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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:51:57 UTC

Update Date

2023-02-21 17:23:52 UTC

HMDB ID

HMDB0034080

Secondary Accession Numbers

HMDB34080

Metabolite Identification

Common Name

3-Methyl-1,2-cyclohexanedione

Description

3-Methyl-1,2-cyclohexanedione belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety. 3-Methyl-1,2-cyclohexanedione is a burnt, coffee, and sugar tasting compound. 3-Methyl-1,2-cyclohexanedione has been detected, but not quantified in, a few different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make 3-methyl-1,2-cyclohexanedione a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Methyl-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-methyl-2-cyclohexen-1-one	HMDB
FEMA 3305	HMDB

Chemical Formula

C₇H₁₀O₂

Average Molecular Weight

126.1531

Monoisotopic Molecular Weight

126.068079564

IUPAC Name

3-methylcyclohexane-1,2-dione

Traditional Name

3-methylcyclohexane-1,2-dione

CAS Registry Number

3008-43-3

SMILES

CC1CCCC(=O)C1=O

InChI Identifier

InChI=1S/C7H10O2/c1-5-3-2-4-6(8)7(5)9/h5H,2-4H2,1H3

InChI Key

JDXJKLGWPNXSHL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclic ketones

Alternative Parents

Substituents

Cyclic ketone
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Ingestion (HMDB: HMDB0034080)

Source

Exogenous

Exogenous (HMDB: HMDB0034080)

Food

Food (HMDB: HMDB0034080)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Endogenous

Plant

Coffea (HMDB: HMDB0034080)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0034080)

Biological role

Nutrient (HMDB: HMDB0034080)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	64 - 65 °C	Not Available
Boiling Point	69.00 to 72.00 °C. @ 1.00 mm Hg	The Good Scents Company Information System
Water Solubility	104800 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.787 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	17.4 g/L	ALOGPS
logP	1.03	ALOGPS
logP	1.88	ChemAxon
logS	-0.86	ALOGPS
pKa (Strongest Acidic)	17.05	ChemAxon
pKa (Strongest Basic)	-8.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	33.57 m³·mol⁻¹	ChemAxon
Polarizability	13.25 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]+	125.938	31661259
DarkChem	[M-H]-	121.774	31661259
DeepCCS	[M+H]+	132.803	30932474
DeepCCS	[M-H]-	130.04	30932474
DeepCCS	[M-2H]-	166.562	30932474
DeepCCS	[M+Na]+	141.325	30932474
AllCCS	[M+H]+	126.3	32859911
AllCCS	[M+H-H2O]+	121.5	32859911
AllCCS	[M+NH4]+	130.7	32859911
AllCCS	[M+Na]+	132.0	32859911
AllCCS	[M-H]-	125.9	32859911
AllCCS	[M+Na-2H]-	128.0	32859911
AllCCS	[M+HCOO]-	130.4	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.	2.97 minutes	32390414
Predicted by Siyang on May 30, 2022	12.5778 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.57 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1676.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	450.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	155.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	285.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	219.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	453.9 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	537.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	105.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1022.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	334.4 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	1079.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	276.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	351.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	428.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	389.9 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	81.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-1,2-cyclohexanedione	CC1CCCC(=O)C1=O	1724.2	Standard polar	33892256
3-Methyl-1,2-cyclohexanedione	CC1CCCC(=O)C1=O	1013.2	Standard non polar	33892256
3-Methyl-1,2-cyclohexanedione	CC1CCCC(=O)C1=O	1127.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-1,2-cyclohexanedione,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(=O)CCC1	1271.6	Semi standard non polar	33892256
3-Methyl-1,2-cyclohexanedione,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(=O)CCC1	1254.9	Standard non polar	33892256
3-Methyl-1,2-cyclohexanedione,1TMS,isomer #2	CC1CCC=C(O[Si](C)(C)C)C1=O	1333.1	Semi standard non polar	33892256
3-Methyl-1,2-cyclohexanedione,1TMS,isomer #2	CC1CCC=C(O[Si](C)(C)C)C1=O	1233.7	Standard non polar	33892256
3-Methyl-1,2-cyclohexanedione,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CCC1	1417.1	Semi standard non polar	33892256
3-Methyl-1,2-cyclohexanedione,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CCC1	1475.2	Standard non polar	33892256
3-Methyl-1,2-cyclohexanedione,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)CCC1	1589.5	Semi standard non polar	33892256
3-Methyl-1,2-cyclohexanedione,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)CCC1	1464.0	Standard non polar	33892256
3-Methyl-1,2-cyclohexanedione,1TBDMS,isomer #2	CC1CCC=C(O[Si](C)(C)C(C)(C)C)C1=O	1564.6	Semi standard non polar	33892256
3-Methyl-1,2-cyclohexanedione,1TBDMS,isomer #2	CC1CCC=C(O[Si](C)(C)C(C)(C)C)C1=O	1442.9	Standard non polar	33892256
3-Methyl-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)=CCC1	1926.3	Semi standard non polar	33892256
3-Methyl-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)=CCC1	1784.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-1,2-cyclohexanedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9100000000-1f1acecfc19c567d50c7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-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-Methyl-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-Methyl-1,2-cyclohexanedione 10V, Positive-QTOF	splash10-004i-1900000000-7b42029d3aaa9e61ec6c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclohexanedione 20V, Positive-QTOF	splash10-056r-8900000000-b799e2f1d5e6ecf4be5c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclohexanedione 40V, Positive-QTOF	splash10-052f-9000000000-c5f5d34c9e18b2dbc78d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclohexanedione 10V, Negative-QTOF	splash10-004i-0900000000-ad62c2519c60710084c3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclohexanedione 20V, Negative-QTOF	splash10-004i-1900000000-b13a7946997ff8e3f1cc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclohexanedione 40V, Negative-QTOF	splash10-0a4i-9200000000-6f2097c0b3a4722216c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclohexanedione 10V, Negative-QTOF	splash10-004i-0900000000-738068b5fb20db20a035	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclohexanedione 20V, Negative-QTOF	splash10-00ba-9700000000-4a08f9da6bb512b197f5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclohexanedione 40V, Negative-QTOF	splash10-0avl-9200000000-2b7e739c1646124b1583	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclohexanedione 10V, Positive-QTOF	splash10-004i-2900000000-04889c3f3176afdcbec4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclohexanedione 20V, Positive-QTOF	splash10-05mo-9000000000-7c1e484daf53c1b3b36c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1,2-cyclohexanedione 40V, Positive-QTOF	splash10-00kf-9000000000-c97252093fa267aaabdd	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 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

Not Available

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

FDB012339

KNApSAcK ID

Not Available

Chemspider ID

2568901

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3321360

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1035751

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-Methyl-1,2-cyclohexanedione (HMDB0034080)

MOL for HMDB0034080 (3-Methyl-1,2-cyclohexanedione)

3D MOL for HMDB0034080 (3-Methyl-1,2-cyclohexanedione)

3D SDF for HMDB0034080 (3-Methyl-1,2-cyclohexanedione)

3D-SDF for HMDB0034080 (3-Methyl-1,2-cyclohexanedione)

PDB for HMDB0034080 (3-Methyl-1,2-cyclohexanedione)

3D PDB for HMDB0034080 (3-Methyl-1,2-cyclohexanedione)

SMILES for HMDB0034080 (3-Methyl-1,2-cyclohexanedione)

INCHI for HMDB0034080 (3-Methyl-1,2-cyclohexanedione)

Structure for HMDB0034080 (3-Methyl-1,2-cyclohexanedione)

3D Structure for HMDB0034080 (3-Methyl-1,2-cyclohexanedione)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra