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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:59:17 UTC
Update Date2023-02-21 17:28:17 UTC
HMDB IDHMDB0040446
Secondary Accession Numbers
  • HMDB40446
Metabolite Identification
Common NameBenzyl acetoacetate
DescriptionBenzyl acetoacetate belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group. Benzyl acetoacetate is a sweet, benzyl acetate, and benzyl propionate tasting compound. Based on a literature review very few articles have been published on Benzyl acetoacetate.
Structure
Data?1677000497
Synonyms
ValueSource
Benzyl acetoacetic acidGenerator
Ac-benzylHMDB
Acetoacetic acid benzyl esterHMDB
Acetoacetic acid, benzyl esterHMDB
Acetoacetic acid, benzyl ester (8ci)HMDB
Benzyl 3-oxobutanoateHMDB
Benzyl acetylacetateHMDB
Benzyl beta-ketobutyrateHMDB
Butanoic acid, 3-oxo-, phenylmethyl esterHMDB
FEMA 2136HMDB
Phenylmethyl 3-oxobutanoateHMDB
Benzyl 3-oxobutanoic acidGenerator
Chemical FormulaC11H12O3
Average Molecular Weight192.2112
Monoisotopic Molecular Weight192.07864425
IUPAC Namebenzyl 3-oxobutanoate
Traditional Namebenzyl 3-oxobutanoate
CAS Registry Number5396-89-4
SMILES
CC(=O)CC(=O)OCC1=CC=CC=C1
InChI Identifier
InChI=1S/C11H12O3/c1-9(12)7-11(13)14-8-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3
InChI KeyWOFAGNLBCJWEOE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzyloxycarbonyls
Direct ParentBenzyloxycarbonyls
Alternative Parents
Substituents
  • Benzyloxycarbonyl
  • Beta-keto acid
  • Fatty acid ester
  • Fatty acyl
  • 1,3-dicarbonyl compound
  • Keto acid
  • Carboxylic acid ester
  • Ketone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • 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 Point162.00 to 164.00 °C. @ 16.00 mm HgThe Good Scents Company Information System
Boiling Point156.00 to 159.00 °C. @ 10.00 mm HgThe Good Scents Company Information System
Water Solubility6531 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.599 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.45 g/LALOGPS
logP1.42ALOGPS
logP1.87ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)10.34ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity51.92 m³·mol⁻¹ChemAxon
Polarizability19.85 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]+146.90631661259
DarkChem[M-H]-143.36431661259
DeepCCS[M+H]+137.34430932474
DeepCCS[M-H]-134.78630932474
DeepCCS[M-2H]-170.42430932474
DeepCCS[M+Na]+145.7330932474
AllCCS[M+H]+141.832859911
AllCCS[M+H-H2O]+137.832859911
AllCCS[M+NH4]+145.532859911
AllCCS[M+Na]+146.632859911
AllCCS[M-H]-144.232859911
AllCCS[M+Na-2H]-144.932859911
AllCCS[M+HCOO]-145.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Benzyl acetoacetateCC(=O)CC(=O)OCC1=CC=CC=C12396.5Standard polar33892256
Benzyl acetoacetateCC(=O)CC(=O)OCC1=CC=CC=C11495.3Standard non polar33892256
Benzyl acetoacetateCC(=O)CC(=O)OCC1=CC=CC=C11498.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Benzyl acetoacetate,1TMS,isomer #1CC(=CC(=O)OCC1=CC=CC=C1)O[Si](C)(C)C1673.6Semi standard non polar33892256
Benzyl acetoacetate,1TMS,isomer #1CC(=CC(=O)OCC1=CC=CC=C1)O[Si](C)(C)C1657.3Standard non polar33892256
Benzyl acetoacetate,1TMS,isomer #2C=C(CC(=O)OCC1=CC=CC=C1)O[Si](C)(C)C1601.3Semi standard non polar33892256
Benzyl acetoacetate,1TMS,isomer #2C=C(CC(=O)OCC1=CC=CC=C1)O[Si](C)(C)C1634.7Standard non polar33892256
Benzyl acetoacetate,1TBDMS,isomer #1CC(=CC(=O)OCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C1906.9Semi standard non polar33892256
Benzyl acetoacetate,1TBDMS,isomer #1CC(=CC(=O)OCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C1876.4Standard non polar33892256
Benzyl acetoacetate,1TBDMS,isomer #2C=C(CC(=O)OCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C1841.6Semi standard non polar33892256
Benzyl acetoacetate,1TBDMS,isomer #2C=C(CC(=O)OCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C1847.4Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Benzyl acetoacetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-6bae91acee540f8cc0e12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzyl acetoacetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl acetoacetate 10V, Positive-QTOFsplash10-0006-6900000000-62344b70f470cc0b85552016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl acetoacetate 20V, Positive-QTOFsplash10-0006-9200000000-7087db0fa6a89c9745b42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl acetoacetate 40V, Positive-QTOFsplash10-0006-9000000000-6ec67218d38ed24819902016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl acetoacetate 10V, Negative-QTOFsplash10-000x-6900000000-78a1a8a5cb37176be6902016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl acetoacetate 20V, Negative-QTOFsplash10-0a59-9600000000-259f094ed1296b4195a72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl acetoacetate 40V, Negative-QTOFsplash10-0a59-9100000000-51de05abd2086f51e6d22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl acetoacetate 10V, Negative-QTOFsplash10-0a6r-4900000000-114c2556c47b19ce6aa12021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl acetoacetate 20V, Negative-QTOFsplash10-0a6r-9600000000-a09250eafa922a1db02c2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl acetoacetate 40V, Negative-QTOFsplash10-004i-9000000000-23eb754ec9000138e5e72021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl acetoacetate 10V, Positive-QTOFsplash10-0006-9000000000-ac6092011a9b5b6dc4732021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl acetoacetate 20V, Positive-QTOFsplash10-0006-9000000000-9adb5302299f76cca9442021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl acetoacetate 40V, Positive-QTOFsplash10-00kf-9000000000-de95915310d7fa79867d2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDFDB020198
KNApSAcK IDNot Available
Chemspider ID125497
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound142266
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1003511
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .