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4-Methoxybenzaldehyde (FDB000872)

Record Information
Version1.0
Creation date2010-04-08 22:04:44 UTC
Update date2019-11-26 02:55:34 UTC
Primary IDFDB000872
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Methoxybenzaldehyde
DescriptionFound in anise oil, fennel and vanilla. Flavouring ingredient Anisaldehyde, or anisic aldehyde, is an organic compound that consists of a benzene ring substituted with an aldehyde and a methoxy group. It is a clear colorless liquid with a strong aroma. It comes in 3 varieties, ortho, meta, and para in which the two functional groups (methoxy and aldehyde) are alpha, beta, and gamma, respectively to each other. The unmodified term anisaldehyde generally refers to the para isomer. Anisaldehyde is found in anise, from which it gets its name. It is similar in structure to vanillin.
CAS Number123-11-5
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.71 g/LALOGPS
logP1.64ALOGPS
logP1.53ChemAxon
logS-1.9ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.11 m³·mol⁻¹ChemAxon
Polarizability14 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H8O2
IUPAC name4-methoxybenzaldehyde
InChI IdentifierInChI=1S/C8H8O2/c1-10-8-4-2-7(6-9)3-5-8/h2-6H,1H3
InChI KeyZRSNZINYAWTAHE-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC=C(C=O)C=C1
Average Molecular Weight136.1479
Monoisotopic Molecular Weight136.0524295
Classification
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
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Benzoyl
  • Benzaldehyde
  • Anisole
  • Aryl-aldehyde
  • Alkyl aryl ether
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aldehyde
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 70.58%; H 5.92%; O 23.50%DFC
Melting PointMp 0°DFC
Boiling PointBp12 134-135°DFC
Experimental Water Solubility4.29 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP1.76HANSCH,C ET AL. (1995)
Experimental pKapKa 15.96 (25°,hydrate, 1% EtOH)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd154 1.12DFC
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-000i-8900000000-2470c82de1eaf7d2642a2015-03-01View Spectrum
GC-MS4-Methoxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-000i-5900000000-f3f464cd23c97578f30cSpectrum
GC-MS4-Methoxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-000i-5900000000-e26ac32161d707d4b67dSpectrum
GC-MS4-Methoxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-000i-9600000000-005ef37f7e37a0e55681Spectrum
GC-MS4-Methoxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-000i-8900000000-d51f38f91dea18a7ca2bSpectrum
GC-MS4-Methoxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-002r-9400000000-bc00e3079ed91b21f4baSpectrum
GC-MS4-Methoxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-000i-5900000000-f3f464cd23c97578f30cSpectrum
GC-MS4-Methoxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-000i-5900000000-e26ac32161d707d4b67dSpectrum
GC-MS4-Methoxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-000i-9600000000-005ef37f7e37a0e55681Spectrum
GC-MS4-Methoxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-000i-8900000000-d51f38f91dea18a7ca2bSpectrum
GC-MS4-Methoxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-002r-9400000000-bc00e3079ed91b21f4baSpectrum
Predicted GC-MS4-Methoxybenzaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4r-5900000000-7529d3b0428c09095b3bSpectrum
Predicted GC-MS4-Methoxybenzaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-26a1b069ae6df01ffff02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-014l-9200000000-bfa432b6662a4ee0dbd72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-2900000000-bf8308aa9be60fc665282021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-b2d6a9d38197c0f6fa062016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-1d9300c2be9fe71e682b2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kl3-9300000000-ed81538d959a9b26cd662016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-ea778719cccbf199adaa2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-6c4fb2d07ea57b35eb7a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-7900000000-292cb3482f5608dd969d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-85183aae6dd12de03af02021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-0900000000-a54ce65ce6c13a79dd832021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9800000000-0e4a6858b345500667502021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0900000000-039acf4403c9b4099eec2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-4900000000-65583d5c117cd8b1920f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-914b4ed5eeddb4a0152d2021-09-24View Spectrum
NMR
TypeDescriptionView
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
ChemSpider ID21105937
ChEMBL IDCHEMBL161598
KEGG Compound IDC10761
Pubchem Compound ID31244
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID727
DrugBank IDNot Available
HMDB IDHMDB29686
CRC / DFC (Dictionary of Food Compounds) IDBLB50-B:BLB50-B
EAFUS ID2203
Dr. Duke IDP-METHOXYBENZALDEHYDE|ANISIC-ALDEHYDE|4-METHOXY-BENZALDEHYDE|ANISALDEHYDE|P-ANISALDEHYDE
BIGG IDNot Available
KNApSAcK IDC00002636
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID123-11-5
GoodScent IDrw1001271
SuperScent ID31244
Wikipedia IDAnisaldehyde
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti mutagenicDUKE
cosmetic64857 The role played by a substance in enhancing the appearance or odour of the human body; a name given to the substance itself or to a component of it.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
irritantDUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
piscicideDUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
tyrosinase inhibitor59997 Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
mint
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
sweet
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
creamy
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
hawthorne
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
anise
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
balsam
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
chocolate
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
cinnamon
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
vanilla
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
berry
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
cherry
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
almond
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
minty
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
powdery
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
mimosa
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
hawthorn
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.