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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:42:10 UTC

Update Date

2023-02-21 17:20:17 UTC

HMDB ID

HMDB0031295

Secondary Accession Numbers

HMDB31295

Metabolite Identification

Common Name

Ethyl pentyl ketone

Description

Ethyl pentyl ketone, also known as 3-oxooctane or EAK, 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. Thus, ethyl pentyl ketone is considered to be an oxygenated hydrocarbon lipid molecule. A dialkyl ketone that is octane in which the two methylene protons at position 3 have been replaced by an oxo group. Ethyl pentyl ketone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Ethyl pentyl ketone has been detected, but not quantified, in cardamoms and lemons. This could make ethyl pentyl ketone a potential biomarker for the consumption of these foods. Ethyl pentyl ketone, with regard to humans, has been linked to the inborn metabolic disorder celiac disease.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Oxooctane	ChEBI
Amyl ethyl ketone	ChEBI
EAK	ChEBI
Ethyl amyl ketone	ChEBI
Ethyl N-amyl ketone	ChEBI
Ethyl N-pentyl ketone	ChEBI
N-Amyl ethyl ketone	ChEBI
Octan-3-one	ChEBI
3-Octanon	HMDB
3-Octanone	HMDB
Ethyl N-amylketone	HMDB
FEMA 2803	HMDB
N-Octanone-3	HMDB
Ethyl pentyl ketone	ChEBI

Chemical Formula

C₈H₁₆O

Average Molecular Weight

128.212

Monoisotopic Molecular Weight

128.120115134

IUPAC Name

octan-3-one

Traditional Name

3-octanone

CAS Registry Number

106-68-3

SMILES

CCCCCC(=O)CC

InChI Identifier

InChI=1S/C8H16O/c1-3-5-6-7-8(9)4-2/h3-7H2,1-2H3

InChI Key

RHLVCLIPMVJYKS-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

ketone (CHEBI:80946 )
Oxygenated hydrocarbons (LMFA12000055 )

Ontology

Sweet

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 24421258)

Excreta

Biofluid or Excreta

Feces (PMID: 21970810)

Cellular substructure

Membrane (HMDB: HMDB0031295)

Source

Exogenous

Exogenous (HMDB: HMDB0031295)

Food

Soy

Soy bean (FooDB: FOOD00085)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Shiitake (FooDB: FOOD00548)

Leaf vegetable

Rocket salad (ssp.) (FooDB: FOOD00077)

Fruit

Berry

Endogenous

Endogenous (HMDB: HMDB0031295)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-23.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	167.00 to 170.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	2.6 mg/mL at 20 °C	Not Available
LogP	2.506 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.48 g/L	ALOGPS
logP	2.61	ALOGPS
logP	2.84	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Basic)	-7.3	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	5	ChemAxon
Refractivity	39.25 m³·mol⁻¹	ChemAxon
Polarizability	16.28 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]+	130.153	31661259
DarkChem	[M-H]-	127.087	31661259
DeepCCS	[M+H]+	134.372	30932474
DeepCCS	[M-H]-	131.567	30932474
DeepCCS	[M-2H]-	168.276	30932474
DeepCCS	[M+Na]+	143.109	30932474
AllCCS	[M+H]+	133.3	32859911
AllCCS	[M+H-H2O]+	129.1	32859911
AllCCS	[M+NH4]+	137.2	32859911
AllCCS	[M+Na]+	138.3	32859911
AllCCS	[M-H]-	135.9	32859911
AllCCS	[M+Na-2H]-	138.6	32859911
AllCCS	[M+HCOO]-	141.7	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. Predicted by Afia on May 17, 2022.	5.4 minutes	32390414
Predicted by Siyang on May 30, 2022	16.081 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.49 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	29.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2062.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	562.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	208.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	368.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	348.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	666.8 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	661.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	112.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1395.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	443.3 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	1388.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	433.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	404.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	489.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	506.3 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	18.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl pentyl ketone	CCCCCC(=O)CC	1251.2	Standard polar	33892256
Ethyl pentyl ketone	CCCCCC(=O)CC	954.5	Standard non polar	33892256
Ethyl pentyl ketone	CCCCCC(=O)CC	972.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ethyl pentyl ketone,1TMS,isomer #1	CC=C(CCCCC)O[Si](C)(C)C	1158.9	Semi standard non polar	33892256
Ethyl pentyl ketone,1TMS,isomer #1	CC=C(CCCCC)O[Si](C)(C)C	1152.1	Standard non polar	33892256
Ethyl pentyl ketone,1TMS,isomer #2	CCCCC=C(CC)O[Si](C)(C)C	1167.3	Semi standard non polar	33892256
Ethyl pentyl ketone,1TMS,isomer #2	CCCCC=C(CC)O[Si](C)(C)C	1151.5	Standard non polar	33892256
Ethyl pentyl ketone,1TBDMS,isomer #1	CC=C(CCCCC)O[Si](C)(C)C(C)(C)C	1376.2	Semi standard non polar	33892256
Ethyl pentyl ketone,1TBDMS,isomer #1	CC=C(CCCCC)O[Si](C)(C)C(C)(C)C	1344.2	Standard non polar	33892256
Ethyl pentyl ketone,1TBDMS,isomer #2	CCCCC=C(CC)O[Si](C)(C)C(C)(C)C	1379.0	Semi standard non polar	33892256
Ethyl pentyl ketone,1TBDMS,isomer #2	CCCCC=C(CC)O[Si](C)(C)C(C)(C)C	1341.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Ethyl pentyl ketone EI-B (Non-derivatized)	splash10-05bf-9000000000-781901ca764a5f841104	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl pentyl ketone EI-B (Non-derivatized)	splash10-05bf-9000000000-c5ad6888f5d8235bbcbd	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl pentyl ketone EI-B (Non-derivatized)	splash10-05bf-9000000000-781901ca764a5f841104	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl pentyl ketone EI-B (Non-derivatized)	splash10-05bf-9000000000-c5ad6888f5d8235bbcbd	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl pentyl ketone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9000000000-c2c048174c4c8d3d8228	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl pentyl ketone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-05i3-9000000000-91e0504d51c6adb6a6dc	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 pentyl ketone 10V, Positive-QTOF	splash10-004i-1900000000-ffaa377d52d739ba9f44	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl pentyl ketone 20V, Positive-QTOF	splash10-0a6r-9400000000-f7381b3ecccb7b1c9936	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl pentyl ketone 40V, Positive-QTOF	splash10-0a4l-9000000000-7f234320bd480d9871b6	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl pentyl ketone 10V, Negative-QTOF	splash10-004i-1900000000-e4a3fd9e0a2d4bb13155	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl pentyl ketone 20V, Negative-QTOF	splash10-004i-7900000000-5ba281eb40ef59122e53	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl pentyl ketone 40V, Negative-QTOF	splash10-0avi-9100000000-0ccdc24b3e039027a03a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl pentyl ketone 10V, Negative-QTOF	splash10-004i-0900000000-e8448bc978ba2df6edde	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl pentyl ketone 20V, Negative-QTOF	splash10-056r-9300000000-2bbefe45e3391c2f9e16	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl pentyl ketone 40V, Negative-QTOF	splash10-0a4i-9000000000-07772b5c8be44e02f68e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl pentyl ketone 10V, Positive-QTOF	splash10-05tf-9000000000-7376e27c0ccc450d2e87	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl pentyl ketone 20V, Positive-QTOF	splash10-052f-9000000000-9a9cbad9068425131f56	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl pentyl ketone 40V, Positive-QTOF	splash10-052f-9000000000-390b61087232d1c44369	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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

Biospecimen Locations

Feces
Saliva

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)	Not Specified	Normal	21970810	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Not Specified	Treated celiac disease	21970810	details

Associated Disorders and Diseases

Disease References

Celiac disease
Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]

Associated OMIM IDs

212750 (Celiac disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

3-Octanone

METLIN ID

Not Available

PubChem Compound

246728

PDB ID

Not Available

ChEBI ID

80946

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1004231

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Ethyl pentyl ketone (HMDB0031295)

MOL for HMDB0031295 (Ethyl pentyl ketone)

3D MOL for HMDB0031295 (Ethyl pentyl ketone)

3D SDF for HMDB0031295 (Ethyl pentyl ketone)

3D-SDF for HMDB0031295 (Ethyl pentyl ketone)

PDB for HMDB0031295 (Ethyl pentyl ketone)

3D PDB for HMDB0031295 (Ethyl pentyl ketone)

SMILES for HMDB0031295 (Ethyl pentyl ketone)

INCHI for HMDB0031295 (Ethyl pentyl ketone)

Structure for HMDB0031295 (Ethyl pentyl ketone)

3D Structure for HMDB0031295 (Ethyl pentyl ketone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra