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Record Information
Version3.6
Creation Date2007-05-22 18:42:13 UTC
Update Date2016-02-11 01:07:25 UTC
HMDB IDHMDB06236
Secondary Accession NumbersNone
Metabolite Identification
Common NamePhenylacetaldehyde
DescriptionPhenylacetaldehyde 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 ).
Structure
Thumb
Synonyms
ValueSource
alpha-TolualdehydeKegg
a-TolualdehydeGenerator
α-tolualdehydeGenerator
.alpha.-toluic aldehydeHMDB
1-oxo-2-PhenylethaneHMDB
2-PhenylacetaldehydeHMDB
2-PhenylethanalHMDB
a-PhenylacetaldehydeHMDB
a-Toluic aldehydeHMDB
alpha-PhenylacetaldehydeHMDB
alpha-Toluic aldehydeHMDB
BenzenacetaldehydeHMDB
BenzeneacetaldehydeHMDB
BenzylcarboxaldehydeHMDB
FEMA no. 2974HMDB
HyacinthinHMDB
OxophenylethaneHMDB
PhenacetaldehydeHMDB
Phenyl-acetaldehydeHMDB
Phenylacetic aldehydeHMDB
PhenylethanalHMDB
Chemical FormulaC8H8O
Average Molecular Weight120.1485
Monoisotopic Molecular Weight120.057514878
IUPAC Name2-phenylacetaldehyde
Traditional Namephenylacetaldehyde
CAS Registry Number122-78-1
SMILES
O=CCC1=CC=CC=C1
InChI Identifier
InChI=1S/C8H8O/c9-7-6-8-4-2-1-3-5-8/h1-5,7H,6H2
InChI KeyInChIKey=DTUQWGWMVIHBKE-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylacetaldehydes. These 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
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
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
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Feces
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableNewborn (0-30 days old)Both
Normal
details
FecesDetected and Quantified0 - 21.52 ppmChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected and Quantified0 - 29.67 ppmChildren (1-13 years old)Not Specified
Treated celiac disease
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012238
KNApSAcK IDC00007535
Chemspider ID13876539
KEGG Compound IDC00601
BioCyc IDHYDRPHENYLAC-CPD
BiGG ID35469
Wikipedia LinkPAA
NuGOwiki LinkHMDB06236
Metagene LinkHMDB06236
METLIN IDNot Available
PubChem Compound998
PDB IDHY1
ChEBI ID16424
References
Synthesis ReferenceSun 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)
General References
  1. Watson WP, Munter T, Golding BT: A new role for glutathione: protection of vitamin B12 from depletion by xenobiotics. Chem Res Toxicol. 2004 Dec;17(12):1562-7. [15606130 ]
  2. Cho IH, Kim SY, Choi HK, Kim YS: Characterization of aroma-active compounds in raw and cooked pine-mushrooms (Tricholoma matsutake Sing.). J Agric Food Chem. 2006 Aug 23;54(17):6332-5. [16910727 ]
  3. Sumner SJ, Fennell TR: Review of the metabolic fate of styrene. Crit Rev Toxicol. 1994;24 Suppl:S11-33. [7818768 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
Reactions
Phenylethylamine + Oxygen + Water → Phenylacetaldehyde + Ammonia + Hydrogen peroxidedetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
Reactions
Phenylethylamine + Oxygen + Water → Phenylacetaldehyde + Ammonia + Hydrogen peroxidedetails
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
Gene Name:
ALDH3A1
Uniprot ID:
P30838
Molecular weight:
50394.57
Reactions
Phenylacetaldehyde + NAD + Water → Phenylacetic acid + NADH + Hydrogen Iondetails
Phenylacetaldehyde + NADP + Water → Phenylacetic acid + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
Reactions
Phenylacetaldehyde + NAD + Water → Phenylacetic acid + NADH + Hydrogen Iondetails
Phenylacetaldehyde + NADP + Water → Phenylacetic acid + NADPH + Hydrogen Iondetails
General function:
Involved in copper ion binding
Specific function:
Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:
ABP1
Uniprot ID:
P19801
Molecular weight:
85377.1
General function:
Involved in copper ion binding
Specific function:
Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity. May play a role in adipogenesis.
Gene Name:
AOC3
Uniprot ID:
Q16853
Molecular weight:
84621.27
Reactions
Phenylethylamine + Oxygen + Water → Phenylacetaldehyde + Ammonia + Hydrogen peroxidedetails
General function:
Involved in copper ion binding
Specific function:
Has a monoamine oxidase activity with substrate specificity for 2-phenylethylamine and tryptamine. May play a role in adipogenesis. May be a critical modulator of signal transmission in retina.
Gene Name:
AOC2
Uniprot ID:
O75106
Molecular weight:
80515.11
Reactions
Phenylethylamine + Oxygen + Water → Phenylacetaldehyde + Ammonia + Hydrogen peroxidedetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH3B2
Uniprot ID:
P48448
Molecular weight:
42623.62
Reactions
Phenylacetaldehyde + NAD + Water → Phenylacetic acid + NADH + Hydrogen Iondetails
Phenylacetaldehyde + NADP + Water → Phenylacetic acid + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:
ALDH3B1
Uniprot ID:
P43353
Molecular weight:
51839.245
Reactions
Phenylacetaldehyde + NAD + Water → Phenylacetic acid + NADH + Hydrogen Iondetails
Phenylacetaldehyde + NADP + Water → Phenylacetic acid + NADPH + Hydrogen Iondetails