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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:15:57 UTC

Update Date

2023-02-21 17:25:33 UTC

HMDB ID

HMDB0037023

Secondary Accession Numbers

HMDB37023

Metabolite Identification

Common Name

2-Hydroxy-2,6,6-trimethylcyclohexanone

Description

2-Hydroxy-2,6,6-trimethylcyclohexanone belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups. 2-Hydroxy-2,6,6-trimethylcyclohexanone is a sweet, herbal, and tobacco tasting compound. 2-Hydroxy-2,6,6-trimethylcyclohexanone has been detected, but not quantified in, several different foods, such as black tea, green tea, herbal tea, red tea, and teas (Camellia sinensis). This could make 2-hydroxy-2,6,6-trimethylcyclohexanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Hydroxy-2,6,6-trimethylcyclohexanone.

Structure

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

COMPND    HMDB0037023
HETATM    1  C1  UNL     1       1.726   0.982   1.154  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.135   0.145   0.028  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.190   0.093  -1.077  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.950  -1.242   0.579  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.299  -1.865   0.050  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.510  -1.043   0.476  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.463   0.236  -0.293  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.336   1.315   0.312  1.00  0.00           C  
HETATM    9  O1  UNL     1      -2.012  -0.034  -1.568  1.00  0.00           O  
HETATM   10  C9  UNL     1      -0.090   0.732  -0.530  1.00  0.00           C  
HETATM   11  O2  UNL     1       0.026   1.715  -1.253  1.00  0.00           O  
HETATM   12  H1  UNL     1       0.977   1.345   1.859  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.497   0.319   1.643  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.336   1.815   0.706  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.580  -0.934  -1.220  1.00  0.00           H  
HETATM   16  H5  UNL     1       3.029   0.791  -0.876  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.751   0.439  -2.053  1.00  0.00           H  
HETATM   18  H7  UNL     1       1.803  -1.903   0.273  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.861  -1.222   1.700  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.418  -2.907   0.339  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.264  -1.766  -1.074  1.00  0.00           H  
HETATM   22  H11 UNL     1      -2.402  -1.664   0.171  1.00  0.00           H  
HETATM   23  H12 UNL     1      -1.585  -0.929   1.561  1.00  0.00           H  
HETATM   24  H13 UNL     1      -2.423   1.242   1.405  1.00  0.00           H  
HETATM   25  H14 UNL     1      -3.352   1.326  -0.173  1.00  0.00           H  
HETATM   26  H15 UNL     1      -1.876   2.289   0.019  1.00  0.00           H  
HETATM   27  H16 UNL     1      -1.831   0.728  -2.158  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4   10
CONECT    3   15   16   17
CONECT    4    5   18   19
CONECT    5    6   20   21
CONECT    6    7   22   23
CONECT    7    8    9   10
CONECT    8   24   25   26
CONECT    9   27
CONECT   10   11   11
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,6,6-Trimethyl-2-hydroxycyclohexanone	HMDB
2-Hydroxy-2,6,6-trimethyl-cyclohexanone	HMDB

Chemical Formula

C₉H₁₆O₂

Average Molecular Weight

156.2221

Monoisotopic Molecular Weight

156.115029756

IUPAC Name

2-hydroxy-2,6,6-trimethylcyclohexan-1-one

Traditional Name

2-hydroxy-2,6,6-trimethylcyclohexan-1-one

CAS Registry Number

7500-42-7

SMILES

CC1(C)CCCC(C)(O)C1=O

InChI Identifier

InChI=1S/C9H16O2/c1-8(2)5-4-6-9(3,11)7(8)10/h11H,4-6H2,1-3H3

InChI Key

FWCGLHYHGUHPRY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Acyloins

Alternative Parents

Substituents

Acyloin
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Ketone
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037023)

Source

Endogenous

Endogenous (HMDB: HMDB0037023)

Plant

Plant (HMDB: HMDB0037023)

Exogenous

Food

Food (HMDB: HMDB0037023)

Tea

Exogenous (HMDB: HMDB0037023)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0037023)

