Identification

PhytoHub ID
PHUB000316
Name
Vanillic acid
Systematic Name
4-hydroxy-3-methoxybenzoic acid
Synonyms
  • 3-Methoxy-4-hydroxybenzoic acid
  • 4-Hydroxy-3-methoxybenzoic acid
  • p-Vanillic acid
CAS Number
121-34-6
Average Mass
168.148
Monoisotopic Mass
168.042258738
Chemical Formula
C8H8O4
IUPAC Name
4-hydroxy-3-methoxybenzoic acid
InChI Key
WKOLLVMJNQIZCI-UHFFFAOYSA-N
InChI Identifier
InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)
SMILES
COC1=CC(=CC=C1O)C(O)=O
Structure

Calculated Properties

Solubility (ALOGPS)
5.70e+00 g/l
LogS (ALOGPS)
-1.47
LogP (ALOGPS)
1.70
Hydrogen Acceptors
4
Hydrogen Donors
2
Rotatable Bond Count
2
Polar Surface Area
66.76
Refractivity
41.7583
Polarizability
15.868081533318291
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-4.901377890748089
pKa (strongest acidic)
4.155416072405769
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
Hydroxybenzoic acids

Taxonomy as Metabolite

Metabolite Family
(Poly)phenol metabolites
Metabolite Class
Phenolic acid metabolites
Metabolite 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
Dihydrocaffeic acidPolyphenolsPhenolic acidsPhenolic acids subclass not specifiedShow Food Phytochemical
Ferulic acidPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical
Orange flavanonesPolyphenolsFlavonoidsFlavanonesShow 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
M-methoxybenzoic acids and derivatives
Alternative Parent Names
["1-hydroxy-2-unsubstituted benzenoids", "Alkyl aryl ethers", "Anisoles", "Benzoic acids", "Benzoyl derivatives", "Carboxylic acids", "Hydrocarbon derivatives", "Hydroxybenzoic acid derivatives", "Methoxybenzenes", "Methoxyphenols", "Monocarboxylic acids and derivatives", "Organic oxides", "Phenoxy compounds"]
External Descriptor Annotations
["methoxybenzoic acid", "monohydroxybenzoic acid"]
Substituent Names
["1-hydroxy-2-unsubstituted benzenoid", "Alkyl aryl ether", "Anisole", "Aromatic homomonocyclic compound", "Benzoic acid", "Benzoyl", "Carboxylic acid", "Carboxylic acid derivative", "Ether", "Hydrocarbon derivative", "Hydroxybenzoic acid", "M-methoxybenzoic acid or derivatives", "Methoxybenzene", "Methoxyphenol", "Monocarboxylic acid or derivatives", "Organic oxide", "Organic oxygen compound", "Organooxygen compound", "Phenol", "Phenol ether", "Phenoxy compound"]

Spectra from Online Resources

Record IDSourceDescriptionView
JP008196MassBankEI-B Spectrum - -, [M]+*View Spectra
KO001150MassBankLC-ESI-QQ Spectrum - 10 V, unspecifiedView Spectra
KO001151MassBankLC-ESI-QQ Spectrum - 20 V, unspecifiedView Spectra
KO001152MassBankLC-ESI-QQ Spectrum - 30 V, unspecifiedView Spectra
KO001153MassBankLC-ESI-QQ Spectrum - 40 V, unspecifiedView Spectra
KO001154MassBankLC-ESI-QQ Spectrum - 50 V, unspecifiedView Spectra
ML005851MassBankLC-ESI-ITFT Spectrum - 50 % (nominal), unspecifiedView Spectra

