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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2007-04-12 15:42:09 UTC

Update Date

2023-02-21 17:17:10 UTC

HMDB ID

HMDB0005846

Secondary Accession Numbers

HMDB05846

Metabolite Identification

Common Name

Ethyl isopropyl ketone

Description

Ethyl isopropyl ketone, also known as 2-methyl-3-pentanal or 2-methylpentan-3-one, 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. Ethyl isopropyl ketone (or ethyl isopropyl ketone) is a volatile organic compound. Ethyl isopropyl ketone is a mint tasting compound. ethyl isopropyl ketone has been detected, but not quantified in corns. This could make ethyl isopropyl ketone a potential biomarker for the consumption of these foods. Volatile organic compounds from feces have the potential to help in the diagnosis of gastrointestinal disease. Ethyl isopropyl ketone is a component of the feces in the normal population and is also occasionally found as a volatile component of normal human biofluids. Ethyl isopropyl ketone is an aliphatic ketone used as a reagent in organic chemistry and as a solvent.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Methyl-3-pentanal	HMDB
2-Methyl-3-pentanone	HMDB
2-Methylpentan-3-one	HMDB
4-Methyl-3-pentanone	HMDB
iso-C3H7COC2H5	HMDB
Isopropyl ethyl ketone	HMDB

Chemical Formula

C₆H₁₂O

Average Molecular Weight

100.1589

Monoisotopic Molecular Weight

100.088815006

IUPAC Name

2-methylpentan-3-one

Traditional Name

4-methyl-3-pentanone

CAS Registry Number

565-69-5

SMILES

CCC(=O)C(C)C

InChI Identifier

InChI=1S/C6H12O/c1-4-6(7)5(2)3/h5H,4H2,1-3H3

InChI Key

HYTRYEXINDDXJK-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

Physiological effect

Organoleptic effect

Odor

Mint

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0005846)
Cell membrane (HMDB: HMDB0005846)

Excreta

Biofluid or Excreta

Feces (PMID: 17314143)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0005846)

Source

Endogenous

Endogenous (HMDB: HMDB0005846)

Plant

Poaceae (HMDB: HMDB0005846)

Exogenous

Food

Food (HMDB: HMDB0005846)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	113.5 °C	Not Available
Water Solubility	15.5 mg/mL at 25 °C	Not Available
LogP	1.331 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	15.9 g/L	ALOGPS
logP	1.45	ALOGPS
logP	2.05	ChemAxon
logS	-0.8	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	2	ChemAxon
Refractivity	30.02 m³·mol⁻¹	ChemAxon
Polarizability	12.05 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]+	121.318	31661259
DarkChem	[M-H]-	116.926	31661259
DeepCCS	[M+H]+	125.588	30932474
DeepCCS	[M-H]-	123.461	30932474
DeepCCS	[M-2H]-	159.314	30932474
DeepCCS	[M+Na]+	134.088	30932474
AllCCS	[M+H]+	125.1	32859911
AllCCS	[M+H-H2O]+	120.8	32859911
AllCCS	[M+NH4]+	129.2	32859911
AllCCS	[M+Na]+	130.3	32859911
AllCCS	[M-H]-	129.1	32859911
AllCCS	[M+Na-2H]-	133.0	32859911
AllCCS	[M+HCOO]-	137.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl isopropyl ketone	CCC(=O)C(C)C	1009.2	Standard polar	33892256
Ethyl isopropyl ketone	CCC(=O)C(C)C	714.8	Standard non polar	33892256
Ethyl isopropyl ketone	CCC(=O)C(C)C	737.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ethyl isopropyl ketone,1TMS,isomer #1	CCC(O[Si](C)(C)C)=C(C)C	983.2	Semi standard non polar	33892256
Ethyl isopropyl ketone,1TMS,isomer #1	CCC(O[Si](C)(C)C)=C(C)C	941.6	Standard non polar	33892256
Ethyl isopropyl ketone,1TMS,isomer #1	CCC(O[Si](C)(C)C)=C(C)C	974.6	Standard polar	33892256
Ethyl isopropyl ketone,1TMS,isomer #2	CC=C(O[Si](C)(C)C)C(C)C	926.4	Semi standard non polar	33892256
Ethyl isopropyl ketone,1TMS,isomer #2	CC=C(O[Si](C)(C)C)C(C)C	887.8	Standard non polar	33892256
Ethyl isopropyl ketone,1TMS,isomer #2	CC=C(O[Si](C)(C)C)C(C)C	1006.5	Standard polar	33892256
Ethyl isopropyl ketone,1TBDMS,isomer #1	CCC(O[Si](C)(C)C(C)(C)C)=C(C)C	1200.1	Semi standard non polar	33892256
Ethyl isopropyl ketone,1TBDMS,isomer #1	CCC(O[Si](C)(C)C(C)(C)C)=C(C)C	1142.2	Standard non polar	33892256
Ethyl isopropyl ketone,1TBDMS,isomer #1	CCC(O[Si](C)(C)C(C)(C)C)=C(C)C	1173.3	Standard polar	33892256
Ethyl isopropyl ketone,1TBDMS,isomer #2	CC=C(O[Si](C)(C)C(C)(C)C)C(C)C	1142.6	Semi standard non polar	33892256
Ethyl isopropyl ketone,1TBDMS,isomer #2	CC=C(O[Si](C)(C)C(C)(C)C)C(C)C	1121.0	Standard non polar	33892256
Ethyl isopropyl ketone,1TBDMS,isomer #2	CC=C(O[Si](C)(C)C(C)(C)C)C(C)C	1196.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl isopropyl ketone GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9000000000-169ad2a703b9155e87e1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl isopropyl ketone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a6u-9000000000-d28dd0d8a918e0f4cc66	2015-03-01	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 - Ethyl isopropyl ketone 10V, Positive-QTOF	splash10-0udi-3900000000-f8fe4280f501b51a75a0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl isopropyl ketone 20V, Positive-QTOF	splash10-0udi-8900000000-f29a5d1fc06f1e264627	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl isopropyl ketone 40V, Positive-QTOF	splash10-0006-9000000000-af27439b3c00cb9f7f99	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl isopropyl ketone 10V, Negative-QTOF	splash10-0002-9000000000-0bab6124e7b3c3f34290	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl isopropyl ketone 20V, Negative-QTOF	splash10-0002-9000000000-a96b32781fe6fa58a9a5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl isopropyl ketone 40V, Negative-QTOF	splash10-05o0-9000000000-9f11e48c43be9ddf2746	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl isopropyl ketone 10V, Positive-QTOF	splash10-0f7o-9200000000-d9aa9c6699ef98b386a7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl isopropyl ketone 20V, Positive-QTOF	splash10-000x-9000000000-1596f7157a58311f2185	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl isopropyl ketone 40V, Positive-QTOF	splash10-0006-9000000000-2f31ecbea2ca586e8109	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl isopropyl ketone 10V, Negative-QTOF	splash10-0002-9000000000-658fe53778817eb82301	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl isopropyl ketone 20V, Negative-QTOF	splash10-0a4i-9000000000-d0bb07edc9d68aebeb9b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl isopropyl ketone 40V, Negative-QTOF	splash10-0a4i-9000000000-6dd1cab74eba4bd80339	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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	Adult (>18 years old)	Both	Normal	17314143	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Campylobacter jejuni infection	17314143	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB007633

KNApSAcK ID

C00052649

Chemspider ID

10791

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ethyl isopropyl ketone

METLIN ID

Not Available

PubChem Compound

11265

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1178591

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [PubMed:5556886 ]
Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]

Showing metabocard for Ethyl isopropyl ketone (HMDB0005846)

MOL for HMDB0005846 (Ethyl isopropyl ketone)

3D MOL for HMDB0005846 (Ethyl isopropyl ketone)

3D SDF for HMDB0005846 (Ethyl isopropyl ketone)

3D-SDF for HMDB0005846 (Ethyl isopropyl ketone)

PDB for HMDB0005846 (Ethyl isopropyl ketone)

3D PDB for HMDB0005846 (Ethyl isopropyl ketone)

SMILES for HMDB0005846 (Ethyl isopropyl ketone)

INCHI for HMDB0005846 (Ethyl isopropyl ketone)

Structure for HMDB0005846 (Ethyl isopropyl ketone)

3D Structure for HMDB0005846 (Ethyl isopropyl ketone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra