Showing Compound 2-Hydroxy-2,6,6-trimethylcyclohexanone (FDB016003)

Record Information

Version

1.0

Creation date

2010-04-08 22:12:11 UTC

Update date

2019-11-26 03:12:35 UTC

Primary ID

FDB016003

Secondary Accession Numbers

Not Available

Chemical Information

FooDB 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.

CAS Number

7500-42-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
2,6,6-Trimethyl-2-hydroxycyclohexanone	HMDB
2,6,6-trimethyl-2-hydroxycyclohexanone	biospider
2-Hydroxy-2,6,6-trimethyl-cyclohexanone	HMDB
2-hydroxy-2,6,6-trimethyl-cyclohexanone	biospider
Cyclohexanone, 2-hydroxy-2,6,6-trimethyl-	biospider

Showing 1 to 5 of 5 entries

Predicted 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

Chemical Formula

C9H16O2

IUPAC name

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

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

Isomeric SMILES

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

Average Molecular Weight

156.2221

Monoisotopic Molecular Weight

156.115029756

Classification

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

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Subcellular:

Cell and elements:

Extracellular

Process

Naturally occurring process:

Biological process:

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 69.19%; H 10.32%; O 20.48%	DFC
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	2-Hydroxy-2,6,6-trimethylcyclohexanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052f-9100000000-188039cffee33a54e5f8	Spectrum
Predicted GC-MS	2-Hydroxy-2,6,6-trimethylcyclohexanone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01xx-9320000000-946947ebc74112a75a4c	Spectrum
Predicted GC-MS	2-Hydroxy-2,6,6-trimethylcyclohexanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Hydroxy-2,6,6-trimethylcyclohexanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-f5098fd2747f89a3aa52	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-5900000000-dbe4884f1d7b23faaf8f	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-015c-9000000000-5f4dcf2fb7221b90ead8	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-fc3691ad4aaa97d1518d	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1900000000-5d50de549f77bb27a68f	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00m0-9300000000-45c7e3c65481757e682c	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-376389ca50b091133eac	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-2900000000-5cb0b45f662d9d1535df	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-3900000000-e9a16d8e98a8fb35dc1f	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-3900000000-18ebf0f49cd1d539d7b3	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000x-9100000000-2896f4c14bfcc8b9ff70	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-e4c4645cd24fd328301d	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

91353

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

101115

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB37023

CRC / DFC (Dictionary of Food Compounds) ID

KLZ22-F:KLZ22-F

EAFUS ID

3754

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1535881

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Flavor	Citations
herbal	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
tobacco	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.