ChemFOnt: Showing chemical card for 2,6,6-Trimethylcyclohex-2-en-1,4-dione (CFc000333497)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:13:38 UTC

Chemfont ID

CFc000333497

Molecule Identification

Common Name

2,6,6-Trimethylcyclohex-2-en-1,4-dione

Definition

2,6,6-trimethyl-2-cyclohexene-1,4-dione, also known as ketoisophorone, is a member of the class of 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. 2,6,6-trimethyl-2-cyclohexene-1,4-dione is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). 2,6,6-trimethyl-2-cyclohexene-1,4-dione is a sweet, leaf, and musty tasting compound found in herbs and spices and tea, which makes 2,6,6-trimethyl-2-cyclohexene-1,4-dione a potential biomarker for the consumption of these food products. 2,6,6-trimethyl-2-cyclohexene-1,4-dione exists in all eukaryotes, ranging from yeast to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,2,6-Trimethyl-2-cyclohexene-1,4-dione (cetoisophorone)	HMDB
2,2,6-Trimethylcyclohex-2-en-1,4-dione (4-oxo-isophorone)	HMDB
2,6,6-Trimethy-2-cyclohexene-1,4-dione (4-oxoisophorone)	HMDB
2,6,6-Trimethyl-2-cyclohexen-1,4-dione	HMDB
2,6,6-Trimethylcyclohex-2-ene-1,4-dione	HMDB
2-Cyclohexen-1,4-dione, 2,6,6-trimethyl	HMDB
3,5,5-Trimethyl-2-cyclohexene-1,4-dione	HMDB
3,5,5-Trimethylcyclohex-2-en-1,4-dione	HMDB
3,5,5-Trimethylcyclohex-2-ene-1,4-dione	HMDB
4-Ketoisophorone	HMDB
4-oxo-alpha-Isophorone	HMDB
4-Oxoisophorone	HMDB
6-Oxoisophorone	HMDB
FEMA 3421	HMDB
Keto-isophorone	HMDB
Ketoisophorone	HMDB
Oxoisophorone	HMDB
Oxopholone	HMDB
Oxophorone	HMDB

Chemical Formula

C₉H₁₂O₂

Average Molecular Weight

152.1904

Monoisotopic Molecular Weight

152.083729628

IUPAC Name

2,6,6-trimethylcyclohex-2-ene-1,4-dione

Traditional Name

2,6,6-trimethylcyclohex-2-ene-1,4-dione

CAS Registry Number

1125-21-9

SMILES

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

InChI Identifier

InChI=1S/C9H12O2/c1-6-4-7(10)5-9(2,3)8(6)11/h4H,5H2,1-3H3

InChI Key

AYJXHIDNNLJQDT-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
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040216)

Source

Endogenous

Endogenous (HMDB: HMDB0040216)

Plant

Plant (HMDB: HMDB0040216)

Exogenous

Food

Food (HMDB: HMDB0040216)

Tea

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0040216)

Role

Biological role

Energy source (HMDB: HMDB0040216)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0040216)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040216)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	8.73 g/L	ALOGPS
logP	1.51	ALOGPS
logP	2.16	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	18.85	ChemAxon
pKa (Strongest Basic)	-6.4	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	43.39 m³·mol⁻¹	ChemAxon
Polarizability	16.33 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

External Links

HMDB ID

HMDB0040216

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB004389

KNApSAcK ID

C00035002

Chemspider ID

56162

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

62374

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 2,6,6-Trimethylcyclohex-2-en-1,4-dione (CFc000333497)

MOL for CFc000333497 (2,6,6-Trimethylcyclohex-2-en-1,4-dione)

3D MOL for CFc000333497 (2,6,6-Trimethylcyclohex-2-en-1,4-dione)

3D SDF for CFc000333497 (2,6,6-Trimethylcyclohex-2-en-1,4-dione)

3D-SDF for CFc000333497 (2,6,6-Trimethylcyclohex-2-en-1,4-dione)

PDB for CFc000333497 (2,6,6-Trimethylcyclohex-2-en-1,4-dione)

3D PDB for CFc000333497 (2,6,6-Trimethylcyclohex-2-en-1,4-dione)

SMILES for CFc000333497 (2,6,6-Trimethylcyclohex-2-en-1,4-dione)

INCHI for CFc000333497 (2,6,6-Trimethylcyclohex-2-en-1,4-dione)

Structure for CFc000333497 (2,6,6-Trimethylcyclohex-2-en-1,4-dione)

3D Structure for CFc000333497 (2,6,6-Trimethylcyclohex-2-en-1,4-dione)