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Showing Compound 3,4-Dihydroxyphenylacetaldehyde (FDB023227)

Record Information
Version1.0
Creation date2011-09-21 00:26:35 UTC
Update date2020-09-17 15:41:36 UTC
Primary IDFDB023227
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3,4-Dihydroxyphenylacetaldehyde
Description3,4-Dihydroxyphenylacetaldehyde, also known as protocatechuatealdehyde or 2-(3,4-dihydroxyphenyl)ethanal, 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. 3,4-Dihydroxyphenylacetaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). 3,4-Dihydroxyphenylacetaldehyde exists in all living organisms, ranging from bacteria to humans. Within humans, 3,4-dihydroxyphenylacetaldehyde participates in a number of enzymatic reactions. In particular, 3,4-dihydroxyphenylacetaldehyde can be biosynthesized from dopamine through its interaction with the enzyme amine oxidase [flavin-containing] a. In addition, 3,4-dihydroxyphenylacetaldehyde can be converted into 3,4-dihydroxybenzeneacetic acid through the action of the enzyme 3,4-dihydroxyphenylacetaldehyde. In humans, 3,4-dihydroxyphenylacetaldehyde is involved in the metabolic disorder called tyrosinemia type I. Outside of the human body, 3,4-Dihydroxyphenylacetaldehyde has been detected, but not quantified in, several different foods, such as pot marjorams, muscadine grapes, rambutans, summer savories, and cottonseeds. This could make 3,4-dihydroxyphenylacetaldehyde a potential biomarker for the consumption of these foods. A phenylacetaldehyde in which the 3 and 4 positions of the phenyl group are substituted by hydroxy groups.
CAS Number5707-55-1
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
2-(3,4-Dihydroxyphenyl)ethanalChEBI
DOPALChEBI
ProtocatechuatealdehydeChEBI
DHPAA aldehydeMeSH
3,4-Dihydroxy-benzeneacetaldehydeHMDB
3,4-dihydroxy-Benzeneacetaldehydehmdb
Predicted Properties
PropertyValueSource
Water Solubility8.72 g/LALOGPS
logP1.15ALOGPS
logP0.85ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)9.27ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.4 m³·mol⁻¹ChemAxon
Polarizability14.78 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H8O3
IUPAC name2-(3,4-dihydroxyphenyl)acetaldehyde
InChI IdentifierInChI=1S/C8H8O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,4-5,10-11H,3H2
InChI KeyIADQVXRMSNIUEL-UHFFFAOYSA-N
Isomeric SMILESOC1=C(O)C=C(CC=O)C=C1
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
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
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 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
Disposition

Route of exposure:

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS3,4-Dihydroxyphenylacetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-3900000000-7f82d1d31cd24be9e865Spectrum
Predicted GC-MS3,4-Dihydroxyphenylacetaldehyde, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00e9-8390000000-bba6c4376314951fb5eeSpectrum
Predicted GC-MS3,4-Dihydroxyphenylacetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-19827d81a06a62c2b70a2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-2900000000-479d55c57638faa6d9cd2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-9400000000-cadc5e95515b4cecf1f72015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-b0ef024b4e5895ddea082015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2900000000-352f5ee2c302c824867e2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500000000-96da2068f1ed3e30ae472015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pb9-0900000000-588f3b3d236131a4fa7a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-3900000000-d3765e83b72ff4e9c9332021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-9100000000-63064bac00f3091d89c32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-b75a7231958cf1fc53ec2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-ed865ca228b5007b7ed42021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9100000000-7cc4c0962b7233330b8c2021-09-22View Spectrum
NMRNot Available
ChemSpider ID106504
ChEMBL IDNot Available
KEGG Compound IDC04043
Pubchem Compound ID119219
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03791
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID43022
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
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Tyrosine MetabolismSMP00006 map00350
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference