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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:14:18 UTC

Update Date

2023-02-21 17:25:10 UTC

HMDB ID

HMDB0036177

Secondary Accession Numbers

HMDB36177

Metabolite Identification

Common Name

3,5,5-Trimethyl-1,2-cyclohexanedione

Description

3,5,5-Trimethyl-1,2-cyclohexanedione belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. 3,5,5-Trimethyl-1,2-cyclohexanedione is a clean, dry, and nutty tasting compound. Based on a literature review very few articles have been published on 3,5,5-Trimethyl-1,2-cyclohexanedione.

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-Hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one, 9ci	HMDB
Benzil-related compound, 52	HMDB

Chemical Formula

C₉H₁₄O₂

Average Molecular Weight

154.2063

Monoisotopic Molecular Weight

154.099379692

IUPAC Name

2-hydroxy-3,5,5-trimethylcyclohex-2-en-1-one

Traditional Name

2-hydroxy-3,5,5-trimethylcyclohex-2-en-1-one

CAS Registry Number

57696-89-6

SMILES

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

InChI Identifier

InChI=1S/C9H14O2/c1-6-4-9(2,3)5-7(10)8(6)11/h11H,4-5H2,1-3H3

InChI Key

DWGZTTFGUFHAJX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Enol
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0036177)

Exogenous

Food

Food (HMDB: HMDB0036177)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0036177)

