phenylacetaldehyde (PAMDB120110)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120110
Identification
Name: phenylacetaldehyde
Description:An aldehyde that consists of acetaldehyde bearing a methyl substituent; the parent member of the phenylacetaldehyde class of compounds.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 1-Oxo-2-phenylethane
  • 2-phenylacetaldehyde
  • 2-Phenylethanal
  • α-phenylacetaldehyde
  • alpha-tolualdehyde
  • alpha-Tolualdehyde
  • α-tolualdehyde
  • α-toluic aldehyde
  • Benzacetaldehyde
  • Benzeneacetaldehyde
  • Hyacinthin
  • Phenacetaldehyde
  • Phenylacetaldehyde
  • PHENYLACETALDEHYDE
  • phenylacetaldehyde
  • Phenylacetic aldehyde
Chemical Formula: C8H8O
Average Molecular Weight: 120.151
Monoisotopic Molecular Weight: 120.05752
InChI Key: DTUQWGWMVIHBKE-UHFFFAOYSA-N
InChI:InChI=1S/C8H8O/c9-7-6-8-4-2-1-3-5-8/h1-5,7H,6H2
CAS number: 122-78-1
IUPAC Name:phenylacetaldehyde
Traditional IUPAC Name: phenylacetaldehyde
SMILES:[CH](=O)CC1(=CC=CC=C1)
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as phenylacetaldehydes. These are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Benzenoids
Sub ClassBenzene and substituted derivatives
Direct Parent Phenylacetaldehydes
Alternative Parents
Substituents
  • Phenylacetaldehyde
  • Alpha-hydrogen aldehyde
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic homomonocyclic compound
Molecular Framework Aromatic homomonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 120.5 - 121.5 °C
Experimental Properties:
PropertyValueReference
Melting Point120.5 - 121.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.78HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility2.08 mg/mLALOGPS
logP1.75ALOGPS
logP1.45ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)14.98ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity36.44 m3·mol-1ChemAxon
Polarizability12.91 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
2-phenylethanol + NAD+ → Hydrogen ion + phenylacetaldehyde + NADH
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-00kf-9400000000-bec6e42b47ad1306960fView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-014l-9700000000-152bdd5b77d6af9657ecView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-4900000000-5001b07cef2fed3caa2cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9100000000-048e2f1b42f7bd5104beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fb9-9000000000-fc1fbd4e7c49f44ba764View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80A) , Positivesplash10-0006-9000000000-bc0fa2967da6872f3a47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-8c96fee71b311d751181View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-2900000000-4b405668c302f69a4bc7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-9300000000-fe46a418a2f0124566c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-4e064e0123dc18b6136aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1900000000-02fff0bd874e6e8616bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-9200000000-340c7a60a7708fa801f1View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-e7ef9a5c5a6cc5674cd1View in MoNA
References
References:
  • Ockey DA, Gadek TR (2004)Discovery of novel PTP1b inhibitors. Bioorganic & medicinal chemistry letters 14, Pubmed: 14698165
  • Hoet S, Stévigny C, Hérent MF, Quetin-Leclercq J (2006)Antitrypanosomal compounds from the leaf essential oil of Strychnos spinosa. Planta medica 72, Pubmed: 16557466
  • Amar-Zrihen N, Aserin A, Garti N (2011)Food volatile compounds facilitating HII mesophase formation: solubilization and stability. Journal of agricultural and food chemistry 59, Pubmed: 21495722
  • Chu FL, Yaylayan VA (2008)Model studies on the oxygen-induced formation of benzaldehyde from phenylacetaldehyde using pyrolysis GC-MS and FTIR. Journal of agricultural and food chemistry 56, Pubmed: 18954073
  • San-Juan F, Ferreira V, Cacho J, Escudero A (2011)Quality and aromatic sensory descriptors (mainly fresh and dry fruit character) of Spanish red wines can be predicted from their aroma-active chemical composition. Journal of agricultural and food chemistry 59, Pubmed: 21627324
Synthesis Reference: Sun Zhirong; Hu Xiang; Zhou Ding Wastewater minimization in indirect electrochemical synthesis of phenylacetaldehyde. TheScientificWorldJournal (2002), 2 48-52.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
METABOLIGHTSMTBLC16424
HMDBHMDB06236
DRUGBANKDB02178
BIGG35469
CHEMSPIDER13876539
PUBCHEM998
CHEBI16424
CAS122-78-1
LIGAND-CPDC00601