![Acetonide skeletal](https://upload.wikimedia.org/wikipedia/commons/2/22/Acetonide_skeletal.svg)
In
organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; ...
, an acetonide is the
functional group
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest ...
composed of the
cyclic
Cycle, cycles, or cyclic may refer to:
Anthropology and social sciences
* Cyclic history, a theory of history
* Cyclical theory, a theory of American political history associated with Arthur Schlesinger, Sr.
* Social cycle, various cycles in s ...
ketal
In organic chemistry, an acetal is a functional group with the connectivity . Here, the R groups can be organic fragments (a carbon atom, with arbitrary other atoms attached to that) or hydrogen, while the R' groups must be organic fragments no ...
of a
diol with
acetone
Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour.
Acetone is miscib ...
. The more systematic name for this structure is an
isopropyl
In organic chemistry, propyl is a three-carbon alkyl substituent with chemical formula for the linear form. This substituent form is obtained by removing one hydrogen atom attached to the terminal carbon of propane. A propyl substituent is ofte ...
idene ketal. Acetonide is a common
protecting group for 1,2- and 1,3-
diols. The protecting group can be removed by
hydrolysis
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...
of the ketal using dilute aqueous
acid
In computer science, ACID ( atomicity, consistency, isolation, durability) is a set of properties of database transactions intended to guarantee data validity despite errors, power failures, and other mishaps. In the context of databases, a sequ ...
.
Example
The acetonides of small di- and triols, as well as many
sugar
Sugar is the generic name for sweet-tasting, soluble carbohydrates, many of which are used in food. Simple sugars, also called monosaccharides, include glucose, fructose, and galactose. Compound sugars, also called disaccharides or double ...
s and
sugar alcohol
Sugar alcohols (also called polyhydric alcohols, polyalcohols, alditols or glycitols) are organic compounds, typically derived from sugars, containing one hydroxyl group (–OH) attached to each carbon atom. They are white, water-soluble solids ...
s, are common. The hexaol
mannitol
Mannitol is a type of sugar alcohol used as a sweetener and medication. It is used as a low calorie sweetener as it is poorly absorbed by the intestines. As a medication, it is used to decrease pressure in the eyes, as in glaucoma, and to lo ...
reacts with
2,2-dimethoxypropane to give the bis-acetonide, which oxidizes to give the acetonide of glyceraldehyde:
:(CHOHCHOHCH
2OH)
2 + 2 (MeO)
2CMe
2 → (CHOHCHCH
2O
2CMe
2)
2 + 4 MeOH
:(CHOHCHOCH
2OCMe
2)
2 +
→ 2 OCHCHCH
2O
2CMe
2 + H
2O
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
Corticosteroids are a class of steroid hormones that are produced in the adrenal cortex of vertebrates, as well as the synthetic analogues of these hormones. Two main classes of corticosteroids, glucocorticoids and mineralocorticoids, are involv ...
are used in
dermatology
Dermatology is the branch of medicine dealing with the skin.''Random House Webster's Unabridged Dictionary.'' Random House, Inc. 2001. Page 537. . It is a speciality with both medical and surgical aspects. A dermatologist is a specialist medical ...
, because their increased
lipophilicity
Lipophilicity (from Greek λίπος "fat" and φίλος "friendly"), refers to the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such non-polar solvents are themselves lipop ...
leads to better penetration into the skin.
*
Fluclorolone acetonide
Fluclorolone acetonide (INN, or flucloronide, USAN
280px, "Samguk Sagi" Book 04. Silla's Records. In 512, Usan-guk(于山國)was Ulleungdo(鬱陵島)
Usan-guk, or the State of Usan, occupied Ulleung-do and the adjacent islands dur ...
*
Fluocinolone acetonide
Fluocinolone acetonide is a corticosteroid primarily used in dermatology to reduce skin inflammation and relieve itching. It is a synthetic hydrocortisone derivative. The fluorine substitution at position 9 in the steroid nucleus greatly enhances ...
*
Triamcinolone acetonide
Triamcinolone acetonide, sold under the brand name Kenalog among others, is a synthetic corticosteroid medication used topically to treat various skin conditions, to relieve the discomfort of mouth sores, and by injection into joints to trea ...
See also
*
Acetophenide
In organic chemistry, acetophenide is a functional group which is composed of the cyclic ketal of a diol with acetophenone. In pharmaceutical chemistry, it is present in algestone acetophenide (dihydroxyprogesterone acetophenide) and amcinafide ( ...
*
Acroleinide
In organic chemistry, acroleinide is a functional group which is composed of a cyclic ketal of a diol with acrolein. In pharmaceutical chemistry, it is present in acrocinonide (triamcinolone acroleinide).
See also
* Acetonide
* Acetophenide
* ...
*
Aminobenzal In organic chemistry, aminobenzal is a functional group which is composed of a cyclic ketal of a diol with 4-dimethylaminobenzylidene. It is seen in triamcinolone aminobenzal benzamidoisobutyrate.
See also
* Acetonide
* Acetophenide
* Acroleinide ...
*
Cyclopentanonide In organic chemistry, cyclopentanonide is a functional group which is composed of a cyclic ketal of a diol with cyclopentanone. It is seen in amcinonide (triamcinolone acetate cyclopentanonide).
See also
* Acetonide
* Acetophenide
* Acroleinide
* ...
*
Pentanonide In organic chemistry, pentanonide is a functional group which is composed of a cyclic ketal of a diol with 3-pentanone. It is seen in amcinafal (triamcinolone pentanonide).
See also
* Acetonide
In organic chemistry, an acetonide is the functio ...
References
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