Tuataric acid

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Tuataric acid
TuataricAcid.png
Names
IUPAC name
(4E,6Z)-Octa-4,6-dienoic acid
Identifiers
Properties
C8H12O2
Molar mass 140.18 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[edit]

  1. ^ "Composition of the cloacal gland secretion of tuatara,Sphenodon punctatus". Chemistry & Biodiversity. 6: 1–37. 2009. doi:10.1002/cbdv.200800265. 
  2. ^ Sarah Everts (February 4, 2009). "Reptile Bouquet". Chemical & Engineering News. American Chemical Society. ISSN 0009-2347.