4-Hydroxyphenylacetaldehyde (ECMDB20093) (M2MDB000941)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (1)Transporters (4)XML
Proteins (181)
Record Information
Version2.0
Creation Date2012-05-31 14:27:05 -0600
Update Date2015-06-03 17:19:18 -0600
Secondary Accession Numbers
  • ECMDB20093
Identification
Name:4-Hydroxyphenylacetaldehyde
Description4-hydroxyphenylacetaldehyde is a member of the chemical class known as Phenylacetaldehydes. These are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (4-hydroxyphenyl)acetaldehyde
  • -dimethylamino
  • 2-(4-Hydroxyphenyl)acetaldehyde
  • 4-(Dimethylamino)azobenzene
  • 4-(Dimethylamino)azobenzol
  • 4-(Dimethylamino)phenylazobenzene
  • 4-(N,N-Dimethylamino)azobenzene
  • 4-(Phenylazo)-N,N-dimethylaniline
  • 4-Dimethylamino
  • 4-Hydroxy-Benzeneacetaldehyde
  • Atul fast yellow R
  • Azobenzene
  • Benzeneazodimethylaniline
  • Brilliant fast oil yellow
  • Brilliant fast spirit yellow
  • Brilliant fast yellow
  • Brilliant oil yellow
  • Brilliant oil yellow (van)
  • Butter or methyl yellow
  • Butter yellow
  • Butyro flavine
  • C.I. Solvent Yellow 2
  • Cerasine yellow GG
  • DAB
  • Dab (carcinogen)
  • Dimethyl yellow
  • Dimethyl yellow analar
  • Dimethyl yellow N, N-dimethylaniline
  • Dimethyl yellow N,N-dimethylaniline
  • Dimethylaminoazobenzene
  • Dimethylaminoazobenzol
  • DMAB
  • Enial Yellow 2G
  • Fast oil yellow b
  • Fast yellow
  • Fat yellow
  • Fat yellow a
  • Fat yellow ad oo
  • Fat yellow es
  • Fat yellow es extra
  • Fat yellow extra conc
  • Fat yellow extra conc.
  • Fat yellow R
  • Fat Yellow R (8186)
  • Grasal brilliant yellow
  • Hydroxyacetophenone
  • Hydrphenylac-CPD
  • Iketon yellow extra
  • Jaune de beurre
  • Jaune de beurre (french)
  • Methyl yellow
  • N, N-Dimethyl-4-(phenylazo)benzamine
  • N, N-Dimethyl-4-(phenylazo)benzenamine
  • N, N-Dimethyl-4-aminoazobenzene
  • N, N-Dimethyl-p-aminoazobenzene
  • N,N-Dimethyl-4-(phenylazo)-Benzenamine
  • N,N-Dimethyl-4-(phenylazo)benzamine
  • N,N-Dimethyl-4-(phenylazo)benzenamine
  • N,N-Dimethyl-4-(phenyldiazenyl)aniline
  • N,N-Dimethyl-4-aminoazobenzene
  • N,N-Dimethyl-4-phenylazoaniline
  • N,N-Dimethyl-4-[(E)-phenyldiazenyl]aniline
  • N,N-Dimethyl-p-(phenylazo)-Aniline
  • N,N-Dimethyl-p-(phenylazo)aniline
  • N,N-Dimethyl-p-aminoazobenzene
  • N,N-Dimethyl-p-azoaniline
  • Nchembio.105-comp15
  • NN-dimethyl-p-(phenylazo)-Aniline
  • Oil yellow
  • Oil Yellow 20
  • Oil Yellow 2G
  • Oil yellow BB
  • Oil yellow D
  • Oil yellow DN
  • Oil yellow FF
  • Oil yellow FN
  • Oil yellow g
  • Oil yellow g (van)
  • Oil Yellow G-2
  • Oil yellow GG
  • Oil yellow GG (van)
  • Oil yellow GR
  • Oil yellow GR (van)
  • Oil yellow N
  • Oil yellow pel
  • Oil yellow S
  • Oleal Yellow 2G
  • Organol yellow adm
  • Orient oil yellow GG
  • P-(Dimethylamino)-Azobenzene
  • P-(Dimethylamino)azobenzene
  • P-Dimethylamino-azobenzol
  • P-Dimethylamino-azobenzol (german)
  • P-Dimethylaminoazobenzen
  • P-Dimethylaminoazobenzen (czech)
  • P-Hydroxyphenylacetaldehyde
  • P.D.a.b.
  • Petrol yellow WT
  • POH-Ph-CH2CHO
  • Resinol yellow GR
  • Resoform yellow gga
  • Silotras Yellow T2G
  • Solvent Yellow 2
  • Somalia yellow a
  • Stear yellow JB
  • Sudan GG
