Identification

PhytoHub ID
PHUB000294
Name
3-Hydroxybenzoic acid
Systematic Name
3-Hydroxybenzoic acid
Synonyms
  • 3-Hydroxybenzenecarboxylic acid
  • m-Hydroxybenzoic acid
CAS Number
99-06-9
Average Mass
138.122
Monoisotopic Mass
138.031694053
Chemical Formula
C7H6O3
IUPAC Name
3-hydroxybenzoic acid
InChI Key
IJFXRHURBJZNAO-UHFFFAOYSA-N
InChI Identifier
InChI=1S/C7H6O3/c8-6-3-1-2-5(4-6)7(9)10/h1-4,8H,(H,9,10)
SMILES
OC(=O)C1=CC(O)=CC=C1
Structure

Calculated Properties

Solubility (ALOGPS)
1.02e+01 g/l
LogS (ALOGPS)
-1.13
LogP (ALOGPS)
1.81
Hydrogen Acceptors
3
Hydrogen Donors
2
Rotatable Bond Count
1
Polar Surface Area
57.53
Refractivity
35.2951
Polarizability
12.919313787333978
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-6.007037034515305
pKa (strongest acidic)
3.844596909709927
Number of Rings
1
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
No
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Metabolite

Family
(Poly)phenol metabolites
Class
Phenolic acid metabolites
Sub-class
Benzoic and hippuric acids

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
Cyanidin 3-O-glucosidePolyphenolsFlavonoidsAnthocyaninsShow 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
Green tea Flavan-3-olsPolyphenolsFlavonoidsFlavan-3-olsShow Food Phytochemical
Cocoa Flavan-3-olsPolyphenolsFlavonoidsFlavan-3-olsShow Food Phytochemical
Black tea Flavan-3-olsPolyphenolsFlavonoidsFlavan-3-olsShow Food Phytochemical
HydroxytyrosolPolyphenolsPhenolic acidsMiscellaneous phenolic acidsShow Food Phytochemical
(+)-GallocatechinPolyphenolsFlavonoidsFlavan-3-olsShow Food Phytochemical

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Benzene and substituted derivatives
Super-class
Benzenoids
Sub-class
Benzoic acids and derivatives
Direct Parent Name
Hydroxybenzoic acid derivatives
Alternative Parent Names
["1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "Benzoic acids", "Benzoyl derivatives", "Carboxylic acids", "Hydrocarbon derivatives", "Monocarboxylic acids and derivatives", "Organic oxides", "Organooxygen compounds"]
External Descriptor Annotations
["monohydroxybenzoic acid"]
Substituent Names
["1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "Aromatic homomonocyclic compound", "Benzoic acid", "Benzoyl", "Carboxylic acid", "Carboxylic acid derivative", "Hydrocarbon derivative", "Hydroxybenzoic acid", "Monocarboxylic acid or derivatives", "Organic oxide", "Organic oxygen compound", "Organooxygen compound", "Phenol"]

Spectra from Online Resources

Record IDSourceDescriptionView
GLS00066MassBankEI-B Spectrum - -, unspecifiedView Spectra
JP010334MassBankEI-B Spectrum - -, [M]+*View Spectra
KO000998MassBankLC-ESI-QQ Spectrum - 10 V, unspecifiedView Spectra
KO000999MassBankLC-ESI-QQ Spectrum - 20 V, unspecifiedView Spectra
KO001000MassBankLC-ESI-QQ Spectrum - 30 V, unspecifiedView Spectra
KO001001MassBankLC-ESI-QQ Spectrum - 40 V, unspecifiedView Spectra
KO001002MassBankLC-ESI-QQ Spectrum - 50 V, unspecifiedView Spectra
ML001351MassBankLC-ESI-ITFT Spectrum - 50 % (nominal), unspecifiedView Spectra

