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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:42:25 UTC

Update Date

2023-02-21 17:20:27 UTC

HMDB ID

HMDB0031344

Secondary Accession Numbers

HMDB31344

Metabolite Identification

Common Name

1,2-Cyclohexanedione

Description

1,2-Cyclohexanedione, also known as cyclohexan-1,2-dione or 1,2-dioxocyclohexane, 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. 1,2-Cyclohexanedione exists in all living organisms, ranging from bacteria to humans. 1,2-Cyclohexanedione is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 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
1,2-Cyclohexadione	ChEBI
1,2-Dioxocyclohexane	ChEBI
Cyclohexan-1,2-dione	ChEBI
1,2-CYCLOHEXANEDIONE,ketone form	HMDB
2-Hydroxy-2-cyclohexen-1-one	HMDB
Cyclohexane-1,2-dione	HMDB
Cyclohexanecarbonitrile	HMDB
1,2-Cyclohexanedione	ChEBI

Chemical Formula

C₆H₈O₂

Average Molecular Weight

112.1265

Monoisotopic Molecular Weight

112.0524295

IUPAC Name

cyclohexane-1,2-dione

Traditional Name

1,2-cyclohexanedione

CAS Registry Number

765-87-7

SMILES

O=C1CCCCC1=O

InChI Identifier

InChI=1S/C6H8O2/c7-5-3-1-2-4-6(5)8/h1-4H2

InChI Key

OILAIQUEIWYQPH-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

cyclohexanedione (CHEBI:41674 )
a ketone (CPD0-1349 )

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Endogenous (HMDB: HMDB0031344)

Exogenous

Food

Food (HMDB: HMDB0031344)

