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Showing Compound 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
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
Benzaldehyde, 4-methoxy-biospider
Formylanisole, p-biospider
p-Anisaldehyde, 8CIdb_source
para-Anisaldehydebiospider
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-mutagenicAn agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.DUKE
Cosmetic64857 A substance used to enhance physical appearance, with no therapeutic effect. It plays a social and psychological role, boosting self-esteem and confidence. Key uses include skincare, haircare, and makeup, with no direct medical applications, but can have indirect benefits such as improving mental well-being.DUKE
Name48318 flavorDUKE
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
Insecticide24852 An agent that kills or repels insects, used to control pests and prevent disease transmission. Therapeutically, insecticides have applications in public health and veterinary medicine, key medical uses include controlling insect-borne diseases such as malaria, typhus, and Lyme disease.DUKE
IrritantAn agent that causes slight inflammation or discomfort, stimulating a biological response. Therapeutically, it can be used to increase blood flow or stimulate healing. Key medical uses include treating wounds, skin conditions, and respiratory issues, such as congestion, by inducing a mild inflammatory response to promote recovery.DUKE
Nematicide25491 An agent that kills nematodes, a type of parasitic worm, used to control infestations in crops and animals, with therapeutic applications in veterinary medicine to treat parasitic infections and promote livestock health.DUKE
Perfumery48318 The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
PiscicideA substance poisonous to fish, used to eliminate dominant or invasive fish species, and combat parasitic fish, allowing for population control and management of aquatic ecosystems.DUKE
Sedative35717 An agent that calms nervous activity, reducing anxiety and inducing relaxation. Its biological role is to slow down brain function, promoting sleep and relieving stress. Therapeutically, sedatives are used to manage insomnia, anxiety disorders, and seizures, as well as to prepare patients for medical procedures.DUKE
Tyrosinase inhibitor59997 An agent that blocks the activity of tyrosinase, an enzyme involved in melanin production, reducing skin pigmentation. Therapeutically used to treat hyperpigmentation disorders, such as melasma and vitiligo, and as a skin-lightening agent in dermatology.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.