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Vanillin (T3D4849)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2014-09-11 05:19:08 UTC
Update Date2014-12-24 20:26:58 UTC
Accession NumberT3D4849
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).
Compound Type
  • Ester
  • Ether
  • Flavouring Agent
  • Food Additive
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
2-Methoxy-4-formylphenol
3-Methoxy-4-hydroxybenzaldehyde
4-Formyl-2-methoxyphenol
4-hydroxy 3-methoxybenzaldehyde
4-Hydroxy-3-methoxy-benzaldehyde
4-Hydroxy-3-methoxy-Benzaldehyde-5-chlorovanillin
4-Hydroxy-3-methoxybenzaldehyde
4-Hydroxy-5-methoxybenzaldehyde
4-Hydroxy-m-anisaldehyde
Lioxin
M-Methoxy-p-hydroxybenzaldehyde
Methyl-Protocatechualdehyde
Methylprotcatechuic aldehyde
Methylprotocatechuic aldehyde
Oleo-Resins vanilla
Oleo-Resins vanilla-bean
Oleoresin vanilla
P-Hydroxy-m-methoxybenzaldehyde
P-Vanillin
Propenylguaethol
Protocatechualdehyde 3-methyl ether
trans-2-Ethoxy-5-(1-propenyl)phenol
Vanilin
Vaniline
Vanilla
Vanilla oleoresin
Vanillaldehyde
Vanillic aldehyde
Vanillin (3-methoxy-4-hydroxy- benzaldehyde)
Vanillin (natural)
Vanillin (NF)
Vanillin sodium salt
Vanilline
Zimco
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=C(O)C=CC(C=O)=C1
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
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
LogP1.21
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 KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-1900000000-46e0edb3260b8896145eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-7900000000-ee0a0ad1232fa889e567JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-9800000000-d8f749f48a78e7c9c3bfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1960000000-b6678c7961ee7df779a1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-1900000000-46e0edb3260b8896145eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-7900000000-ee0a0ad1232fa889e567JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-9800000000-d8f749f48a78e7c9c3bfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1960000000-b6678c7961ee7df779a1JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-1900000000-68ebbe847e88a001f8faJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-7950000000-08c9e1cb0dbb3704f8eeJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0udi-0900000000-334e2cf1c60f75229fd1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0uy0-0900200200-4cbd13b45290ded181eeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udr-0900000000-d67b08f1b4f6e90cd270JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-e949414f752aab5e9606JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-1dcee0be3ba8e1431a7cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ff9-9400000000-dcd0372357bd9c46926dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-6cc5e0ed993af0b790e6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-cf1b6af77251971154f9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-9500000000-302ce8740fbb7b9295b9JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0udi-5900000000-907c9684d5ac0386d522JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB12308
PubChem Compound ID1183
ChEMBL IDCHEMBL13883
ChemSpider ID13860434
KEGG IDC00755
UniProt IDNot Available
OMIM ID
ChEBI ID18346
BioCyc IDVANILLIN
CTD IDNot Available
Stitch IDNot Available
PDB IDV55
ACToR IDNot Available
Wikipedia LinkVanillin
References
Synthesis ReferenceNot Available
MSDSLink
General ReferencesNot Available
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Stromelysin-1
General Function:
Zinc ion binding
Specific Function:
Can degrade fibronectin, laminin, gelatins of type I, III, IV, and V; collagens III, IV, X, and IX, and cartilage proteoglycans. Activates procollagenase.
Gene Name:
MMP3
Uniprot ID:
P08254
Molecular Weight:
53976.84 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC503.79 uMNVS_ENZ_hMMP3Novascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]