Food Sources

No food source information available

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
(+)-GallocatechinBlack teaTeas and herbal teas PublicationsShow
Cyanidin 3-O-glucosideBlackberryFruit, Berries PublicationsShow
Caffeic acidBlackberryFruit, Berries PublicationsShow
5-O-Caffeoylquinic acidBlackberryFruit, Berries PublicationsShow
Ferulic acidBlackberryFruit, Berries PublicationsShow
Cyanidin 3-O-glucosideBlackcurrantFruit, 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
Cyanidin 3-O-glucosideElderberryFruit, Berries PublicationsShow
Caffeic acidEuropean cranberryFruit, Berries PublicationsShow
5-O-Caffeoylquinic acidEuropean cranberryFruit, Berries PublicationsShow
Ferulic acidEuropean cranberryFruit, Berries PublicationsShow
Cyanidin 3-O-glucosideEuropean 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
Ferulic acidGrapefruitFruit, Citrus PublicationsShow
5-O-Caffeoylquinic acidGreen teaTeas and herbal teas PublicationsShow
(+)-GallocatechinGreen teaTeas and herbal teas PublicationsShow
Ferulic acidHard wheatCereals and cereal products PublicationsShow
Cyanidin 3-O-glucosideLettuceVegetables, Leaf vegetables PublicationsShow
5-O-Caffeoylquinic acidLettuceVegetables, Leaf vegetables PublicationsShow
Caffeic acidMateTeas and herbal teas PublicationsShow
5-O-Caffeoylquinic acidMateTeas and herbal teas PublicationsShow
Cyanidin 3-O-glucosideOlive, blackFruit, Drupes PublicationsShow
Caffeic acidOlive, blackFruit, Drupes PublicationsShow
5-O-Caffeoylquinic acidOlive, blackFruit, Drupes PublicationsShow
Ferulic acidOlive, blackFruit, Drupes PublicationsShow
HydroxytyrosolOlive, blackFruit, Drupes PublicationsShow
Caffeic acidOlive, greenFruit, Drupes PublicationsShow
Ferulic acidOlive, greenFruit, Drupes PublicationsShow
HydroxytyrosolOlive, greenFruit, Drupes PublicationsShow
Ferulic acidOrange juiceBeverages, Non-alcoholic PublicationsShow
Cyanidin 3-O-glucosidePeachFruit, Drupes PublicationsShow
5-O-Caffeoylquinic acidPeachFruit, Drupes PublicationsShow
Caffeic acidPearFruit, Pomes PublicationsShow
5-O-Caffeoylquinic acidPearFruit, Pomes PublicationsShow
Cyanidin 3-O-glucosidePomegranate juiceBeverages, Non-alcoholic PublicationsShow
5-O-Caffeoylquinic acidPotatoVegetables, Tubers PublicationsShow
Ferulic acidRapeseedOilseed crops PublicationsShow
Cyanidin 3-O-glucosideRed raspberryFruit, Berries 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
Cyanidin 3-O-glucosideStrawberryFruit, Berries PublicationsShow
Caffeic acidStrawberryFruit, Berries PublicationsShow
5-O-Caffeoylquinic acidStrawberryFruit, Berries PublicationsShow
Ferulic acidStrawberryFruit, Berries PublicationsShow
Cyanidin 3-O-glucosideSweet cherryFruit, Drupes 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
Cyanidin 3-O-glucoside 3-Hydroxybenzoic acidhumanfeces, urineNot AvailableNot AvailableNot AvailableNot AvailableC7H6O3138.031694053 Publications
Caffeic acid 3-Hydroxybenzoic acidhuman in vitro (human) ratfeces, urinehost-gut microbiota co-metaboliteNot AvailableNot AvailableNot AvailableC7H6O3138.031694053 Publications
5-O-Caffeoylquinic acid 3-Hydroxybenzoic acidraturinehost-gut microbiota co-metaboliteNot AvailableNot AvailableNot AvailableC7H6O3138.031694053
Ferulic acid 3-Hydroxybenzoic acidhuman ratplasma, urinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC7H6O3138.031694053 Publications
Orange flavanones 3-Hydroxybenzoic acidhumanurinegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC7H6O3138.031694053 Detailed Intervention Studies Publications
Green tea Flavan-3-ols 3-Hydroxybenzoic acidNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC7H6O3138.031694053 Detailed Intervention Studies
Cocoa Flavan-3-ols 3-Hydroxybenzoic acidhumanurinegut microbiota metaboliteNot AvailableNot Available<1%C7H6O3138.031694053 Detailed Intervention Studies Publications
Black tea Flavan-3-ols 3-Hydroxybenzoic acidhumanurinegut microbiota metaboliteNot AvailableNot Available<1%C7H6O3138.031694053 Detailed Intervention Studies Publications
Hydroxytyrosol 3-Hydroxybenzoic acidhumanplasmagut microbiota metaboliteNot Available2-5┬Ámol/LNot AvailableC7H6O3138.031694053 Detailed Intervention Studies Publications
(+)-Gallocatechin 3-Hydroxybenzoic acidhumanurinegut microbiota metaboliteNot AvailableNot Available<1%C7H6O3138.031694053 Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
(+)-Gallocatechin 3-Hydroxybenzoic acidMicrobiotaEffect, clusters Publications
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