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cyclododecanone
Sign in to saveCyclododecanone is an organic compound with the formula (CH2)11CO. It is a cyclic ketone that exists as a white solid at room temperature. Like its smaller analogs but unlike the larger ones, it has a camphor-like odor. ==History and synthesis== It was first obtained by Ružička et al. in 1926 by ketonic decarboxylation. A higher-yield method by acyloin condensation was devised by Prelog et al. in 1947.
Chemical data
- Formula
- C12H22O
- Molecular weight
- 182.3 g/mol
- IUPAC name
- cyclododecanone
- SMILES
- C1CCCCCC(=O)CCCCC1
- InChIKey
- SXVPOSFURRDKBO-UHFFFAOYSA-N
- XLogP
- 4.2
- Polar surface area
- 17.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 182.167
Show 4 more facts
- chemical formula
- C₁₂H₂₂O
- canonical SMILES
- C1CCCCCC(=O)CCCCC1
- melting point
- 61.0
- Commons category
- Cyclododecanone
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- History and synthesis
- Uses
- References
Cyclododecanone is an organic compound with the formula (CH2)11CO. It is a cyclic ketone that exists as a white solid at room temperature. Like its smaller analogs but unlike the larger ones, it has a camphor-like odor. ==History and synthesis== It was first obtained by Ružička et al. in 1926 by ketonic decarboxylation. A higher-yield method by acyloin condensation was devised by Prelog et al. in 1947.
It is now industrially produced by the oxidation of cyclododecane via cyclododecanol. ==Uses== Cyclododecanone is oxidized on an industrial scale to give the corresponding dicarboxylic acid 1,12-dodecanedioic acid and laurolactam, which are precursors to certain specialized nylons. It is also precursor to cyclohexadecanone, which is used in some fragrances.
Excerpted from Wikipedia’s “cyclododecanone” article, available under the CC BY-SA 4.0 licence.