Cyclohexanone
PubChem CID: 7967
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| Compound Synonyms | CYCLOHEXANONE, 108-94-1, Ketohexamethylene, Pimelic ketone, Sextone, Nadone, Anone, Anon, Cyclohexanon, Hexanon, Hytrol O, ketocyclohexane, oxocyclohexane, Pimelin ketone, Cicloesanone, Cykloheksanon, Hytrolo, Cyclic ketone, NCI-C55005, Cyclohexanon [Dutch], RCRA waste number U057, Caswell No. 270, Cicloesanone [Italian], Cykloheksanon [Polish], NSC 5711, CCRIS 5897, UNII-5QOR3YM052, MFCD00001625, HSDB 186, EINECS 203-631-1, UN1915, EPA Pesticide Chemical Code 025902, 5QOR3YM052, DTXSID6020359, CHEBI:17854, AI3-00041, NSC-5711, CYCLOHEXANONE [MI], CYCLOHEXANONE [FHFI], CYCLOHEXANONE [HSDB], CYCLOHEXANONE [IARC], CHEMBL18850, DTXCID00359, EC 203-631-1, UN 1915, CYCLOHEXANON (DUTCH), CYCLOHEXANONE (IARC), CYH, CICLOESANONE (ITALIAN), CYKLOHEKSANON (POLISH), CAS-108-94-1, RCRA waste no. U057, cylcohexanone, cylohexanone, cyclo-hexanone, 2-cyclohexanone, 4-cyclohexanone, Cyclohexanone,(S), Cyclohexanon(dutch), Caswell no 270, Cyclohexanone ACS grade, BDBM6, Cyclohexanone, 99.8%, WLN: L6VTJ, bmse000405, CYCLOHEXANONE [INCI], Cyclohexanone (ACGIH:OSHA), MLS002152896, BIDD:ER0292, Cyclohexanone, LR, >=99%, Cyclohexanone, p.a., 99.0%, Cyclohexanone, AR, >=99.5%, NSC5711, Cyclohexanone, analytical standard, HMS3039C04, Tox21_202121, Tox21_302750, s6236, STL183287, AKOS000119815, DB02060, FC02353, Cyclohexanone, ACS reagent, >=99.0%, Cyclohexanone, ReagentPlus(R), 99.8%, NCGC00091786-01, NCGC00091786-02, NCGC00256489-01, NCGC00259670-01, 9075-99-4, SMR001224507, Cyclohexanone 5000 microg/mL in Methanol, Cyclohexanone, puriss., >=99.5% (GC), Cyclohexanone, SAJ first grade, >=98.0%, DB-059799, Cyclohexanone, Selectophore(TM), >=99.5%, NS00001732, Cyclohexanone [UN1915] [Flammable liquid], Cyclohexanone, JIS special grade, >=99.0%, Cyclohexanone, Vetec(TM) reagent grade, 98%, EN300-19567, C00414, Cyclohexanone, puriss. p.a., >=99.5% (GC), Q409178, F0001-0185, Z104474256, 203-631-1 |
|---|---|
| Ghose Rule | False |
| Classyfire Kingdom | Organic compounds |
| Topological Polar Surface Area | 17.1 |
| Hydrogen Bond Donor Count | 0.0 |
| Pfizer 3 75 Rule | False |
| Scaffold Graph Level | CC1CCCCC1 |
| Deep Smiles | O=CCCCCC6 |
| Heavy Atom Count | 7.0 |
| Classyfire Class | Organooxygen compounds |
| 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 |
| Scaffold Graph Node Level | OC1CCCCC1 |
| Classyfire Subclass | Carbonyl compounds |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 68.2 |
| Database Name | cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 0.0 |
| Uniprot Id | P10938, P00352, P83916, O89049, P84022, O75496 |
| Iupac Name | cyclohexanone |
| Prediction Hob | 1.0 |
| Class | Carbonyl compounds |
| Veber Rule | True |
| Classyfire Superclass | Organic oxygen compounds |
| Target Id | NPT94 |
| Xlogp | 0.8 |
| Superclass | Organooxygen compounds |
| Subclass | Ketones |
| Gsk 4 400 Rule | True |
| Molecular Formula | C6H10O |
| Scaffold Graph Node Bond Level | O=C1CCCCC1 |
| Prediction Swissadme | 0.0 |
| Inchi Key | JHIVVAPYMSGYDF-UHFFFAOYSA-N |
| Silicos It Class | Soluble |
| Fcsp3 | 0.8333333333333334 |
| Logs | -0.199 |
| Rotatable Bond Count | 0.0 |
| State | Liquid |
| Logd | 0.429 |
| Synonyms | ANON, Anone, Cicloesanone, Cyclic ketone, Cyclohexanon, Cyclohexanone [UN1915] [Flammable liquid], Cyclohexanone homopolymer, Cyclohexanone, acs, Cyclohexanone, homopolymer, Cyclohexyl ketone, CYH, Cykloheksanon, FEMA 3909, Hexanon, Hytrol o, Hytrolo, Ketocyclohexane, Ketohexamethylene, Nadone, Oxocyclohexane, Pimelic ketone, Pimelin ketone, Rcra waste number u057, Sextone, Hytrol O, cyclohexanone |
| Substituent Name | Cyclohexanone, Hydrocarbon derivative, Aliphatic homomonocyclic compound |
| Esol Class | Very soluble |
| Functional Groups | CC(C)=O |
| Compound Name | Cyclohexanone |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 98.0732 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 98.0732 |
| Hydrogen Bond Acceptor Count | 1.0 |
| Molecular Weight | 98.14 |
| Gi Absorption | True |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 0.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aliphatic homomonocyclic compounds |
| Lipinski Rule Of 5 | True |
| Esol | -0.958799 |
| Inchi | InChI=1S/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2 |
| Smiles | C1CCC(=O)CC1 |
| Nring | 1.0 |
| Defined Bond Stereocenter Count | 0.0 |
| Egan Rule | True |
| Taxonomy Direct Parent | Cyclic ketones |
- 1. Outgoing r'ship
FOUND_INto/from Agastache Rugosa (Plant) Rel Props:Reference:https://doi.org/10.1080/0972060x.2012.10644084 - 2. Outgoing r'ship
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FOUND_INto/from Ocimum Basilicum (Plant) Rel Props:Source_db:fooddb_chem_all - 8. Outgoing r'ship
FOUND_INto/from Ocimum Gratissimum (Plant) Rel Props:Reference:ISBN:9788185042114 - 9. Outgoing r'ship
FOUND_INto/from Rheum Palmatum (Plant) Rel Props:Reference:https://doi.org/10.1002/(sici)1099-1026(199601)11:1<57::aid-ffj549>3.0.co;2-k - 10. Outgoing r'ship
FOUND_INto/from Spondias Dulcis (Plant) Rel Props:Reference:https://doi.org/10.1080/10412905.2001.9699686