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Vanillin (FDB000838)

Record Information
Version1.0
Creation date2010-04-08 22:04:44 UTC
Update date2019-11-26 02:55:29 UTC
Primary IDFDB000838
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameVanillin
DescriptionVanillin, also known as vanillaldehyde or 5-bromovanillin, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Vanillin exists in all living species, ranging from bacteria to plants to humans. Vanillin is a sweet, chocolate, and creamy tasting compound. Vanillin is found, on average, in the highest concentration within a few different foods, such as corns (Zea mays), ryes (Secale cereale), and sherry and in a lower concentration in sunflowers (Helianthus annuus), spirit, and oats (Avena sativa). Vanillin has also been detected, but not quantified in, several different foods, such as blackcurrants (Ribes nigrum), daikon radishes (Raphanus sativus var. longipinnatus), conches (Strombidae), white mustards (Sinapis alba), and fireweeds (Chamerion angustifolium). This could make vanillin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Vanillin.
CAS Number121-33-5
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.05 g/LALOGPS
logP1.31ALOGPS
logP1.22ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)7.81ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.09 m³·mol⁻¹ChemAxon
Polarizability14.82 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H8O3
IUPAC name4-hydroxy-3-methoxybenzaldehyde
InChI IdentifierInChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3
InChI KeyMWOOGOJBHIARFG-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(C=O)=CC=C1O
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
Classification
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Hydroxybenzaldehyde
  • Anisole
  • Benzaldehyde
  • Benzoyl
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • Aryl-aldehyde
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Ether
  • Organooxygen compound
  • Aldehyde
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Foods
  • Cocoa and cocoa products

    • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionC 63.15%; H 5.30%; O 31.55%DFC
    Melting PointMp 77-79° (dimorph.)DFC
    Boiling PointBp15 170°DFC
    Experimental Water Solubility11 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
    Experimental logP1.21HANSCH,C ET AL. (1995)
    Experimental pKapKa1 7.4 (25°)DFC
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV Data319 (e 25200) (MeOH-NaOH) (Berdy)DFC
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    EI-MSMass Spectrum (Electron Ionization)splash10-0udi-5900000000-907c9684d5ac0386d5222014-09-20View Spectrum
    GC-MSVanillin, non-derivatized, GC-MS Spectrumsplash10-0udi-1900000000-46e0edb3260b8896145eSpectrum
    GC-MSVanillin, non-derivatized, GC-MS Spectrumsplash10-0udi-7900000000-ee0a0ad1232fa889e567Spectrum
    GC-MSVanillin, non-derivatized, GC-MS Spectrumsplash10-0udi-9800000000-d8f749f48a78e7c9c3bfSpectrum
    GC-MSVanillin, non-derivatized, GC-MS Spectrumsplash10-00di-1960000000-b6678c7961ee7df779a1Spectrum
    GC-MSVanillin, non-derivatized, GC-MS Spectrumsplash10-0udi-1900000000-46e0edb3260b8896145eSpectrum
    GC-MSVanillin, non-derivatized, GC-MS Spectrumsplash10-0udi-7900000000-ee0a0ad1232fa889e567Spectrum
    GC-MSVanillin, non-derivatized, GC-MS Spectrumsplash10-0udi-9800000000-d8f749f48a78e7c9c3bfSpectrum
    GC-MSVanillin, non-derivatized, GC-MS Spectrumsplash10-00di-1960000000-b6678c7961ee7df779a1Spectrum
    Predicted GC-MSVanillin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fk9-1900000000-68ebbe847e88a001f8faSpectrum
    Predicted GC-MSVanillin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fr-7950000000-08c9e1cb0dbb3704f8eeSpectrum
    Predicted GC-MSVanillin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0udi-0900000000-334e2cf1c60f75229fd12017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0uy0-0900200200-4cbd13b45290ded181ee2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udr-0900000000-d67b08f1b4f6e90cd2702017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-9fc5182650ced222b1a12021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-052b-9800000000-312c82e1fbcda8abeaf72021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-0a4j-9700000000-c0da5ed12872161ea30e2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000l-5900000000-8c4d3cd8abfc264729a32021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-a9b7f966d85c30f6174c2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-d1e812bea83f6f84570d2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000f-7900000000-9d9283afc35603b0121c2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-146c4b184605c821d8222021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00kf-9500000000-f5a8328127a89c12c19e2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-014i-9000000000-44efadd4b0c1fe89c39c2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-014i-9100000000-70cac2e87a3ecb4ec8672021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0udr-0900000000-10b0539cab1169d8d8772021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-0900000000-17943fa1f4f19dd4878a2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0udr-0900000000-2e50ec52313e18cddbd02021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0f79-1900000000-98d502286eb47c703f642021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-052e-9800000000-03597a1112a480b91d5e2021-09-20View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-e949414f752aab5e96062015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-1dcee0be3ba8e1431a7c2015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ff9-9400000000-dcd0372357bd9c46926d2015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-6cc5e0ed993af0b790e62015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-cf1b6af77251971154f92015-05-27View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-9500000000-302ce8740fbb7b9295b92015-05-27View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, 25.16 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 ID13860434
    ChEMBL IDCHEMBL13883
    KEGG Compound IDC00755
    Pubchem Compound ID1183
    Pubchem Substance IDNot Available
    ChEBI ID18346
    Phenol-Explorer ID724
    DrugBank IDNot Available
    HMDB IDHMDB12308
    CRC / DFC (Dictionary of Food Compounds) IDHCW75-Q:BJR54-T
    EAFUS ID3830
    Dr. Duke IDVANILLIC-ALDEHYDE|VANILLIN|4-HYDROXY-3-METHOXYBENZALDEHYDE
    BIGG IDNot Available
    KNApSAcK IDC00029531
    HET IDV55
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet ID121-33-5
    GoodScent IDrw1011711
    SuperScent IDNot Available
    Wikipedia IDVanillin
    Phenol-Explorer Metabolite ID724
    Duplicate IDS
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / Bioactivities
    DescriptorIDDefinitionReference
    allelochemicDUKE
    allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
    anti anemic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    anti drepanocyticDUKE
    anti escherichicDUKE
    anti lactobacillic33282 A substance that kills or slows the growth of bacteria.DUKE
    anti listeria33282 A substance that kills or slows the growth of bacteria.DUKE
    anti mutagenicDUKE
    antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
    anti polio22587 A substance that destroys or inhibits replication of viruses.DUKE
    anti radicularDUKE
    anti sicklingDUKE
    antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    antitumor promoter35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
    anti yeast33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
    bacteristat33282 A substance that kills or slows the growth of bacteria.DUKE
    cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    candidicideDUKE
    cholereticDUKE
    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
    immunosuppressant35705 An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.DUKE
    insectifuge24852 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
    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
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    Flavours
    FlavorCitations
    vanilla
    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.
    sweet
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    creamy
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    chocolate
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    Files
    MSDSshow
    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.