Aceturic acid

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Aceturic acid
N-acetylglycine Structural Formula V.1.svg
Names
Preferred IUPAC name
Acetamidoacetic acid
Other names
Acetylglycine
N-Acetylglycine
2-Acetamidoacetic acid
Acetylglycocoll
Identifiers
3D model (JSmol)
AbbreviationsAcGly
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.008.036 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-839-6
PubChem CID
UNII
  • InChI=1S/C4H7NO3/c1-3(6)5-2-4(7)8/h2H2,1H3,(H,5,6)(H,7,8)
    Key: OKJIRPAQVSHGFK-UHFFFAOYSA-N
  • CC(=O)NCC(=O)O
Properties
C4H7NO3
Molar mass 117.104 g·mol−1
AppearanceWhite powder or needles
Melting point 206 to 208 °C (403 to 406 °F; 479 to 481 K)
2.7% at 15 °C
Acidity (pKa)3.67 (H2O) [1]
Related compounds
Related compounds
N-Acetylglycinamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Aceturic acid (N-acetylglycine) is a derivative of the amino acid glycine. The conjugate base of this carboxylic acid is called aceturate, a term used for its esters and salts.

Contents

Preparation

Aceturic acid can be prepared by warming glycine either with a slight excess of acetic anhydride in benzene, [2] or with an equal molar amount of acetic anhydride in glacial (concentrated) acetic acid. [3]

See also

Related Research Articles

<span class="mw-page-title-main">Glycine</span> Amino acid

Glycine (symbol Gly or G; ) is an amino acid that has a single hydrogen atom as its side chain. It is the simplest stable amino acid (carbamic acid is unstable), with the chemical formula NH2CH2‐COOH. Glycine is one of the proteinogenic amino acids. It is encoded by all the codons starting with GG (GGU, GGC, GGA, GGG). Glycine is integral to the formation of alpha-helices in secondary protein structure due to the "flexibility" caused by such a small R group. Glycine is also an inhibitory neurotransmitter – interference with its release within the spinal cord (such as during a Clostridium tetani infection) can cause spastic paralysis due to uninhibited muscle contraction.

<span class="mw-page-title-main">Acetyl group</span> Chemical group, –C(=O)CH₃

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. In IUPAC nomenclature, acetyl is called ethanoyl.

In chemistry, acetylation is an organic esterification reaction with acetic acid. It introduces an acetyl group into a chemical compound. Such compounds are termed acetate esters or simply acetates. Deacetylation is the opposite reaction, the removal of an acetyl group from a chemical compound.

<span class="mw-page-title-main">Acetic anhydride</span> Organic compound with formula (CH₃CO)₂O

Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air.

The Perkin reaction is an organic reaction developed by English chemist William Henry Perkin that is used to make cinnamic acids. It gives an α,β-unsaturated aromatic acid or α-substituted β-aryl acrylic acid by the aldol condensation of an aromatic aldehyde and an acid anhydride, in the presence of an alkali salt of the acid. The alkali salt acts as a base catalyst, and other bases can be used instead.

<span class="mw-page-title-main">Organic acid anhydride</span> Any chemical compound having two acyl groups bonded to the same oxygen atom

An organic acid anhydride is an acid anhydride that is also an organic compound. An acid anhydride is a compound that has two acyl groups bonded to the same oxygen atom. A common type of organic acid anhydride is a carboxylic anhydride, where the parent acid is a carboxylic acid, the formula of the anhydride being (RC(O))2O. Symmetrical acid anhydrides of this type are named by replacing the word acid in the name of the parent carboxylic acid by the word anhydride. Thus, (CH3CO)2O is called acetic anhydride.Mixed (or unsymmetrical) acid anhydrides, such as acetic formic anhydride (see below), are known, whereby reaction occurs between two different carboxylic acids. Nomenclature of unsymmetrical acid anhydrides list the names of both of the reacted carboxylic acids before the word "anhydride" (for example, the dehydration reaction between benzoic acid and propanoic acid would yield "benzoic propanoic anhydride").

4-Dimethylaminopyridine (DMAP) is a derivative of pyridine with the chemical formula (CH3)2NC5H4N. This white solid is of interest because it is more basic than pyridine, owing to the resonance stabilisation from the NMe2 substituent.

<span class="mw-page-title-main">Curtius rearrangement</span> Chemical reaction

The Curtius rearrangement, first defined by Theodor Curtius in 1885, is the thermal decomposition of an acyl azide to an isocyanate with loss of nitrogen gas. The isocyanate then undergoes attack by a variety of nucleophiles such as water, alcohols and amines, to yield a primary amine, carbamate or urea derivative respectively. Several reviews have been published.

Hydrazides in organic chemistry are a class of organic compounds with the formula R−NR1−NR2R3 where R is acyl, sulfonyl, phosphoryl, phosphonyl and similar groups, R1, R2, R3 and R' are any groups. Unlike hydrazine and alkylhydrazines, hydrazides are nonbasic owing to the inductive influence of the acyl, sulfonyl, or phosphoryl substituent.

