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Carbon monoxide

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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Infobox references

In organic chemistry, acetyl is a moiety, the acyl with chemical formula CH3CO. It is sometimes represented by the symbol Ac[5] (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
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).

Contents

1 Acetylation

1.1 In nature 1.2 Synthetic organic and pharmaceutical chemistry

2 Pharmacology 3 See also 4 References

Acetylation[edit] In nature[edit] 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
Acetyl-CoA
is an intermediate both in the biological synthesis and in the breakdown of many organic molecules. Acetyl-CoA
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.[6] In addition to HDACs, Methyl
Methyl
group additions are able to bind DNA resulting in DNA methylation, and this is another common way to block DNA acetylation and inhibit gene transcription.[citation needed] Synthetic organic and pharmaceutical chemistry[edit] Acetylation
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:[7]

H2NCH2CO2H + (CH3CO)2O → CH3C(O)NHCH2CO2H + CH3CO2H

Pharmacology[edit] Acetylated organic molecules exhibit increased ability to cross the selectively permeable blood–brain barrier.[citation needed] Acetylation
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.[citation needed] 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 heroin (diacetylmorphine). There is some evidence that acetyl- L-carnitine
L-carnitine
may be more effective for some applications than L-carnitine.[8] Acetylation
Acetylation
of resveratrol holds promise as one of the first anti-radiation medicines for human populations.[9] See also[edit]

Acetylaldehyde Acetoxy group Histone
Histone
acetylation and deacetylation Polyoxymethylene plastic, a.k.a. acetal resin, a thermoplastic

References[edit]

^ "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
IUPAC
Nomenclature of Organic Compounds (Recommendations 1993), 1993, Blackwell Scientific publications, Copyright 1993 IUPAC.  ^ IUPAC
IUPAC
Chemical Nomenclature and Structure Representation Division (2013). "P-65.1.7.2.1". In Favre, Henri A.; Powell, Warren H. Nomenclature of Organic Chemistry: IUPAC
IUPAC
Recommendations and Preferred Names 2013. IUPAC–RSC. ISBN 978-0-85404-182-4.  ^ "Acetyl". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute.  ^ Hanson, James A. (2001). Functional group
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. ISBN 1-57259-153-6.  ^ 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
L-carnitine
and acetyl- L-carnitine
L-carnitine
on 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 Prodrug for Resveratrol
Resveratrol
Protects Mice from γ-Irradiation-Induced Death". ACS Medicinal Chemistry Letters. 2 (4): 270–274. doi:10.1021/ml100159p. PMC 3151144 . PMID 21826253. 

v t e

Functional groups

Only carbon, hydrogen and oxygen

Hydrocarbons

Allene Alkene
Alkene
(Allyl, Vinyl) Alkyl
Alkyl
(Methyl, Ethyl, Propyl, Butyl, Pentyl) Alkyne Benzyl Carbene Cumulene Methylene bridge Methylene group Methine Phenyl

Other

Acetoxy Acetyl Acryloyl Acyl Aldehyde Alkoxy (Methoxy) Benzoyl Carbonyl Carboxyl Dioxirane Epoxide Ester Ether Ethylenedioxy Hydroxy Ketone Methylenedioxy Peroxide
Peroxide
(Organic) Ynone

Only one element apart from C, H, O

Nitrogen

Amine Azo compound Cyanate Hydrazone Imide Imine Isocyanate Isonitrile Nitrene Nitrile Nitro compound Nitroso
Nitroso
compound Organic amide Oxime

Phosphorus

Phosphonate Phosphonous

Sulfur

Disulfide Sulfone Sulfonic acid Sulfoxide Thial Thioester Thioether Thioketone Thiol

Selenium

Selenol Selenonic acid Seleninic acid Selenenic acid

Tellurium

Tellurol

Other

Isothiocyanate Phosphoramide Sulfenyl chloride Sulfonamide Thiocyanate

See also chemical classification, chemical nomenclature (inorgan

.