Penta-2,3-dienedioic acid

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Penta-2,3-dienedioic acid
Penta-2,3-dienedioic acid.png
(R)-Penta-2,3-dienedioic acid.png
(R) enantiomer
(S)-Penta-2,3-dienedioic acid.png
(S) enantiomer
Names
IUPAC name
5-Hydroxy-5-oxopent-3-enoate
Other names
  • 1,3-Allenedicarboxylic acid
  • Diacrylic acid
  • Glutinic acid
  • Penta-2,3-dienedioic acid
  • 2,3-Pentadienedioic acid
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
Properties
C5H4O4
Molar mass 128.083 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Penta-2,3-dienedioic acid (one of two chemicals called glutinic acid), is in allene-containing dicarboxylic acid. It was the first allene to be synthesized, in 1887, but the structure of it was thought to be a propyne core instead of an allene. The correct structural isomeric identity was not determined until 1954. [1]

Literature confusion

A diterpene, chemical name (4aR,5S,6R,8aR)-5-[(Z)-4-carboxy-3-methylbut-3-enyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid (CID 6444268 from PubChem ), is also called glutinic acid. Some database entries for "glutinic acid" incorrectly identify it as this diterpene rather than the allene meaning in the underlying publications. [2]

Related Research Articles

Acetylene Unsaturated hydrocarbon with formula C2H2

Acetylene (systematic name: ethyne) is the chemical compound with the formula C2H2. It is a hydrocarbon and the simplest alkyne. This colorless gas (lower hydrocarbons are generally gaseous in nature) is widely used as a fuel and a chemical building block. It is unstable in its pure form and thus is usually handled as a solution. Pure acetylene is odorless, but commercial grades usually have a marked odor due to impurities.

Allenes

Allenes are organic compounds in which one carbon atom has double bonds with each of its two adjacent carbon centres. Allenes are classified as cumulated dienes. The parent compound of this class is propadiene, which is itself also called allene. Compounds with an allene-type structure but with more than three carbon atoms are members of a larger class of compounds called cumulenes with X=C=Y bonding.

Alkyne Acyclic hydrocarbon

In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and no other functional groups form a homologous series with the general chemical formula CnH2n−2. Alkynes are traditionally known as acetylenes, although the name acetylene also refers specifically to C2H2, known formally as ethyne using IUPAC nomenclature. Like other hydrocarbons, alkynes are generally hydrophobic.

The compound hydrogen chloride has the chemical formula HCl and as such is a hydrogen halide. At room temperature, it is a colourless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric water vapor. Hydrogen chloride gas and hydrochloric acid are important in technology and industry. Hydrochloric acid, the aqueous solution of hydrogen chloride, is also commonly given the formula HCl.

Terpene Class of oily organic compounds found in plants

Terpenes are a class of natural products consisting of compounds with the formula (C5H8)n. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. Terpenes are further classified by the number of carbons: monoterpenes (C10), sesquiterpenes (C15), diterpenes (C20), etc. A well known monoterpene is alpha-pinene, a major component of turpentine.

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Linoleic acid is an organic compound with the formula COOH(CH2)7CH=CHCH2CH=CH(CH2)4CH3. Both alkene groups are cis. It is a fatty acid sometimes denoted 18:2 (n-6) or 18:2 cis-9,12. A linoleate is a salt or ester of this acid.

Imide

In organic chemistry, an imide is a functional group consisting of two acyl groups bound to nitrogen. The compounds are structurally related to acid anhydrides, although imides are more resistant toward hydrolysis. In terms of commercial applications, imides are best known as components of high-strength polymers, called polyimides. Inorganic imides are also known as solid state or gaseous compounds, and the imido group (=NH) can also act as a ligand.

Carbo-mer

In organic chemistry, a carbo-mer (often carbo-mer or carbomer) is an expanded molecule obtained by insertion of C2 units into a given molecule. Carbo-mers differ from their templates in size but not in symmetry when each C–C single bond is replaced by an alkyne bond C-C≡C-C, each C=C double bond is replaced by an allene bond C=C=C=C, and each C≡C triple bond is replaced by C≡C-C≡C. The size of the carbo-mer continues to increase when more C2 units are inserted, so carbo-mers are also called carbon-molecules, where "n" is the number of acetylene or allene groups in an n-expansion unit. This concept, devised by Rémi Chauvin in 1995, is aimed at introducing new chemical properties for existing chemical motifs.

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Polyyne

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n
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Isocyanic acid

Isocyanic acid is a chemical compound with the structural formula HNCO, which is often written as H–N=C=O. It is a colourless substance, volatile and poisonous, with a boiling point of 23.5 °C. It is the predominant tautomer of cyanic acid H–O–C≡N.

Vinylacetylene

Vinylacetylene is the organic compound with the formula C4H4. The colourless gas was once used in the polymer industry. It is composed of both alkyne and alkene groups and is the simplest enyne.

In organic chemistry, a cycloalkyne is the cyclic analog of an alkyne. A cycloalkyne consists of a closed ring of carbon atoms containing one or more triple bonds. Cycloalkynes have a general formula CnH2n−4. Because of the linear nature of the C–C≡C–C alkyne unit, cycloalkynes can be highly strained and can only exist when the number of carbon atoms in the ring is great enough to provide the flexibility necessary to accommodate this geometry. Large alkyne-containing carbocycles may be virtually unstrained, while the smallest constituents of this class of molecules may experience so much strain that they have yet to be observed experimentally. Cyclooctyne (C8H12) is the smallest cycloalkyne capable of being isolated and stored as a stable compound. Despite this, smaller cycloalkynes can be produced and trapped through reactions with other organic molecules or through complexation to transition metals.

Mercury(II) sulfate

Mercury(II) sulfate, commonly called mercuric sulfate, is the chemical compound Hg S O4. It is an odorless solid that forms white granules or crystalline powder. In water, it separates into an insoluble sulfate with a yellow color and sulfuric acid.

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References

  1. Jones, E. R. H.; Mansfield, G. H.; Whiting, M. C. (1954-01-01). "Researches on acetylenic compounds. Part XLVII. The prototropic rearrangements of some acetylenic dicarboxylic acids". Journal of the Chemical Society (Resumed): 3208–3212. doi:10.1039/JR9540003208. ISSN   0368-1769.
  2. See patents listed for CID 6444268 from PubChem