Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Version1.0
Created at2007-04-24 13:52:54 UTC
Updated at2021-08-19 23:58:47 UTC
NP-MRD IDNP0001105
Secondary Accession NumbersNone
Natural Product 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
Benzaldehyde, formyl-(14)C-labeledHMDB
Chemical FormulaC7H6O
Average Mass106.1219 Da
Monoisotopic Mass106.04186 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)V.dorna832021-08-09View Spectrum
Species
Species of Origin
Species NameSourceReference
Carica papayaKNApSAcK Database
Centaurea armenaKNApSAcK Database
Centaurea atropurpureaKNApSAcK Database
Centaurea orientalisKNApSAcK Database
Centaurea sessilisKNApSAcK Database
Citrus aurantifoliaKNApSAcK Database
Citrus aurantiumKNApSAcK Database
Citrus limonKNApSAcK Database
Citrus paradisiKNApSAcK Database
Citrus reticulataKNApSAcK Database
Citrus sinensisKNApSAcK Database
Coffea arabicaKNApSAcK Database
Coffea canephoraKNApSAcK Database
Dianthus caryophyllus L.KNApSAcK Database
Dittrichia graveolensKNApSAcK Database
Foeniculum vulgareKNApSAcK Database
Hesperis matronalisKNApSAcK Database
Laminaria japonicaKNApSAcK Database
Mandragora autumnalisKNApSAcK Database
Marsupella emarginataKNApSAcK Database
Medicago sativaKNApSAcK Database
Melaleuca leucadendra L.KNApSAcK Database
Nicotiana alataKNApSAcK Database
Nicotiana langsdorffiiKNApSAcK Database
Nymphaea lasiophyllaKNApSAcK Database
Petiveria alliaceaKNApSAcK Database
Prunus aviumKNApSAcK Database
Rhodiola rosea L.KNApSAcK Database
Santolina corsica Jordan et FourrKNApSAcK Database
Silene latifoliaKNApSAcK Database
Solanum lycopersicum Mill.KNApSAcK Database
Tanacetum macrophyllumKNApSAcK Database
Species Where Detected
Species NameSourceReference
Mycobacterium bovisKNApSAcK Database
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-26 °CNot Available
Boiling Point62.00 to 63.00 °C. @ 10.00 mm HgThe Good Scents Company Information System
Water Solubility6.95 mg/mL at 25 °CNot Available
LogP1.48HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility5.44 g/LALOGPS
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
External Links
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
Good Scents IDrw1001491
References
General References
  1. Andersen A: Final report on the safety assessment of benzaldehyde. Int J Toxicol. 2006;25 Suppl 1:11-27. [PubMed:16835129 ]
  2. Bozza T, Feinstein P, Zheng C, Mombaerts P: Odorant receptor expression defines functional units in the mouse olfactory system. J Neurosci. 2002 Apr 15;22(8):3033-43. doi: 20026321. [PubMed:11943806 ]
  3. Authors unspecified: NTP Toxicology and Carcinogenesis Studies of Benzaldehyde (CAS No. 100-52-7) in F344/N Rats and B6C3F1 Mice (Gavage Studies). Natl Toxicol Program Tech Rep Ser. 1990 Mar;378:1-191. [PubMed:12692643 ]
  4. Silk PJ, Macaulay JB: Stereoselective biosynthesis of chloroarylpropane diols by the basidiomycete Bjerkandera adusta. Chemosphere. 2003 Jul;52(2):503-12. doi: 10.1016/S0045-6535(03)00203-0. [PubMed:12738275 ]
  5. Rahnasto M, Raunio H, Poso A, Juvonen RO: More potent inhibition of human CYP2A6 than mouse CYP2A5 enzyme activities by derivatives of phenylethylamine and benzaldehyde. Xenobiotica. 2003 May;33(5):529-39. doi: 10.1080/0049825031000085979. [PubMed:12746108 ]