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Acetyl group
Names
IUPAC name
Acetyl (preferred to ethanoyl)[1][2][3]
Systematic IUPAC name
Methyloxidocarbon(•)[4] (additive)
Identifiers
CAS Number
3170-69-2N
3D model (JSmol)
Interactive image
Abbreviations
Ac
Beilstein Reference
1697938
ChEBI
CHEBI:46887Y
ChemSpider
121499Y
Gmelin Reference
786
PubChem CID
137849
InChI
InChI=1S/C2H3O/c1-2-3/h1H3Y
Key: TUCNEACPLKLKNU-UHFFFAOYSA-NY
SMILES
C[C]=O
Properties
Chemical formula
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).
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Infobox references
Chemical compound
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 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).
^"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. IUPAC–RSC. 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.
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...
Acetyl chloride (CH3COCl) is an acyl chloride derived from acetic acid (CH3COOH). It belongs to the class of organic compounds called acid halides. It...
from the acetylgroup (−C(=O)−CH3) by the presence of an additional oxygen atom. The name acetoxy is the short form of acetyl-oxy. An acetoxy group may be...
E260 as an acidity regulator and as a condiment. In biochemistry, the acetylgroup, derived from acetic acid, is fundamental to all forms of life. When...
an organic esterification reaction with acetic acid. It introduces an acetylgroup into a chemical compound. Such compounds are termed acetate esters or...
reactions in cells; acetyl-CoA is the primary substrate for the Krebs cycle, once it is de-acetylated, it must be re-charged with an acetyl-group in order for...
sodium acetate, and EtOAc for ethyl acetate (as Ac is common symbol for acetylgroup CH3CO).The pseudoelement symbol "Ac" is also sometimes encountered in...
transferring an acetylgroup from acetyl-CoA to form ε-N-acetyllysine. DNA is wrapped around histones, and, by transferring an acetylgroup to the histones...
reactions to release the energy stored in nutrients through the oxidation of acetyl-CoA derived from carbohydrates, fats, and proteins. The chemical energy...
Acetylation is the process where an acetyl functional group is transferred from one molecule (in this case, acetyl coenzyme A) to another. Deacetylation...
into acetyl-CoA (acetyl-Coenzyme A)—which then enters the citric acid cycle (Krebs cycle) and is oxidized for energy. These liver-derived ketone groups include...
identical to carnosine with the exception that it carries an additional acetylgroup. The acetylation makes NAC more resistant to degradation by carnosinase...
neurotransmitter acetylcholine. ChAT catalyzes the transfer of an acetylgroup from the coenzyme acetyl-CoA to choline, yielding acetylcholine (ACh). ChAT is found...
and then TPP connects the acetylgroup after the reaction. The carbonyl group of the acetylgroup reacts with the carbonyl group of the carbon negative ion...
exhaustive halogenation of an acetylgroup (R−C(=O)CH3, where R can be either a hydrogen atom, an alkyl or an aryl group), in the presence of a base. The...
functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo...
that react well with bromine water are phenols, alkenes, enols, the acetylgroup, aniline, and glucose. In addition, bromine water is commonly used to...
β-galactoside transacetylase and GAT) is an enzyme that transfers an acetylgroup from acetyl-CoA to β-galactosides, glucosides and lactosides. It is coded for...
Friedel–Crafts acylation uses acetyl chloride (CH3COCl) as the agent and aluminum chloride (AlCl3) as a catalyst to add an acetylgroup to benzene: This reaction...
thromboxane synthesis. Aspirin acts as an acetylating agent where an acetylgroup is covalently attached to a serine residue in the active site of the...
by enzymes, to further harness the energy from the acetylgroup. The energy from the acetylgroup, in the form of electrons, is used to reduce NAD+ and...
4-acetyl-3,5-dimethylpyrrole-2-carboxylate, where "OEt" = R1 = R3 = Me, and R2 = COOEt. The 4-acetylgroup could easily be converted to a 4-ethyl group...
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