Role

Biological role

Energy source (HMDB: HMDB0037023)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037023)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	232.00 to 233.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	6304 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.924 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	13 g/L	ALOGPS
logP	1.27	ALOGPS
logP	2.15	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	13.26	ChemAxon
pKa (Strongest Basic)	-3.6	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	43.53 m³·mol⁻¹	ChemAxon
Polarizability	17.46 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]+	135.026	31661259
DarkChem	[M-H]-	131.871	31661259
DeepCCS	[M+H]+	139.066	30932474
DeepCCS	[M-H]-	135.248	30932474
DeepCCS	[M-2H]-	172.702	30932474
DeepCCS	[M+Na]+	148.182	30932474
AllCCS	[M+H]+	133.1	32859911
AllCCS	[M+H-H2O]+	128.7	32859911
AllCCS	[M+NH4]+	137.1	32859911
AllCCS	[M+Na]+	138.3	32859911
AllCCS	[M-H]-	135.6	32859911
AllCCS	[M+Na-2H]-	137.3	32859911
AllCCS	[M+HCOO]-	139.2	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.	3.31 minutes	32390414
Predicted by Siyang on May 30, 2022	12.2408 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.89 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1866.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	371.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	145.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	201.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	132.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	522.4 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	593.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	84.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	979.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	351.6 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	1163.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	352.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	323.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	397.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	439.3 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	17.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxy-2,6,6-trimethylcyclohexanone	CC1(C)CCCC(C)(O)C1=O	1594.4	Standard polar	33892256
2-Hydroxy-2,6,6-trimethylcyclohexanone	CC1(C)CCCC(C)(O)C1=O	1087.0	Standard non polar	33892256
2-Hydroxy-2,6,6-trimethylcyclohexanone	CC1(C)CCCC(C)(O)C1=O	1097.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxy-2,6,6-trimethylcyclohexanone,1TMS,isomer #1	CC1(C)CCCC(C)(O[Si](C)(C)C)C1=O	1275.9	Semi standard non polar	33892256
2-Hydroxy-2,6,6-trimethylcyclohexanone,1TBDMS,isomer #1	CC1(C)CCCC(C)(O[Si](C)(C)C(C)(C)C)C1=O	1525.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9100000000-188039cffee33a54e5f8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone GC-MS (1 TMS) - 70eV, Positive	splash10-01xx-9320000000-946947ebc74112a75a4c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone 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 - 2-Hydroxy-2,6,6-trimethylcyclohexanone 10V, Positive-QTOF	splash10-0a4i-0900000000-f5098fd2747f89a3aa52	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone 20V, Positive-QTOF	splash10-0a4i-5900000000-dbe4884f1d7b23faaf8f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone 40V, Positive-QTOF	splash10-015c-9000000000-5f4dcf2fb7221b90ead8	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone 10V, Negative-QTOF	splash10-0a4i-0900000000-fc3691ad4aaa97d1518d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone 20V, Negative-QTOF	splash10-0a4i-1900000000-5d50de549f77bb27a68f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone 40V, Negative-QTOF	splash10-00m0-9300000000-45c7e3c65481757e682c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone 10V, Negative-QTOF	splash10-0a4i-0900000000-376389ca50b091133eac	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone 20V, Negative-QTOF	splash10-0a4i-2900000000-5cb0b45f662d9d1535df	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone 40V, Negative-QTOF	splash10-0a4i-3900000000-e9a16d8e98a8fb35dc1f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone 10V, Positive-QTOF	splash10-0a4i-3900000000-18ebf0f49cd1d539d7b3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone 20V, Positive-QTOF	splash10-000x-9100000000-2896f4c14bfcc8b9ff70	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-2,6,6-trimethylcyclohexanone 40V, Positive-QTOF	splash10-00kf-9000000000-e4c4645cd24fd328301d	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+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
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

FDB016003

KNApSAcK ID

Not Available

Chemspider ID

91353

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101115

PDB ID

Not Available

ChEBI ID

171777

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1535881

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 2-Hydroxy-2,6,6-trimethylcyclohexanone (HMDB0037023)

MOL for HMDB0037023 (2-Hydroxy-2,6,6-trimethylcyclohexanone)

3D MOL for HMDB0037023 (2-Hydroxy-2,6,6-trimethylcyclohexanone)

3D SDF for HMDB0037023 (2-Hydroxy-2,6,6-trimethylcyclohexanone)

3D-SDF for HMDB0037023 (2-Hydroxy-2,6,6-trimethylcyclohexanone)

PDB for HMDB0037023 (2-Hydroxy-2,6,6-trimethylcyclohexanone)

3D PDB for HMDB0037023 (2-Hydroxy-2,6,6-trimethylcyclohexanone)

SMILES for HMDB0037023 (2-Hydroxy-2,6,6-trimethylcyclohexanone)

INCHI for HMDB0037023 (2-Hydroxy-2,6,6-trimethylcyclohexanone)

Structure for HMDB0037023 (2-Hydroxy-2,6,6-trimethylcyclohexanone)

3D Structure for HMDB0037023 (2-Hydroxy-2,6,6-trimethylcyclohexanone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra