Identification

PhytoHub ID
PHUB000604
Name
Dihydrocaffeic acid
Systematic Name
3-(3',4'-dihydroxyphenyl)propanoic acid
Synonyms
  • 2,3-Dihydrocaffeic acid
  • 3-(3,4-dihydroxyphenyl)propanoic acid
  • 3-(3,4-dihydroxyphenyl)propionic acid
  • 3-(3',4'-Dihydroxyphenyl)propionic acid
  • 3,4-dihydroxy-dihydrocinnamic acid
  • 3,4-dihydroxybenzenepropanoic acid
  • hydrocaffeic acid
CAS Number
1078-61-1
Average Mass
182.175
Monoisotopic Mass
182.057908802
Chemical Formula
C9H10O4
IUPAC Name
3-(3,4-dihydroxyphenyl)propanoic acid
InChI Key
DZAUWHJDUNRCTF-UHFFFAOYSA-N
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)
SMILES
OC(=O)CCC1=CC(O)=C(O)C=C1
Structure

Calculated Properties

Solubility (ALOGPS)
2.62e+00 g/l
LogS (ALOGPS)
-1.84
LogP (ALOGPS)
1.04
Hydrogen Acceptors
4
Hydrogen Donors
3
Rotatable Bond Count
3
Polar Surface Area
77.76
Refractivity
45.9284
Polarizability
17.84878987605153
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-6.289086658260411
pKa (strongest acidic)
3.8379150142223004
Number of Rings
1
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Food Phytochemical

Family
Polyphenols
Class
Phenolic acids
Sub-class
Phenolic acids subclass not specified

Taxonomy as Metabolite

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

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
EriocitrinPolyphenolsFlavonoidsFlavanonesShow Food Phytochemical
EriodictyolPolyphenolsFlavonoidsFlavanonesShow Food Phytochemical
Caffeic acidPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
5-O-Caffeoylquinic acidPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Ferulic acidPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Orange flavanonesPolyphenolsFlavonoidsFlavanonesShow Food Phytochemical
Cocoa Flavan-3-olsPolyphenolsFlavonoidsFlavan-3-olsShow Food Phytochemical
Black tea Flavan-3-olsPolyphenolsFlavonoidsFlavan-3-olsShow Food Phytochemical
Coffee Chlorogenic acidsPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Yerba mate 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", "Catechols", "Hydrocarbon derivatives", "Monocarboxylic acids and derivatives", "Organic oxides"]
External Descriptor Annotations
["catechols", "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", "Catechol", "Hydrocarbon derivative", "Monocarboxylic acid or derivatives", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organooxygen compound", "Phenol"]

Spectra from Online Resources

Record IDSourceDescriptionView
KO000584MassBankLC-ESI-QQ Spectrum - 10 V, unspecifiedView Spectra
KO000585MassBankLC-ESI-QQ Spectrum - 20 V, unspecifiedView Spectra
KO000586MassBankLC-ESI-QQ Spectrum - 30 V, unspecifiedView Spectra
KO000587MassBankLC-ESI-QQ Spectrum - 40 V, unspecifiedView Spectra
KO000588MassBankLC-ESI-QQ Spectrum - 50 V, unspecifiedView Spectra

Food Sources

NameGroup
BlueberryFruit, BerriesShow
BroccoliVegetables, CabbagesShow
CiderBeverages, AlcoholicShow
CoffeeCoffee and coffee productsShow
Common wheatCereals and cereal productsShow
CornCereals and cereal productsShow
GrapesFruit, BerriesShow
LemonFruit, CitrusShow
LettuceVegetables, Leaf vegetablesShow
LimeFruit, CitrusShow
Olive, blackFruit, Drupes PublicationsShow
Olive, greenFruit, Drupes PublicationsShow
SpinachVegetables, Leaf vegetablesShow
Wheat breadCereals and cereal productsShow

Food Sources of its Food Phytochemical(s)

Food PhytochemicalFood SourceFood Source Group
Caffeic acidAmerican cranberryFruit, Berries PublicationsShow
Ferulic acidAmerican cranberryFruit, Berries PublicationsShow
Caffeic acidAppleFruit, Pomes PublicationsShow
5-O-Caffeoylquinic acidAppleFruit, Pomes PublicationsShow
5-O-Caffeoylquinic acidApple ciderBeverages, Alcoholic PublicationsShow
Caffeic acidApple juiceBeverages, Non-alcoholic PublicationsShow
5-O-Caffeoylquinic acidApple juiceBeverages, Non-alcoholic PublicationsShow
Ferulic acidApple juiceBeverages, Non-alcoholic PublicationsShow
5-O-Caffeoylquinic acidApricotFruit, Drupes PublicationsShow
Caffeic acidBeerBeverages, Alcoholic PublicationsShow
Ferulic acidBeerBeverages, Alcoholic PublicationsShow
Ferulic acidBilberryFruit, Berries PublicationsShow
Ferulic acidBlack mulberryFruit, 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
Ferulic acidBlueberryFruit, Berries PublicationsShow
Caffeic acidBroccoliVegetables, Cabbages PublicationsShow
5-O-Caffeoylquinic acidBroccoliVegetables, Cabbages PublicationsShow
Ferulic acidBroccoliVegetables, Cabbages PublicationsShow
Caffeic acidCarrotVegetables, Root vegetables PublicationsShow
5-O-Caffeoylquinic acidCarrotVegetables, Root vegetables PublicationsShow
5-O-Caffeoylquinic acidCherry tomatoVegetables, Fruit vegetables PublicationsShow
Caffeic acidCiderBeverages, Alcoholic PublicationsShow
5-O-Caffeoylquinic acidCiderBeverages, Alcoholic PublicationsShow
Ferulic acidCocoa beanCocoa and cocoa products PublicationsShow
Caffeic acidCoffeeCoffee and coffee products PublicationsShow
5-O-Caffeoylquinic acidCoffeeCoffee and coffee products PublicationsShow
Ferulic acidCoffeeCoffee and coffee products PublicationsShow
Ferulic acidCommon beanPulses and beans PublicationsShow
Ferulic acidCommon walnutNuts PublicationsShow
Caffeic acidCommon wheatCereals and cereal products PublicationsShow
Ferulic acidCommon wheatCereals and cereal products PublicationsShow
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
Caffeic acidEuropean cranberryFruit, Berries PublicationsShow
5-O-Caffeoylquinic acidEuropean cranberryFruit, Berries PublicationsShow
Ferulic acidEuropean cranberryFruit, Berries 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
Ferulic acidGrapefruitFruit, Citrus PublicationsShow
5-O-Caffeoylquinic acidGreen teaTeas and herbal teas PublicationsShow
Ferulic acidHard wheatCereals and cereal products PublicationsShow
EriocitrinLemonFruit, Citrus PublicationsShow
5-O-Caffeoylquinic acidLettuceVegetables, Leaf vegetables PublicationsShow
EriocitrinLimeFruit, Citrus PublicationsShow
Caffeic acidMateTeas and herbal teas PublicationsShow
5-O-Caffeoylquinic acidMateTeas and herbal teas PublicationsShow
Caffeic acidOlive, blackFruit, Drupes PublicationsShow
5-O-Caffeoylquinic acidOlive, blackFruit, Drupes PublicationsShow
Ferulic acidOlive, blackFruit, Drupes PublicationsShow
Caffeic acidOlive, greenFruit, Drupes PublicationsShow
Ferulic acidOlive, greenFruit, Drupes PublicationsShow
Ferulic acidOrange juiceBeverages, Non-alcoholic PublicationsShow
5-O-Caffeoylquinic acidPeachFruit, Drupes PublicationsShow
Caffeic acidPearFruit, Pomes PublicationsShow
5-O-Caffeoylquinic acidPearFruit, Pomes PublicationsShow
5-O-Caffeoylquinic acidPotatoVegetables, Tubers PublicationsShow
Ferulic acidRapeseedOilseed crops PublicationsShow
Ferulic acidRed raspberryFruit, Berries PublicationsShow
Ferulic acidRiceCereals and cereal products PublicationsShow
5-O-Caffeoylquinic acidRoasted coffeeCoffee and coffee products PublicationsShow
Ferulic acidRosemaryHerbs and Spices PublicationsShow
Ferulic acidRye breadCereals and cereal products PublicationsShow
