Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120585
Identification
Name: benzaldehyde
Description:An arenecarbaldehyde that consists of benzene bearing a single formyl substituent; the simplest aromatic aldehyde and parent of the class of benzaldehydes.
Structure
Thumb
Synonyms:
  • Artificial almond oil
  • Benzaldehyde
  • benzaldehyde
  • Benzanoaldehyde
  • Benzene carbaldehyde
  • Benzene carboxaldehyde
  • Benzenecarbonal
  • Benzenecarboxaldehyde
  • Benzenemethylal
  • Benzoic acid aldehyde
  • Benzoic aldehyde
  • Benzoic aldehyde
  • Benzylaldehyde
  • Ethereal oil of bitter almonds
  • Phenylformaldehyde
  • Phenylmethanal
  • Synthetic oil of bitter almond
Chemical Formula: C7H6O
Average Molecular Weight: 106.124
Monoisotopic Molecular Weight: 106.04186
InChI Key: HUMNYLRZRPPJDN-UHFFFAOYSA-N
InChI:InChI=1S/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H
CAS number: 100-52-7
IUPAC Name:benzaldehyde
Traditional IUPAC Name: benzaldehyde
SMILES:C(=O)C1(=CC=CC=C1)
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-).
Kingdom Chemical entities
Super ClassOrganic compounds
Class Benzenoids
Sub ClassBenzene and substituted derivatives
Direct Parent Benzoyl derivatives
Alternative Parents
Substituents
  • Benzoyl
  • Benzaldehyde
  • Aryl-aldehyde
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aldehyde
  • Aromatic homomonocyclic compound
Molecular Framework Aromatic homomonocyclic compounds
External Descriptors
Physical Properties
State: Liquid
Charge:0
Melting point: -26 °C
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
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
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
References
References:
  • Bozza T, Feinstein P, Zheng C, Mombaerts P (2002)Odorant receptor expression defines functional units in the mouse olfactory system. The Journal of neuroscience : the official journal of the Society for Neuroscience 22, Pubmed: 11943806
  • Rahnasto M, Raunio H, Poso A, Juvonen RO (2003)More potent inhibition of human CYP2A6 than mouse CYP2A5 enzyme activities by derivatives of phenylethylamine and benzaldehyde. Xenobiotica; the fate of foreign compounds in biological systems 33, Pubmed: 12746108
  • Stevenson DE, Feng R, Dumas F, Groleau D, Mihoc A, Storer AC (1992)Mechanistic and structural studies on Rhodococcus ATCC 39484 nitrilase. Biotechnology and applied biochemistry 15, Pubmed: 1388821
  • Silk PJ, Macaulay JB (2003)Stereoselective biosynthesis of chloroarylpropane diols by the basidiomycete Bjerkandera adusta. Chemosphere 52, Pubmed: 12738275
  • National Toxicology Program (1990)NTP Toxicology and Carcinogenesis Studies of Benzaldehyde (CAS No. 100-52-7) in F344/N Rats and B6C3F1 Mice (Gavage Studies). National Toxicology Program technical report series 378, Pubmed: 12692643
  • Kim H, Park BS, Lee KG, Choi CY, Jang SS, Kim YH, Lee SE (2005)Effects of naturally occurring compounds on fibril formation and oxidative stress of beta-amyloid. Journal of agricultural and food chemistry 53, Pubmed: 16248550
  • Yokota J, Takuma D, Hamada A, Onogawa M, Yoshioka S, Kusunose M, Miyamura M, Kyotani S, Nishioka Y (2006)Scavenging of reactive oxygen species by Eriobotrya japonica seed extract. Biological & pharmaceutical bulletin 29, Pubmed: 16508147
  • Philips N, Burchill D, O'Donoghue D, Keller T, Gonzalez S (2004)Identification of benzene metabolites in dermal fibroblasts as nonphenolic: regulation of cell viability, apoptosis, lipid peroxidation and expression of matrix metalloproteinase 1 and elastin by benzene metabolites. Skin pharmacology and physiology 17, Pubmed: 15087594
  • Hoet S, Stévigny C, Hérent MF, Quetin-Leclercq J (2006)Antitrypanosomal compounds from the leaf essential oil of Strychnos spinosa. Planta medica 72, Pubmed: 16557466
  • Rahnasto M, Raunio H, Poso A, Wittekindt C, Juvonen RO (2005)Quantitative structure-activity relationship analysis of inhibitors of the nicotine metabolizing CYP2A6 enzyme. Journal of medicinal chemistry 48, Pubmed: 15658857
  • Schmidt MF, Isidro-Llobet A, Lisurek M, El-Dahshan A, Tan J, Hilgenfeld R, Rademann J (2008)Sensitized detection of inhibitory fragments and iterative development of non-peptidic protease inhibitors by dynamic ligation screening. Angewandte Chemie (International ed. in English) 47, Pubmed: 18348134
  • Sankar M, Nowicka E, Tiruvalam R, He Q, Taylor SH, Kiely CJ, Bethell D, Knight DW, Hutchings GJ (2011)Controlling the duality of the mechanism in liquid-phase oxidation of benzyl alcohol catalysed by supported Au-Pd nanoparticles. Chemistry (Weinheim an der Bergstrasse, Germany) 17, Pubmed: 21538605
  • Niu Q, Huang X, Zhang L, Xu J, Yang D, Wei K, Niu X, An Z, Bennett JW, Zou C, Yang J, Zhang KQ (2010)A Trojan horse mechanism of bacterial pathogenesis against nematodes. Proceedings of the National Academy of Sciences of the United States of America 107, Pubmed: 20733068
  • Khan TR, Daugulis AJ (2011)The effects of polymer phase ratio and feeding strategy on solid-liquid TPPBs for the production of L-phenylacetylcarbinol from benzaldehyde using Candida utilis. Biotechnology letters 33, Pubmed: 20878540
  • Tan H, Chen W, Liu D, Feng X, Li Y, Yan A, Wang E (2011)Two diphosphonate-functionalized asymmetric polyoxomolybdates with catalytic activity for oxidation of benzyl alcohol to benzaldehyde. Dalton transactions (Cambridge, England : 2003) 40, Pubmed: 21773601
  • Kastner PE, Le Calvé S, Diss L, Sauveplane V, Franke R, Schreiber L, Pinot F (2011)Specific accumulation of CYP94A1 transcripts after exposure to gaseous benzaldehyde: induction of lauric acid ?-hydroxylase activity in Vicia sativa exposed to atmospheric pollutants. Environmental research 111, Pubmed: 21035797
  • Mashayekhi HA, Rezaee M, Garmaroudi SS, Montazeri N, Ahmadi SJ (2011)Rapid and sensitive determination of benzaldehyde arising from benzyl alcohol used as preservative in an injectable formulation solution using dispersive liquid-liquid microextraction followed by gas chromatography. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 27, Pubmed: 21828928
  • Ulker Z, Alpsoy L, Mihmanli A (2013)Assessment of cytotoxic and apoptotic effects of benzaldehyde using different assays. Human & experimental toxicology 32, Pubmed: 23263855
Synthesis Reference: Oxidation 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)
External Links:
ResourceLink
METABOLIGHTSMTBLC17169
HMDBHMDB06115
CHEMSPIDER235
PUBCHEM240
CHEBI17169
LIGAND-CPDC00261
CAS100-52-7