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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:56:36 UTC
Update Date2022-03-07 02:55:27 UTC
HMDB IDHMDB0037681
Secondary Accession Numbers
  • HMDB37681
Metabolite Identification
Common NameVanillin isobutyrate
DescriptionVanillin isobutyrate 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 a sweet, caramel, and chocolate tasting compound. Based on a literature review very few articles have been published on Vanillin isobutyrate.
Structure
Data?1563863072
Synonyms
ValueSource
Vanillin isobutyric acidGenerator
FEMA 3754HMDB
IsobutavanHMDB
4-Formyl-2-methoxyphenyl 2-methylpropanoic acidGenerator
Chemical FormulaC12H14O4
Average Molecular Weight222.2372
Monoisotopic Molecular Weight222.089208936
IUPAC Name4-formyl-2-methoxyphenyl 2-methylpropanoate
Traditional Name4-formyl-2-methoxyphenyl 2-methylpropanoate
CAS Registry Number20665-85-4
SMILES
COC1=C(OC(=O)C(C)C)C=CC(C=O)=C1
InChI Identifier
InChI=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
Chemical Taxonomy
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
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point165.00 to 166.00 °C. @ 2.00 mm HgThe Good Scents Company Information System
Water Solubility0The Good Scents Company Information System
LogP1.980 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+151.87631661259
DarkChem[M-H]-151.91931661259
DeepCCS[M+H]+152.54330932474
DeepCCS[M-H]-150.18530932474
DeepCCS[M-2H]-183.18130932474
DeepCCS[M+Na]+158.63630932474
AllCCS[M+H]+149.232859911
AllCCS[M+H-H2O]+145.532859911
AllCCS[M+NH4]+152.832859911
AllCCS[M+Na]+153.832859911
AllCCS[M-H]-151.832859911
AllCCS[M+Na-2H]-152.232859911
AllCCS[M+HCOO]-152.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Vanillin isobutyrateCOC1=C(OC(=O)C(C)C)C=CC(C=O)=C12680.8Standard polar33892256
Vanillin isobutyrateCOC1=C(OC(=O)C(C)C)C=CC(C=O)=C11705.1Standard non polar33892256
Vanillin isobutyrateCOC1=C(OC(=O)C(C)C)C=CC(C=O)=C11703.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Vanillin isobutyrate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fdo-8910000000-2d7cfa83307798d0afbf2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillin isobutyrate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vanillin isobutyrate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillin isobutyrate 30V, Positive-QTOFsplash10-004i-0900000000-e14af552e9b8db2e93642021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillin isobutyrate 15V, Positive-QTOFsplash10-014i-9000000000-ed8d9d8c1adcba78ab3e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillin isobutyrate 45V, Positive-QTOFsplash10-00ou-9800000000-3e69e882204361a9a2572021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillin isobutyrate 60V, Positive-QTOFsplash10-00bc-3900000000-20330bc7cb80b4cf2ef22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillin isobutyrate 30V, Negative-QTOFsplash10-00di-0900000000-1a1e3d54f88fd157a5de2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillin isobutyrate 15V, Negative-QTOFsplash10-00di-0910000000-70714079ed7e95d6ef742021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillin isobutyrate 75V, Positive-QTOFsplash10-0umj-5900000000-82639734b79004580e2b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillin isobutyrate 90V, Positive-QTOFsplash10-0udj-7900000000-a0eea15924ac087b77f82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillin isobutyrate 90V, Negative-QTOFsplash10-004i-9200000000-bab0e6b59be9a589fdf82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillin isobutyrate 75V, Negative-QTOFsplash10-00b9-9700000000-2002a92aa776f731f5472021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillin isobutyrate 45V, Negative-QTOFsplash10-00di-0900000000-3a6c7d7f9113fed591742021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vanillin isobutyrate 60V, Negative-QTOFsplash10-00di-3900000000-a00fe976c698b4ed63252021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillin isobutyrate 10V, Positive-QTOFsplash10-00di-4290000000-5ab713e0abcc3537b1052016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillin isobutyrate 20V, Positive-QTOFsplash10-00dl-9220000000-bf4860b04da09072ce682016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillin isobutyrate 40V, Positive-QTOFsplash10-05fu-9200000000-e1d19d9c5fa12d20d89d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillin isobutyrate 10V, Negative-QTOFsplash10-00di-0190000000-04c60ba217267f4408112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillin isobutyrate 20V, Negative-QTOFsplash10-00di-3890000000-5182553d6b920ad8598c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillin isobutyrate 40V, Negative-QTOFsplash10-014r-9600000000-b70b1735f77e1b1a194e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillin isobutyrate 10V, Negative-QTOFsplash10-00dr-8090000000-4152470ffe84d9eca4c82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillin isobutyrate 20V, Negative-QTOFsplash10-000i-9740000000-6b680ec6779d356e92b82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillin isobutyrate 40V, Negative-QTOFsplash10-014r-9230000000-a17cfa7b37261c0463db2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillin isobutyrate 10V, Positive-QTOFsplash10-00di-1190000000-a0add6e6a2add28948c52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillin isobutyrate 20V, Positive-QTOFsplash10-05fu-9660000000-81e2f89e6192568e3bc42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vanillin isobutyrate 40V, Positive-QTOFsplash10-0f6x-9600000000-82f6a1d940d36f040b682021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB016808
KNApSAcK IDNot Available
Chemspider ID470078
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound539829
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1024071
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .