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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:32:03 UTC
Update Date2022-03-07 02:52:15 UTC
HMDB IDHMDB0029686
Secondary Accession Numbers
  • HMDB29686
Metabolite Identification
Common Name4-Methoxybenzaldehyde
Description4-Methoxybenzaldehyde, also known as 4-anisaldehyde or p-formylanisole, belongs to the class of organic compounds known as benzoyl derivatives, with the chemical formula CH3OC6H4CHO. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-). Anisaldehyde is prepared commercially by oxidation of 4-methoxytoluene (p-cresyl methyl ether) using manganese dioxide to convert a methyl group to the aldehyde group. 4-Methoxybenzaldehyde is a sweet, almond, and anise tasting compound. 4-Methoxybenzaldehyde can be found, on average, in the highest concentration within a few different foods, such as cumins, star anises, and fennels. 4-Methoxybenzaldehyde has also been detected, but not quantified, in several different foods, such as cornmints, anises, herbs and spices, tarragons, and tea. The related ortho isomer has a scent of licorice. It is a colorless liquid with a strong aroma. A solution of para-anisaldehyde in acid and ethanol is a useful stain in thin layer chromatography. Different chemical compounds on the plate can give different colors, allowing easy distinction. It is used as an intermediate in the synthesis of other compounds important in pharmaceuticals and perfumery.
Structure
Data?1582753451
Synonyms
ValueSource
4-AnisaldehydeChEBI
4-Methoxy-benzaldehydeChEBI
AnisalChEBI
p-AnisaldehydeChEBI
p-Anisic aldehydeChEBI
p-FormylanisoleChEBI
Para-anisaldehydeChEBI
4-Anisaldehyde, 1,2,3,4,5,6-(14)C6-labeledMeSH
4-Anisaldehyde, 18O-labeledMeSH
4-Anisaldehyde, formyl-(14)C-labeledMeSH
AnisaldehydeMeSH
p-MethoxybenzaldehydeMeSH
4-MethoxybenzaldehydeChEMBL, MeSH
Anisic aldehydeHMDB
AubepineHMDB
CrategineHMDB
FEMA 2670HMDB
ObepinHMDB
P-Anisaldehyde, 8ciHMDB
Chemical FormulaC8H8O2
Average Molecular Weight136.1479
Monoisotopic Molecular Weight136.0524295
IUPAC Name4-methoxybenzaldehyde
Traditional Nameanisaldehyde
CAS Registry Number123-11-5
SMILES
COC1=CC=C(C=O)C=C1
InChI Identifier
InChI=1S/C8H8O2/c1-10-8-4-2-7(6-9)3-5-8/h2-6H,1H3
InChI KeyZRSNZINYAWTAHE-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
  • 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

Biological location

Source

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point0 °CNot Available
Boiling Point248.00 to 249.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility4.29 mg/mL at 25 °CNot Available
LogP1.76Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+129.78431661259
DarkChem[M-H]-128.46831661259
DeepCCS[M+H]+129.19130932474
DeepCCS[M-H]-125.36130932474
DeepCCS[M-2H]-162.80730932474
DeepCCS[M+Na]+138.34630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-MethoxybenzaldehydeCOC1=CC=C(C=O)C=C12069.4Standard polar33892256
4-MethoxybenzaldehydeCOC1=CC=C(C=O)C=C11198.2Standard non polar33892256
4-MethoxybenzaldehydeCOC1=CC=C(C=O)C=C11246.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 4-Methoxybenzaldehyde EI-B (Non-derivatized)splash10-000i-5900000000-f3f464cd23c97578f30c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methoxybenzaldehyde EI-B (Non-derivatized)splash10-000i-5900000000-e26ac32161d707d4b67d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methoxybenzaldehyde EI-B (Non-derivatized)splash10-000i-9600000000-005ef37f7e37a0e556812017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methoxybenzaldehyde EI-B (Non-derivatized)splash10-000i-8900000000-d51f38f91dea18a7ca2b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methoxybenzaldehyde EI-B (Non-derivatized)splash10-002r-9400000000-bc00e3079ed91b21f4ba2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methoxybenzaldehyde EI-B (Non-derivatized)splash10-000i-5900000000-f3f464cd23c97578f30c2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methoxybenzaldehyde EI-B (Non-derivatized)splash10-000i-5900000000-e26ac32161d707d4b67d2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methoxybenzaldehyde EI-B (Non-derivatized)splash10-000i-9600000000-005ef37f7e37a0e556812018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methoxybenzaldehyde EI-B (Non-derivatized)splash10-000i-8900000000-d51f38f91dea18a7ca2b2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methoxybenzaldehyde EI-B (Non-derivatized)splash10-002r-9400000000-bc00e3079ed91b21f4ba2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Methoxybenzaldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-5900000000-7529d3b0428c09095b3b2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Methoxybenzaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-000i-8900000000-2470c82de1eaf7d2642a2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methoxybenzaldehyde 40V, Positive-QTOFsplash10-014i-9000000000-26a1b069ae6df01ffff02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methoxybenzaldehyde 20V, Positive-QTOFsplash10-014l-9200000000-bfa432b6662a4ee0dbd72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methoxybenzaldehyde 10V, Positive-QTOFsplash10-000i-2900000000-bf8308aa9be60fc665282021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methoxybenzaldehyde 10V, Positive-QTOFsplash10-000i-0900000000-b2d6a9d38197c0f6fa062016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methoxybenzaldehyde 20V, Positive-QTOFsplash10-000i-0900000000-1d9300c2be9fe71e682b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methoxybenzaldehyde 40V, Positive-QTOFsplash10-0kl3-9300000000-ed81538d959a9b26cd662016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methoxybenzaldehyde 10V, Negative-QTOFsplash10-000i-0900000000-ea778719cccbf199adaa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methoxybenzaldehyde 20V, Negative-QTOFsplash10-000i-0900000000-6c4fb2d07ea57b35eb7a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methoxybenzaldehyde 40V, Negative-QTOFsplash10-066r-7900000000-292cb3482f5608dd969d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methoxybenzaldehyde 10V, Negative-QTOFsplash10-000i-0900000000-85183aae6dd12de03af02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methoxybenzaldehyde 20V, Negative-QTOFsplash10-052r-0900000000-a54ce65ce6c13a79dd832021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methoxybenzaldehyde 40V, Negative-QTOFsplash10-014i-9800000000-0e4a6858b345500667502021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methoxybenzaldehyde 10V, Positive-QTOFsplash10-052r-0900000000-039acf4403c9b4099eec2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methoxybenzaldehyde 20V, Positive-QTOFsplash10-052r-4900000000-65583d5c117cd8b1920f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methoxybenzaldehyde 40V, Positive-QTOFsplash10-0udi-9000000000-914b4ed5eeddb4a0152d2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID727
FooDB IDFDB000872
KNApSAcK IDC00002636
Chemspider ID21105937
KEGG Compound IDC10761
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAnisaldehyde
METLIN IDNot Available
PubChem Compound31244
PDB IDNot Available
ChEBI ID28235
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1001272
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .