Record Information
Version1.0
Creation date2010-04-08 22:09:09 UTC
Update date2018-05-28 22:48:15 UTC
Primary IDFDB010504
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Hydroxybenzaldehyde
DescriptionOccurs naturally combined in many glycosides. Constituent of vanillin. Isol. in free state from opium poppy (Papaver somniferum) 4-Hydroxybenzaldehyde reacts with NAD+ and H2O to produce 4-hydroxybenzoate, NADH, and 2 protons. The reaction is catalyzed by 4-hydroxybenzaldehyde dehydrogenase.; ; 4-Hydroxybenzaldehyde is found in the benzoate degradation via hydroxylation, bisphenol A degradation, toluene and xylene degradation, and biosynthesis of phenylpropanoids pathways.
CAS Number123-08-0
Structure
Thumb
Synonyms
SynonymSource
4-FormylphenolChEBI
p-FormylphenolChEBI
p-HydroxybenzaldehydeChEBI
4-Hydroxy-benzaldehydeHMDB
4-HydroxybenzenecarbonalHMDB
p-Hydroxy-benzaldehydeHMDB
p-OxybenzaldehydeHMDB
ParahydroxybenzaldehydeHMDB
Usaf m-6HMDB
Para-hydroxybenzaldehydeHMDB
4-hydroxy-Benzaldehydebiospider
4-Hydroxybenzaldehyde, homopolymerbiospider
Benzaldehyde, 4-hydroxy-biospider
Benzaldehyde, 4-hydroxy-, homopolymerbiospider
Benzaldehyde, p-hydroxy-biospider
HBAbiospider
P-Hydroxy-benzaldehydeHMDB
P-hydroxybenzaldehydebiospider
P-oxybenzaldehydebiospider
P-oxybenzaldehyde;p-hydroxy-benzaldehydebiospider
PHBbiospider
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
Physico-Chemical Properties - Experimental
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-8900000000-4eff34096f6bd4f30d10View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-9800000000-c8646d08ef8e23a3d49bView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-8900000000-60621d4d9871b2d7587dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05i0-1970000000-7ef151eab685361413a6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00b9-1940000000-fa6b812457f26dce7720View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00b9-2940000000-0bfc68ade3f25f6ba1f2View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00b9-2940000000-b50ed8954cb10b92a30bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00b9-2930000000-671031e52722de3402ecView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-8900000000-4eff34096f6bd4f30d10View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-9800000000-c8646d08ef8e23a3d49bView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-8900000000-60621d4d9871b2d7587dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05i0-1970000000-7ef151eab685361413a6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00b9-1940000000-fa6b812457f26dce7720View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00b9-2940000000-0bfc68ade3f25f6ba1f2View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00b9-2940000000-b50ed8954cb10b92a30bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00b9-2930000000-671031e52722de3402ecView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-6900000000-ea309e8826550692ddebView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-8900000000-781df730e85ee6b33891View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0900000000-99136b39c7ec11a7bbcaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-00di-0900000000-ab4c213ba9a645517aa3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-298ab6a83ac989405983View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-12ad1640340af91bc8e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0036-9000000000-ddc48e682b255bd53c5eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-785058db9c1fbc1b5950View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-c22365c838c065b99ed8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0100-9300000000-491fc6287b2479ddc1a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-298ab6a83ac989405983View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-12ad1640340af91bc8e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0036-9000000000-ddc48e682b255bd53c5eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-785058db9c1fbc1b5950View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-c22365c838c065b99ed8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0100-9300000000-491fc6287b2479ddc1a6View in MoNA
MSMass Spectrum (Electron Ionization)splash10-00di-9500000000-2c1739a8a2bc288e4a5cView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
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
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.