Showing Compound Card for p-Hydroxybenzaldehyde (CDB005797)

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Record Information
Version1.0
Created at2020-04-27 16:57:32 UTC
Updated at2021-01-04 18:49:21 UTC
CannabisDB IDCDB005797
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namep-Hydroxybenzaldehyde
Description4-Hydroxybenzaldehyde, also known as p-Formylphenol or p-Hydroxybenzaldehyde, is a hydroxylated derivative of benzaldehyde. It 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 is one of the three isomers of hydroxybenzaldehyde wherein the hydroxyl group is substituted at one of three postions (the ortho, meta and para positions) of benzaldehyde. 4-Hydroxybenzaldehyde exists as a yellow to tan powder and is moderately soluble in water. It is found in all living organisms, ranging from bacteria to plants to humans. 4-Hydroxybenzaldehyde has a sweet, nutty, almond, or balsam odor and has a creamy, honey or vanilla like taste. It and can be found in certain orchid species (PMID: 11025174 ; PMID: 8009989 ) including vanilla. 4-Hydroxybenzaldehyde occurs naturally and is found many plants and plant foods including bamboo, bilbeerries, grape leaves, sorghum, tomatoes, vanilla, certain vinegars, oats, durians, carrots, sweet marjorams, lingonberries, and savoy cabbages. This could make 4-hydroxybenzaldehyde a potential biomarker for the consumption of these foods. p-Hydroxybenzaldehyde is also a constituent of cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-FormylphenolChEBI
p-FormylphenolChEBI
p-HydroxybenzaldehydeChEBI
4-Hydroxy-benzaldehydeHMDB
4-HydroxybenzenecarbonalHMDB
P-Hydroxy-benzaldehydeHMDB
p-OxybenzaldehydeHMDB
ParahydroxybenzaldehydeHMDB
Usaf m-6HMDB
Para-hydroxybenzaldehydeMeSH, HMDB
4-HydroxybenzaldehydePhytoBank
Chemical FormulaC7H6O2
Average Molecular Weight122.12
Monoisotopic Molecular Weight122.0368
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:

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
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00di-9500000000-2c1739a8a2bc288e4a5c2015-03-01View Spectrum
GC-MSp-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00di-8900000000-4eff34096f6bd4f30d10Spectrum
GC-MSp-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00di-9800000000-c8646d08ef8e23a3d49bSpectrum
GC-MSp-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00di-8900000000-60621d4d9871b2d7587dSpectrum
GC-MSp-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-05i0-1970000000-7ef151eab685361413a6Spectrum
GC-MSp-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00b9-1940000000-fa6b812457f26dce7720Spectrum
GC-MSp-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00b9-2940000000-0bfc68ade3f25f6ba1f2Spectrum
GC-MSp-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00b9-2940000000-b50ed8954cb10b92a30bSpectrum
GC-MSp-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00b9-2930000000-671031e52722de3402ecSpectrum
GC-MSp-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00di-8900000000-4eff34096f6bd4f30d10Spectrum
GC-MSp-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00di-9800000000-c8646d08ef8e23a3d49bSpectrum
GC-MSp-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00di-8900000000-60621d4d9871b2d7587dSpectrum
GC-MSp-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-05i0-1970000000-7ef151eab685361413a6Spectrum
GC-MSp-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00b9-1940000000-fa6b812457f26dce7720Spectrum
GC-MSp-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00b9-2940000000-0bfc68ade3f25f6ba1f2Spectrum
GC-MSp-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00b9-2940000000-b50ed8954cb10b92a30bSpectrum
GC-MSp-Hydroxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-00b9-2930000000-671031e52722de3402ecSpectrum
Predicted GC-MSp-Hydroxybenzaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-6900000000-ea309e8826550692ddebSpectrum
Predicted GC-MSp-Hydroxybenzaldehyde, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-8900000000-781df730e85ee6b33891Spectrum
Predicted GC-MSp-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
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0011718
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
General References
  1. Ha JH, Lee DU, Lee JT, Kim JS, Yong CS, Kim JA, Ha JS, Huh K: 4-Hydroxybenzaldehyde from Gastrodia elata B1. is active in the antioxidation and GABAergic neuromodulation of the rat brain. J Ethnopharmacol. 2000 Nov;73(1-2):329-33. doi: 10.1016/s0378-8741(00)00313-5. [PubMed:11025174 ]
  2. Li YM, Zhou ZL, Hong YF: [Studies on the phenolic derivatives from Galeola faberi Rolfe]. Yao Xue Xue Bao. 1993;28(10):766-71. [PubMed:8009989 ]