Tuataric acid

Tuataric acid
Names
	Preferred IUPAC name (4E,6Z)-Octa-4,6-dienoic acid
Identifiers
CAS Number	1147102-65-5 [EPA];
3D model (JSmol)	Interactive image;
ChemSpider	(4E,6E): 4519120;
PubChem CID	28766189;
CompTox Dashboard (EPA)	DTXSID801046815 ;
	InChI 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;
	SMILES C/C=C\C=C\CCC(=O)O;
Properties
Chemical formula	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). verify (what is ?) 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

^ 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.
^ Sarah Everts (February 4, 2009). "Reptile Bouquet". Chemical & Engineering News. American Chemical Society. ISSN 0009-2347.

[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.

[1]

[2]