Acetyl group

Source: Wikipedia, the free encyclopedia.
Not to be confused with Acetal.
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
3D model (
JSmol
)
Abbreviations Ac
1697938
ChEBI
ChemSpider
786
  • InChI=1S/C2H3O/c1-2-3/h1H3 checkY
    Key: TUCNEACPLKLKNU-UHFFFAOYSA-N checkY
  • C[C]=O
Properties
C2H3O
Molar mass 43.045 g·mol−1
Thermochemistry
Std enthalpy of
formation
(ΔfH⦵298)
 −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 ?)

In organic 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

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

acetaminophen (also known as paracetamol), and acetylsalicylic acid (also known as aspirin
).

Acetylation

In nature

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 dehydrogenase on pyruvic acid.[7]

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

N-acetylglycine:[9]

Pharmacology

Acetylated organic molecules exhibit increased ability to cross the selectively permeable

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

L-carnitine.[10] Acetylation of resveratrol holds promise as one of the first anti-radiation medicines for human populations.[11]

Etymology

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

References

  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.
  2. ^ "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.
  3. ISBN 978-0-85404-182-4
    .
  4. ^ "Acetyl". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute.
  5. S2CID 262269861
    .
  6. ISBN 0-85404-627-5
    .
  7. PMID 24798336
    .
  8. ISBN 1-57259-153-6
    .
  9. ^ Herbst, R. M.; Shemin, D. (1943). "Acetylglycine". Organic Syntheses; Collected Volumes, vol. 2, p. 11.
  10. S2CID 24221474
    .
  11. PMID 21826253
    .
  12. ISSN 2624-8549
    .
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