Food Sources

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
Caffeic acidApple juiceBeverages, Non-alcoholic PublicationsShow
Ferulic acidApple juiceBeverages, Non-alcoholic PublicationsShow
Caffeic acidBeerBeverages, Alcoholic PublicationsShow
Ferulic acidBeerBeverages, Alcoholic PublicationsShow
Ferulic acidBilberryFruit, Berries PublicationsShow
Ferulic acidBlack mulberryFruit, Berries PublicationsShow
Cyanidin 3-O-glucosideBlackberryFruit, Berries PublicationsShow
Caffeic acidBlackberryFruit, Berries PublicationsShow
Ferulic acidBlackberryFruit, Berries PublicationsShow
Cyanidin 3-O-glucosideBlackcurrantFruit, Berries PublicationsShow
Caffeic acidBlueberryFruit, Berries PublicationsShow
Dihydrocaffeic acidBlueberryFruit, BerriesShow
Ferulic acidBlueberryFruit, Berries PublicationsShow
Caffeic acidBroccoliVegetables, Cabbages PublicationsShow
Dihydrocaffeic acidBroccoliVegetables, CabbagesShow
Ferulic acidBroccoliVegetables, Cabbages PublicationsShow
Caffeic acidCarrotVegetables, Root vegetables PublicationsShow
Caffeic acidCiderBeverages, Alcoholic PublicationsShow
Dihydrocaffeic acidCiderBeverages, AlcoholicShow
Ferulic acidCocoa beanCocoa and cocoa products PublicationsShow
Caffeic acidCoffeeCoffee and coffee products PublicationsShow
Dihydrocaffeic acidCoffeeCoffee and coffee productsShow
Ferulic acidCoffeeCoffee and coffee products PublicationsShow
Ferulic acidCommon beanPulses and beans 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
Ferulic acidEggplantVegetables, Fruit vegetables PublicationsShow
Cyanidin 3-O-glucosideElderberryFruit, Berries PublicationsShow
Caffeic acidEuropean cranberryFruit, Berries PublicationsShow
Ferulic acidEuropean cranberryFruit, Berries PublicationsShow
Cyanidin 3-O-glucosideEuropean plumFruit, Drupes PublicationsShow
Caffeic acidEuropean plumFruit, Drupes PublicationsShow
Ferulic acidFennelHerbs and Spices PublicationsShow
Ferulic acidGrapefruitFruit, Citrus PublicationsShow
Dihydrocaffeic acidGrapesFruit, BerriesShow
Ferulic acidHard wheatCereals and cereal products PublicationsShow
Dihydrocaffeic acidLemonFruit, CitrusShow
Cyanidin 3-O-glucosideLettuceVegetables, Leaf vegetables PublicationsShow
Dihydrocaffeic acidLettuceVegetables, Leaf vegetablesShow
Dihydrocaffeic acidLimeFruit, CitrusShow
Caffeic acidMateTeas and herbal teas PublicationsShow
Cyanidin 3-O-glucosideOlive, blackFruit, Drupes PublicationsShow
Caffeic 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
Ferulic acidOrange juiceBeverages, Non-alcoholic PublicationsShow
Cyanidin 3-O-glucosidePeachFruit, Drupes PublicationsShow
Caffeic acidPearFruit, Pomes PublicationsShow
Cyanidin 3-O-glucosidePomegranate juiceBeverages, Non-alcoholic PublicationsShow
Ferulic acidRapeseedOilseed crops PublicationsShow
Cyanidin 3-O-glucosideRed raspberryFruit, Berries PublicationsShow
Ferulic acidRed raspberryFruit, Berries PublicationsShow
Ferulic acidRiceCereals and cereal products PublicationsShow
Ferulic acidRosemaryHerbs and Spices PublicationsShow
Ferulic acidRye breadCereals and cereal products PublicationsShow
Dihydrocaffeic acidSpinachVegetables, Leaf vegetablesShow
Ferulic acidSpinachVegetables, Leaf vegetables PublicationsShow
Cyanidin 3-O-glucosideStrawberryFruit, Berries PublicationsShow
Caffeic acidStrawberryFruit, Berries PublicationsShow
Ferulic acidStrawberryFruit, Berries PublicationsShow
Cyanidin 3-O-glucosideSweet cherryFruit, Drupes PublicationsShow
Caffeic acidSweet cherryFruit, Drupes PublicationsShow
Ferulic acidSweet orangeFruit, Citrus PublicationsShow
Ferulic acidTarragonHerbs and Spices PublicationsShow
Caffeic 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
Vanillic acid Vanillic acid-4-O-sulfatehumanplasmahost metabolismNot Available0.5-2┬Ámol/LNot AvailableC8H8O7S247.999073772 Detailed Intervention Studies Publications
Cyanidin 3-O-glucoside Vanillic acidhumanfeces, serum, urineNot AvailableNot AvailableNot AvailableNot AvailableC8H8O4168.042258738 Publications
Caffeic acid Vanillic acidhumanurinehost metabolismNot AvailableNot AvailableNot AvailableC8H8O4168.042258738 Publications
Dihydrocaffeic acid Vanillic acidraturineNot AvailableNot AvailableNot AvailableNot AvailableC8H8O4168.042258738
Ferulic acid Vanillic acidhuman raturineNot AvailableNot AvailableNot AvailableNot AvailableC8H8O4168.042258738 Publications
Orange flavanones Vanillic acidhumanurinehost-gut microbiota co-metaboliteNot AvailableNot AvailableNot AvailableC8H8O4168.042258738 Detailed Intervention Studies Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
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