• Source: Acetonide

In organic chemistry, an acetonide is the functional group composed of the cyclic ketal of a diol with acetone. The more systematic name for this structure is an isopropylidene ketal. Acetonide is a common protecting group for 1,2- and 1,3-diols. The protecting group can be removed by hydrolysis of the ketal using dilute aqueous acid.




Example


The acetonides of small di- and triols, as well as many sugars and sugar alcohols, are common. The hexaol mannitol reacts with 2,2-dimethoxypropane to give the bis-acetonide, which oxidizes to give the acetonide of glyceraldehyde:

(CHOHCHOHCH2OH)2 + 2 (MeO)2CMe2 → (CHOHCHCH2O2CMe2)2 + 4 MeOH
(CHOHCHOCH2OCMe2)2 + [O] → 2 OCHCHCH2O2CMe2 + H2O
An example of its use as a protecting group in a complex organic synthesis is the Nicolaou Taxol total synthesis. It is a common protecting group for sugars and sugar alcohols, a simple example being solketal.
The acetonides of corticosteroid are used in dermatology, because their increased lipophilicity leads to better penetration into the skin.

Fluclorolone acetonide
Fluocinolone acetonide
Triamcinolone acetonide




See also


Acetophenide
Acroleinide
Aminobenzal
Cyclopentanonide
Pentanonide




References

Kata Kunci Pencarian:

• Triamsinolon
• Fluosinolon asetonida
• Rinitis alergi
• Triamcinolone acetonide
• Fluocinolone acetonide
• Acetonide
• Triamcinolone
• Topical steroid
• ATC code D07
• Fluocinolone
• Corticosteroid
• Fluclorolone acetonide
• Keloid