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4-Hydroxybenzaldehyde (FDB010504)

Record Information
Version1.0
Creation date2010-04-08 22:09:09 UTC
Update date2019-11-26 03:03:39 UTC
Primary IDFDB010504
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Hydroxybenzaldehyde
Description4-Hydroxybenzaldehyde, also known as 4-formylphenol, 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. 4-Hydroxybenzaldehyde exists in all living organisms, ranging from bacteria to humans. 4-Hydroxybenzaldehyde is a sweet, almond, and balsam tasting compound. 4-Hydroxybenzaldehyde is found, on average, in the highest concentration within a few different foods, such as vinegar, oats (Avena sativa), and beer. 4-Hydroxybenzaldehyde has also been detected, but not quantified in, several different foods, such as horseradish trees (Moringa oleifera), chayotes (Sechium edule), peanuts (Arachis hypogaea), yardlong beans (Vigna unguiculata ssp. sesquipedalis), and mixed nuts. This could make 4-hydroxybenzaldehyde a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 4-Hydroxybenzaldehyde.
CAS Number123-08-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility9.51 g/LALOGPS
logP1.27ALOGPS
logP1.38ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)7.32ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.62 m³·mol⁻¹ChemAxon
Polarizability11.98 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H6O2
IUPAC name4-hydroxybenzaldehyde
InChI IdentifierInChI=1S/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9H
InChI KeyRGHHSNMVTDWUBI-UHFFFAOYSA-N
Isomeric SMILESOC1=CC=C(C=O)C=C1
Average Molecular Weight122.1213
Monoisotopic Molecular Weight122.036779436
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
  • Benzoyl
  • 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

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

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 stateSolid
    Physical DescriptionNot Available
    Mass CompositionC 68.85%; H 4.95%; O 26.20%DFC
    Melting PointMp 115-116°DFC
    Boiling PointNot Available
    Experimental Water Solubility8.45 mg/mL at 25 oCJIN,LJ et al. (1998)
    Experimental logP1.35HANSCH,C ET AL. (1995)
    Experimental pKapKa 7.62 (25°, H2O)DFC
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV Data330 (e 6600) (EtOH) (Berdy)DFC
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    EI-MSMass Spectrum (Electron Ionization)splash10-00di-9500000000-2c1739a8a2bc288e4a5c2015-03-01View Spectrum
    GC-MS4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00di-8900000000-4eff34096f6bd4f30d10Spectrum
    GC-MS4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00di-9800000000-c8646d08ef8e23a3d49bSpectrum
    GC-MS4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00di-8900000000-60621d4d9871b2d7587dSpectrum
    GC-MS4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-05i0-1970000000-7ef151eab685361413a6Spectrum
    GC-MS4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00b9-1940000000-fa6b812457f26dce7720Spectrum
    GC-MS4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00b9-2940000000-0bfc68ade3f25f6ba1f2Spectrum
    GC-MS4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00b9-2940000000-b50ed8954cb10b92a30bSpectrum
    GC-MS4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00b9-2930000000-671031e52722de3402ecSpectrum
    GC-MS4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00di-8900000000-4eff34096f6bd4f30d10Spectrum
    GC-MS4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00di-9800000000-c8646d08ef8e23a3d49bSpectrum
    GC-MS4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00di-8900000000-60621d4d9871b2d7587dSpectrum
    GC-MS4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-05i0-1970000000-7ef151eab685361413a6Spectrum
    GC-MS4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00b9-1940000000-fa6b812457f26dce7720Spectrum
    GC-MS4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00b9-2940000000-0bfc68ade3f25f6ba1f2Spectrum
    GC-MS4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00b9-2940000000-b50ed8954cb10b92a30bSpectrum
    GC-MS4-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00b9-2930000000-671031e52722de3402ecSpectrum
    Predicted GC-MS4-Hydroxybenzaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-6900000000-ea309e8826550692ddebSpectrum
    Predicted GC-MS4-Hydroxybenzaldehyde, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-8900000000-781df730e85ee6b33891Spectrum
    Predicted GC-MS4-Hydroxybenzaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0900000000-99136b39c7ec11a7bbca2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - , negativesplash10-00di-0900000000-ab4c213ba9a645517aa32017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-9300000000-7a1d8d268b763ce713312020-07-21View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-002g-9000000000-e9050639f16e3b6d79392020-07-21View Spectrum
    MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-00di-0900000000-27effb3a35bdb0d723102020-07-22View Spectrum
    MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-00di-1900000000-731f917249c17a761e0f2020-07-22View Spectrum
    MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-00dj-5900000000-c46a92738e14de26b66c2020-07-22View Spectrum
    MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-006t-9500000000-7f1f8c64931b0dc6f66f2020-07-22View Spectrum
    MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0002-9100000000-39037b9523c5f3c7ed6c2020-07-22View Spectrum
    MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0002-9000000000-06c809ed4b25327e8b092020-07-22View Spectrum
    MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-002b-9000000000-b93cdaad48fe246028dd2020-07-22View Spectrum
    MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-002b-9000000000-16e7fae11656d4e6cd8a2020-07-22View Spectrum
    MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-0fba-9000000000-96924ab5b95b0d4fb8572020-07-22View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-298ab6a83ac9894059832015-04-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-12ad1640340af91bc8e82015-04-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0036-9000000000-ddc48e682b255bd53c5e2015-04-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-785058db9c1fbc1b59502015-04-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-c22365c838c065b99ed82015-04-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0100-9300000000-491fc6287b2479ddc1a62015-04-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-298ab6a83ac9894059832015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-12ad1640340af91bc8e82015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0036-9000000000-ddc48e682b255bd53c5e2015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-785058db9c1fbc1b59502015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-c22365c838c065b99ed82015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0100-9300000000-491fc6287b2479ddc1a62015-05-27View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
    ChemSpider ID123
    ChEMBL IDCHEMBL14193
    KEGG Compound IDC00633
    Pubchem Compound ID126
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID725
    DrugBank IDDB03560
    HMDB IDHMDB11718
    CRC / DFC (Dictionary of Food Compounds) IDFBR96-V:FBR96-V
    EAFUS ID1724
    Dr. Duke ID4-HYDROXYBENZALDEHYDE|P-HYDROXYBENZALDEHYDE
    BIGG IDNot Available
    KNApSAcK IDC00002657
    HET IDHBA
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDrw1040191
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite IDNot Available
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / Bioactivities
    DescriptorIDDefinitionReference
    allelochemicDUKE
    anti feedantDUKE
    cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
    tyrosinase inhibitor59997 Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.DUKE
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    Flavours
    FlavorCitations
    sweet
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    nutty
    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.
    balsam
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    woody
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    Files
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— 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.
    — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
    — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.