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Record Information
Version1.0
Creation Date2014-09-11 05:19:08 UTC
Update Date2016-11-09 01:09:13 UTC
Accession NumberCHEM003805
Identification
Common NameVanillin
ClassSmall Molecule
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).
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • Tobacco Smoke Compounds
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Ether
  • Flavouring Agent
  • Food Additive
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Synthetic Compound
Chemical 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
Vanillin, sodium saltHMDB
5-BromovanillinHMDB
5-ChlorovanillinHMDB
4-Hydroxy-3-methoxy-benzyldehydePhytoBank
VanillumPhytoBank
VanillinHMDB
Chemical FormulaC8H8O3
Average Molecular Mass152.147 g/mol
Monoisotopic Mass152.047 g/mol
CAS Registry Number121-33-5
IUPAC Name4-hydroxy-3-methoxybenzaldehyde
Traditional Namevanillin
SMILESCOC1=CC(C=O)=CC=C1O
InChI IdentifierInChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3
InChI KeyMWOOGOJBHIARFG-UHFFFAOYSA-N
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point81.5 °C
Boiling Point285°C (545°F)
Solubility11 mg/mL at 25 °C
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-0fk9-1900000000-68ebbe847e88a001f8faView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0udi-1900000000-46e0edb3260b8896145eView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0udi-7900000000-ee0a0ad1232fa889e567View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0udi-9800000000-d8f749f48a78e7c9c3bfView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-1960000000-b6678c7961ee7df779a1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS)splash10-05fr-7950000000-08c9e1cb0dbb3704f8eeView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0udi-1900000000-46e0edb3260b8896145eView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0udi-7900000000-ee0a0ad1232fa889e567View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0udi-9800000000-d8f749f48a78e7c9c3bfView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-1960000000-b6678c7961ee7df779a1View 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 Available
1D NMR13C NMR SpectrumNot Available
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0012308
FooDB IDFDB000838
Phenol Explorer ID724
KNApSAcK IDC00029531
BiGG IDNot Available
BioCyc IDVANILLIN
METLIN IDNot Available
PDB IDV55
Wikipedia LinkVanillin
Chemspider ID13860434
ChEBI ID18346
PubChem Compound ID1183
Kegg Compound IDC00755
YMDB IDYMDB01803
ECMDB IDM2MDB005004
References
Synthesis ReferenceNot Available
MSDSLink
General ReferencesNot Available