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Identification
YMDB IDYMDB01803
NameVanillin
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionVanillin, also known as vanillaldehyde or lioxin, 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. Vanillin is an extremely weak basic (essentially neutral) compound (based on its pKa). Vanillin exists in all living species, ranging from bacteria to humans. Vanillin is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 4-Hydroxy-3-methoxybenzaldehyde
  • 5-Bromovanillin
  • 5-Chlorovanillin
  • Vanillaldehyde
  • Vanillin, sodium salt
  • 3-Methoxy-4-hydroxybenzaldehyde
  • 4-Formyl-2-methoxyphenol
  • 4-Hydroxy-3-methoxy-benzaldehyde
  • 4-Hydroxy-m-anisaldehyde
  • Methylprotocatechuic aldehyde
  • p-Hydroxy-m-methoxybenzaldehyde
  • p-Vanillin
  • Vaniline
  • Vanillic aldehyde
  • 2-Methoxy-4-formylphenol
  • 4-Hydroxy 3-methoxybenzaldehyde
  • 4-Hydroxy-3-methoxy-benzaldehyde-5-chlorovanillin
  • 4-Hydroxy-3-methoxybenzaldehyde (acd/name 4.0)
  • 4-Hydroxy-5-methoxybenzaldehyde
  • Lioxin
  • m-Methoxy-p-hydroxybenzaldehyde
  • Methyl-protocatechualdehyde
  • Methylprotcatechuic aldehyde
  • Oleo-resins vanilla
  • Oleo-resins vanilla-bean
  • Oleoresin vanilla
  • Propenylguaethol
  • Protocatechualdehyde 3-methyl ether
  • trans-2-Ethoxy-5-(1-propenyl)phenol
  • Vanilin
  • Vanilla
  • Vanilla oleoresin
  • Vanillin (3-methoxy-4-hydroxy- benzaldehyde)
  • Vanillin (natural)
  • Vanillin (NF)
  • Vanillin sodium salt
  • Vanilline
  • Zimco
CAS number121-33-5
WeightAverage: 152.1473
Monoisotopic: 152.047344122
InChI KeyMWOOGOJBHIARFG-UHFFFAOYSA-N
InChIInChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3
IUPAC Name4-hydroxy-3-methoxybenzaldehyde
Traditional IUPAC Namevanillin
Chemical FormulaC8H8O3
SMILESCOC1=CC(C=O)=CC=C1O
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
Physical Properties
StateSolid
Charge0
Melting point81.5 °C
Experimental Properties
PropertyValueReference
Water Solubility11 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP1.21 [HANSCH,C ET AL. (1995)]PhysProp
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
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
ChocolateFDB000838
CreamyFDB000838
SweetFDB000838
VanillaFDB000838
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Loscos, N., Hernandez-Orte, P., Cacho, J., Ferreira, V. (2007). "Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions." J Agric Food Chem 55:6674-6684.17616208
  • Chatonnet, P., Dubourdieu, D., & Boidron, J. N. (1992a) Incidence des conditions de fermentation et d’elevage des vins blanc secs en barriques sur leur composition en substances cedees par le bois de chene. Science des Aliments, 12, 665–685.
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID18346
HMDB IDHMDB12308
Pubchem Compound ID1183
Kegg IDC00755
ChemSpider ID13860434
FOODB IDFDB000838
Wikipedia IDVanillin
BioCyc IDNot Available