<span class="mw-page-title-main">Trifluoroacetic acid</span> Chemical compound

Trifluoroacetic acid (TFA) is an organofluorine compound with the chemical formula CF3CO2H. It is a structural analogue of acetic acid with all three of the acetyl group's hydrogen atoms replaced by fluorine atoms and is a colorless liquid with a vinegar-like odor.

<span class="mw-page-title-main">Robinson–Gabriel synthesis</span> Organic reaction

The Robinson–Gabriel synthesis is an organic reaction in which a 2-acylamino-ketone reacts intramolecularly followed by a dehydration to give an oxazole. A cyclodehydrating agent is needed to catalyze the reaction It is named after Sir Robert Robinson and Siegmund Gabriel who described the reaction in 1909 and 1910, respectively.

<span class="mw-page-title-main">Erlenmeyer–Plöchl azlactone and amino-acid synthesis</span>

The Erlenmeyer–Plöchl azlactone and amino acid synthesis, named after Friedrich Gustav Carl Emil Erlenmeyer who partly discovered the reaction, is a series of chemical reactions which transform an N-acyl glycine to various other amino acids via an oxazolone.

Acetyl iodide is an organoiodine compound with the formula CH3COI. It is a colourless liquid. It is formally derived from acetic acid. Although far rarer in the laboratory than the related acetyl bromide and acetyl chloride, acetyl iodide is produced, transiently at least, on a far larger scale than any other acid halide. Specifically, it is generated by the carbonylation of methyl iodide in the Cativa and Monsanto processes, which are the main industrial processes that generate acetic acid. It is also an intermediate in the production of acetic anhydride from methyl acetate.

<span class="mw-page-title-main">Ethenone</span> Organic compound with the formula H2C=C=O

In organic chemistry, ethenone is the formal name for ketene, an organic compound with formula C2H2O or H2C=C=O. It is the simplest member of the ketene class. It is an important reagent for acetylations.

<span class="mw-page-title-main">Trifluoroacetic anhydride</span> Chemical compound

Trifluoroacetic anhydride (TFAA) is the acid anhydride of trifluoroacetic acid. It is the perfluorinated derivative of acetic anhydride.

<span class="mw-page-title-main">Acetic acid</span> Colorless and faint organic acid found in vinegar

Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. It has been used, as a component of vinegar, throughout history from at least the third century BC.

<span class="mw-page-title-main">Formic anhydride</span> Chemical compound

Formic anhydride, also called methanoic anhydride, is an organic compound with the chemical formula C
2
H
2
O
3
and a structural formula of (H(C=O)−)2O. It can be viewed as the anhydride of formic acid (HCOOH).

<span class="mw-page-title-main">1-Tetralone</span> Chemical compound

1-Tetralone is a bicyclic aromatic hydrocarbon and a ketone. In terms of its structure, it can also be regarded as benzo-fused cyclohexanone. It is a colorless oil with a faint odor. It is used as starting material for agricultural and pharmaceutical agents. The carbon skeleton of 1-tetralone is found in natural products such as Aristelegone A (4,7-dimethyl-6-methoxy-1-tetralone) from the family of Aristolochiaceae used in traditional Chinese medicine.

<span class="mw-page-title-main">2-Carboxybenzaldehyde</span> Chemical compound

2-Carboxybenzaldehyde is a chemical compound. It consists of a benzene ring, with an aldehyde and a carboxylic acid as substituents that are ortho to each other. The compound exhibits ring–chain tautomerism: the two substituents can react with each other to form 3-hydroxyphthalide, a cyclic lactol. This lactol reacts readily with Grignard reagents, forming alkyl- and aryl-substituted phthalides. Other benzo-fused heterocyclic compounds can be derived from 2-carboxybenzaldehyde, including isoindolinones and phthalazinones, with a variety of pharmacological properties, such as the antihistamine azelastine.

<span class="mw-page-title-main">Diethyl acetamidomalonate</span> Chemical compound

Diethyl acetamidomalonate (DEAM) is a derivative of malonic acid diethyl ester. Formally, it is derived through the acetylation of ester from the unstable aminomalonic acid. DEAM serves as a starting material for racemates including both, natural and unnatural α-amino acids or hydroxycarboxylic acids. It is also usable as a precursor in pharmaceutical formulations, particularly in the cases of active ingredients like fingolimod, which is used to treat multiple sclerosis.

References

  1. Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 5–88. ISBN   978-1498754286.
  2. Curtius, Th.; Radenhausen, R. (1895). "Hydrazide und Azide organischer Säuren. X Abhandlung. 35. Ueber Hydrazide substituirter Amidosäuren und das Hydrazid der Fumarsäure". J. Prakt. Chem. 52 (1): 433–454. doi:10.1002/prac.18950520134.
  3. Dakin, H. D. (1929). "The Condensation of Aromatic Aldehydes with Glycine and Acetylglycine" (PDF). J. Biol. Chem. 82 (2): 439–446. doi: 10.1016/S0021-9258(20)78291-8 .