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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:43:00 UTC

Update Date

2022-03-07 02:52:58 UTC

HMDB ID

HMDB0031417

Secondary Accession Numbers

HMDB31417

Metabolite Identification

Common Name

2,6-Dimethyl-4-heptanone

Description

2,6-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

COMPND    HMDB0031417
HETATM    1  C1  UNL     1      -3.163  -0.096  -0.892  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.243  -0.853   0.019  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.399  -0.294   1.418  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.816  -0.843  -0.447  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.240   0.503  -0.550  1.00  0.00           C  
HETATM    6  O1  UNL     1      -0.924   1.469  -0.264  1.00  0.00           O  
HETATM    7  C6  UNL     1       1.158   0.691  -0.995  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.089   1.053   0.136  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.116  -0.013   1.194  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.482   1.171  -0.445  1.00  0.00           C  
HETATM   11  H1  UNL     1      -4.164  -0.572  -0.837  1.00  0.00           H  
HETATM   12  H2  UNL     1      -3.318   0.966  -0.548  1.00  0.00           H  
HETATM   13  H3  UNL     1      -2.825  -0.071  -1.948  1.00  0.00           H  
HETATM   14  H4  UNL     1      -2.574  -1.931   0.022  1.00  0.00           H  
HETATM   15  H5  UNL     1      -1.671  -0.722   2.134  1.00  0.00           H  
HETATM   16  H6  UNL     1      -2.430   0.804   1.418  1.00  0.00           H  
HETATM   17  H7  UNL     1      -3.417  -0.633   1.763  1.00  0.00           H  
HETATM   18  H8  UNL     1      -0.229  -1.461   0.276  1.00  0.00           H  
HETATM   19  H9  UNL     1      -0.780  -1.359  -1.425  1.00  0.00           H  
HETATM   20  H10 UNL     1       1.230   1.459  -1.786  1.00  0.00           H  
HETATM   21  H11 UNL     1       1.534  -0.271  -1.439  1.00  0.00           H  
HETATM   22  H12 UNL     1       1.796   1.998   0.621  1.00  0.00           H  
HETATM   23  H13 UNL     1       2.093  -1.027   0.709  1.00  0.00           H  
HETATM   24  H14 UNL     1       3.038   0.101   1.806  1.00  0.00           H  
HETATM   25  H15 UNL     1       1.268   0.077   1.905  1.00  0.00           H  
HETATM   26  H16 UNL     1       3.547   0.454  -1.280  1.00  0.00           H  
HETATM   27  H17 UNL     1       3.569   2.203  -0.892  1.00  0.00           H  
HETATM   28  H18 UNL     1       4.273   1.021   0.326  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    4   14
CONECT    3   15   16   17
CONECT    4    5   18   19
CONECT    5    6    6    7
CONECT    7    8   20   21
CONECT    8    9   10   22
CONECT    9   23   24   25
CONECT   10   26   27   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Isobutyl N-propyl ketone	HMDB
Isobutyl propyl ketone	HMDB
DIBK	MeSH, HMDB
Diisobutyl ketone	MeSH, HMDB
2,6-Dimethyl-4-heptanone	MeSH
DIBC	HMDB
Isobutyl ketone	HMDB
Isovalerone	HMDB
s-Diisopropylacetone	HMDB

