Chemistry:Penta-2,3-dienedioic acid

Penta-2,3-dienedioic acid

(R) enantiomer (S) enantiomer
Names
IUPAC name Penta-2,3-dienedioic acid
Other names 1,3-Allenedicarboxylic acid Diacrylic acid Glutinic acid 2,3-Pentadienedioic acid
Identifiers
CAS Number	32804-68-5
3D model (JSmol)	Interactive image
ChemSpider	4411426
PubChem CID	135471958
InChI InChI=1S/C5H4O4/c6-4(7)2-1-3-5(8)9/h2-3H,(H,6,7)(H,8,9) Key: FEFVVCZNGBRBSB-UHFFFAOYSA-N
SMILES O=C(O)C=C=CC(O)=O
Properties
Chemical formula	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.

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 (Template: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.