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]

References

1. Fatope, Majekodunmi O., Oumar A. Adoum & Yoshio Takeda. (2000) C18 Acetylenic Fatty Acids of Ximenia americana with Potential Pesticidal Activity. Journal of Agricultural and Food Chemistry 48 (5): 1872–1874 doi:10.1021/jf990550k
2. Arnaud LA (1902). "Constitution of Tariric Acid". Journal of the Chemical Society. 82 Part 1: 342. and "Abstracts of Papers on Organic Chemistry". JCS.Abstracts: 342. 1902.
3. Arnaud A (1892). "Sur un novel acide gras non saturé de la série C
   _nH
   _2n–4O
   ₂" [On a novel unsaturated fatty acid of the series C
   _nH
   _2n–4O
   ₂]. Comptes rendus de l'Académie des Sciences (in French). 114: 79.
4. Grützner B (1893). "Ueber einen krystallisirten Bestandtheil der Früchte von Picramnia camboita" [On a crystallized component of the fruit of Picramnia camboita]. Chemiker Zeitung (in German). 100: 1851.
5. Grimme C (1910). "Über einige seltene Ölfrüchte" [On some rare oilseeds]. Chemische Revue über die Fett- und Harzindustrie (in German). 17 (7): 156. doi:10.1002/lipi.19100170705.
6. Grimme C (1912). "Über das Fett von Picramnia lindeniana" [On the fat of Picramnia lindeniana]. Chemische Revue über die Fett- und Harzindustrie (in German). 19 (3): 51. doi:10.1002/lipi.19120190305.
7. Anna Ohtera, Yusaku Miyamae, Naomi Nakai, Atsushi Kawachi, Kiyokazu Kawada, Junkyu Han, Hiroko Isoda, Mohamed Neffati, Toru Akita, Kazuhiro Maejima, Seiji Masuda, Taiho Kambe, Naoki Mori, Kazuhiro Irie, and Masaya Nagao (2013): "Identification of 6-octadecynoic acid from a methanol extract of Marrubium vulgare L. as a peroxisome proliferator-activated receptor γ agonist". Biochemical and Biophysical Research Communications, volume 440, issue 2, pages 204-209. doi:10.1016/j.bbrc.2013.09.003
8. G. F. Spencer, R. Kleiman, F. R. Earle & I. A. Wolff. (1970) The trans-6 fatty acids of Picramnia sellowii seed oil. Lipids 5:285
9. M. B. Pearl, R. Kleiman & F. R. Earle. (1973) Acetylenic acids of Alvaradoa amorphoides seed oil. Lipids 8:627
10. R. Hänsel, 22. Lipide in: R. Hänsel, O. Sticher (Hrsg.) Pharmakognosie Phytopharmazie 9. Auflage (2010) 673–674 Springer, Heidelberg ISBN 978-3-642-00962-4 (Google Books)
11. Stuhlfauth T, Fock H, Huber H, Klug K (1985). "The distribution of fatty acids including petroselinic and tariric acids in the fruit and seed oils of the Pittosporaceae, Araliaceae, Umbelliferae, Simaroubaceae and Rutaceae". Biochemical Systematics and Ecology. 13 (4): 447–453. Bibcode:1985BioSE..13..447S. doi:10.1016/0305-1978(85)90091-2.
12. B. Breuer, T. Stuhlfauth, H. P. Fock (1987). "Separation of fatty acids or methyl esters including positional and geometric isomers by alumina argentation thin-layer chromatography". J. Chromatogr. Sci. 25 (7): 302–306. doi:10.1093/chromsci/25.7.302. PMID 3611285.