  • Sudan yellow
  • Sudan yellow GG
  • Sudan yellow gga
  • Toyo oil yellow g
  • Tranlisant
  • Waxoline yellow ad
  • Waxoline yellow ads
  • Yellow g soluble in grease
  • Zlut maselna
  • Zlut maselna (czech)
  • Zlut rozpoustedlova 2
Chemical Formula:C8H8O2
Weight:Average: 136.1479
Monoisotopic: 136.0524295
InChI Key:IPRPPFIAVHPVJH-UHFFFAOYSA-N
InChI:InChI=1S/C8H8O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,6,10H,5H2
CAS number:60-11-7
IUPAC Name:2-(4-hydroxyphenyl)acetaldehyde
Traditional IUPAC Name:p-hydroxyphenylacetaldehyde
SMILES:OC1=CC=C(CC=O)C=C1
Chemical Taxonomy
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
Physical Properties
State:Solid
Charge:0
Melting point:117 °C
Experimental Properties:
PropertyValueSource
Water Solubility:0.00023 mg/mL at 25 oC [BAUGHMAN,GL & PERENICH,TA (1988)]PhysProp
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Water + Oxygen + Tyramine > 4-Hydroxyphenylacetaldehyde + Hydrogen peroxide + Ammonium
Tyramine + Water + Oxygen <> 4-Hydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxide
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-5900000000-dee6bd2327885b9b9c35View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05g0-5900000000-052b7c5a508b36e0512fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-c592acce12d2ba134040View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-2900000000-90058ffcbfd58f5dff5bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0690-9500000000-a8abea2510950f337295View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-3f4ed034f10b0d6a25b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1900000000-99115e80b538ba6b2306View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-6c9913d203a267c92186View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-4900000000-e2bf91e8ab2ae47d9096View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9600000000-ff10a0510f947f476688View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004l-9100000000-b447fa4b15009b677f8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-2900000000-59dcda3398a30862c88dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1900000000-7a7b9a9d95399c23529bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-b2c6c4e6f393a7458822View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID15621
HMDB IDHMDB03767
Pubchem Compound ID440113
Kegg IDC03765
ChemSpider ID389113
Wikipedia ID4-Hydroxyphenylacetaldehyde
BioCyc IDHYDRPHENYLAC-CPD
EcoCyc IDHYDRPHENYLAC-CPD

Enzymes

Protein Details
1. Primary amine oxidase
General function:
Involved in copper ion binding
Specific function:
The enzyme prefers aromatic over aliphatic amines
Gene Name:
tynA
Uniprot ID:
P46883
Molecular weight:
84378
Reactions
RCH(2)NH(2) + H(2)O + O(2) = RCHO + NH(3) + H(2)O(2).
2-phenylethylamine + H(2)O + O(2) = phenylacetaldehyde + NH(3) + H(2)O(2).

Transporters

Protein Details
1. Outer membrane protein N
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
Protein Details
2. Outer membrane pore protein E
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
Protein Details
3. Outer membrane protein F
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
Protein Details
4. Outer membrane protein C
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368