Exogenous (HMDB: HMDB0031344)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	38 - 40 °C	Not Available
Boiling Point	193.00 to 195.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	267900 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.252 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	39.9 g/L	ALOGPS
logP	0.77	ALOGPS
logP	1.33	ChemAxon
logS	-0.45	ALOGPS
pKa (Strongest Acidic)	16.9	ChemAxon
pKa (Strongest Basic)	-8.5	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	28.99 m³·mol⁻¹	ChemAxon
Polarizability	11.31 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]+	123.193	31661259
DarkChem	[M-H]-	117.172	31661259
DeepCCS	[M+H]+	129.013	30932474
DeepCCS	[M-H]-	126.642	30932474
DeepCCS	[M-2H]-	162.69	30932474
DeepCCS	[M+Na]+	137.491	30932474
AllCCS	[M+H]+	124.2	32859911
AllCCS	[M+H-H2O]+	119.4	32859911
AllCCS	[M+NH4]+	128.8	32859911
AllCCS	[M+Na]+	130.1	32859911
AllCCS	[M-H]-	121.2	32859911
AllCCS	[M+Na-2H]-	123.8	32859911
AllCCS	[M+HCOO]-	126.6	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.	2.68 minutes	32390414
Predicted by Siyang on May 30, 2022	11.2664 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.14 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1471.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	406.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	138.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	264.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	227.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	363.5 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	471.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	112.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	958.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	296.2 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	933.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	241.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	323.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	510.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	354.8 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	129.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,2-Cyclohexanedione	O=C1CCCCC1=O	1705.1	Standard polar	33892256
1,2-Cyclohexanedione	O=C1CCCCC1=O	928.3	Standard non polar	33892256
1,2-Cyclohexanedione	O=C1CCCCC1=O	1073.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1,2-Cyclohexanedione,1TMS,isomer #1	C[Si](C)(C)OC1=CCCCC1=O	1308.9	Semi standard non polar	33892256
1,2-Cyclohexanedione,1TMS,isomer #1	C[Si](C)(C)OC1=CCCCC1=O	1221.5	Standard non polar	33892256
1,2-Cyclohexanedione,2TMS,isomer #1	C[Si](C)(C)OC1=CCCC=C1O[Si](C)(C)C	1426.7	Semi standard non polar	33892256
1,2-Cyclohexanedione,2TMS,isomer #1	C[Si](C)(C)OC1=CCCC=C1O[Si](C)(C)C	1339.6	Standard non polar	33892256
1,2-Cyclohexanedione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CCCCC1=O	1545.9	Semi standard non polar	33892256
1,2-Cyclohexanedione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CCCCC1=O	1419.7	Standard non polar	33892256
1,2-Cyclohexanedione,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CCCC=C1O[Si](C)(C)C(C)(C)C	1908.3	Semi standard non polar	33892256
1,2-Cyclohexanedione,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CCCC=C1O[Si](C)(C)C(C)(C)C	1688.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 1,2-Cyclohexanedione EI-B (Non-derivatized)	splash10-0btc-9100000000-3d5ad1ace9b6e2c89289	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2-Cyclohexanedione GC-EI-TOF (Non-derivatized)	splash10-0a4i-1900000000-2e5a6e06ef55c3e49dbf	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2-Cyclohexanedione GC-EI-TOF (Non-derivatized)	splash10-000i-7920000000-1460cee8e2bcb83147ea	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2-Cyclohexanedione GC-EI-TOF (Non-derivatized)	splash10-002r-5910000000-e65d353ffae9815b4d27	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2-Cyclohexanedione GC-EI-TOF (Non-derivatized)	splash10-00ba-0910000000-b6c1f0d43e329df34569	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2-Cyclohexanedione EI-B (Non-derivatized)	splash10-0btc-9100000000-3d5ad1ace9b6e2c89289	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2-Cyclohexanedione GC-EI-TOF (Non-derivatized)	splash10-0a4i-1900000000-2e5a6e06ef55c3e49dbf	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2-Cyclohexanedione GC-EI-TOF (Non-derivatized)	splash10-000i-7920000000-1460cee8e2bcb83147ea	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2-Cyclohexanedione GC-EI-TOF (Non-derivatized)	splash10-002r-5910000000-e65d353ffae9815b4d27	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2-Cyclohexanedione GC-EI-TOF (Non-derivatized)	splash10-00ba-0910000000-b6c1f0d43e329df34569	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Cyclohexanedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9000000000-acc17143efdaace3b312	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 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 - 1,2-Cyclohexanedione 10V, Positive-QTOF	splash10-03di-2900000000-2259ed4ff6285cf86ecd	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Cyclohexanedione 20V, Positive-QTOF	splash10-03di-6900000000-e956344b066027936fcd	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Cyclohexanedione 40V, Positive-QTOF	splash10-0a4l-9000000000-77ff2252637d4d339120	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Cyclohexanedione 10V, Negative-QTOF	splash10-03di-0900000000-a8bb463b50174a7135f0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Cyclohexanedione 20V, Negative-QTOF	splash10-03di-1900000000-3aac8fb749c7b5a45614	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Cyclohexanedione 40V, Negative-QTOF	splash10-0gvo-9100000000-f510b709eb6b933186b9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Cyclohexanedione 10V, Negative-QTOF	splash10-03di-0900000000-2aa00323e84aa0faf579	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Cyclohexanedione 20V, Negative-QTOF	splash10-03di-3900000000-a0ff2f4db35bf5dc8af1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Cyclohexanedione 40V, Negative-QTOF	splash10-0006-9000000000-156983626f26591859be	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Cyclohexanedione 10V, Positive-QTOF	splash10-03di-9600000000-5674226176fe1326994f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Cyclohexanedione 20V, Positive-QTOF	splash10-052f-9000000000-988d462b943c421ac852	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Cyclohexanedione 40V, Positive-QTOF	splash10-052o-9000000000-58b0ce29e2dabf58547a	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	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

FDB003408

KNApSAcK ID

Not Available

Chemspider ID

12465

KEGG Compound ID

C06105

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

1,2-Cyclohexanedione

METLIN ID

Not Available

PubChem Compound

13006

PDB ID

Not Available

ChEBI ID

41674

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1145191

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 1,2-Cyclohexanedione (HMDB0031344)

MOL for HMDB0031344 (1,2-Cyclohexanedione)

3D MOL for HMDB0031344 (1,2-Cyclohexanedione)

3D SDF for HMDB0031344 (1,2-Cyclohexanedione)

3D-SDF for HMDB0031344 (1,2-Cyclohexanedione)

PDB for HMDB0031344 (1,2-Cyclohexanedione)

3D PDB for HMDB0031344 (1,2-Cyclohexanedione)

SMILES for HMDB0031344 (1,2-Cyclohexanedione)

INCHI for HMDB0031344 (1,2-Cyclohexanedione)

Structure for HMDB0031344 (1,2-Cyclohexanedione)

3D Structure for HMDB0031344 (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