Record Information
Version1.0
Creation date2010-04-08 22:10:04 UTC
Update date2019-11-27 17:21:12 UTC
Primary IDFDB012238
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePhenylacetaldehyde
DescriptionFound in some essential oils, e.g. Citrus subspecies, Tagetes minuta (Mexican marigold) and in the mushroom Phallus impudicus (common stinkhorn). Flavouring ingredient Phenylacetaldehyde is one important oxidation-related aldehyde. Exposure to styrene gives phenylacetaldehyde as a secondary metabolite. Styrene has been implicated as reproductive toxicant, neurotoxicant, or carcinogen in vivo or in vitro. Phenylacetaldehyde could be formed by diverse thermal reactions during the cooking process together with C8 compounds is identified as a major aroma- active compound in cooked pine mushroom. Phenylacetaldehyde is readily oxidized to phenylacetic acid. Therefore will eventually be hydrolyzed and oxidized to yield phenylacetic acid that will be excreted primarily in the urine in conjugated form. (PMID: 16910727, 7818768, 15606130).
CAS Number122-78-1
Structure
Thumb
Synonyms
SynonymSource
1-oxo-2-PhenylethaneChEBI
2-PhenylacetaldehydeChEBI
2-PhenylethanalChEBI
alpha-PhenylacetaldehydeChEBI
alpha-TolualdehydeChEBI
alpha-Toluic aldehydeChEBI
BenzacetaldehydeChEBI
BenzeneacetaldehydeChEBI
HyacinthinChEBI
PhenacetaldehydeChEBI
Phenylacetic aldehydeChEBI
a-PhenylacetaldehydeGenerator
Α-phenylacetaldehydeGenerator
a-TolualdehydeGenerator
Α-tolualdehydeGenerator
a-Toluic aldehydeGenerator
Α-toluic aldehydeGenerator
.alpha.-toluic aldehydeHMDB
BenzenacetaldehydeHMDB
BenzylcarboxaldehydeHMDB
FEMA no. 2974HMDB
OxophenylethaneHMDB
Phenyl-acetaldehydeHMDB
PhenylethanalHMDB
Benzeneacetaldehyde, 9CIdb_source
FEMA 2874db_source
α-phenylacetaldehydeGenerator
α-tolualdehydeGenerator
α-toluic aldehydeGenerator
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00kf-9400000000-bec6e42b47ad1306960fView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014l-9700000000-152bdd5b77d6af9657ecView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-d37cbef4100302e951deView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00kf-9400000000-bec6e42b47ad1306960fView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014l-9700000000-152bdd5b77d6af9657ecView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kf-9400000000-e75d2f0bf82f16a80388View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kf-9400000000-32573b7f6ab690a27e3eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-5900000000-21e85148d15d190553c4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-5900000000-4471e0916a32cf4df7acView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-5900000000-650012e69d0a89a2fd4aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-5900000000-c80b65e383f833509e0fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-b3923f5fae42c664ac4aView in MoNA
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
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.