Record Information
Version3.6
Creation Date2009-04-06 16:22:43 UTC
Update Date2013-02-09 00:28:46 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
  1. 2-Methoxy-4-formylphenol
  2. 3-Methoxy-4-hydroxybenzaldehyde
  3. 3-Methoxy-4-hydroxybenzaldehyde (vanillin)
  4. 4-Formyl-2-methoxyphenol
  5. 4-hydroxy 3-methoxybenzaldehyde
  6. 4-Hydroxy-3-methoxy-benzaldehyde
  7. 4-Hydroxy-3-methoxy-Benzaldehyde-5-chlorovanillin
  8. 4-Hydroxy-3-methoxybenzaldehyde
  9. 4-Hydroxy-3-methoxybenzaldehyde (ACD/Name 4.0)
  10. 4-Hydroxy-3-methoxybenzaldehyde (vanillin)
  11. 4-Hydroxy-5-methoxybenzaldehyde
  12. 4-Hydroxy-m-anisaldehyde
  13. Lioxin
  14. M-Methoxy-p-hydroxybenzaldehyde
  15. Methyl-Protocatechualdehyde
  16. Methylprotcatechuic aldehyde
  17. Methylprotocatechuic aldehyde
  18. Oleo-Resins vanilla
  19. Oleo-Resins vanilla-bean
  20. Oleoresin vanilla
  21. P-Hydroxy-m-methoxybenzaldehyde
  22. P-Vanillin
  23. Propenylguaethol
  24. Protocatechualdehyde 3-methyl ether
  25. trans-2-Ethoxy-5-(1-propenyl)phenol
  26. Vanilin
  27. Vaniline
  28. Vanilla
  29. Vanilla oleoresin
  30. Vanilla oleoresin (vanilla SPP)
  31. Vanillaldehyde
  32. Vanillic aldehyde
  33. Vanillin (3-methoxy-4-hydroxy- benzaldehyde)
  34. Vanillin (natural)
  35. Vanillin (NF)
  36. Vanillin sodium salt
  37. Vanillin [usan]
  38. Vanilline
  39. Zimco
Chemical FormulaC8H8O3
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
IUPAC Name4-hydroxy-3-methoxybenzaldehyde
Traditional IUPAC 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 KeyMWOOGOJBHIARFG-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassPhenols and Derivatives
Sub ClassMethoxyphenols and Derivatives
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • a small molecule(Cyc)
  • benzaldehydes(ChEBI)
  • phenols(ChEBI)
Substituents
  • Aldehyde
  • Alkyl Aryl Ether
  • Anisole
  • Benzaldehyde
  • Benzoyl
Direct ParentMethoxyphenols and Derivatives
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 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 area46.53ChemAxon
rotatable bond count2ChemAxon
refractivity41.09ChemAxon
polarizability14.82ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified5.298 +/- 0.902 uMAdult (>18 years old)MaleCommentNormal
BloodDetected and Quantified3.764 +/- 0.869 uMAdult (>18 years old)MaleCommentNormal
BloodDetected and Quantified4.976 +/- 0.971 uMAdult (>18 years old)MaleCommentNormal
BloodDetected and Quantified8.309 +/- 3.765 uMAdult (>18 years old)MaleCommentNormal
BloodDetected and Quantified4.951 +/- 0.92 uMAdult (>18 years old)MaleCommentNormal
BloodDetected and Quantified5.375 +/- 0.91 uMAdult (>18 years old)MaleCommentNormal
BloodDetected and Quantified4.468 +/- 0.815 uMAdult (>18 years old)MaleCommentNormal
BloodDetected and Quantified28.258 +/- 24.808 uMAdult (>18 years old)MaleCommentNormal
UrineDetected and Quantified0.362 +/- 0.053 umol/mmol creatinineAdult (>18 years old)MaleCommentNormal
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)Not Available
General ReferencesNot Available