Chemical Formula

C₉H₁₈O

Average Molecular Weight

142.2386

Monoisotopic Molecular Weight

142.135765198

IUPAC Name

2,6-dimethylheptan-4-one

Traditional Name

2,6-dimethyl-4-heptanone

CAS Registry Number

108-83-8

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 Key

PTTPXKJBFFKCEK-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Ketones

Alternative Parents

Substituents

Ketone
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-41.5 °C	Not Available
Boiling Point	169.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	2.64 mg/mL at 24 °C	Not Available
LogP	2.560	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.98 g/L	ALOGPS
logP	2.71	ALOGPS
logP	2.97	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	43.75 m³·mol⁻¹	ChemAxon
Polarizability	17.77 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	134.618	31661259
DarkChem	[M-H]-	131.678	31661259
DeepCCS	[M+H]+	145.046	30932474
DeepCCS	[M-H]-	142.431	30932474
DeepCCS	[M-2H]-	178.979	30932474
DeepCCS	[M+Na]+	154.304	30932474
AllCCS	[M+H]+	133.5	32859911
AllCCS	[M+H-H2O]+	129.4	32859911
AllCCS	[M+NH4]+	137.2	32859911
AllCCS	[M+Na]+	138.3	32859911
AllCCS	[M-H]-	137.7	32859911
AllCCS	[M+Na-2H]-	140.2	32859911
AllCCS	[M+HCOO]-	143.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	5.42 minutes	32390414
Predicted by Siyang on May 30, 2022	16.7943 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.35 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2228.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	623.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	218.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	382.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	220.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	709.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	726.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	86.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1280.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	490.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1472.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	396.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	395.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	420.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	513.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	12.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,6-Dimethyl-4-heptanone	CC(C)CC(=O)CC(C)C	1185.6	Standard polar	33892256
2,6-Dimethyl-4-heptanone	CC(C)CC(=O)CC(C)C	962.5	Standard non polar	33892256
2,6-Dimethyl-4-heptanone	CC(C)CC(=O)CC(C)C	954.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,6-Dimethyl-4-heptanone,1TMS,isomer #1	CC(C)C=C(CC(C)C)O[Si](C)(C)C	1154.6	Semi standard non polar	33892256
2,6-Dimethyl-4-heptanone,1TMS,isomer #1	CC(C)C=C(CC(C)C)O[Si](C)(C)C	1139.7	Standard non polar	33892256
2,6-Dimethyl-4-heptanone,1TBDMS,isomer #1	CC(C)C=C(CC(C)C)O[Si](C)(C)C(C)(C)C	1357.9	Semi standard non polar	33892256
2,6-Dimethyl-4-heptanone,1TBDMS,isomer #1	CC(C)C=C(CC(C)C)O[Si](C)(C)C(C)(C)C	1331.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2,6-Dimethyl-4-heptanone EI-B (Non-derivatized)	splash10-0a4r-9000000000-9382d11942152900dc11	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,6-Dimethyl-4-heptanone EI-B (Non-derivatized)	splash10-052r-9100000000-9e44efa94d39c79fda18	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,6-Dimethyl-4-heptanone EI-B (Non-derivatized)	splash10-0a4r-9000000000-1969d8f7cb8d04d73fe5	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,6-Dimethyl-4-heptanone EI-B (Non-derivatized)	splash10-0a4r-9000000000-9382d11942152900dc11	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,6-Dimethyl-4-heptanone EI-B (Non-derivatized)	splash10-052r-9100000000-9e44efa94d39c79fda18	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,6-Dimethyl-4-heptanone EI-B (Non-derivatized)	splash10-0a4r-9000000000-1969d8f7cb8d04d73fe5	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,6-Dimethyl-4-heptanone EI-B (Non-derivatized)	splash10-0a4r-9000000000-9382d11942152900dc11	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,6-Dimethyl-4-heptanone EI-B (Non-derivatized)	splash10-052r-9100000000-9e44efa94d39c79fda18	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,6-Dimethyl-4-heptanone EI-B (Non-derivatized)	splash10-0a4r-9000000000-1969d8f7cb8d04d73fe5	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,6-Dimethyl-4-heptanone EI-B (Non-derivatized)	splash10-0a4r-9000000000-9382d11942152900dc11	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,6-Dimethyl-4-heptanone EI-B (Non-derivatized)	splash10-052r-9100000000-9e44efa94d39c79fda18	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,6-Dimethyl-4-heptanone EI-B (Non-derivatized)	splash10-0a4r-9000000000-1969d8f7cb8d04d73fe5	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dimethyl-4-heptanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-9000000000-701180f8d1e0dc3c58b1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,6-Dimethyl-4-heptanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4r-9000000000-9fe0d157a8b7ac394c53	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-4-heptanone 10V, Positive-QTOF	splash10-0006-1900000000-d164beed8d14b9553579	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-4-heptanone 20V, Positive-QTOF	splash10-052f-9400000000-8ae2e3879d0d03172db4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-4-heptanone 40V, Positive-QTOF	splash10-0a4l-9000000000-99428e335596fe56c29c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-4-heptanone 10V, Negative-QTOF	splash10-0006-1900000000-c4ce22e000a4fd332b2e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-4-heptanone 20V, Negative-QTOF	splash10-0006-5900000000-2b9194a6e7eb8115410c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-4-heptanone 40V, Negative-QTOF	splash10-0a4i-9100000000-fdaec16602306530a9e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-4-heptanone 10V, Positive-QTOF	splash10-000f-9700000000-070208453b6c2c82a8a4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-4-heptanone 20V, Positive-QTOF	splash10-001i-9000000000-f3555d87c8ca11d4515d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-4-heptanone 40V, Positive-QTOF	splash10-0a5c-9000000000-5ca25c77f9e1d0a97dda	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-4-heptanone 10V, Negative-QTOF	splash10-0006-0900000000-31a4c0b614cfbc7c3156	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-4-heptanone 20V, Negative-QTOF	splash10-0a4l-9400000000-6ee1ede4154a6ee5af3f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,6-Dimethyl-4-heptanone 40V, Negative-QTOF	splash10-00l6-9000000000-24ededd73984f33919dd	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Normal	24130822	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24922509	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Autism	24130822	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Pervasive Developmental Disorder Not Otherwise Specified	24130822	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Immunoglobulin A nephropathy (IgAN) non progressor	24922509	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Immunoglobulin A nephropathy (IgAN) progressor	24922509	details

Associated Disorders and Diseases

Disease References

Autism
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
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

209850 (Autism)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003494

KNApSAcK ID

Not Available

Chemspider ID

7670

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7958

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1036771

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2,6-Dimethyl-4-heptanone (HMDB0031417)

MOL for HMDB0031417 (2,6-Dimethyl-4-heptanone)

3D MOL for HMDB0031417 (2,6-Dimethyl-4-heptanone)

3D SDF for HMDB0031417 (2,6-Dimethyl-4-heptanone)

3D-SDF for HMDB0031417 (2,6-Dimethyl-4-heptanone)

PDB for HMDB0031417 (2,6-Dimethyl-4-heptanone)

3D PDB for HMDB0031417 (2,6-Dimethyl-4-heptanone)

SMILES for HMDB0031417 (2,6-Dimethyl-4-heptanone)

INCHI for HMDB0031417 (2,6-Dimethyl-4-heptanone)

Structure for HMDB0031417 (2,6-Dimethyl-4-heptanone)

3D Structure for HMDB0031417 (2,6-Dimethyl-4-heptanone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra