Record Information
Version1.0
Creation date2011-09-21 00:26:33 UTC
Update date2020-09-17 15:40:43 UTC
Primary IDFDB023224
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Hydroxyphenylacetaldehyde
Description4-Hydroxyphenylacetaldehyde, also known as POH-PH-CH2CHO, belongs to the class of organic compounds known as phenylacetaldehydes. Phenylacetaldehydes are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde. 4-Hydroxyphenylacetaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 4-Hydroxyphenylacetaldehyde has been detected, but not quantified in, several different foods, such as purple mangosteens, cottonseeds, garden cress, borages, and colorado pinyons. This could make 4-hydroxyphenylacetaldehyde a potential biomarker for the consumption of these foods. The condensation of 4-hydroxyphenylacetaldehyde and dopamine is a key step in the biosynthesis of benzylisoquinoline alkaloids. In both species, it is subsequently metabolized into 4-hydroxyphenylacetate by aldehyde dehydrogenase (ALDH) enzymes in humans and the phenylacetaldehyde dehydrogenase (feaB) enzyme in E. coli. These natural products include berberine and morphine.
CAS Number7339-87-9
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility5.93 g/LALOGPS
logP1.59ALOGPS
logP1.15ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)9.5ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.42 m³·mol⁻¹ChemAxon
Polarizability13.87 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H8O2
IUPAC name2-(4-hydroxyphenyl)acetaldehyde
InChI IdentifierInChI=1S/C8H8O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,6,10H,5H2
InChI KeyIPRPPFIAVHPVJH-UHFFFAOYSA-N
Isomeric SMILESOC1=CC=C(CC=O)C=C1
Average Molecular Weight136.1479
Monoisotopic Molecular Weight136.0524295
Classification
Description Belongs to the class of organic compounds known as phenylacetaldehydes. Phenylacetaldehydes are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetaldehydes
Direct ParentPhenylacetaldehydes
Alternative Parents
Substituents
  • Phenylacetaldehyde
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alpha-hydrogen aldehyde
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS4-Hydroxyphenylacetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4r-5900000000-dee6bd2327885b9b9c35Spectrum
Predicted GC-MS4-Hydroxyphenylacetaldehyde, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05g0-5900000000-052b7c5a508b36e0512fSpectrum
Predicted GC-MS4-Hydroxyphenylacetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-c592acce12d2ba1340402015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-2900000000-90058ffcbfd58f5dff5b2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0690-9500000000-a8abea2510950f3372952015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-3f4ed034f10b0d6a25b42015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1900000000-99115e80b538ba6b23062015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-6c9913d203a267c921862015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-4900000000-e2bf91e8ab2ae47d90962021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9600000000-ff10a0510f947f4766882021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004l-9100000000-b447fa4b15009b677f8f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-2900000000-59dcda3398a30862c88d2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1900000000-7a7b9a9d95399c23529b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-b2c6c4e6f393a74588222021-09-24View Spectrum
NMRNot Available
ChemSpider ID389113
ChEMBL IDNot Available
KEGG Compound IDC03765
Pubchem Compound ID440113
Pubchem Substance IDNot Available
ChEBI ID15666
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03767
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID42489
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference