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
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:
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 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
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 IDNot Available
BioCyc IDHYDRPHENYLAC-CPD
EcoCyc IDHYDRPHENYLAC-CPD

Enzymes

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

General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
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
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
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