Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
In organic chemistry, acetyl is a moiety, the acyl with chemical
formula CH3CO. It is sometimes represented by the symbol Ac (not to
be confused with the element actinium). The acetyl group contains a
methyl group single-bonded to a carbonyl. The carbonyl center of an
acyl radical has one nonbonded electron with which it forms a chemical
bond to the remainder R of the molecule. In
IUPAC nomenclature, acetyl
is called ethanoyl, although this term is rarely heard.[citation
needed] The acetyl moiety is a component of many organic compounds,
including acetic acid, the neurotransmitter acetylcholine, acetyl-CoA,
acetylcysteine, and the analgesics acetaminophen (also known as
paracetamol) and acetylsalicylic acid (better known as aspirin).
1.1 In nature
1.2 Synthetic organic and pharmaceutical chemistry
3 See also
The introduction of an acetyl group into a molecule is called
acetylation. In biological organisms, acetyl groups are commonly
transferred from acetyl-CoA to coenzyme A (CoA).
Acetyl-CoA is an
intermediate both in the biological synthesis and in the breakdown of
many organic molecules.
Acetyl-CoA is also created during the second
stage of cellular respiration, the Krebs Cycle, by the action of
pyruvate dehydrogenase on pyruvic acid.
Histones and other proteins are often modified by acetylation. For
example, on the DNA level, histone acetylation by acetyltransferases
(HATs) causes an expansion of chromatin architecture, allowing for
genetic transcription to occur. However, removal of the acetyl group
by histone deacetylases (HDACs) condenses DNA structure, thereby
preventing transcription. In addition to HDACs,
additions are able to bind DNA resulting in DNA methylation, and this
is another common way to block DNA acetylation and inhibit gene
Synthetic organic and pharmaceutical chemistry
Acetylation can be achieved using a variety of methods, the most
common one being via the use of acetic anhydride or acetyl chloride,
often in the presence of a tertiary or aromatic amine base. A typical
acetylation is the conversion of glycine to N-acetylglycine:
H2NCH2CO2H + (CH3CO)2O → CH3C(O)NHCH2CO2H + CH3CO2H
Acetylated organic molecules exhibit increased ability to cross the
selectively permeable blood–brain barrier.
Acetylation helps a given drug reach the brain more quickly, making
the drug's effects more intense and increasing the effectiveness of a
given dose. The acetyl group in acetylsalicylic acid
(aspirin) enhances its effectiveness relative to the natural
anti-inflammatant salicylic acid. In similar manner, acetylation
converts the natural painkiller morphine into the far more potent
There is some evidence that acetyl-
L-carnitine may be more effective
for some applications than L-carnitine.
Acetylation of resveratrol
holds promise as one of the first anti-radiation medicines for human
Histone acetylation and deacetylation
Polyoxymethylene plastic, a.k.a. acetal resin, a thermoplastic
^ "List of Radical Names Beginning from "A"". Nomenclature of Organic
Chemistry, Sections A, B, C, D, E, F, and H, Pergamon Press, Oxford,
1979. Copyright 1979 IUPAC.
^ "R-5.7.1 Carboxylic acids, where acetyl appears as an example".
IUPAC, Commission on Nomenclature of Organic Chemistry. A Guide to
IUPAC Nomenclature of Organic Compounds (Recommendations 1993), 1993,
Blackwell Scientific publications, Copyright 1993 IUPAC.
IUPAC Chemical Nomenclature and Structure Representation Division
(2013). "P-22.214.171.124.1". In Favre, Henri A.; Powell, Warren H.
Nomenclature of Organic Chemistry:
IUPAC Recommendations and Preferred
Names 2013. IUPAC–RSC. ISBN 978-0-85404-182-4.
^ "Acetyl". Chemical Entities of Biological Interest. UK: European
^ Hanson, James A. (2001).
Functional group chemistry. Cambridge, Eng:
Royal Society of Chemistry. p. 11. ISBN 0-85404-627-5.
^ Cox, David L. Nelson, Michael M. (2000). Lehninger principles of
biochemistry (3rd ed.). New York: Worth Publishers.
^ R. M. Herbst and D. Shemin (1943). "Acetylglycine". Organic
Syntheses. ; Collective Volume, 2, p. 11
^ Liu, J; Head, E; Kuratsune, H; Cotman, C. W.; Ames, B. N. (2004).
"Comparison of the effects of
L-carnitine and acetyl-
carnitine levels, ambulatory activity, and oxidative stress biomarkers
in the brain of old rats". Annals of the New York Academy of Sciences.
1033: 117–31. Bibcode:2004NYASA1033..117L.
doi:10.1196/annals.1320.011. PMID 15591009.
^ Koide, Kazunori; Osman, Sami; Garner, Amanda L.; Song, Fengling;
Dixon, Tracy; Greenberger, Joel S.; Epperly, Michael W. (14 April
2011). "The Use of 3,5,4′-Tri-acetylresveratrol as a Potential
Resveratrol Protects Mice from γ-Irradiation-Induced
Death". ACS Medicinal Chemistry Letters. 2 (4): 270–274.
doi:10.1021/ml100159p. PMC 3151144 . PMID 21826253.
Alkene (Allyl, Vinyl)
Alkyl (Methyl, Ethyl, Propyl, Butyl, Pentyl)
C, H, O
See also chemical classification, chemical nomenclature (inorgan