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3,4-Dihydroxybenzaldehyde (FDB012060)

Record Information
Version1.0
Creation date2010-04-08 22:09:58 UTC
Update date2019-11-26 03:06:06 UTC
Primary IDFDB012060
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3,4-Dihydroxybenzaldehyde
DescriptionProtocatechualdehyde, also known as rancinamycin iv or 1,2-dihydroxy-4-formylbenzene, is a member of the class of compounds known as hydroxybenzaldehydes. Hydroxybenzaldehydes are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. Protocatechualdehyde is soluble (in water) and a very weakly acidic compound (based on its pKa). Protocatechualdehyde is an almond, bitter, and dry tasting compound and can be found in a number of food items such as plains prickly pear, mugwort, silver linden, and cardamom, which makes protocatechualdehyde a potential biomarker for the consumption of these food products. Protocatechualdehyde can be found primarily in urine. This molecule can be used as a precursor in the vanillin synthesis by biotransformation by cell cultures of Capsicum frutescens, a type of Chili pepper. It is also found in the mushroom Phellinus linteus .
CAS Number139-85-5
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility14.3 g/LALOGPS
logP0.89ALOGPS
logP1.08ChemAxon
logS-0.99ALOGPS
pKa (Strongest Acidic)7.46ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.6 m³·mol⁻¹ChemAxon
Polarizability12.87 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H6O3
IUPAC name3,4-dihydroxybenzaldehyde
InChI IdentifierInChI=1S/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H
InChI KeyIBGBGRVKPALMCQ-UHFFFAOYSA-N
Isomeric SMILESOC1=CC=C(C=O)C=C1O
Average Molecular Weight138.1207
Monoisotopic Molecular Weight138.031694058
Classification
Description Belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentHydroxybenzaldehydes
Alternative Parents
Substituents
  • Hydroxybenzaldehyde
  • Catechol
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Foods
  • Cocoa and cocoa products

    • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateNot Available
    Physical DescriptionNot Available
    Mass CompositionC 60.87%; H 4.38%; O 34.75%DFC
    Melting PointNot Available
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV Data[neutral] lmax 220 (e 9500) (95% EtOH) (Derep)DFC
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    Predicted GC-MS3,4-Dihydroxybenzaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052r-2900000000-fd0d28650a72226166e6Spectrum
    Predicted GC-MS3,4-Dihydroxybenzaldehyde, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00yi-8690000000-16ccc54dcf22361cffb1Spectrum
    Predicted GC-MS3,4-Dihydroxybenzaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0002-0040900010-522c055741661bbc5ba82017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0002-0040900010-522c055741661bbc5ba82017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0002-0040900010-522c055741661bbc5ba82017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-002r-0905000000-7987816fb8648b0eea182017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0900000000-aa91c9c469ec394504352017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-000i-0900000000-25b5b2bc87af9df04e912017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0900000000-03d9e2dbe57c9bcfb9ab2017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-002r-0905000000-7987816fb8648b0eea182017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-000i-0900000000-aa91c9c469ec394504352017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-000i-0900000000-25b5b2bc87af9df04e912017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-aa91c9c469ec394504352021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-25b5b2bc87af9df04e912021-09-20View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-db13978cfcbc33c6da322015-05-26View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1900000000-ed3a0258f14e4361b25c2015-05-26View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-9200000000-cdb54c915314193962132015-05-26View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-db13978cfcbc33c6da322015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1900000000-ed3a0258f14e4361b25c2015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-9200000000-cdb54c915314193962132015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-882b8375384be94a34912015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1900000000-25b2a170eaf9dd74c4a02015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kw4-9300000000-e349b638bc98dcdf0ade2015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-882b8375384be94a34912015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1900000000-25b2a170eaf9dd74c4a02015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kw4-9300000000-e349b638bc98dcdf0ade2015-05-27View Spectrum
    NMRNot Available
    ChemSpider IDNot Available
    ChEMBL IDNot Available
    KEGG Compound IDNot Available
    Pubchem Compound IDNot Available
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID723
    DrugBank IDNot Available
    HMDB IDNot Available
    CRC / DFC (Dictionary of Food Compounds) IDHCW75-Q:HCW75-Q
    EAFUS IDNot Available
    Dr. Duke IDPROTOCATECHUIC-ALDEHYDE|3,4-DIHYDROXYBENZALDEHYDE|PROTOCATECHUALDEHYDE
    BIGG IDNot Available
    KNApSAcK IDNot Available
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDrw1040061
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite ID723
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / Bioactivities
    DescriptorIDDefinitionReference
    anti aggregantDUKE
    anti coagulant50249 An agent that prevents blood clotting.DUKE
    antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    Flavours
    FlavorCitations
    dry
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    medical
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    bitter
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    almond
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    Files
    MSDSNot Available
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
    — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.