Ferulic acidSpinachVegetables, Leaf vegetables PublicationsShow
Caffeic acidStrawberryFruit, Berries PublicationsShow
5-O-Caffeoylquinic acidStrawberryFruit, Berries PublicationsShow
Ferulic acidStrawberryFruit, Berries PublicationsShow
Caffeic acidSweet cherryFruit, Drupes PublicationsShow
5-O-Caffeoylquinic acidSweet cherryFruit, Drupes PublicationsShow
Ferulic acidSweet orangeFruit, Citrus PublicationsShow
Ferulic acidTarragonHerbs and Spices PublicationsShow
Caffeic acidTomatoVegetables, Fruit vegetables PublicationsShow
5-O-Caffeoylquinic acidTomatoVegetables, Fruit vegetables PublicationsShow
Ferulic acidTomatoVegetables, Fruit vegetables PublicationsShow
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
Dihydrocaffeic acid Vanillic acidraturineNot AvailableNot AvailableNot AvailableNot AvailableC8H8O4168.042258738
Dihydrocaffeic acid Isoferulic acidraturineNot AvailableNot AvailableNot AvailableNot AvailableC10H10O4194.057908802
Dihydrocaffeic acid 3-(3'-Hydroxyphenyl)propionic acidraturineNot AvailableNot AvailableNot AvailableNot AvailableC9H10O3166.062994182 Publications
Dihydrocaffeic acid Dihydroferulic acidraturineNot AvailableNot AvailableNot AvailableNot AvailableC10H12O4196.073558866 Publications
Dihydrocaffeic acid Ferulic acid-4'-sulfateraturineNot AvailableNot AvailableNot AvailableNot AvailableC10H10O7S274.014723836 Publications
Dihydrocaffeic acid Dihydrocaffeic acid-3'-O-glucuronideraturineNot AvailableNot AvailableNot AvailableNot AvailableC15H18O10358.08999678 Publications
Dihydrocaffeic acid Dihydrocaffeic acid-4'-O-glucuronideraturineNot AvailableNot AvailableNot AvailableNot AvailableC15H18O10358.08999678 Publications
Dihydrocaffeic acid Dihydrocaffeic acid-4'-sulfateraturineNot AvailableNot AvailableNot AvailableNot AvailableC9H10O7S262.014723836 Publications
Eriocitrin Dihydrocaffeic acidin vitro (human) ratplasma (major), urine (major)gut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H10O4182.057908802 Publications
Eriodictyol Dihydrocaffeic acidin vitro (human) raturinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H10O4182.057908802 Publications
Caffeic acid Dihydrocaffeic acidraturinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H10O4182.057908802 Publications
5-O-Caffeoylquinic acid Dihydrocaffeic acidraturinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H10O4182.057908802 Publications
Ferulic acid Dihydrocaffeic acidhumanurinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H10O4182.057908802
Orange flavanones Dihydrocaffeic acidhumanplasma, urinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC9H10O4182.057908802 Detailed Intervention Studies Publications
Cocoa Flavan-3-ols Dihydrocaffeic acidhumanurinegut microbiota metaboliteNot AvailableNot Available<1%C9H10O4182.057908802 Detailed Intervention Studies Publications
Black tea Flavan-3-ols Dihydrocaffeic acidhumanurinegut microbiota metaboliteNot AvailableNot Available<1%C9H10O4182.057908802 Detailed Intervention Studies Publications
Coffee Chlorogenic acids Dihydrocaffeic acidhumanplasma, urinegut microbiota metabolite5h-8h50-200 nmol/L<1%C9H10O4182.057908802 Detailed Intervention Studies Publications
Yerba mate Chlorogenic acids Dihydrocaffeic acidhumanplasma, urinegut microbiota metabolite5h-8h20-50 nmol/L<1%C9H10O4182.057908802 Detailed Intervention Studies Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
Cocoa Flavan-3-ols Dihydrocaffeic acidMicrobiotaEffect, clusters Publications
Coffee Chlorogenic acids Dihydrocaffeic acidMicrobiotaEffect, clusters Publications
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