Showing Compound Card for Benzaldehyde (CDB000562)

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Record Information
Version1.0
Created at2020-03-19 00:43:51 UTC
Updated at2020-12-07 19:07:31 UTC
CannabisDB IDCDB000562
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameBenzaldehyde
DescriptionBenzaldehyde, also known as benzenecarbonal or benzenemethylal, 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-). Benzaldehyde is a colorless liquid with a characteristic almond-like odor. It is a strong, sweet, and almond tasting compound. Benzaldehyde is found, on average, in the highest concentration within a few different foods, such as black walnuts, almonds, and corns and in a lower concentration in safflowers, kohlrabis, and ceylon cinnamons. Benzaldehyde has also been detected, but not quantified in, Mexican oregano, winter savories, strawberries, lingonberries, and common persimmons. Benzaldehyde has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499 ). It is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis ( Ref:DOI ). Benzaldehyde is an aromatic aldehyde used in cosmetics as a denaturant, a flavoring agent, and as a fragrance. It is currently used in only seven cosmetic products, with the highest reported used concentration of 0.5 %, in perfumes. Benzaldehyde is a “Generally Regarded As Safe” (GRAS) food additive in the U.S.A. and is accepted as a flavoring substance in the European Union. Although there is limited data available in regards of potential skin irritation and sensitization caused by benzaldehyde, the available data on the safety of the use of benzoic acid is currently used to support the safe use of benzaldehyde. (PMID: 16835129 , Int J Toxicol. 2006;25 Suppl 1:11-27.). This is because benzaldehyde rapidly metabolizes to benzoic acid in the skin, rendering the available dermal irritation and sensitization data on the latter sufficient to support the safety of Benzaldehyde. Benzaldehyde is absorbed through the 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 ( Ref:DOI ). Overall, at the concentrations used in cosmetics, benzaldehyde is not considered a carcinogenic risk to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
Benzaldehyde, formyl-(14)C-labeledMeSH, HMDB
Chemical FormulaC7H6O
Average Molecular Weight106.12
Monoisotopic Molecular Weight106.0419
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 KeyHUMNYLRZRPPJDN-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aldehyde
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-26 °CNot Available
Boiling Point178.1 °CWikipedia
Water Solubility6.95 mg/mL at 25 °CNot Available
logP1.48HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP1.6ALOGPS
logP1.69ChemAxon
logS-1.3ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.64 m³·mol⁻¹ChemAxon
Polarizability11.02 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0pdi-9600000000-2c76a7cdbd4023dd3eff2015-03-01View Spectrum
GC-MSBenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-0a6r-9600000000-731755b6449c9d44f340Spectrum
GC-MSBenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-0a6r-7900000000-7d98ce9e964eb9bae123Spectrum
GC-MSBenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-0a6r-9700000000-af6ef18ad5441da71000Spectrum
GC-MSBenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-0pdi-9500000000-eee2fac3cee7076204caSpectrum
GC-MSBenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-0a6r-9600000000-731755b6449c9d44f340Spectrum
GC-MSBenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-0a6r-7900000000-7d98ce9e964eb9bae123Spectrum
GC-MSBenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-0a6r-9700000000-af6ef18ad5441da71000Spectrum
GC-MSBenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-0pdi-9500000000-eee2fac3cee7076204caSpectrum
Predicted GC-MSBenzaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9800000000-930ad158d75deff2317aSpectrum
Predicted GC-MSBenzaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-056r-9400000000-d5e049f5a5c77b8864cb2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9100000000-dca76d402f152bd3f5622012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9100000000-ce8274b57c274e79f8942012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positivesplash10-0a6r-9600000000-731755b6449c9d44f3402012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positivesplash10-0a6r-7900000000-7d98ce9e964eb9bae1232012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-0a6r-9700000000-e4f830b1b360289036652012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HP 5970) , Positivesplash10-0pdi-9500000000-eee2fac3cee7076204ca2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-2900000000-effe07b6b286033801ed2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-6345a1cf40f283a793a22015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-296abcf15a77a1f53d6a2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9200000000-086efee77b92115c17ca2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-266f38215789f236324e2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-266f38215789f236324e2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7900000000-828e61a7919a0eb819402015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-2900000000-18b3fa1f2954aac5b3232021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-9500000000-66c17c5a52895b2cc4d32021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-fc58e0949de9ca4842ff2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-8900000000-aae71de8ab13b4993f862021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9200000000-84ecaabc5b5d7c2807f52021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-99509376f83dc0a534322021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Aldehyde dehydrogenase family 8 member A1ALDH8A16q23.2Q9H2A2 details
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0006115
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014661
KNApSAcK IDC00034452
Chemspider ID235
KEGG Compound IDC00261
BioCyc IDBENZALDEHYDE
BiGG IDNot Available
Wikipedia LinkBenzaldehyde
METLIN IDNot Available
PubChem Compound240
PDB IDNot Available
ChEBI ID17169
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]
  2. Andersen A: Final report on the safety assessment of benzaldehyde. Int J Toxicol. 2006;25 Suppl 1:11-27. doi: 10.1080/10915810600716612. [PubMed:16835129 ]

Enzymes

Enzyme Details
1. Aldehyde dehydrogenase family 8 member A1
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