Record Information
Version1.0
Creation date2010-04-08 22:12:39 UTC
Update date2015-07-20 23:32:45 UTC
Primary IDFDB016808
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameVanillin isobutyrate
DescriptionVanillin isobutyrate, also known as fema 3754 or isobutavan, belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group. Vanillin isobutyrate is an extremely weak basic (essentially neutral) compound (based on its pKa). Vanillin isobutyrate is a sweet, caramel, and chocolate tasting compound.
CAS Number20665-85-4
Structure
Thumb
Synonyms
SynonymSource
Vanillin isobutyric acidGenerator
FEMA 3754HMDB
IsobutavanHMDB
4-Formyl-2-methoxyphenyl 2-methylpropanoic acidGenerator
Vanillin isobutyratedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.42 g/LALOGPS
logP2.25ALOGPS
logP2.38ChemAxon
logS-2.7ALOGPS
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity59.44 m³·mol⁻¹ChemAxon
Polarizability23.14 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC12H14O4
IUPAC name4-formyl-2-methoxyphenyl 2-methylpropanoate
InChI IdentifierInChI=1S/C12H14O4/c1-8(2)12(14)16-10-5-4-9(7-13)6-11(10)15-3/h4-8H,1-3H3
InChI KeyBGKAKRUFBSTALK-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(OC(=O)C(C)C)C=CC(C=O)=C1
Average Molecular Weight222.2372
Monoisotopic Molecular Weight222.089208936
Classification
Description belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol esters
Sub ClassNot Available
Direct ParentPhenol esters
Alternative Parents
Substituents
  • Phenol ester
  • Phenoxy compound
  • Anisole
  • Benzaldehyde
  • Methoxybenzene
  • Phenol ether
  • Benzoyl
  • Alkyl aryl ether
  • Aryl-aldehyde
  • Monocyclic benzene moiety
  • Carboxylic acid ester
  • Ether
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organooxygen compound
  • Aldehyde
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 64.85%; H 6.35%; O 28.80%DFC
Melting PointNot Available
Boiling PointBp5.5 155°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd20 0.99DFC
Refractive Indexn20D 1.5219DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fdo-8910000000-2d7cfa83307798d0afbfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-4290000000-5ab713e0abcc3537b105JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-9220000000-bf4860b04da09072ce68JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fu-9200000000-e1d19d9c5fa12d20d89dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0190000000-04c60ba217267f440811JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-3890000000-5182553d6b920ad8598cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-9600000000-b70b1735f77e1b1a194eJSpectraViewer
ChemSpider ID470078
ChEMBL IDCHEMBL3188782
KEGG Compound IDNot Available
Pubchem Compound ID539829
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB37681
CRC / DFC (Dictionary of Food Compounds) IDHCW75-Q:KTJ44-P
EAFUS ID3833
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1024071
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
vanilla
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
creamy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fruity
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
caramel
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
chocolate
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference