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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:44:04 UTC

Update Date

2023-02-21 17:20:50 UTC

HMDB ID

HMDB0031563

Secondary Accession Numbers

HMDB31563

Metabolite Identification

Common Name

4-Methyl-3-penten-2-one, 9CI

Description

4-Methyl-3-penten-2-one, also known as isopropylidene acetone or (CH3)2C=chc(=o)CH3, belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'. 4-Methyl-3-penten-2-one is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, 4-methyl-3-penten-2-one is considered to be an oxygenated hydrocarbon lipid molecule. 4-Methyl-3-penten-2-one is a sweet, acrylic, and chemical tasting compound. 4-Methyl-3-penten-2-one has been detected, but not quantified, in several different foods, such as orange bell peppers, pepper (c. frutescens), herbs and spices, yellow bell peppers, and green bell peppers. This could make 4-methyl-3-penten-2-one a potential biomarker for the consumption of these foods. With regards to humans, 4-Methyl-3-penten-2-one 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
(CH3)2C=chc(=o)CH3	HMDB
1-Methylpent-2-en-4-one	HMDB
2,2-Dimethylvinyl methyl ketone	HMDB
2-Methyl-2-penten-4-one	HMDB
2-Methyl-2-pentenone-4	HMDB
2-Methyl-4-oxo-2-pentene	HMDB
3-Isohexen-2-one	HMDB
3-PENTEN,2-one,4-methyl mesityloxide	HMDB
4-Methyl-3-penten-2-ON	HMDB
4-Methyl-3-penten-2-one	HMDB
4-Methyl-3-penten-2-one (mesityl oxide)	HMDB
4-Methyl-3-pentene-2-one	HMDB
4-Methylpent-3-en-2-one	HMDB
4-Metil-3-penten-2-one	HMDB
FEMA 3368	HMDB
Isobutenyl methyl ketone	HMDB
Isopropylidene acetone	HMDB
Isopropylidene-acetone	HMDB
Isopropylideneacetone	HMDB
Mesityl oxide	HMDB
Mesityloxid	HMDB
Mesityloxyde	HMDB
Methyl 2,2-dimethylvinyl ketone	HMDB
Methyl 2-methyl-1-propenyl ketone	HMDB
Methyl isobutenyl ketone	HMDB
ossido Di mesitile	HMDB
Oxyde de mesityle	HMDB

Chemical Formula

C₆H₁₀O

Average Molecular Weight

98.143

Monoisotopic Molecular Weight

98.073164942

IUPAC Name

4-methylpent-3-en-2-one

Traditional Name

mesityl oxide

CAS Registry Number

141-79-7

SMILES

CC(C)=CC(C)=O

InChI Identifier

InChI=1S/C6H10O/c1-5(2)4-6(3)7/h4H,1-3H3

InChI Key

SHOJXDKTYKFBRD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Enones

Alternative Parents

Substituents

Enone
Acryloyl-group
Ketone
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Oxygenated hydrocarbons (LMFA12000030 )

Ontology

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 24657864)

Excreta

Biofluid or Excreta

Feces (PMID: 17314143)

Cellular substructure

Extracellular (HMDB: HMDB0031563)
Cytoplasm (HMDB: HMDB0031563)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031563)

Source

Endogenous

Endogenous (HMDB: HMDB0031563)

Plant

Plant (HMDB: HMDB0031563)

Exogenous

Food

Food (HMDB: HMDB0031563)

Vegetable

Fruit vegetable

Pepper (FooDB: FOOD00040)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Pepper (C. frutescens) (FooDB: FOOD00428)
Orange bell pepper (FooDB: FOOD00879)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0031563)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031563)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-41.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	28.9 mg/mL at 20 °C	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	20.5 g/L	ALOGPS
logP	1.01	ALOGPS
logP	1.49	ChemAxon
logS	-0.68	ALOGPS
pKa (Strongest Acidic)	19.78	ChemAxon
pKa (Strongest Basic)	-4.3	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	1	ChemAxon
Refractivity	30.8 m³·mol⁻¹	ChemAxon
Polarizability	11.52 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]+	122.839	31661259
DarkChem	[M-H]-	116.145	31661259
DeepCCS	[M+H]+	125.511	30932474
DeepCCS	[M-H]-	123.616	30932474
DeepCCS	[M-2H]-	159.346	30932474
DeepCCS	[M+Na]+	133.855	30932474
AllCCS	[M+H]+	122.4	32859911
AllCCS	[M+H-H2O]+	118.0	32859911
AllCCS	[M+NH4]+	126.5	32859911
AllCCS	[M+Na]+	127.7	32859911
AllCCS	[M-H]-	125.0	32859911
AllCCS	[M+Na-2H]-	128.9	32859911
AllCCS	[M+HCOO]-	133.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Methyl-3-penten-2-one, 9CI	CC(C)=CC(C)=O	1151.8	Standard polar	33892256
4-Methyl-3-penten-2-one, 9CI	CC(C)=CC(C)=O	784.1	Standard non polar	33892256
4-Methyl-3-penten-2-one, 9CI	CC(C)=CC(C)=O	803.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Methyl-3-penten-2-one, 9CI,1TMS,isomer #1	C=C(C=C(C)C)O[Si](C)(C)C	992.9	Semi standard non polar	33892256
4-Methyl-3-penten-2-one, 9CI,1TMS,isomer #1	C=C(C=C(C)C)O[Si](C)(C)C	959.2	Standard non polar	33892256
4-Methyl-3-penten-2-one, 9CI,1TBDMS,isomer #1	C=C(C=C(C)C)O[Si](C)(C)C(C)(C)C	1204.1	Semi standard non polar	33892256
4-Methyl-3-penten-2-one, 9CI,1TBDMS,isomer #1	C=C(C=C(C)C)O[Si](C)(C)C(C)(C)C	1194.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 4-Methyl-3-penten-2-one, 9CI EI-B (Non-derivatized)	splash10-0a7i-9000000000-3661666f8de0c561e186	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Methyl-3-penten-2-one, 9CI EI-B (Non-derivatized)	splash10-0a7l-9000000000-3abe2bd4b3b37c4ed2cc	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Methyl-3-penten-2-one, 9CI EI-B (Non-derivatized)	splash10-0a7i-9000000000-3661666f8de0c561e186	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Methyl-3-penten-2-one, 9CI EI-B (Non-derivatized)	splash10-0a7l-9000000000-3abe2bd4b3b37c4ed2cc	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methyl-3-penten-2-one, 9CI GC-MS (Non-derivatized) - 70eV, Positive	splash10-0536-9000000000-2812ff25d24931b41744	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methyl-3-penten-2-one, 9CI GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methyl-3-penten-2-one, 9CI GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-053s-9000000000-6fe7e7a277af44176ff4	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 - 4-Methyl-3-penten-2-one, 9CI 10V, Positive-QTOF	splash10-000t-9000000000-1cada987a9858a217a77	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-3-penten-2-one, 9CI 20V, Positive-QTOF	splash10-001j-9000000000-e609ed7c7875fbd22551	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-3-penten-2-one, 9CI 40V, Positive-QTOF	splash10-00lr-9000000000-fe1499144a8401242c76	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-3-penten-2-one, 9CI 10V, Negative-QTOF	splash10-0002-9000000000-623d2802baf709699403	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-3-penten-2-one, 9CI 20V, Negative-QTOF	splash10-052b-9000000000-16572bb315d857e26b9b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-3-penten-2-one, 9CI 40V, Negative-QTOF	splash10-0a7i-9000000000-59b1a0eada94cc3c451e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-3-penten-2-one, 9CI 10V, Negative-QTOF	splash10-0002-9000000000-21c5ae8d52f2e0f4cd33	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-3-penten-2-one, 9CI 20V, Negative-QTOF	splash10-0002-9000000000-eed82ff9c391c5362464	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-3-penten-2-one, 9CI 40V, Negative-QTOF	splash10-03fr-9000000000-c60c0aab8dedee066bd2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-3-penten-2-one, 9CI 10V, Positive-QTOF	splash10-000x-9000000000-87409e2f1170b30e777d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-3-penten-2-one, 9CI 20V, Positive-QTOF	splash10-0006-9000000000-6d052a8bde956f1f244e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-3-penten-2-one, 9CI 40V, Positive-QTOF	splash10-000f-9000000000-e4044459c1588578e40a	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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	Adult (>18 years old)	Both	Normal	24922509	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	17314143	details
Saliva	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Normal	24657864	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	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
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Campylobacter jejuni infection	17314143	details
Saliva	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Celiac disease	24657864	details

Associated Disorders and Diseases

Disease References

Celiac disease
Francavilla R, Ercolini D, Piccolo M, Vannini L, Siragusa S, De Filippis F, De Pasquale I, Di Cagno R, Di Toma M, Gozzi G, Serrazanetti DI, De Angelis M, Gobbetti M: Salivary microbiota and metabolome associated with celiac disease. Appl Environ Microbiol. 2014 Jun;80(11):3416-25. doi: 10.1128/AEM.00362-14. Epub 2014 Mar 21. [PubMed:24657864 ]

Associated OMIM IDs

212750 (Celiac disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008178

KNApSAcK ID

C00051541

Chemspider ID

8526

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

8858

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 4-Methyl-3-penten-2-one, 9CI (HMDB0031563)

MOL for HMDB0031563 (4-Methyl-3-penten-2-one, 9CI)

3D MOL for HMDB0031563 (4-Methyl-3-penten-2-one, 9CI)

3D SDF for HMDB0031563 (4-Methyl-3-penten-2-one, 9CI)

3D-SDF for HMDB0031563 (4-Methyl-3-penten-2-one, 9CI)

PDB for HMDB0031563 (4-Methyl-3-penten-2-one, 9CI)

3D PDB for HMDB0031563 (4-Methyl-3-penten-2-one, 9CI)

SMILES for HMDB0031563 (4-Methyl-3-penten-2-one, 9CI)

INCHI for HMDB0031563 (4-Methyl-3-penten-2-one, 9CI)

Structure for HMDB0031563 (4-Methyl-3-penten-2-one, 9CI)

3D Structure for HMDB0031563 (4-Methyl-3-penten-2-one, 9CI)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra