Tariric acid

Tariric acid is an acetylenic fatty acid that can be found in the tallow-wood tree, Ximenia americana.^[1]

Tariric acid

Names
Preferred IUPAC name Octadec-6-ynoic acid
Other names 6-octadecynoic acid
Identifiers
CAS Number	544-74-1 Y
3D model (JSmol)	Interactive image
ChemSpider	205669
PubChem CID	235711
UNII	J6D59J8RYW Y
CompTox Dashboard (EPA)	DTXSID10284475
InChI InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-11,14-17H2,1H3,(H,19,20) Key: GVZXZHWIIXHZOB-UHFFFAOYSA-N InChI=1/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-11,14-17H2,1H3,(H,19,20) Key: GVZXZHWIIXHZOB-UHFFFAOYAC
SMILES CCCCCCCCCCCC#CCCCCC(=O)O
Properties
Chemical formula	C18H32O2
Molar mass	280.44 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Léon-Albert Arnaud (1853–1915) was the first scientist to describe the chemical make-up of tariric acid, an extraction from the glucoside of the "tariri plant" found in Guatemala.^[2]

Occurrence

Tariric acid has been found in several oils and fats of plant origin. It was first isolated in 1892 from the seed oil of a species of Picramnia.^[3] It appears in Picramnia camboita from Brazil,^[4] Picramnia carpinterae from Guatemala,^[5] and Picramnia lindeniana from Mexico.^[6]

Tariric acid also occurs in the herb Marrubium vulgare (White horehound), where it is conjectured to have an anti-fungal role. It was found to stimulate lipid accumulation by adipocytes in vitro.^[7]

Tariric acid is biosynthesised from petroselinic acid; both fatty acids have been found together in Picramnia and Alvaradoa species.^[8][9] The occurrence of tariric acid as the major fatty acid is typical for the Picramniaceae.^[10]

Production and chemical behavior

Tariric acid can be synthesised from commercially available petroselinic acid.^[11]

In chemical analysis, tariric acid can be separated from other fatty acids by gas chromatography of methyl esters; additionally, a separation of unsaturated fatty acids is possible by argentation thin-layer chromatography.^[12]