Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:47 UTC |
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Update date | 2019-11-26 02:59:11 UTC |
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Primary ID | FDB003418 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Cyclohexanone |
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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 |
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CAS Number | 108-94-1 |
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Structure | |
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Synonyms | Synonym | Source |
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Cyclohexyl ketone | ChEBI | Ketocyclohexane | ChEBI | Ketohexamethylene | ChEBI | Oxocyclohexane | ChEBI | ANON | HMDB | Anone | HMDB | Cicloesanone | HMDB | Cyclic ketone | HMDB | Cyclohexanon | HMDB | Cyclohexanone homopolymer | HMDB | Cykloheksanon | HMDB | Hexanon | HMDB | Hytrol O | HMDB | Hytrolo | HMDB | Nadone | HMDB | Pimelic ketone | HMDB | Pimelin ketone | HMDB | Rcra waste number u057 | HMDB | Sextone | HMDB | Cyclohexanone [UN1915] [Flammable liquid] | biospider | Cyclohexanone, acs | biospider | Cyclohexanone, homopolymer | biospider | CYH | biospider | FEMA 3909 | db_source | Hytrol o | biospider |
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Predicted Properties | |
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Chemical Formula | C6H10O |
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IUPAC name | cyclohexanone |
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InChI Identifier | InChI=1S/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2 |
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InChI Key | JHIVVAPYMSGYDF-UHFFFAOYSA-N |
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Isomeric SMILES | O=C1CCCCC1 |
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Average Molecular Weight | 98.143 |
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Monoisotopic Molecular Weight | 98.073164942 |
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Classification |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbonyl compounds |
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Direct Parent | Cyclic ketones |
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Alternative Parents | |
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Substituents | - Cyclic ketone
- Organic oxide
- Hydrocarbon derivative
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Biological location: Source: |
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Role | Industrial application: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Liquid | |
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Physical Description | Not Available | |
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Mass Composition | C 73.43%; H 10.27%; O 16.30% | DFC |
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Melting Point | Mp -45° (-32°) | DFC |
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Boiling Point | Bp15 47° | DFC |
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Experimental Water Solubility | 25 mg/mL at 25 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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Experimental logP | 0.81 | HANSCH,C ET AL. (1995) |
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Experimental pKa | pKa 16.7 | DFC |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | d204 0.95 | DFC |
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Refractive Index | n20D 1.4500 | DFC |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-052f-9000000000-033d5d3e517e312e7ca4 | 2015-03-01 | View Spectrum | GC-MS | Cyclohexanone, non-derivatized, GC-MS Spectrum | splash10-052b-9000000000-7f647b6a300fe214ba1c | Spectrum | GC-MS | Cyclohexanone, non-derivatized, GC-MS Spectrum | splash10-052f-9000000000-88641988de1851f0ca4a | Spectrum | GC-MS | Cyclohexanone, non-derivatized, GC-MS Spectrum | splash10-0a4l-9000000000-ef33444a3514a2701f27 | Spectrum | GC-MS | Cyclohexanone, non-derivatized, GC-MS Spectrum | splash10-052f-9000000000-e12b443f04b3874cc4a3 | Spectrum | GC-MS | Cyclohexanone, non-derivatized, GC-MS Spectrum | splash10-052f-9000000000-6c26c5016354e3daff39 | Spectrum | GC-MS | Cyclohexanone, non-derivatized, GC-MS Spectrum | splash10-0a4m-9000000000-cc5c0d1047cc29ad4505 | Spectrum | GC-MS | Cyclohexanone, non-derivatized, GC-MS Spectrum | splash10-052b-9000000000-7f647b6a300fe214ba1c | Spectrum | GC-MS | Cyclohexanone, non-derivatized, GC-MS Spectrum | splash10-052f-9000000000-88641988de1851f0ca4a | Spectrum | GC-MS | Cyclohexanone, non-derivatized, GC-MS Spectrum | splash10-0a4l-9000000000-ef33444a3514a2701f27 | Spectrum | GC-MS | Cyclohexanone, non-derivatized, GC-MS Spectrum | splash10-052f-9000000000-e12b443f04b3874cc4a3 | Spectrum | GC-MS | Cyclohexanone, non-derivatized, GC-MS Spectrum | splash10-052f-9000000000-6c26c5016354e3daff39 | Spectrum | GC-MS | Cyclohexanone, non-derivatized, GC-MS Spectrum | splash10-0a4m-9000000000-cc5c0d1047cc29ad4505 | Spectrum | Predicted GC-MS | Cyclohexanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-052f-9000000000-676979762c05de37295f | Spectrum | Predicted GC-MS | Cyclohexanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-001i-9000000000-ca81dd5928fb0f8c16fc | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0036-9000000000-f3a92fc2703dc2e7ac49 | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0036-9000000000-96a8b1e4fcd8526498c7 | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive | splash10-052b-9000000000-61827fde8b35540ae236 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive | splash10-052f-9000000000-88641988de1851f0ca4a | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive | splash10-0a4l-9000000000-a54e798882ebeac562d5 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive | splash10-052f-9000000000-6a7154ca19de3cc98715 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive | splash10-052f-9000000000-b22778e6dc417b973b8d | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive | splash10-0a4m-9000000000-cc5c0d1047cc29ad4505 | 2012-08-31 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-9000000000-7d7a09c152ff6936e906 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-9000000000-1ccd9e64aac47d6a0d5b | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9000000000-7df9b0d241ad009abf2f | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-9000000000-9faec66ab8e398a57ac8 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-9000000000-9faec66ab8e398a57ac8 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00kg-9000000000-7ab3d0ee8fbd2e735805 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-9000000000-21c5ae8d52f2e0f4cd33 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-9000000000-be188196f07ccf1be01c | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0002-9000000000-f4aaa1a445ebe821a986 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0532-9000000000-b4fe4dffc288586a2cdc | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-9000000000-f7bae72cd20f0ffb5390 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-76725ae76099c3e8afc0 | 2021-09-24 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 7679 |
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ChEMBL ID | CHEMBL18850 |
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KEGG Compound ID | C00414 |
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Pubchem Compound ID | 7967 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 17854 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB02060 |
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HMDB ID | HMDB03315 |
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CRC / DFC (Dictionary of Food Compounds) ID | CXZ75-T:CXZ75-T |
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EAFUS ID | 792 |
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Dr. Duke ID | CYCLOHEXANONE |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | CYH |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | rw1098591 |
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SuperScent ID | Not Available |
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Wikipedia ID | Cyclohexanone |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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minty |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| acetone |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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