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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:10:06 UTC

Update Date

2023-02-21 17:23:19 UTC

HMDB ID

HMDB0033434

Secondary Accession Numbers

HMDB33434

Metabolite Identification

Common Name

4-Acetyl-1-methylcyclohexene

Description

4-Acetyl-1-methylcyclohexene 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. 4-Acetyl-1-methylcyclohexene is a spice tasting compound. 4-Acetyl-1-methylcyclohexene has been detected, but not quantified in, breakfast cereal and cereals and cereal products. This could make 4-acetyl-1-methylcyclohexene a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Acetyl-1-methylcyclohexene.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1',2',3',6'-tetrahydro-4'-Methylacetophenone	HMDB
1-(4-Methyl-3-cyclohexen-1-yl)-ethanone	HMDB
1-(4-Methyl-3-cyclohexen-1-yl)ethanone	HMDB
1-(4-Methyl-3-cyclohexen-1-yl)ethanone, 9ci	HMDB
1-Methyl-4-acetylcyclohex-1-ene	HMDB
1H-Indole-3-ethanamine, N,N-diethyl- (9ci)	HMDB
3-(2-(diethylamino)Ethyl)-indole	HMDB
3-(2-Diethylaminoethyl)indole	HMDB
4-Acetyl-1-methyl-1-cyclohexene	HMDB
4-Acetyl-1-methylcyclohex-1-ene	HMDB
Cyclohexene, 1-methyl-4-acetyl	HMDB
Cyclohexene, 4-acetyl-1-methyl	HMDB
D.e.t.	HMDB
DET	HMDB
Diethyltryptamine	HMDB
N,N-Diethyl-1H-indole-3-ethanamine	HMDB
N,N-Diethyl-2-(1H-indol-3-yl)ethanamine	HMDB
N,N-Diethyltryptamine	HMDB
tetrahydro-P-Acetyltoluene	HMDB
AMCH CPD	MeSH, HMDB
4-Acetyl-1-methylcyclohexene	MeSH

Chemical Formula

C₉H₁₄O

Average Molecular Weight

138.2069

Monoisotopic Molecular Weight

138.10446507

IUPAC Name

1-(4-methylcyclohex-3-en-1-yl)ethan-1-one

Traditional Name

4-acetyl-1-methylcyclohexene

CAS Registry Number

6090-09-1

SMILES

CC(=O)C1CCC(C)=CC1

InChI Identifier

InChI=1S/C9H14O/c1-7-3-5-9(6-4-7)8(2)10/h3,9H,4-6H2,1-2H3

InChI Key

HOBBEYSRFFJETF-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 homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Odor

Spice

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033434)
Cytoplasm (HMDB: HMDB0033434)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033434)

Source

Exogenous

Food

Food (HMDB: HMDB0033434)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Endogenous

Plant

Plant (HMDB: HMDB0033434)
Poaceae (HMDB: HMDB0033434)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033434)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	189.50 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	811 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.190 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.4 g/L	ALOGPS
logP	2.3	ALOGPS
logP	2.1	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	19.43	ChemAxon
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	1	ChemAxon
Refractivity	42.8 m³·mol⁻¹	ChemAxon
Polarizability	16.26 Å³	ChemAxon
Number of Rings	1	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]+	132.479	31661259
DarkChem	[M-H]-	127.155	31661259
DeepCCS	[M+H]+	132.463	30932474
DeepCCS	[M-H]-	129.567	30932474
DeepCCS	[M-2H]-	166.276	30932474
DeepCCS	[M+Na]+	141.661	30932474
AllCCS	[M+H]+	129.0	32859911
AllCCS	[M+H-H2O]+	124.4	32859911
AllCCS	[M+NH4]+	133.3	32859911
AllCCS	[M+Na]+	134.6	32859911
AllCCS	[M-H]-	133.4	32859911
AllCCS	[M+Na-2H]-	135.3	32859911
AllCCS	[M+HCOO]-	137.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Acetyl-1-methylcyclohexene	CC(=O)C1CCC(C)=CC1	1552.3	Standard polar	33892256
4-Acetyl-1-methylcyclohexene	CC(=O)C1CCC(C)=CC1	1091.4	Standard non polar	33892256
4-Acetyl-1-methylcyclohexene	CC(=O)C1CCC(C)=CC1	1111.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Acetyl-1-methylcyclohexene,1TMS,isomer #1	CC1=CCC(=C(C)O[Si](C)(C)C)CC1	1312.1	Semi standard non polar	33892256
4-Acetyl-1-methylcyclohexene,1TMS,isomer #1	CC1=CCC(=C(C)O[Si](C)(C)C)CC1	1305.8	Standard non polar	33892256
4-Acetyl-1-methylcyclohexene,1TMS,isomer #2	C=C(O[Si](C)(C)C)C1CC=C(C)CC1	1252.8	Semi standard non polar	33892256
4-Acetyl-1-methylcyclohexene,1TMS,isomer #2	C=C(O[Si](C)(C)C)C1CC=C(C)CC1	1280.6	Standard non polar	33892256
4-Acetyl-1-methylcyclohexene,1TBDMS,isomer #1	CC1=CCC(=C(C)O[Si](C)(C)C(C)(C)C)CC1	1565.7	Semi standard non polar	33892256
4-Acetyl-1-methylcyclohexene,1TBDMS,isomer #1	CC1=CCC(=C(C)O[Si](C)(C)C(C)(C)C)CC1	1513.3	Standard non polar	33892256
4-Acetyl-1-methylcyclohexene,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C1CC=C(C)CC1	1499.2	Semi standard non polar	33892256
4-Acetyl-1-methylcyclohexene,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C1CC=C(C)CC1	1469.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 4-Acetyl-1-methylcyclohexene EI-B (Non-derivatized)	splash10-000g-9200000000-c7a992e3f2edf78ecf36	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Acetyl-1-methylcyclohexene EI-B (Non-derivatized)	splash10-000g-9200000000-c7a992e3f2edf78ecf36	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Acetyl-1-methylcyclohexene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9100000000-1f8cc5f10f998a5a80c2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Acetyl-1-methylcyclohexene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-1-methylcyclohexene 10V, Positive-QTOF	splash10-000i-1900000000-40a5e31d03941b9352d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-1-methylcyclohexene 20V, Positive-QTOF	splash10-000i-9800000000-7411bb0d1faa37c7c2ce	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-1-methylcyclohexene 40V, Positive-QTOF	splash10-0udi-9000000000-dcd30aea4d4a02bde400	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-1-methylcyclohexene 10V, Negative-QTOF	splash10-000i-0900000000-896a39d66c8f7aed574a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-1-methylcyclohexene 20V, Negative-QTOF	splash10-000i-2900000000-09b676a36f17434b8340	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-1-methylcyclohexene 40V, Negative-QTOF	splash10-010a-9500000000-95265caeeacb9a18e0cc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-1-methylcyclohexene 10V, Negative-QTOF	splash10-000i-0900000000-928b413704490084a303	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-1-methylcyclohexene 20V, Negative-QTOF	splash10-000l-7900000000-48ac329d943a43e16a29	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-1-methylcyclohexene 40V, Negative-QTOF	splash10-0006-9100000000-288f28617f8b6aa10081	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-1-methylcyclohexene 10V, Positive-QTOF	splash10-000l-9700000000-5c325adc8c67562b83d9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-1-methylcyclohexene 20V, Positive-QTOF	splash10-0006-9000000000-d2bca87634aeed57b8c6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-1-methylcyclohexene 40V, Positive-QTOF	splash10-0006-9000000000-2a805cbf1174f8aba67a	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)	2021-09-25	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

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

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

FDB011472

KNApSAcK ID

C00054113

Chemspider ID

83972

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

93019

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1445381

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-Acetyl-1-methylcyclohexene (HMDB0033434)

MOL for HMDB0033434 (4-Acetyl-1-methylcyclohexene)

3D MOL for HMDB0033434 (4-Acetyl-1-methylcyclohexene)

3D SDF for HMDB0033434 (4-Acetyl-1-methylcyclohexene)

3D-SDF for HMDB0033434 (4-Acetyl-1-methylcyclohexene)

PDB for HMDB0033434 (4-Acetyl-1-methylcyclohexene)

3D PDB for HMDB0033434 (4-Acetyl-1-methylcyclohexene)

SMILES for HMDB0033434 (4-Acetyl-1-methylcyclohexene)

INCHI for HMDB0033434 (4-Acetyl-1-methylcyclohexene)

Structure for HMDB0033434 (4-Acetyl-1-methylcyclohexene)

3D Structure for HMDB0033434 (4-Acetyl-1-methylcyclohexene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra