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Phenylacetaldehyde (FDB012238)

Record Information
Version1.0
Creation date2010-04-08 22:10:04 UTC
Update date2020-09-17 15:39:20 UTC
Primary IDFDB012238
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePhenylacetaldehyde
DescriptionPhenylacetaldehyde, also known as alpha-tolualdehyde or 2-phenylethanal, 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. Phenylacetaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Phenylacetaldehyde exists in all living species, ranging from bacteria to humans. Phenylacetaldehyde is a sweet, bitter, and clover tasting compound. Outside of the human body, Phenylacetaldehyde is found, on average, in the highest concentration within a few different foods, such as corns, beers, and white wines and in a lower concentration in safflowers, taco, and bilberries. Phenylacetaldehyde has also been detected, but not quantified in, several different foods, such as small-leaf lindens, green beans, sweet oranges, mountain yams, and common thymes. This could make phenylacetaldehyde a potential biomarker for the consumption of these foods. An aldehyde that consists of acetaldehyde bearing a methyl substituent; the parent member of the phenylacetaldehyde class of compounds. Phenylacetaldehyde is a potentially toxic compound.
CAS Number122-78-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.08 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity36.44 m³·mol⁻¹ChemAxon
Polarizability12.91 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H8O
IUPAC name2-phenylacetaldehyde
InChI IdentifierInChI=1S/C8H8O/c9-7-6-8-4-2-1-3-5-8/h1-5,7H,6H2
InChI KeyDTUQWGWMVIHBKE-UHFFFAOYSA-N
Isomeric SMILESO=CCC1=CC=CC=C1
Average Molecular Weight120.1485
Monoisotopic Molecular Weight120.057514878
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
  • 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:

Biological location:

Process

Industrial process:

Role

Environmental role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 79.97%; H 6.71%; O 13.32%DFC
Melting Point120.5-121.5 oC
Boiling PointBp10 78°DFC
Experimental Water SolubilityNot Available
Experimental logP1.78HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
Charge0
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd19.64 1.03DFC
Refractive Indexn20D 1.5290DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-e7ef9a5c5a6cc5674cd12014-09-20View Spectrum
GC-MSPhenylacetaldehyde, non-derivatized, GC-MS Spectrumsplash10-00kf-9400000000-bec6e42b47ad1306960fSpectrum
GC-MSPhenylacetaldehyde, non-derivatized, GC-MS Spectrumsplash10-014l-9700000000-152bdd5b77d6af9657ecSpectrum
GC-MSPhenylacetaldehyde, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-d37cbef4100302e951deSpectrum
GC-MSPhenylacetaldehyde, non-derivatized, GC-MS Spectrumsplash10-00kf-9400000000-bec6e42b47ad1306960fSpectrum
GC-MSPhenylacetaldehyde, non-derivatized, GC-MS Spectrumsplash10-014l-9700000000-152bdd5b77d6af9657ecSpectrum
GC-MSPhenylacetaldehyde, non-derivatized, GC-MS Spectrumsplash10-00kf-9400000000-e75d2f0bf82f16a80388Spectrum
GC-MSPhenylacetaldehyde, non-derivatized, GC-MS Spectrumsplash10-00kf-9400000000-32573b7f6ab690a27e3eSpectrum
GC-MSPhenylacetaldehyde, non-derivatized, GC-MS Spectrumsplash10-0006-5900000000-21e85148d15d190553c4Spectrum
GC-MSPhenylacetaldehyde, non-derivatized, GC-MS Spectrumsplash10-0006-5900000000-4471e0916a32cf4df7acSpectrum
GC-MSPhenylacetaldehyde, non-derivatized, GC-MS Spectrumsplash10-0006-5900000000-650012e69d0a89a2fd4aSpectrum
GC-MSPhenylacetaldehyde, non-derivatized, GC-MS Spectrumsplash10-0006-5900000000-c80b65e383f833509e0fSpectrum
Predicted GC-MSPhenylacetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9200000000-b3923f5fae42c664ac4aSpectrum
Predicted GC-MSPhenylacetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhenylacetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-4900000000-5001b07cef2fed3caa2c2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9100000000-048e2f1b42f7bd5104be2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fb9-9000000000-fc1fbd4e7c49f44ba7642012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80A) , Positivesplash10-0006-9000000000-bc0fa2967da6872f3a472012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0ufr-9700000000-507b63b585578b6706282021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-8c96fee71b311d7511812015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-2900000000-4b405668c302f69a4bc72015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-9300000000-fe46a418a2f0124566c32015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-4e064e0123dc18b6136a2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1900000000-02fff0bd874e6e8616bb2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-9200000000-340c7a60a7708fa801f12015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-9000000000-e37fda57674e1a53ea102021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-2071e5b3f45157a1da9c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-9100000000-219bfc0a5188714799772021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kf-9300000000-3fb47a0274f5792b4bd12021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-5671d4c535a6553aaf0d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-cc66f13f72898a397be62021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
ChemSpider ID13876539
ChEMBL IDCHEMBL1233464
KEGG Compound IDC00601
Pubchem Compound ID998
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB02178
HMDB IDHMDB06236
CRC / DFC (Dictionary of Food Compounds) IDHFG98-S:HFG98-S
EAFUS ID2985
Dr. Duke ID2-PHENYLACETALDEHYDE|PHENYL-ACETALDEHYDE
BIGG ID35469
KNApSAcK IDC00007535
HET IDHY1
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID122-78-1
GoodScent IDrw1009931
SuperScent ID998
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 / Bioactivities
DescriptorIDDefinitionReference
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
hawthorne
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
honey
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
hyacinth
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
grapefruit
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
peanut
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
green
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
clover
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cocoa
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
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References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.