Tuataric acid
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| Names | |
|---|---|
| IUPAC name
(4E,6Z)-Octa-4,6-dienoic acid
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| Identifiers | |
CompTox Dashboard (EPA)
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| 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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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]
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
- ^ "Composition of the cloacal gland secretion of tuatara,Sphenodon punctatus". Chemistry & Biodiversity. 6: 1–37. 2009. doi:10.1002/cbdv.200800265.