FComEx: Cyclohexanone (PC000831)

Record Information

Version

1.0

Creation date

2015-10-09 22:32:57 UTC

Update date

2017-01-19 02:36:37 UTC

FoodComEx ID

PC000831

FoodDB Record

FDB003418

Chemical Information

Name

Cyclohexanone

Description

Cyclohexanone is a food flavourant. Present in various plant spp. e.g. Cistus ladaniferus (labdanum). Cyclohexanone is a colorless oily liquid with an odor resembling acetone and peppermint. Cyclohexanone is occasionally found as a volatile component of human urine. Biological fluids such as blood and urine have been shown to contain a large number of components, some of them volatiles (low boiling point) apparently present in all individuals, while others such are much more variable. In some cases differences up to an order of magnitude are observed. Although some of these changes may have dietary origins, others seem to be characteristic of the individual. Cyclohexanone is obtained through oxidation of cyclohexane or dehydrogenation of phenol. Approx. 95% of its manuf. is used for the production of nylon. Information on toxicity to human beings is fragmentary. Acute exposure is characterized by irritation of the eyes, nose, and throat. In two persons, drowsiness and renal impairment were found; Like cyclohexanol, cyclohexanone is not carcinogenic and is only moderately toxic, with a TLV of 25 ppm for the vapor. It is an irritant.; The great majority of cyclohexanone is consumed in the production of precursors to Nylon 66 and Nylon 6. About half of the world's supply is converted to adipic acid, one of two precursors for nylon 66. For this application, the KA oil (see above) is oxidized with nitric acid. The other half of the cyclohexanone supply is converted to the oxime. In the presence of sulfuric acid catalyst, the oxime rearranges to caprolactam, a precursor to nylon 6:; however, there were embryotoxic effects and influence on reproduction Cyclohexanone is well absorbed through the skin, respiratory tract, and alimentary tract. The main metabolic pathway leads to cyclohexanol, which is excreted in urine coupled with glucuronic acid. A high correlation was found between the concentration of cyclohexanone in the working environment and its concentration in urine. Cyclohexanone is formed from the hydrocarbons cyclohexane and 1-, 2-, and 3-hexanol. A patient's case report documents the development of anosmia (an olfactory disorder) and rhinitis caused by occupational exposure to organic solvents, including cyclohexanone (PMID: 10476412, 16925936, 16477465); however, these workers were also exposed to other compounds. Hepatic disorders were found in a group of workers exposed for over five years. In animals, cyclohexanone is characterized by relatively low acute toxicity (DL50 by intragastric administration is approx. 2 g/kg body wt.). Effects on the central nervous system (CNS) were found (narcosis), as well as irritation of the eyes and skin. Following multiple administration, effects were found in the CNS, liver, and kidneys as well as irritation of the conjunctiva. Mutagenic and genotoxic effects were found, but no teratogenic effects were detected

CAS Number

108-94-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
ANON	biospider
Anone	biospider
Cicloesanone	biospider
Cyclic ketone	biospider
Cyclohexanon	biospider
Cyclohexanone [UN1915] [Flammable liquid]	biospider
Cyclohexanone homopolymer	biospider
Cyclohexanone, acs	biospider
Cyclohexanone, homopolymer	biospider
Cyclohexyl ketone	biospider
CYH	biospider
Cykloheksanon	biospider
FEMA 3909	db_source
Hexanon	biospider
Hytrol o	biospider
Hytrolo	biospider
Ketocyclohexane	db_source
Ketohexamethylene	biospider
Nadone	db_source
Oxocyclohexane	db_source
Pimelic ketone	biospider
Pimelin ketone	biospider
Rcra waste number u057	HMDB
Sextone	db_source

Chemical Formula

C6H10O

IUPAC name

cyclohexanone

InChI Identifier

InChI=1S/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2

InChI Key

JHIVVAPYMSGYDF-UHFFFAOYSA-N

Isomeric SMILES

O=C1CCCCC1

Average Molecular Weight

98.143

Monoisotopic Molecular Weight

98.073164942

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

cyclohexanones (CHEBI:17854 )
a small molecule (CYCLOHEXANONE )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	0.81	HANSCH,C ET AL. (1995)
Experimental Water Solubility	25 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point	Mp -45° (-32°)	DFC

Foods of Origin