Record Information
Version1.0
Creation date2010-04-08 22:04:44 UTC
Update date2015-07-20 21:34:56 UTC
Primary IDFDB000838
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameVanillin
DescriptionConstit. of vanilla (Vanilla spp.) and many other plants, e.g. Peru balsam, clove bud oil. Widely used flavouring agent esp. in cocoa products. Obt. from spent wood-pulp liquors
CAS Number121-33-5
Structure
Thumb
Synonyms
SynonymSource
2-Methoxy-4-formylphenolbiospider
3-Methoxy-4-hydroxybenzaldehydebiospider
4-Formyl-2-methoxyphenolbiospider
4-Hydroxy 3-methoxybenzaldehydeHMDB
4-Hydroxy-3-methoxy-benzaldehydebiospider
4-Hydroxy-3-methoxy-benzaldehyde-5-chlorovanillinHMDB
4-Hydroxy-3-methoxybenzaldehydeChEBI
4-Hydroxy-3-methoxybenzaldehyde (acd/name 4.0)HMDB
4-Hydroxy-5-methoxybenzaldehydebiospider
4-Hydroxy-m-anisaldehydebiospider
Benzaldehyde, 4-hydroxy-3-methoxy-biospider
FEMA 3107db_source
Lioxinbiospider
m-Anisaldehyde, 4-hydroxy-biospider
m-Methoxy-p-hydroxybenzaldehydebiospider
Methyl-protocatechualdehydeHMDB
Methylprotcatechuic aldehydeHMDB
Methylprotocatechuic aldehydebiospider
Oleo-resins vanillaHMDB
Oleo-resins vanilla-beanHMDB
Oleoresin vanillaHMDB
p-Hydroxy-m-methoxybenzaldehydebiospider
p-Vanillinbiospider
Protocatechualdehyde 3-methyl etherbiospider
VanilinHMDB
VanilineChEBI
VanillaHMDB
Vanilla oleoresinHMDB
Vanillaldehydedb_source
Vanillic aldehydebiospider
Vanillin (3-methoxy-4-hydroxy- benzaldehyde)HMDB
Vanillin (natural)HMDB
Vanillin (NF)HMDB
Vanillin sodium saltHMDB
Vanillin, USANdb_source
VanillineHMDB
ZimcoHMDB
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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 KeyInChIKey=MWOOGOJBHIARFG-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C=CC(C=O)=C1
Average Molecular Weight152
Monoisotopic Molecular Weight152
Classification
DescriptionThis compound belongs to the class of chemical entities known as methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassPhenols
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
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-1900000000-46e0edb3260b8896145eView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-7900000000-ee0a0ad1232fa889e567View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-9800000000-d8f749f48a78e7c9c3bfView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1960000000-b6678c7961ee7df779a1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-1900000000-68ebbe847e88a001f8faView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-7950000000-08c9e1cb0dbb3704f8eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0udi-0900000000-334e2cf1c60f75229fd1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0uy0-0900200200-4cbd13b45290ded181eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udr-0900000000-d67b08f1b4f6e90cd270View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-e949414f752aab5e9606View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-1dcee0be3ba8e1431a7cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ff9-9400000000-dcd0372357bd9c46926dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-6cc5e0ed993af0b790e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-cf1b6af77251971154f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-9500000000-302ce8740fbb7b9295b9View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0udi-5900000000-907c9684d5ac0386d522View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
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
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.