4-Pyrone

Last updated • a couple of secsFrom Wikipedia, The Free Encyclopedia
4-Pyrone [1]
4-Pyranone.png
Names
Preferred IUPAC name
4H-Pyran-4-one
Other names
γ-Pyrone
4-Pyranone
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.305 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C5H4O2/c6-5-1-3-7-4-2-5/h1-4H Yes check.svgY
    Key: CVQUWLDCFXOXEN-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C5H4O2/c6-5-1-3-7-4-2-5/h1-4H
    Key: CVQUWLDCFXOXEN-UHFFFAOYAG
  • C1=COC=CC1=O
  • O=C\1/C=C\O/C=C/1
Properties
C5H4O2
Molar mass 96.08
Melting point 32 to 34 °C (90 to 93 °F; 305 to 307 K)
Boiling point 210 to 215 °C (410 to 419 °F; 483 to 488 K)
Hazards
Flash point 101 °C (214 °F; 374 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

4-Pyrone (γ-pyrone or pyran-4-one) is an unsaturated cyclic chemical compound with the molecular formula C5H4O2.It is isomeric with 2-pyrone.

Contents

Preparation

4-Pyrone is prepared via the thermal decarboxylation of chelidonic acid. [2]

Reactions

4-Pyrone and its derivatives react with amines in protic solvents to form 4-Pyridones. [2] [3] [4]

Derivatives

4-Pyrone forms the central core of several natural chemical compounds, [5] including maltol, meconic acid, kojic acid, and of the important class of the Flavones.

Maltol.svg KojicAcid.png
MaltolKojic acid

See also

Related Research Articles

In chemistry, pyran, or oxine, is a six-membered heterocyclic, non-aromatic ring, consisting of five carbon atoms and one oxygen atom and containing two double bonds. The molecular formula is C5H6O. There are two isomers of pyran that differ by the location of the double bonds. In 2H-pyran, the saturated carbon is at position 2, whereas, in 4H-pyran, the saturated carbon is at position 4.

<span class="mw-page-title-main">Nitro compound</span> Organic compound containing an −NO₂ group

In organic chemistry, nitro compounds are organic compounds that contain one or more nitro functional groups. The nitro group is one of the most common explosophores used globally. The nitro group is also strongly electron-withdrawing. Because of this property, C−H bonds alpha (adjacent) to the nitro group can be acidic. For similar reasons, the presence of nitro groups in aromatic compounds retards electrophilic aromatic substitution but facilitates nucleophilic aromatic substitution. Nitro groups are rarely found in nature. They are almost invariably produced by nitration reactions starting with nitric acid.

<span class="mw-page-title-main">Tautomer</span> Structural isomers of chemical compounds that readily interconvert

Tautomers are structural isomers of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the relocation of a hydrogen atom within the compound. The phenomenon of tautomerization is called tautomerism, also called desmotropism. Tautomerism is for example relevant to the behavior of amino acids and nucleic acids, two of the fundamental building blocks of life.

In organic chemistry, the Ugi reaction is a multi-component reaction involving a ketone or aldehyde, an amine, an isocyanide and a carboxylic acid to form a bis-amide. The reaction is named after Ivar Karl Ugi, who first reported this reaction in 1959.

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

2-Pyridone is an organic compound with the formula C
5
H
4
NH(O)
. It is a colourless solid. It is well known to form hydrogen bonded dimers and it is also a classic case of a compound that exists as tautomers.

Pyrones or pyranones are a class of heterocyclic chemical compounds. They contain an unsaturated six-membered lactone ring, which has one oxygen atom and an adjacent ketone functional group. There are two isomers denoted as 2-pyrone and 4-pyrone. The 2-pyrone structure is found in nature as part of the coumarin ring system. 4-Pyrone is found in some natural chemical compounds such as chromone, maltol and kojic acid.

Pyrylium is a cation with formula C5H5O+, consisting of a six-membered ring of five carbon atoms, each with one hydrogen atom, and one positively charged oxygen atom. The bonds in the ring are conjugated as in benzene, giving it an aromatic character. In particular, because of the positive charge, the oxygen atom is trivalent. Pyrilium is a mono-cyclic and heterocyclic compound, one of the oxonium ions.

