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.

Cyclododecanone
Names
Preferred IUPAC name
Cyclododecanone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.450
UNII
  • InChI=1S/C12H22O/c13-12-10-8-6-4-2-1-3-5-7-9-11-12/h1-11H2
    Key: SXVPOSFURRDKBO-UHFFFAOYSA-N
  • C1CCCCCC(=O)CCCCC1
Properties
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

Synthesis

It is produced by the oxidation of cyclododecane via cyclododecanol.[1]

Uses
  • Cyclododecanone is mainly consumed as a precursor to 1,12-dodecanedioic acid and laurolactam, which are precursors to certain specialized nylons.
  • Small amounts are also converted to cyclohexadecanone, which is used in some fragrances.[2]

Drug Use
Pimagedine-cyclodecanone hydrazone.

Hydrazone formation with pimagedine leads to a hypoglycemic formula.[3] Notice that the shape of the molecule can be made to appear like a pharmacy cross symbol.

References
  1. Schiffer, T.; Oenbrink, G. "Cyclododecanol, Cyclododecanone, and Laurolactam" in Ullman’s Encyclopedia of Industrial Chemistry: Wiley-VCH, 2009. doi:10.1002/14356007.a08_201.pub2
  2. Johannes Panten and Horst Surburg "Flavors and Fragrances, 2. Aliphatic Compounds" in Ullmann's Encyclopedia of Industrial Chemistry, 2015, Wiley-VCH, Weinheim.doi:10.1002/14356007.t11_t01
  3. J Nordmann, et al. U.S. Patent 3,746,764 (1973 to Ugine Kuhlmann SA).


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