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Record Information
Version3.6
Creation Date2007-04-24 13:52:54 UTC
Update Date2016-02-11 01:07:23 UTC
HMDB IDHMDB06115
Secondary Accession NumbersNone
Metabolite Identification
Common NameBenzaldehyde
DescriptionBenzaldehyde is occasionally found as a volatile component of urine. Benzaldehyde is an aromatic aldehyde used in cosmetics as a denaturant, a flavoring agent, and as a fragrance. Currently used in only seven cosmetic products, its highest reported concentration of use was 0.5% in perfumes. Benzaldehyde is a generally regarded as safe (GRAS) food additive in the United States and is accepted as a flavoring substance in the European Union. Because Benzaldehyde rapidly metabolizes to Benzoic Acid in the skin, the available dermal irritation and sensitization data demonstrating no adverse reactions to Benzoic Acid were considered supportive of the safety of Benzaldehyde. Benzaldehyde is absorbed through skin and by the lungs, distributes to all well-perfused organs, but does not accumulate in any specific tissue type. After being metabolized to benzoic acid, conjugates are formed with glycine or glucuronic acid, and excreted in the urine. Several studies have suggested that Benzaldehyde can have carcinostatic or antitumor properties. Overall, at the concentrations used in cosmetics, Benzaldehyde was not considered a carcinogenic risk to humans. Although there are limited irritation and sensitization data available for Benzaldehyde, the available dermal irritation and sensitization data and ultraviolet (UV) absorption and phototoxicity data demonstrating no adverse reactions to Benzoic Acid support the safety of Benzaldehyde as currently used in cosmetic products. (PMID: 16835129 , Int J Toxicol. 2006;25 Suppl 1:11-27.).
Structure
Thumb
Synonyms
ValueSource
Artificial almond oilChEBI
BenzanoaldehydeChEBI
Benzene carbaldehydeChEBI
Benzene carboxaldehydeChEBI
BenzenecarbonalChEBI
BenzenecarboxaldehydeChEBI
BenzenemethylalChEBI
Benzoic acid aldehydeChEBI
Benzoic aldehydeChEBI
BenzylaldehydeChEBI
Ethereal oil OF bitter almondsChEBI
PhenylformaldehydeChEBI
PhenylmethanalChEBI
Synthetic oil OF bitter almondChEBI
Benzoate aldehydeGenerator
Almond artificial essential oilHMDB
Artificial bitter almond oilHMDB
Artificial essential oil OF almondHMDB
BenzadehydeHMDB
Benzaldehyde FFCHMDB
Benzene methylalHMDB
BenzoateHMDB
Benzoic acidHMDB
Benzoyl hydrideHMDB
BenzyaldehydeHMDB
BEZHMDB
Caswell no. 076HMDB
FEMA no. 2127HMDB
Oil OF bitter almondHMDB
Phenylmethanal benzenecarboxaldehydeHMDB
Chemical FormulaC7H6O
Average Molecular Weight106.1219
Monoisotopic Molecular Weight106.041864814
IUPAC Namebenzaldehyde
Traditional Namebenzaldehyde
CAS Registry Number100-52-7
SMILES
O=CC1=CC=CC=C1
InChI Identifier
InChI=1S/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H
InChI KeyInChIKey=HUMNYLRZRPPJDN-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-).
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoyl derivatives
Direct ParentBenzoyl derivatives
Alternative Parents
Substituents
  • Benzoyl
  • Benzaldehyde
  • Aryl-aldehyde
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-26 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility6.95 mg/mL at 25 °CNot Available
LogP1.48HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility5.44 mg/mLALOGPS
logP1.6ALOGPS
logP1.69ChemAxon
logS-1.3ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.64 m3·mol-1ChemAxon
Polarizability11.02 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-056r-9400000000-d5e049f5a5c77b8864cbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9100000000-dca76d402f152bd3f562View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9100000000-ce8274b57c274e79f894View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positivesplash10-0a6r-9600000000-731755b6449c9d44f340View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positivesplash10-0a6r-7900000000-7d98ce9e964eb9bae123View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-0a6r-9700000000-e4f830b1b36028903665View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HP 5970) , Positivesplash10-0pdi-9500000000-eee2fac3cee7076204caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-6345a1cf40f283a793a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-296abcf15a77a1f53d6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9200000000-086efee77b92115c17caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-266f38215789f236324eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-266f38215789f236324eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7900000000-828e61a7919a0eb81940View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0pdi-9600000000-2c76a7cdbd4023dd3effView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableNewborn (0-30 days 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
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
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 but not QuantifiedNot ApplicableChildren (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 IDFDB014661
KNApSAcK IDC00034452
Chemspider ID235
KEGG Compound IDC00193
BioCyc IDCPD-1131
BiGG IDNot Available
Wikipedia LinkBenzaldehyde
NuGOwiki LinkHMDB06115
Metagene LinkHMDB06115
METLIN IDNot Available
PubChem Compound240
PDB IDHBX
ChEBI ID17169
References
Synthesis ReferenceOxidation products of aromatic hydrocarbons with methyl groups, substituting methyl groups or their derivatives. (1903), DE 175295 19030730 CAN 1:4512 AN 1907:4512
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Andersen A: Final report on the safety assessment of benzaldehyde. Int J Toxicol. 2006;25 Suppl 1:11-27. [16835129 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Converts 9-cis-retinal to 9-cis-retinoic acid. Has lower activity towards 13-cis-retinal. Has much lower activity towards all-trans-retinal. Has highest activity with benzaldehyde and decanal (in vitro). Has a preference for NAD, but shows considerable activity with NADP (in vitro)
Gene Name:
ALDH8A1
Uniprot ID:
Q9H2A2
Molecular weight:
53400.9