Jump to content
 







Main menu
   


Navigation  



Main page
Contents
Current events
Random article
About Wikipedia
Contact us
Donate
 




Contribute  



Help
Learn to edit
Community portal
Recent changes
Upload file
 








Search  



























Create account

Log in
 









Create account
 Log in
 




Pages for logged out editors learn more  



Contributions
Talk
 



















Contents

   



(Top)
 


1Acetylation
 


1.1In nature
 




1.2Synthetic organic and pharmaceutical chemistry
 






2Pharmacology
 




3Etymology
 




4See also
 




5References
 













Acetyl group






العربية
تۆرکجه

Català
Čeština
Dansk
Deutsch
Eesti
Ελληνικά
Español
Euskara
فارسی
Français
Galego

Bahasa Indonesia
Italiano
Magyar
Bahasa Melayu
Nederlands

Nordfriisk
Norsk bokmål
Norsk nynorsk
Polski
Português
Română
Simple English
Slovenčina
Српски / srpski
Srpskohrvatski / српскохрватски
Suomi
Svenska
Türkçe
Українська
Tiếng Vit

 

Edit links
 









Article
Talk
 

















Read
Edit
View history
 








Tools
   


Actions  



Read
Edit
View history
 




General  



What links here
Related changes
Upload file
Special pages
Permanent link
Page information
Cite this page
Get shortened URL
Download QR code
Wikidata item
 




Print/export  



Download as PDF
Printable version
 




In other projects  



Wikimedia Commons
 


















From Wikipedia, the free encyclopedia
 

(Redirected from Acetyl)

Acetyl group
Skeletal formula of acetyl with all implicit hydrogens shown
Names
IUPAC name

Acetyl (preferred to ethanoyl)[1][2][3]

Systematic IUPAC name

Methyloxidocarbon(•)[4] (additive)

Identifiers

CAS Number

3D model (JSmol)

Abbreviations Ac

Beilstein Reference

1697938
ChEBI
ChemSpider

Gmelin Reference

786

PubChem CID

  • InChI=1S/C2H3O/c1-2-3/h1H3 checkY

    Key: TUCNEACPLKLKNU-UHFFFAOYSA-N checkY

  • C[C]=O

Properties

Chemical formula

C2H3O
Molar mass 43.045 g·mol−1
Thermochemistry

Std enthalpy of
formation
fH298)

−15 to −9 kJ mol−1
Related compounds

Related compounds

Acetone
Carbon monoxide
Acetic acid

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

☒N verify (what is checkY☒N ?)

Infobox references

Inorganic chemistry, acetyl is a functional group with the chemical formula −COCH3 and the structure −C(=O)−CH3. It is sometimes represented by the symbol Ac[5][6] (not to be confused with the element actinium). In IUPAC nomenclature, acetyl is called ethanoyl.

The acetyl group contains a methyl group (−CH3) single-bonded to a carbonyl (C=O), making it an acyl group. 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.

The acetyl moiety is a component of many organic compounds, including acetic acid, the neurotransmitter acetylcholine, acetyl-CoA, acetylcysteine, acetaminophen (also known as paracetamol), and acetylsalicylic acid (also known as aspirin).

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 other organic molecules. 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, pyruvate decarboxylation, by the action of pyruvate dehydrogenaseonpyruvic acid.[7]

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.[8]

Synthetic organic and pharmaceutical chemistry[edit]

Acetylation can be achieved using a variety of methods, most commonly with the use of acetic anhydrideoracetyl chloride, often in the presence of a tertiary or aromatic amine base. A typical acetylation is the conversion of glycinetoN-acetylglycine:[9]

Pharmacology[edit]

Acetylated organic molecules exhibit increased ability to cross the selectively permeable blood–brain barrier.[citation needed] 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 may be more effective for some applications than L-carnitine.[10] Acetylation of resveratrol holds promise as one of the first anti-radiation medicines for human populations.[11]

Etymology[edit]

The term was coined by Justus von Liebig in 1839 to denote what he believed to be the radical of the acetic acid, and what we now call the vinyl group (coined in 1851). When it became a scientific consensus that his theory was wrong and the acid had a different radical, the name was carried over to the correct one, but the name of acetylene (coined in 1860) was retained.[12]

See also[edit]

References[edit]

  1. ^ "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-65.1.7.2.1". In Favre, Henri A.; Powell, Warren H. (eds.). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. IUPACRSC. ISBN 978-0-85404-182-4.
  • ^ "Acetyl". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute.
  • ^ Banik, Gregory M.; Baysinger, Grace; Kamat, Prashant V.; Pienta, Norbert, eds. (January 2020). The ACS Guide to Scholarly Communication. Washington, DC: American Chemical Society. doi:10.1021/acsguide.50308. ISBN 978-0-8412-3586-1. S2CID 262269861.
  • ^ Hanson, James A. (2001). Functional group chemistry. Cambridge, Eng: Royal Society of Chemistry. p. 11. ISBN 0-85404-627-5.
  • ^ Patel, Mulchand (June 13, 2014). "The Pyruvate Dehydrogenase Complexes: Structure-based Function and Regulation". The Journal of Biological Chemistry. 289 (24): 16615–16623. doi:10.1074/jbc.R114.563148. PMC 4059105. PMID 24798336.
  • ^ Nelson, David L.; Cox, Michael M. (2000). Lehninger principles of biochemistry (3rd ed.). New York: Worth Publishers. ISBN 1-57259-153-6.
  • ^ Herbst, R. M.; Shemin, D. (1943). "Acetylglycine". Organic Syntheses; Collected Volumes, vol. 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-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 (1): 117–31. Bibcode:2004NYASA1033..117L. doi:10.1196/annals.1320.011. PMID 15591009. S2CID 24221474.
  • ^ 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 Protects Mice from γ-Irradiation-Induced Death". ACS Medicinal Chemistry Letters. 2 (4): 270–274. doi:10.1021/ml100159p. PMC 3151144. PMID 21826253.
  • ^ Constable, Edwin C.; Housecroft, Catherine E. (2020-04-20). "Before Radicals Were Free – the Radical Particulier of de Morveau". Chemistry. 2 (2): 293–304. doi:10.3390/chemistry2020019. ISSN 2624-8549.

  • Retrieved from "https://en.wikipedia.org/w/index.php?title=Acetyl_group&oldid=1223691510"

    Category: 
    Acyl groups
    Hidden categories: 
    Articles with short description
    Short description is different from Wikidata
    Articles needing additional references from January 2016
    All articles needing additional references
    Articles without InChI source
    Articles without KEGG source
    Articles without UNII source
    Articles with changed CASNo identifier
    Articles containing unverified chemical infoboxes
    Chembox image size set
    All articles with unsourced statements
    Articles with unsourced statements from January 2016
    Articles to be expanded from January 2023
    All articles to be expanded
    Articles using small message boxes
     



    This page was last edited on 13 May 2024, at 18:59 (UTC).

    Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization.



    Privacy policy

    About Wikipedia

    Disclaimers

    Contact Wikipedia

    Code of Conduct

    Developers

    Statistics

    Cookie statement

    Mobile view



    Wikimedia Foundation
    Powered by MediaWiki