, Fruit vegetables PublicationsShow
Dihydrocaffeic acidWheat breadCereals and cereal productsShow
Ferulic acidWhite wineBeverages, Alcoholic PublicationsShow
Caffeic acidWhite wine grapeFruit, Berries PublicationsShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
(-)-Epicatechin 3-(3'-Hydroxyphenyl)propionic acidin vitro (human)Not Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H10O3166.062994182 Publications
Procyanidin dimer A2 3-(3'-Hydroxyphenyl)propionic acidin vitro (human)Not Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H10O3166.062994182 Publications
Procyanidin dimer B2 3-(3'-Hydroxyphenyl)propionic acidin vitro (human)Not Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H10O3166.062994182 Publications
Hesperetin 3-(3'-Hydroxyphenyl)propionic acidin vitro (pig)Not Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H10O3166.062994182 Publications
Caffeic acid 3-(3'-Hydroxyphenyl)propionic acidratplasma, urinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H10O3166.062994182 Publications
Caftaric acid 3-(3'-Hydroxyphenyl)propionic acidNot AvailableNot Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H10O3166.062994182 Publications
5-O-Caffeoylquinic acid 3-(3'-Hydroxyphenyl)propionic acidratplasma, urinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H10O3166.062994182 Publications
Dihydrocaffeic acid 3-(3'-Hydroxyphenyl)propionic acidraturineNot AvailableNot AvailableNot AvailableNot AvailableC9H10O3166.062994182 Publications
Ferulic acid 3-(3'-Hydroxyphenyl)propionic acidhuman ratplasma, urinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H10O3166.062994182
Rosmarinic acid 3-(3'-Hydroxyphenyl)propionic acidratplasma, urineNot AvailableNot AvailableNot AvailableNot AvailableC9H10O3166.062994182 Publications
Orange flavanones 3-(3'-Hydroxyphenyl)propionic acidhumanplasmagut microbiota metabolite5h-8h<20 nmol/LNot AvailableC9H10O3166.062994182 Detailed Intervention Studies Publications
Cocoa Flavan-3-ols 3-(3'-Hydroxyphenyl)propionic acidhumanurinegut microbiota metaboliteNot AvailableNot Available<1%C9H10O3166.062994182 Detailed Intervention Studies Publications
Coffee Chlorogenic acids 3-(3'-Hydroxyphenyl)propionic acidNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC9H10O3166.062994182 Detailed Intervention Studies

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
Cocoa Flavan-3-ols 3-(3'-Hydroxyphenyl)propionic acidMicrobiotaEffect, clusters Publications
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