Tuataric acid
Names
Preferred IUPAC name
(4E,6Z)-Octa-4,6-dienoic acid
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C8H12O2/c1-2-3-4-5-6-7-8(9)10/h2-5H,6-7H2,1H3,(H,9,10)/b3-2-,5-4+
    Key: GVKGXDFZFAFBIW-AWYLAFAOSA-N
  • C/C=C\C=C\CCC(=O)O
Properties
C8H12O2
Molar mass 140.182 g·mol−1
Appearance Colorless Solid
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

Tuataric acid is an organic compound and an unsaturated carboxylic acid. This colourless compound was isolated in 2009 from the cloacal glands of the tuatara, a lizard-like reptile native to New Zealand. Its formal name is (4E,6Z)-octa-4,6-dienoic acid, and it consists of an unusual pair of conjugated alkene units with the E and Z configurations.[1][2]

Tuataric acid can be prepared from pent-4-yn-1-ol through a sequence that begins with the extension of the alkyne terminus by hydroboration and ends with the oxidation of the alcohol.

References

  1. ↑ Flachsbarth, Birte; Fritzsche, Matthias; Weldon, Paul J.; Schulz, Stefan (2009). "Composition of the cloacal gland secretion of tuatara,Sphenodon punctatus". Chemistry & Biodiversity. 6 (1): 1–37. doi:10.1002/cbdv.200800265. PMID 19180453. S2CID 31080296.
  2. ↑ Sarah Everts (February 4, 2009). "Reptile Bouquet". Chemical & Engineering News. American Chemical Society. ISSN 0009-2347.
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