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Record Information
Version3.6
Creation Date2009-04-06 16:22:43 UTC
Update Date2016-02-11 01:24:15 UTC
HMDB IDHMDB12308
Secondary Accession NumbersNone
Metabolite Identification
Common NameVanillin
DescriptionVanillin is the primary component of the extract of the vanilla bean. Synthetic vanillin, instead of natural vanilla extract, is sometimes used as a flavouring agent in foods, beverages, and pharmaceuticals. It is used by the food industry as well as ethylvanillin.Artificial vanilla flavoring is a solution of pure vanillin, usually of synthetic origin. Because of the scarcity and expense of natural vanilla extract, there has long been interest in the synthetic preparation of its predominant component. The first commercial synthesis of vanillin began with the more readily available natural compound eugenol. Today, artificial vanillin is made from either guaiacol or from lignin, a constituent of wood which is a byproduct of the paper industry. (Wiki).
Structure
Thumb
Synonyms
ValueSource
3-Methoxy-4-hydroxybenzaldehydeChEBI
4-Formyl-2-methoxyphenolChEBI
4-Hydroxy-3-methoxy-benzaldehydeChEBI
4-Hydroxy-3-methoxybenzaldehydeChEBI
4-Hydroxy-m-anisaldehydeChEBI
Methylprotocatechuic aldehydeChEBI
P-Hydroxy-m-methoxybenzaldehydeChEBI
P-VanillinChEBI
VanilineChEBI
VanillaldehydeChEBI
Vanillic aldehydeChEBI
2-Methoxy-4-formylphenolHMDB
4-Hydroxy 3-methoxybenzaldehydeHMDB
4-Hydroxy-3-methoxy-benzaldehyde-5-chlorovanillinHMDB
4-Hydroxy-3-methoxybenzaldehyde (acd/name 4.0)HMDB
4-Hydroxy-5-methoxybenzaldehydeHMDB
LioxinHMDB
m-Methoxy-P-hydroxybenzaldehydeHMDB
Methyl-protocatechualdehydeHMDB
Methylprotcatechuic aldehydeHMDB
oleo-Resins vanillaHMDB
oleo-Resins vanilla-beanHMDB
Oleoresin vanillaHMDB
PropenylguaetholHMDB
Protocatechualdehyde 3-methyl etherHMDB
trans-2-Ethoxy-5-(1-propenyl)phenolHMDB
VanilinHMDB
VanillaHMDB
Vanilla oleoresinHMDB
Vanillin (3-methoxy-4-hydroxy- benzaldehyde)HMDB
Vanillin (natural)HMDB
Vanillin (NF)HMDB
Vanillin sodium saltHMDB
VanillineHMDB
ZimcoHMDB
Chemical FormulaC8H8O3
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
IUPAC Name4-hydroxy-3-methoxybenzaldehyde
Traditional Namevanillin
CAS Registry Number121-33-5
SMILES
COC1=CC(C=O)=CC=C1O
InChI Identifier
InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3
InChI KeyInChIKey=MWOOGOJBHIARFG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Hydroxybenzaldehyde
  • Methoxybenzene
  • Phenol ether
  • Benzoyl
  • Benzaldehyde
  • Anisole
  • Aryl-aldehyde
  • Alkyl aryl ether
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point81.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility11 mg/mL at 25 °CNot Available
LogP1.21HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility5.05 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.09 m3·mol-1ChemAxon
Polarizability14.82 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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 Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified5.298 +/- 0.902 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified3.764 +/- 0.869 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified4.976 +/- 0.971 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified8.309 +/- 3.765 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified4.951 +/- 0.92 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified5.375 +/- 0.91 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified4.468 +/- 0.815 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified28.258 +/- 24.808 uMAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.362 +/- 0.053 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID724
Phenol Explorer Metabolite ID724
FoodDB IDFDB000838
KNApSAcK IDC00029531
Chemspider ID13860434
KEGG Compound IDC00755
BioCyc IDVANILLIN
BiGG IDNot Available
Wikipedia LinkVanillin
NuGOwiki LinkHMDB12308
Metagene LinkHMDB12308
METLIN IDNot Available
PubChem Compound1183
PDB IDV55
ChEBI ID18346
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available