Cyclododecanone

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.^[1]

Cyclododecanone

Names
Preferred IUPAC name Cyclododecanone
Identifiers
CAS Number	830-13-7 Y
3D model (JSmol)	Interactive image
ChemSpider	12690
ECHA InfoCard	100.011.450
PubChem CID	13246
UNII	WL053118A9 Y
CompTox Dashboard (EPA)	DTXSID3027322
InChI InChI=1S/C12H22O/c13-12-10-8-6-4-2-1-3-5-7-9-11-12/h1-11H2 Key: SXVPOSFURRDKBO-UHFFFAOYSA-N
SMILES C1CCCCCC(=O)CCCCC1
Properties
Chemical formula	C12H22O
Molar mass	182.307 g·mol−1
Appearance	white solid
Melting point	60.8 °C (141.4 °F; 333.9 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

History and synthesis

It was first obtained by Ružička et al. in 1926 by ketonic decarboxylation.^[2] A higher-yield method by acyloin condensation was devised by Prelog et al. in 1947.^[3]

It is now industrially produced by the oxidation of cyclododecane via cyclododecanol.^[4]

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.^[5] It is also precursor to cyclohexadecanone, which is used in some fragrances.^[6]

Pimagedine-cyclodecanone hydrazone.

Hydrazone formation with pimagedine leads to a hypoglycemic formula.^[7] Notice that the shape of the molecule can be made to appear like a pharmacy cross symbol.