tariric acid
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{{Chembox
| ImageFile = Tariric acid.svg
| ImageSize = 200px
| ImageAlt = Chemical structure of tariric acid
| PIN = Octadec-6-ynoic acid
| OtherNames = 6-octadecynoic acid
|Section1={{Chembox Identifiers
| CASNo = 544-74-1
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = J6D59J8RYW
| PubChem = 235711
| SMILES = CCCCCCCCCCCC#CCCCCC(=O)O
| ChemSpiderID = 205669
| 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)
| InChIKey = GVZXZHWIIXHZOB-UHFFFAOYAC
| StdInChI = 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)
| StdInChIKey = GVZXZHWIIXHZOB-UHFFFAOYSA-N
}}
|Section2 = {{Chembox Properties
| C = 18 | H = 32 | O = 2
| MolarMass = 280.44 g/mol
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
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|Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
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Tariric acid is an acetylenic fatty acid that can be found in the tallow-wood tree, Ximenia americana.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}}
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.{{cite journal |last=Arnaud |first=Léon-Albert |year=1902 |title=Constitution of Tariric Acid |journal=Journal of the Chemical Society |volume=82 Part 1 |page=[https://books.google.com/books?id=NPU4AAAAMAAJ&q=Guatemala 342]}} and {{cite journal |title=Abstracts of Papers on Organic Chemistry |journal=JCS.Abstracts |year=1902 |page=[https://archive.org/details/sim_journal-of-the-chemical-society-abstracts_1902_82_part-i/page/342/mode/1up 342]}}
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.{{cite journal |last=Arnaud |first=A. |year=1892 |title=Sur un novel acide gras non saturé de la série {{chem|C|n|H|2n–4|O|2}} |trans-title=On a novel unsaturated fatty acid of the series {{chem|C|n|H|2n–4|O|2}} |journal=Comptes rendus de l'Académie des Sciences |volume=114 |page=79 |lang=fr}} It appears in Picramnia camboita from Brazil,{{cite journal |last=Grützner |first=B. |year=1893 |title=Ueber einen krystallisirten Bestandtheil der Früchte von Picramnia camboita |trans-title=On a crystallized component of the fruit of Picramnia camboita |journal=Chemiker Zeitung |volume=100 |page=1851 |lang=de}} Picramnia carpinterae from Guatemala,{{cite journal |last=Grimme |first=Cl. |year=1910 |title=Über einige seltene Ölfrüchte |trans-title=On some rare oilseeds |journal=Chemische Revue über die Fett- und Harzindustrie |volume=17 |issue=7 |page=156 |doi=10.1002/lipi.19100170705 |url=https://zenodo.org/record/1522944 |lang=de}} and Picramnia lindeniana from Mexico.{{cite journal |last=Grimme |first=Cl. |year=1912 |title=Über das Fett von Picramnia lindeniana |trans-title=On the fat of Picramnia lindeniana |journal=Chemische Revue über die Fett- und Harzindustrie |volume=19 |issue=3 |page=51 |doi=10.1002/lipi.19120190305 |url=https://zenodo.org/record/2521180 |lang=de}}
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.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}}
Tariric acid is biosynthesised from petroselinic acid; both fatty acids have been found together in Picramnia and Alvaradoa species.G. F. Spencer, R. Kleiman, F. R. Earle & I. A. Wolff. (1970) The trans-6 fatty acids of Picramnia sellowii seed oil. Lipids 5:285M. B. Pearl, R. Kleiman & F. R. Earle. (1973) Acetylenic acids of Alvaradoa amorphoides seed oil. Lipids 8:627 The occurrence of tariric acid as the major fatty acid is typical for the Picramniaceae.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}} ([https://books.google.com/books?id=GXCmaxpNAkYC&pg=PA674 Google Books])
Production and chemical behavior
Tariric acid can be synthesised from commercially available petroselinic acid.{{cite journal | vauthors = Stuhlfauth T, Fock H, Huber H, Klug K | title = The distribution of fatty acids including petroselinic and tariric acids in the fruit and seed oils of the Pittosporaceae, Araliaceae, Umbelliferae, Simaroubaceae and Rutaceae | journal = Biochemical Systematics and Ecology | volume = 13 | issue = 4 | year = 1985 | pages = 447–453 | doi = 10.1016/0305-1978(85)90091-2| bibcode = 1985BioSE..13..447S }}
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.{{cite journal |author1=B. Breuer, T. Stuhlfauth |author2=H. P. Fock | title = Separation of fatty acids or methyl esters including positional and geometric isomers by alumina argentation thin-layer chromatography | journal = J. Chromatogr. Sci. | volume = 25 | year = 1987 | pages = 302–306 | url = http://chromsci.oxfordjournals.org/content/25/7/302.abstract | doi = 10.1093/chromsci/25.7.302 | issue = 7 | pmid=3611285}}