Role

Biological role

Energy source (HMDB: HMDB0036177)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036177)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0036177)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	89 - 91 °C	Not Available
Boiling Point	214.00 to 215.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	14430 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.630	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.9 g/L	ALOGPS
logP	1.14	ALOGPS
logP	1.8	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	9.56	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	44.61 m³·mol⁻¹	ChemAxon
Polarizability	17.04 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
DeepCCS	[M+H]+	142.402	30932474
DeepCCS	[M-H]-	139.914	30932474
DeepCCS	[M-2H]-	175.325	30932474
DeepCCS	[M+Na]+	150.615	30932474
AllCCS	[M+H]+	131.9	32859911
AllCCS	[M+H-H2O]+	127.5	32859911
AllCCS	[M+NH4]+	136.0	32859911
AllCCS	[M+Na]+	137.2	32859911
AllCCS	[M-H]-	133.9	32859911
AllCCS	[M+Na-2H]-	135.5	32859911
AllCCS	[M+HCOO]-	137.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,5,5-Trimethyl-1,2-cyclohexanedione	CC1=C(O)C(=O)CC(C)(C)C1	1657.0	Standard polar	33892256
3,5,5-Trimethyl-1,2-cyclohexanedione	CC1=C(O)C(=O)CC(C)(C)C1	1197.5	Standard non polar	33892256
3,5,5-Trimethyl-1,2-cyclohexanedione	CC1=C(O)C(=O)CC(C)(C)C1	1164.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,5,5-Trimethyl-1,2-cyclohexanedione,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(=O)CC(C)(C)C1	1377.5	Semi standard non polar	33892256
3,5,5-Trimethyl-1,2-cyclohexanedione,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(=O)CC(C)(C)C1	1377.5	Semi standard non polar	33892256
3,5,5-Trimethyl-1,2-cyclohexanedione,1TMS,isomer #2	CC1=C(O)C(O[Si](C)(C)C)=CC(C)(C)C1	1441.5	Semi standard non polar	33892256
3,5,5-Trimethyl-1,2-cyclohexanedione,1TMS,isomer #2	CC1=C(O)C(O[Si](C)(C)C)=CC(C)(C)C1	1441.5	Semi standard non polar	33892256
3,5,5-Trimethyl-1,2-cyclohexanedione,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC(C)(C)C1	1477.7	Semi standard non polar	33892256
3,5,5-Trimethyl-1,2-cyclohexanedione,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC(C)(C)C1	1491.3	Standard non polar	33892256
3,5,5-Trimethyl-1,2-cyclohexanedione,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)CC(C)(C)C1	1651.9	Semi standard non polar	33892256
3,5,5-Trimethyl-1,2-cyclohexanedione,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)CC(C)(C)C1	1651.9	Semi standard non polar	33892256
3,5,5-Trimethyl-1,2-cyclohexanedione,1TBDMS,isomer #2	CC1=C(O)C(O[Si](C)(C)C(C)(C)C)=CC(C)(C)C1	1646.9	Semi standard non polar	33892256
3,5,5-Trimethyl-1,2-cyclohexanedione,1TBDMS,isomer #2	CC1=C(O)C(O[Si](C)(C)C(C)(C)C)=CC(C)(C)C1	1646.9	Semi standard non polar	33892256
3,5,5-Trimethyl-1,2-cyclohexanedione,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC(C)(C)C1	1912.1	Semi standard non polar	33892256
3,5,5-Trimethyl-1,2-cyclohexanedione,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC(C)(C)C1	1844.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5,5-Trimethyl-1,2-cyclohexanedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ars-9300000000-9f1ac794a812e7423ca1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5,5-Trimethyl-1,2-cyclohexanedione GC-MS (1 TMS) - 70eV, Positive	splash10-020r-9530000000-4a5e28c45b4c5ef1ae7f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5,5-Trimethyl-1,2-cyclohexanedione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5,5-Trimethyl-1,2-cyclohexanedione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5,5-Trimethyl-1,2-cyclohexanedione 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 - 3,5,5-Trimethyl-1,2-cyclohexanedione 10V, Positive-QTOF	splash10-0a4i-0900000000-9ef06de287e0517060ef	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-1,2-cyclohexanedione 20V, Positive-QTOF	splash10-0a4i-6900000000-0ec07c19cb68f653f4e4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-1,2-cyclohexanedione 40V, Positive-QTOF	splash10-0a5d-9000000000-55124772220314f0e401	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-1,2-cyclohexanedione 10V, Negative-QTOF	splash10-0udi-0900000000-3f4df2c91b2074dac493	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-1,2-cyclohexanedione 20V, Negative-QTOF	splash10-0udi-1900000000-ad670b94f28d21606da5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-1,2-cyclohexanedione 40V, Negative-QTOF	splash10-0f7w-9500000000-f4a16bc5e4638280e22a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-1,2-cyclohexanedione 10V, Positive-QTOF	splash10-0a4i-2900000000-f4ce8e1d338e7944477f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-1,2-cyclohexanedione 20V, Positive-QTOF	splash10-0a5i-9400000000-c9e1fd1ae9d5649acae8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-1,2-cyclohexanedione 40V, Positive-QTOF	splash10-0536-9000000000-33bb199f1ab85f29b787	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-1,2-cyclohexanedione 10V, Negative-QTOF	splash10-0udi-0900000000-2b724c24a95a3652b801	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-1,2-cyclohexanedione 20V, Negative-QTOF	splash10-0udi-0900000000-f004c8afc9a72c32925b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5,5-Trimethyl-1,2-cyclohexanedione 40V, Negative-QTOF	splash10-0udr-4900000000-2c3b62387bc795b85384	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
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

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+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

Extracellular
Membrane

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

FDB015097

KNApSAcK ID

Not Available

Chemspider ID

479415

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

551084

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1444061

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 3,5,5-Trimethyl-1,2-cyclohexanedione (HMDB0036177)

MOL for HMDB0036177 (3,5,5-Trimethyl-1,2-cyclohexanedione)

3D MOL for HMDB0036177 (3,5,5-Trimethyl-1,2-cyclohexanedione)

3D SDF for HMDB0036177 (3,5,5-Trimethyl-1,2-cyclohexanedione)

3D-SDF for HMDB0036177 (3,5,5-Trimethyl-1,2-cyclohexanedione)

PDB for HMDB0036177 (3,5,5-Trimethyl-1,2-cyclohexanedione)

3D PDB for HMDB0036177 (3,5,5-Trimethyl-1,2-cyclohexanedione)

SMILES for HMDB0036177 (3,5,5-Trimethyl-1,2-cyclohexanedione)

INCHI for HMDB0036177 (3,5,5-Trimethyl-1,2-cyclohexanedione)

Structure for HMDB0036177 (3,5,5-Trimethyl-1,2-cyclohexanedione)

3D Structure for HMDB0036177 (3,5,5-Trimethyl-1,2-cyclohexanedione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra