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

1. Triamcinolone acetonide
2. Fluocinolone acetonide
3. Fluclorolone acetonide
4. Topical steroid
5. Triamcinolone
6. Algestone acetonide
7. Corticosteroid
8. Fluocinolone
9. Keloid
10. Descinolone acetonide
11. ATC code D07
12. List of corticosteroids
13. Intravitreal injection
14. Flupamesone
15. Acetal
16. 2,2-Dimethoxypropane
17. Prednisone
18. Cortisol
19. Desonide
20. Betamethasone dipropionate