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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-02-24 16:13:29 UTC
Update Date2018-05-20 18:52:41 UTC
HMDB IDHMDB0011718
Secondary Accession Numbers
  • HMDB11718
Metabolite Identification
Common Name4-Hydroxybenzaldehyde
Description4-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.
Structure
Thumb
Synonyms
ValueSource
4-FormylphenolChEBI
P-FormylphenolChEBI
P-HydroxybenzaldehydeChEBI
4-Hydroxy-benzaldehydeHMDB
4-HydroxybenzenecarbonalHMDB
P-Hydroxy-benzaldehydeHMDB
P-OxybenzaldehydeHMDB
ParahydroxybenzaldehydeHMDB
Usaf m-6HMDB
Para-hydroxybenzaldehydeMeSH
Chemical FormulaC7H6O2
Average Molecular Weight122.1213
Monoisotopic Molecular Weight122.036779436
IUPAC Name4-hydroxybenzaldehyde
Traditional NameP-hydroxybenzaldehyde
CAS Registry Number123-08-0
SMILES
OC1=CC=C(C=O)C=C1
InChI Identifier
InChI=1S/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9H
InChI KeyRGHHSNMVTDWUBI-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point117 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility8.45 mg/mL at 25 °CNot Available
LogP1.35HANSCH,C ET AL. (1995)
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
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
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
UrineDetected and Quantified16.961 +/- 2.481 umol/mmol creatinineAdolescent (13-18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.5 (0.0-1.0) uMAdult (>18 years old)Both
Prostate Cancer
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified6.703 +/- 1.305 umol/mmol creatinineAdolescent (13-18 years old)Both
Obese
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Obesity
  1. Cho K, Moon JS, Kang JH, Jang HB, Lee HJ, Park SI, Yu KS, Cho JY: Combined untargeted and targeted metabolomic profiling reveals urinary biomarkers for discriminating obese from normal-weight adolescents. Pediatr Obes. 2017 Apr;12(2):93-101. doi: 10.1111/ijpo.12114. Epub 2016 Feb 22. [PubMed:26910390 ]
Prostate cancer
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Associated OMIM IDs
DrugBank IDDB03560
Phenol Explorer Compound ID725
FoodDB IDFDB010504
KNApSAcK IDC00002657
Chemspider ID123
KEGG Compound IDC00633
BioCyc ID4-HYDROXYBENZALDEHYDE
BiGG IDNot Available
Wikipedia Link4-Hydroxybenzaldehyde
METLIN IDNot Available
PubChem Compound126
PDB IDHBA
ChEBI ID17597
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Hext PM, Rose FA: The Sulphation of p-hydroxyphenylpyruvic acid and related compounds by the rat liver cytosol. Biochem J. 1975 Aug;150(2):175-81. [PubMed:1180912 ]