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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-02-24 16:13:29 UTC
Update Date2021-09-07 17:05:28 UTC
HMDB IDHMDB0011718
Secondary Accession Numbers
  • HMDB11718
Metabolite Identification
Common Name4-Hydroxybenzaldehyde
Description4-Hydroxybenzaldehyde, also known as 4-formylphenol or 4-hydroxybenzenecarbonal, 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. A hydroxybenzaldehyde that is benzaldehyde substituted with a hydroxy group at position C-4. 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 vinegars and oats. 4-Hydroxybenzaldehyde has also been detected, but not quantified, in several different foods, such as cardoons, colorado pinyons, oyster mushrooms, common chokecherries, and potato. This could make 4-hydroxybenzaldehyde a potential biomarker for the consumption of these foods.
Structure
Data?1582752943
Synonyms
ValueSource
4-FormylphenolChEBI
p-FormylphenolChEBI
p-HydroxybenzaldehydeChEBI
4-Hydroxy-benzaldehydeHMDB
4-HydroxybenzenecarbonalHMDB
p-Hydroxy-benzaldehydeHMDB
p-OxybenzaldehydeHMDB
ParahydroxybenzaldehydeHMDB
Usaf m-6HMDB
Para-hydroxybenzaldehydeHMDB
4-HydroxybenzaldehydePhytoBank
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
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:

Physical Properties
StateSolid
Experimental Molecular 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 Molecular 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
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
AllCCS[M-H]-ExperimentalNot Available119.4http://allccs.zhulab.cn/database/detail?ID=AllCCS00002108
DarkChem[M+H]+PredictedNot Available123.19631661259
DarkChem[M-H]-PredictedNot Available119.95431661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
4-Hydroxybenzaldehyde,1TMS,#11367.131https://arxiv.org/abs/1905.12712
4-Hydroxybenzaldehyde,1TBDMS,#11636.7496https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-8900000000-4eff34096f6bd4f30d102017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-9800000000-c8646d08ef8e23a3d49b2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-8900000000-60621d4d9871b2d7587d2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05i0-1970000000-7ef151eab685361413a62017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00b9-1940000000-fa6b812457f26dce77202017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00b9-2940000000-0bfc68ade3f25f6ba1f22017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00b9-2940000000-b50ed8954cb10b92a30b2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00b9-2930000000-671031e52722de3402ec2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-8900000000-4eff34096f6bd4f30d102018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-9800000000-c8646d08ef8e23a3d49b2018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-8900000000-60621d4d9871b2d7587d2018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05i0-1970000000-7ef151eab685361413a62018-05-18View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00b9-1940000000-fa6b812457f26dce77202018-05-18View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00b9-2940000000-0bfc68ade3f25f6ba1f22018-05-18View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00b9-2940000000-b50ed8954cb10b92a30b2018-05-18View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00b9-2930000000-671031e52722de3402ec2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-6900000000-ea309e8826550692ddeb2017-07-27View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-8900000000-781df730e85ee6b338912017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-9500000000-2c1739a8a2bc288e4a5c2015-03-01View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-8900000000-5b42adf83e422cffefb62021-09-18View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-24fa3ff739ff064312ab2021-09-18View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0900000000-99136b39c7ec11a7bbca2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-00di-0900000000-ab4c213ba9a645517aa32017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-9300000000-7a1d8d268b763ce713312020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-002g-9000000000-e9050639f16e3b6d79392020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-00di-0900000000-27effb3a35bdb0d723102020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-00di-1900000000-731f917249c17a761e0f2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-00dj-5900000000-c46a92738e14de26b66c2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-006t-9500000000-7f1f8c64931b0dc6f66f2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0002-9100000000-39037b9523c5f3c7ed6c2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0002-9000000000-06c809ed4b25327e8b092020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-002b-9000000000-b93cdaad48fe246028dd2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-002b-9000000000-16e7fae11656d4e6cd8a2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-0fba-9000000000-96924ab5b95b0d4fb8572020-07-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-298ab6a83ac9894059832015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-12ad1640340af91bc8e82015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0036-9000000000-ddc48e682b255bd53c5e2015-04-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-785058db9c1fbc1b59502015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-c22365c838c065b99ed82015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0100-9300000000-491fc6287b2479ddc1a62015-04-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-298ab6a83ac9894059832015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-12ad1640340af91bc8e82015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0036-9000000000-ddc48e682b255bd53c5e2015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-785058db9c1fbc1b59502015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-c22365c838c065b99ed82015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0100-9300000000-491fc6287b2479ddc1a62015-05-27View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)2015-03-01View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)2015-03-12View Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>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 QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>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
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 ]
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 ]
Associated OMIM IDs
DrugBank IDDB03560
Phenol Explorer Compound ID725
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000845
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 ]