Human Metabolome Database Version 3.5

Showing metabocard for Vanillin (HMDB12308)

Record Information
Version 3.5
Creation Date 2009-04-06 10:22:43 -0600
Update Date 2013-02-08 17:28:46 -0700
HMDB ID HMDB12308
Secondary Accession Numbers None
Metabolite Identification
Common Name Vanillin
Description Vanillin 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
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Display: 2D Structure | 3D Structure
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 Formula C8H8O3
Average Molecular Weight 152.1473
Monoisotopic Molecular Weight 152.047344122
IUPAC Name 4-hydroxy-3-methoxybenzaldehyde
Traditional IUPAC Name vanillin
CAS Registry Number 121-33-5
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 Key MWOOGOJBHIARFG-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Phenols and Derivatives
Sub Class Methoxyphenols and Derivatives
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • a small molecule(Cyc)
  • benzaldehydes(ChEBI)
  • phenols(ChEBI)
Substituents
  • Aldehyde
  • Alkyl Aryl Ether
  • Anisole
  • Benzaldehyde
  • Benzoyl
Direct Parent Methoxyphenols and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 81.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 11 mg/mL at 25 °C Not Available
LogP 1.21 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 5.05 g/L ALOGPS
LogP 1.31 ALOGPS
LogP 1.22 ChemAxon
LogS -1.48 ALOGPS
pKa (strongest acidic) 7.81 ChemAxon
pKa (strongest basic) -4.9 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 46.53 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 41.09 ChemAxon
Polarizability 14.82 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
5.298 +/- 0.902 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
3.764 +/- 0.869 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
4.976 +/- 0.971 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
8.309 +/- 3.765 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
4.951 +/- 0.92 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
5.375 +/- 0.91 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
4.468 +/- 0.815 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
28.258 +/- 24.808 uM Adult (>18 years old) Male Comment Normal
Urine Detected and Quantified
0.362 +/- 0.053 umol/mmol creatinine Adult (>18 years old) Male Comment Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID 724 Link_out
Phenol Explorer Metabolite ID 724 Link_out
FoodDB ID FDB000838
KNApSAcK ID C00029531 Link_out
Chemspider ID 13860434 Link_out
KEGG Compound ID C00755 Link_out
BioCyc ID VANILLIN Link_out
BiGG ID Not Available
Wikipedia Link Vanillin Link_out
NuGOwiki Link HMDB12308 Link_out
Metagene Link HMDB12308 Link_out
METLIN ID Not Available
PubChem Compound 1183 Link_out
PDB ID V55 Link_out
ChEBI ID 18346 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References Not Available