Acetyl
81632
224132218
2008-07-07T13:32:30Z
Puppy8800
5404759
iw
[[Image:Acetyl.png|thumb|Chemical structure of an acetyl group bound to the remainder R of a molecule.]]
In [[organic chemistry]], '''acetyl''' (ethanoyl), is a [[functional group]], the [[acyl]] of [[acetic acid]], with [[chemical formula]] -[[Carbon|C]][[Oxygen|O]][[Carbon|C]][[Hydrogen|H]]<sub>3</sub>. It is sometimes abbreviated as '''Ac''' (not to be confused with the [[Chemical element|element]] [[actinium]]). The acetyl radical contains a [[methyl]] group single-bonded to a [[carbonyl]]. The [[carbon]] of the carbonyl has a lone [[electron]] available, with which it forms a [[chemical bond]] to the remainder ''R'' of the molecule.
The acetyl radical is a component of many [[organic compound]]s, including the [[neurotransmitter]] [[acetylcholine]], and [[acetyl-CoA]], and the [[analgesic]]s [[acetaminophen]] and acetylsalicylic acid (better known as [[aspirin]]).
==Acetylation==
The introduction of an acetyl group into a molecule is called [[acetylation]] (or ethanoylation). In biological organisms, acetyl groups are commonly transferred bound to [[Coenzyme A]] (CoA), in the form of acetyl-CoA. Acetyl-CoA is an important intermediate both in the biological synthesis and in the breakdown of many organic molecules.
Acetyl groups are also frequently added to [[histone]]s and other [[protein]]s modifying their properties. For example, on the DNA level, histone acetylation by [[acetyltransferase]]s (HATs) causes an expansion of chromatin architecture allowing for [[Transcription (genetics)|genetic transcription]] to take place. Conversely, removal of the acetyl group by [[histone deacetylase]]s (HDACs) condenses DNA structure, thereby preventing transcription.<ref>{{cite journal |author=North B, Verdin E |title=Sirtuins: Sir2-related NAD-dependent protein deacetylases |journal=Genome Biol |volume=5 |issue=5 |pages=224 |year=2004 |pmid=15128440 | doi = 10.1186/gb-2004-5-5-224}}</ref>
Chemical [[acetylation]] can be achieved using a variety of methods, most commonly by the use of [[acetic anhydride]] or [[acetyl chloride]] in the presence of a tertiary or aromatic [[amine]] [[base (chemistry)|base]].
==Pharmacology==
When acetyl groups are bound to certain other organic molecules, they impart an increased ability to cross the [[blood-brain barrier]]. This makes the drug reach the brain more quickly, making the drug's effects more intense and increasing the effectiveness of a given dose. Acetyl groups are used to make the natural [[anti-inflammatant]] [[salicylic acid]] into the more effective [[acetylsalicylic acid]], or [[aspirin]]. Similarly, they make the natural painkiller [[morphine]] into [[diacetylmorphine]], or [[heroin]].
==References==
<references/>
== See also ==
* [[Acetoxy group]]
* [[Functional group]]
* [[Histone acetylation and deacetylation]]
[[Category:functional groups]]
{{orgchem-stub}}
[[da:Acetyl]]
[[de:Acetylgruppe]]
[[fr:Acétyle]]
[[hu:Acetilcsoport]]
[[nl:Acetyl]]
[[ja:アセチル基]]
[[nb:Acetyl]]
[[nn:Acetyl]]
[[pl:Grupa acetylowa]]
[[pt:Acetila]]
[[fi:Asetyyli]]
[[sv:Acetyl]]
[[zh:乙酰基]]