# Acetonide

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{{Short description|Chemical compound}}
[[File:Acetonide skeletal.svg|thumb|class=skin-invert-image|General structure of a 1,2-acetonide. The [diol](/source/diol) is shown in blue, the [acetone](/source/acetone) part in red.]]

In [organic chemistry](/source/organic_chemistry), an '''acetonide''' is the [functional group](/source/functional_group) composed of the [cyclic](/source/cyclic_compound) [ketal](/source/ketal) of a [diol](/source/diol) with [acetone](/source/acetone). The more systematic name for this structure is an [isopropyl](/source/isopropyl)idene ketal. Acetonide is a common [protecting group](/source/protecting_group) for 1,2- and 1,3-[diol](/source/diol)s.<ref>{{cite book |title= Protecting Groups |last= Kocieński |first= Philip j. |year= 1994 |publisher= [Thieme Medical Publishers](/source/Thieme_Medical_Publishers) |series= Foundations of Organic Chemistry Series |chapter= 3.2.2: Diol Protecting Groups—Acetals—Isopropylidene Acetals |page=103}}</ref> The protecting group can be removed by [hydrolysis](/source/hydrolysis) of the ketal using dilute aqueous [acid](/source/acid).

==Example==
The acetonides of small di- and triols, as well as many [sugar](/source/sugar)s and [sugar alcohol](/source/sugar_alcohol)s, are common.<ref>{{cite journal|author1=Rychnovsky, S. D.|author2=Rogers, B. N.|author3=Richardson, T. I. |title=Configurational Assignment of Polyene Macrolide Antibiotics Using the [13c]Acetonide Analysis|journal=Acc. Chem. Res.|year=1998|volume=31|pages=9–17|doi=10.1021/AR960223N}}</ref> The hexaol [mannitol](/source/mannitol) reacts with [2,2-dimethoxypropane](/source/2%2C2-dimethoxypropane) to give the bis-acetonide, which oxidizes to give the acetonide of glyceraldehyde:<ref>{{cite journal|title=D-(R)-Glyceraldehyde Acetonide|author1=Christopher R. Schmid|author2=Jerry D. Bryant|journal=Org. Synth.|year=1995|volume=72|page=6|doi=10.15227/orgsyn.072.0006}}</ref><ref>{{cite journal|title=L-(S)-glyceraldehyde Acetonide
|author1=Christian Hubschwerlen|author2=Jean-luc Specklin|author3=J. Higelin|journal=Org. Synth.|year=1995|volume=72|page=1|doi=10.15227/orgsyn.072.0001}}</ref>

:(CHOHCHOHCH<sub>2</sub>OH)<sub>2</sub> + 2 (MeO)<sub>2</sub>CMe<sub>2</sub> → (CHOHCHCH<sub>2</sub>O<sub>2</sub>CMe<sub>2</sub>)<sub>2</sub> + 4 MeOH
:(CHOHCHOCH<sub>2</sub>OCMe<sub>2</sub>)<sub>2</sub> + [O] → 2 OCHCHCH<sub>2</sub>O<sub>2</sub>CMe<sub>2</sub> + H<sub>2</sub>O

An example of its use as a protecting group in a complex organic synthesis is the [Nicolaou Taxol total synthesis](/source/Nicolaou_Taxol_total_synthesis). It is a common protecting group for sugars and sugar alcohols, a simple example being [solketal](/source/solketal).

The acetonides of [corticosteroid](/source/corticosteroid) are used in [dermatology](/source/dermatology), because their increased [lipophilicity](/source/lipophilicity) leads to better penetration into the skin.<ref>{{cite book|title=Medizinische Chemie|page=337|last1=Steinhilber|first1=D|last2=Schubert-Zsilavecz|first2=M|last3=Roth|first3=HJ|publisher=Deutscher Apotheker Verlag|location=Stuttgart|year=2005|isbn=3-7692-3483-9|language=German}}</ref><ref>{{cite journal|author1=Derendorf, H.|author2=Hochhaus, G.|author3=Meibohm, B.|author4=Mollmann, H.|author5=Barth, J.|title=Pharmacokinetics and Pharmacodynamics of Inhaled Corticosteroids|journal=J. Allergy Clin. Immunol.|year=1998|volume=101|pages=S440-S446|doi=10.1016/S0091-6749(98)70156-3|doi-access=free}}</ref>

* [Fluclorolone acetonide](/source/Fluclorolone_acetonide)
* [Fluocinolone acetonide](/source/Fluocinolone_acetonide)
* [Triamcinolone acetonide](/source/Triamcinolone_acetonide)

==See also==
* [Acetophenide](/source/Acetophenide)
* [Acroleinide](/source/Acroleinide)
* [Aminobenzal](/source/Aminobenzal)
* [Cyclopentanonide](/source/Cyclopentanonide)
* [Pentanonide](/source/Pentanonide)

==References==
{{Reflist|2}}

Category:Acetonides

{{organic-chemistry-stub}}

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Adapted from the Wikipedia article [Acetonide](https://en.wikipedia.org/wiki/Acetonide) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Acetonide?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.