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
dihydrocaffeic 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

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

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

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
PrecursorFood 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
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 acidMateBeverages, Non-alcoholic PublicationsShow
5-O-Caffeoylquinic acidMateBeverages, Non-alcoholic 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

Metabolism

PrecursorMetaboliteSpeciesBiofluidsOriginFormulaMonoisotopic mass
Dihydrocaffeic acid Vanillic acidraturineNot AvailableC8H8O4168.042258738
Dihydrocaffeic acid Isoferulic acidraturineNot AvailableC10H10O4194.057908802
Dihydrocaffeic acid 3-(3'-Hydroxyphenyl)propionic acidraturineNot AvailableC9H10O3166.062994182 Publications
Dihydrocaffeic acid Dihydroferulic acidraturineNot AvailableC10H12O4196.073558866 Publications
Dihydrocaffeic acid Ferulic acid-4'-sulfateraturineNot AvailableC10H10O7S274.014723836 Publications
Dihydrocaffeic acid Dihydrocaffeic acid-3'-O-glucuronideraturineNot AvailableC15H18O10358.08999678 Publications
Dihydrocaffeic acid Dihydrocaffeic acid-4'-O-glucuronideraturineNot AvailableC15H18O10358.08999678 Publications
Dihydrocaffeic acid Dihydrocaffeic acid-4'-sulfateraturineNot AvailableC9H10O7S262.014723836 Publications
Dihydrocaffeic acid Isoferulic acid-3'-sulfateraturineNot AvailableC10H10O7S274.014723836 Publications
Eriocitrin Dihydrocaffeic acidin vitro (human) ratplasma (major), urine (major)gut microbiota metaboliteC9H10O4182.057908802 Publications
Eriodictyol Dihydrocaffeic acidin vitro (human) raturinegut microbiota metaboliteC9H10O4182.057908802 Publications
Caffeic acid Dihydrocaffeic acidraturinegut microbiota metaboliteC9H10O4182.057908802 Publications
5-O-Caffeoylquinic acid Dihydrocaffeic acidraturinegut microbiota metaboliteC9H10O4182.057908802 Publications
Ferulic acid Dihydrocaffeic acidhumanurinegut microbiota metaboliteC9H10O4182.057908802
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