Tuataric acid

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| Watchedfields = changed

| verifiedrevid = 451275527

| ImageFile = Tuataric acid.svg

| PIN=(4E,6Z)-Octa-4,6-dienoic acid

| Section1 = {{Chembox Identifiers

| CASNo = 1147102-65-5

| CASNo_Ref = {{Cascite|changed|EPA}}

| index1_label = (4E,6E)

| ChemSpiderID1 = 4519120

| PubChem = 28766189

| StdInChI=1S/C8H12O2/c1-2-3-4-5-6-7-8(9)10/h2-5H,6-7H2,1H3,(H,9,10)/b3-2-,5-4+

| StdInChIKey = GVKGXDFZFAFBIW-AWYLAFAOSA-N

| SMILES = C/C=C\C=C\CCC(=O)O

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| Section2 = {{Chembox Properties

| C=8

| H=12

| O=2

| Appearance = Colorless Solid

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| Section3 = {{Chembox Hazards

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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.{{Cite journal | title = Composition of the cloacal gland secretion of tuatara,Sphenodon punctatus | journal = Chemistry & Biodiversity | date = 2009| volume =6 | issue = 1 | pages = 1–37 | doi =10.1002/cbdv.200800265| pmid = 19180453 | last1 = Flachsbarth | first1 = Birte | last2 = Fritzsche | first2 = Matthias | last3 = Weldon | first3 = Paul J. | last4 = Schulz | first4 = Stefan | s2cid = 31080296 }}{{cite journal|title=Reptile Bouquet|author=Sarah Everts|publisher=American Chemical Society|journal=Chemical & Engineering News|date=February 4, 2009|issn=0009-2347}}

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.