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

Kojic acid is an organic compound with the formula HOCH2C5H2O2OH. It is a derivative of 4-pyrone that functions in nature as a chelation agent produced by several species of fungi, especially Aspergillus oryzae, which has the Japanese common name koji. Kojic acid is a by-product in the fermentation process of malting rice, for use in the manufacturing of sake, the Japanese rice wine. It is a mild inhibitor of the formation of pigment in plant and animal tissues, and is used in food and cosmetics to preserve or change colors of substances. It forms a bright red complex with ferric ions.

<span class="mw-page-title-main">Boronic acid</span> Organic compound of the form R–B(OH)2

A boronic acid is an organic compound related to boric acid in which one of the three hydroxyl groups is replaced by an alkyl or aryl group. As a compound containing a carbon–boron bond, members of this class thus belong to the larger class of organoboranes.

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

Dehydroacetic acid is an organic compound which has several industrial applications. The compound is classified as a pyrone derivative. It presents as an odorless, colorless to white crystalline powder, almost insoluble in water and moderately soluble in most organic solvents.

<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.

2-Pyrone (α-pyrone or pyran-2-one) is an unsaturated cyclic chemical compound with the molecular formula C5H4O2. It is isomeric with 4-pyrone.

<span class="mw-page-title-main">Jocelyn Field Thorpe</span> British chemist

Sir Jocelyn Field Thorpe FRS was a British chemist who made major contributions to organic chemistry, including the Thorpe-Ingold effect and three named reactions.

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

2-Mercaptopyridine is an organosulfur compound with the formula HSC5H4N. This yellow crystalline solid is a derivative of pyridine. The compound and its derivatives serve primarily as acylating agents. A few of 2-mercaptopyridine’s other uses include serving as a protecting group for amines and imides as well as forming a selective reducing agent. 2-Mercaptopyridine oxidizes to 2,2’-dipyridyl disulfide.

The retro-Diels–Alder reaction is the reverse of the Diels–Alder (DA) reaction, a [4+2] cycloelimination. It involves the formation of a diene and dienophile from a cyclohexene. It can be accomplished spontaneously with heat, or with acid or base mediation.

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

Endothion is an organic compound used as an insecticide and acaricides. It is part of the chemical class of organophosphorus compounds. It is generally described as white crystals with a slight odor. It is used as an insecticide, but not sold in the United States or Canada.

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

Chelidonic acid is a heterocyclic organic acid with a pyran skeleton.

<span class="mw-page-title-main">4-Pyridone</span> Chemical compound

4-Pyridone is an organic compound with the formula C
5
H
4
NH(O)
. It is a colorless solid.

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

Tetronic acid is a chemical compound, classified as a γ-lactone, with the molecular formula C4H4O3.

<span class="mw-page-title-main">6-Amyl-α-pyrone</span> Chemical compound

6-Amyl-α-pyrone, also 6-pentyl-2-pyrone or 6PP, is an unsaturated lactone molecule. It contains two double bonds in the ring and a pentyl substituent at carbon adjacent to the ring oxygen. It is a colorless liquid which possesses characteristic coconut aroma, produced biologically by Trichoderma species. It is found in animal foods, peach, and heated beef.

References

  1. 4H-Pyran-4-one at Sigma-Aldrich
  2. 1 2 Weygand, Conrad (1972). Hilgetag, G.; Martini, A. (eds.). Weygand/Hilgetag Preparative Organic Chemistry (4th ed.). New York: John Wiley & Sons, Inc. pp. 533–534, & 1009. ISBN   0471937495.
  3. Van Allan, J. A.; Reynolds, G. A.; Alessi, J. T.; Chie Chang, S.; C. Joines, R. (1971). "Reactions of 4-pyrones with primary amines. A new class of ionic associates". Journal of Heterocyclic Chemistry. 8 (6): 919–922. doi:10.1002/jhet.5570080606.
  4. Cook, Denys (1963). "The Preparation, Properties, and Structure of 2,6-bis-(Alkyamino)-2,5-heptadien-4-ones". Canadian Journal of Chemistry. 41 (6): 1435–1440. doi:10.1139/v63-195.
  5. Wilk, Wolfram; Waldmann, Herbert; Kaiser, Markus (2009). "Γ-Pyrone natural products—A privileged compound class provided by nature". Bioorganic & Medicinal Chemistry. 17 (6): 2304–2309. doi:10.1016/j.bmc.2008.11.001. PMID   19042133.