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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:43:00 UTC
Update Date2022-03-07 02:52:58 UTC
HMDB IDHMDB0031417
Secondary Accession Numbers
  • HMDB31417
Metabolite Identification
Common Name2,6-Dimethyl-4-heptanone
Description2,6-Dimethyl-4-heptanone, also known as isobutyl N-propyl ketone or diisobutyl ketone, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. 2,6-Dimethyl-4-heptanone is a flavouring ingredient belonging to the family of Ketones. 2,6-Dimethyl-4-heptanone is a banana, fruity, and green tasting compound. 2,6-Dimethyl-4-heptanone is a potentially toxic compound.
Structure
Data?1563862123
Synonyms
ValueSource
Isobutyl N-propyl ketoneHMDB
Isobutyl propyl ketoneHMDB
DIBKMeSH, HMDB
Diisobutyl ketoneMeSH, HMDB
2,6-Dimethyl-4-heptanoneMeSH
DIBCHMDB
Isobutyl ketoneHMDB
IsovaleroneHMDB
s-DiisopropylacetoneHMDB
Chemical FormulaC9H18O
Average Molecular Weight142.2386
Monoisotopic Molecular Weight142.135765198
IUPAC Name2,6-dimethylheptan-4-one
Traditional Name2,6-dimethyl-4-heptanone
CAS Registry Number108-83-8
SMILES
CC(C)CC(=O)CC(C)C
InChI Identifier
InChI=1S/C9H18O/c1-7(2)5-9(10)6-8(3)4/h7-8H,5-6H2,1-4H3
InChI KeyPTTPXKJBFFKCEK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-41.5 °CNot Available
Boiling Point169.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility2.64 mg/mL at 24 °CNot Available
LogP2.560The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.98 g/LALOGPS
logP2.71ALOGPS
logP2.97ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity43.75 m³·mol⁻¹ChemAxon
Polarizability17.77 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.61831661259
DarkChem[M-H]-131.67831661259
DeepCCS[M+H]+145.04630932474
DeepCCS[M-H]-142.43130932474
DeepCCS[M-2H]-178.97930932474
DeepCCS[M+Na]+154.30430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,6-Dimethyl-4-heptanoneCC(C)CC(=O)CC(C)C1185.6Standard polar33892256
2,6-Dimethyl-4-heptanoneCC(C)CC(=O)CC(C)C962.5Standard non polar33892256
2,6-Dimethyl-4-heptanoneCC(C)CC(=O)CC(C)C954.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2,6-Dimethyl-4-heptanone,1TMS,isomer #1CC(C)C=C(CC(C)C)O[Si](C)(C)C1154.6Semi standard non polar33892256
2,6-Dimethyl-4-heptanone,1TMS,isomer #1CC(C)C=C(CC(C)C)O[Si](C)(C)C1139.7Standard non polar33892256
2,6-Dimethyl-4-heptanone,1TBDMS,isomer #1CC(C)C=C(CC(C)C)O[Si](C)(C)C(C)(C)C1357.9Semi standard non polar33892256
2,6-Dimethyl-4-heptanone,1TBDMS,isomer #1CC(C)C=C(CC(C)C)O[Si](C)(C)C(C)(C)C1331.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2,6-Dimethyl-4-heptanone EI-B (Non-derivatized)splash10-0a4r-9000000000-9382d11942152900dc112017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Dimethyl-4-heptanone EI-B (Non-derivatized)splash10-052r-9100000000-9e44efa94d39c79fda182017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Dimethyl-4-heptanone EI-B (Non-derivatized)splash10-0a4r-9000000000-1969d8f7cb8d04d73fe52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Dimethyl-4-heptanone EI-B (Non-derivatized)splash10-0a4r-9000000000-9382d11942152900dc112018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Dimethyl-4-heptanone EI-B (Non-derivatized)splash10-052r-9100000000-9e44efa94d39c79fda182018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Dimethyl-4-heptanone EI-B (Non-derivatized)splash10-0a4r-9000000000-1969d8f7cb8d04d73fe52018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Dimethyl-4-heptanone EI-B (Non-derivatized)splash10-0a4r-9000000000-9382d11942152900dc112018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Dimethyl-4-heptanone EI-B (Non-derivatized)splash10-052r-9100000000-9e44efa94d39c79fda182018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Dimethyl-4-heptanone EI-B (Non-derivatized)splash10-0a4r-9000000000-1969d8f7cb8d04d73fe52018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Dimethyl-4-heptanone EI-B (Non-derivatized)splash10-0a4r-9000000000-9382d11942152900dc112018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Dimethyl-4-heptanone EI-B (Non-derivatized)splash10-052r-9100000000-9e44efa94d39c79fda182018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Dimethyl-4-heptanone EI-B (Non-derivatized)splash10-0a4r-9000000000-1969d8f7cb8d04d73fe52018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,6-Dimethyl-4-heptanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9000000000-701180f8d1e0dc3c58b12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,6-Dimethyl-4-heptanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4r-9000000000-9fe0d157a8b7ac394c532014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Dimethyl-4-heptanone 10V, Positive-QTOFsplash10-0006-1900000000-d164beed8d14b95535792016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Dimethyl-4-heptanone 20V, Positive-QTOFsplash10-052f-9400000000-8ae2e3879d0d03172db42016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Dimethyl-4-heptanone 40V, Positive-QTOFsplash10-0a4l-9000000000-99428e335596fe56c29c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Dimethyl-4-heptanone 10V, Negative-QTOFsplash10-0006-1900000000-c4ce22e000a4fd332b2e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Dimethyl-4-heptanone 20V, Negative-QTOFsplash10-0006-5900000000-2b9194a6e7eb8115410c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Dimethyl-4-heptanone 40V, Negative-QTOFsplash10-0a4i-9100000000-fdaec16602306530a9e02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Dimethyl-4-heptanone 10V, Positive-QTOFsplash10-000f-9700000000-070208453b6c2c82a8a42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Dimethyl-4-heptanone 20V, Positive-QTOFsplash10-001i-9000000000-f3555d87c8ca11d4515d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Dimethyl-4-heptanone 40V, Positive-QTOFsplash10-0a5c-9000000000-5ca25c77f9e1d0a97dda2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Dimethyl-4-heptanone 10V, Negative-QTOFsplash10-0006-0900000000-31a4c0b614cfbc7c31562021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Dimethyl-4-heptanone 20V, Negative-QTOFsplash10-0a4l-9400000000-6ee1ede4154a6ee5af3f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Dimethyl-4-heptanone 40V, Negative-QTOFsplash10-00l6-9000000000-24ededd73984f33919dd2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) non progressor details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothAutism details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothPervasive Developmental Disorder Not Otherwise Specified details
Associated Disorders and Diseases
Disease References
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003494
KNApSAcK IDNot Available
Chemspider ID7670
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7958
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1036771
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.. .