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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:16:00 UTC

Update Date

2023-02-21 17:25:33 UTC

HMDB ID

HMDB0037024

Secondary Accession Numbers

HMDB37024

Metabolite Identification

Common Name

4-Acetyl-1,4-dimethyl-1-cyclohexene

Description

4-Acetyl-1,4-dimethyl-1-cyclohexene 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, 4-acetyl-1,4-dimethyl-1-cyclohexene is considered to be an isoprenoid. 4-Acetyl-1,4-dimethyl-1-cyclohexene is a fruity tasting compound. Based on a literature review very few articles have been published on 4-Acetyl-1,4-dimethyl-1-cyclohexene.

Structure

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

COMPND    HMDB0037024
HETATM    1  C1  UNL     1      -2.862   1.017   0.467  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.742   0.106   0.793  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.574  -0.265   1.941  1.00  0.00           O  
HETATM    4  C3  UNL     1      -0.787  -0.395  -0.234  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.641  -1.161  -1.255  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.170   0.753  -0.968  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.263   0.957  -0.658  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.960   0.312   0.234  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.400   0.631   0.431  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.342  -0.732   1.056  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.183  -1.367   0.336  1.00  0.00           C  
HETATM   12  H1  UNL     1      -3.246   0.893  -0.552  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.704   0.834   1.160  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.529   2.072   0.679  1.00  0.00           H  
HETATM   15  H4  UNL     1      -1.793  -0.573  -2.178  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.600  -1.478  -0.810  1.00  0.00           H  
HETATM   17  H6  UNL     1      -1.126  -2.106  -1.565  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.247   0.659  -2.077  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.675   1.734  -0.742  1.00  0.00           H  
HETATM   20  H9  UNL     1       1.775   1.726  -1.243  1.00  0.00           H  
HETATM   21  H10 UNL     1       3.584   0.995   1.471  1.00  0.00           H  
HETATM   22  H11 UNL     1       3.710   1.481  -0.229  1.00  0.00           H  
HETATM   23  H12 UNL     1       4.056  -0.219   0.177  1.00  0.00           H  
HETATM   24  H13 UNL     1       1.044  -0.321   2.050  1.00  0.00           H  
HETATM   25  H14 UNL     1       2.098  -1.531   1.225  1.00  0.00           H  
HETATM   26  H15 UNL     1      -0.341  -2.063   1.003  1.00  0.00           H  
HETATM   27  H16 UNL     1       0.622  -1.959  -0.513  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3    4
CONECT    4    5    6   11
CONECT    5   15   16   17
CONECT    6    7   18   19
CONECT    7    8    8   20
CONECT    8    9   10
CONECT    9   21   22   23
CONECT   10   11   24   25
CONECT   11   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,4-Dimethyl-3-cyclohexenyl methyl ketone	HMDB
1,4-Dimethyl-4-acetyl-1-cyclohexene	HMDB
1,4-Dimethyl-4-acetylcyclohexene	HMDB
1,4-Dimethyl-cyclohex-3-enyl methyl ketone	HMDB
1,4-Dimethyl-laquo deltaraquo -3-tetrahydroacetophenone	HMDB
1,4-Dimethylcyclohex-3-enyl methyl ketone	HMDB
1-(1,4-Dimethyl-3-cyclohexen-1-yl)-ethanone	HMDB
1-(1,4-Dimethyl-3-cyclohexen-1-yl)ethanone	HMDB
1-(1,4-Dimethyl-3-cyclohexenyl)ethanone	HMDB
1-(1,4-Dimethylcyclohex-3-en-1-yl)ethan-1-one	HMDB
1-(1,4-Dimethylcyclohex-3-enyl)ethanone	HMDB
FEMA 3449	HMDB

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

1-(1,4-dimethylcyclohex-3-en-1-yl)ethan-1-one

Traditional Name

1-(1,4-dimethylcyclohex-3-en-1-yl)ethanone

CAS Registry Number

43219-68-7

SMILES

CC(=O)C1(C)CCC(C)=CC1

InChI Identifier

InChI=1S/C10H16O/c1-8-4-6-10(3,7-5-8)9(2)11/h4H,5-7H2,1-3H3

InChI Key

BIUSXTISNNLMOR-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

Other cyclohexane monoterpenoids (LMPR0102100001 )

Ontology

Physiological effect

Organoleptic effect

Odor

Fruity

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0037024)
Cytoplasm (HMDB: HMDB0037024)

Source

Exogenous

Food

Food (HMDB: HMDB0037024)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037024)

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0037024)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	208.00 to 211.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	289.5 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.558 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.99 g/L	ALOGPS
logP	2.4	ALOGPS
logP	2.66	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	19.3	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	47.3 m³·mol⁻¹	ChemAxon
Polarizability	18.01 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]+	135.237	31661259
DarkChem	[M-H]-	131.634	31661259
DeepCCS	[M+H]+	139.318	30932474
DeepCCS	[M-H]-	136.472	30932474
DeepCCS	[M-2H]-	172.994	30932474
DeepCCS	[M+Na]+	148.532	30932474
AllCCS	[M+H]+	132.2	32859911
AllCCS	[M+H-H2O]+	127.7	32859911
AllCCS	[M+NH4]+	136.3	32859911
AllCCS	[M+Na]+	137.5	32859911
AllCCS	[M-H]-	137.3	32859911
AllCCS	[M+Na-2H]-	138.9	32859911
AllCCS	[M+HCOO]-	140.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Acetyl-1,4-dimethyl-1-cyclohexene	CC(=O)C1(C)CCC(C)=CC1	1563.0	Standard polar	33892256
4-Acetyl-1,4-dimethyl-1-cyclohexene	CC(=O)C1(C)CCC(C)=CC1	1147.8	Standard non polar	33892256
4-Acetyl-1,4-dimethyl-1-cyclohexene	CC(=O)C1(C)CCC(C)=CC1	1171.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Acetyl-1,4-dimethyl-1-cyclohexene,1TMS,isomer #1	C=C(O[Si](C)(C)C)C1(C)CC=C(C)CC1	1273.6	Semi standard non polar	33892256
4-Acetyl-1,4-dimethyl-1-cyclohexene,1TMS,isomer #1	C=C(O[Si](C)(C)C)C1(C)CC=C(C)CC1	1327.2	Standard non polar	33892256
4-Acetyl-1,4-dimethyl-1-cyclohexene,1TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C1(C)CC=C(C)CC1	1528.4	Semi standard non polar	33892256
4-Acetyl-1,4-dimethyl-1-cyclohexene,1TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C1(C)CC=C(C)CC1	1507.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Acetyl-1,4-dimethyl-1-cyclohexene GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9500000000-75959f285c5f543a9a9f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Acetyl-1,4-dimethyl-1-cyclohexene 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-1,4-dimethyl-1-cyclohexene 10V, Positive-QTOF	splash10-0udi-0900000000-08b94ad232a9d9ff4cfa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-1,4-dimethyl-1-cyclohexene 20V, Positive-QTOF	splash10-0udi-6900000000-44839a581fede5c45338	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-1,4-dimethyl-1-cyclohexene 40V, Positive-QTOF	splash10-0zfr-9100000000-e4aa420290d603e278f2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-1,4-dimethyl-1-cyclohexene 10V, Negative-QTOF	splash10-0udi-0900000000-9660b5753a8569252584	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-1,4-dimethyl-1-cyclohexene 20V, Negative-QTOF	splash10-0udi-0900000000-973b6ed6f277bddbfdf4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-1,4-dimethyl-1-cyclohexene 40V, Negative-QTOF	splash10-052u-6900000000-56512cbc49d52c14d17d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-1,4-dimethyl-1-cyclohexene 10V, Positive-QTOF	splash10-0a4i-2900000000-f10145b7f93be88bcb75	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-1,4-dimethyl-1-cyclohexene 20V, Positive-QTOF	splash10-066u-9500000000-c65d42b1960837f42572	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-1,4-dimethyl-1-cyclohexene 40V, Positive-QTOF	splash10-0006-9100000000-0bf69753f2a092d26628	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-1,4-dimethyl-1-cyclohexene 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-1,4-dimethyl-1-cyclohexene 20V, Negative-QTOF	splash10-0udi-2900000000-7b7dbd02a69c0f67b12e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Acetyl-1,4-dimethyl-1-cyclohexene 40V, Negative-QTOF	splash10-0f6x-9200000000-9625e02376d61fa1e43c	2021-09-24	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

FDB016004

KNApSAcK ID

C00010978

Chemspider ID

58780

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

65289

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1036221

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-1,4-dimethyl-1-cyclohexene (HMDB0037024)

MOL for HMDB0037024 (4-Acetyl-1,4-dimethyl-1-cyclohexene)

3D MOL for HMDB0037024 (4-Acetyl-1,4-dimethyl-1-cyclohexene)

3D SDF for HMDB0037024 (4-Acetyl-1,4-dimethyl-1-cyclohexene)

3D-SDF for HMDB0037024 (4-Acetyl-1,4-dimethyl-1-cyclohexene)

PDB for HMDB0037024 (4-Acetyl-1,4-dimethyl-1-cyclohexene)

3D PDB for HMDB0037024 (4-Acetyl-1,4-dimethyl-1-cyclohexene)

SMILES for HMDB0037024 (4-Acetyl-1,4-dimethyl-1-cyclohexene)

INCHI for HMDB0037024 (4-Acetyl-1,4-dimethyl-1-cyclohexene)

Structure for HMDB0037024 (4-Acetyl-1,4-dimethyl-1-cyclohexene)

3D Structure for HMDB0037024 (4-Acetyl-1,4-dimethyl-1-cyclohexene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra