Tariric acid
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| Names | |
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| Preferred IUPAC name
Octadec-6-ynoic acid | |
| Other names
6-octadecynoic acid
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| Identifiers | |
3D model (JSmol)
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PubChemCID
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CompTox Dashboard(EPA)
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| Properties | |
| C18H32O2 | |
| Molar mass | 280.44 g/mol |
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).
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Tariric acidis anacetylenicfatty acid that can be found in the tallow-wood tree,Ximenia americana.[1]
Léon-Albert Arnaud(1853–1915) was the first scientist to describe the chemical make-up of tariric acid, an extraction from theglucosideof the "tariri plant"found inGuatemala.[2]
Occurrence
[edit]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 ofPicramnia.[3]It appears inPicramnia camboitafrom Brazil,[4]Picramnia carpinteraefrom Guatemala,[5]andPicramnia lindenianafrom Mexico.[6]
Tariric acid also occurs in the herbMarrubium vulgare(White horehound), where it is conjectured to have ananti-fungalrole. It was found to stimulatelipidaccumulation byadipocytesin vitro.[7]
Tariric acid is biosynthesised frompetroselinic acid;both fatty acids have been found together inPicramniaandAlvaradoaspecies.[8][9]The occurrence of tariric acid as the major fatty acid is typical for thePicramniaceae.[10]
Production and chemical behavior
[edit]Tariric acid can be synthesised from commercially available petroselinic acid.[11]
In chemical analysis, tariric acid can be separated from other fatty acids bygas chromatographyof methyl esters; additionally, a separation of unsaturated fatty acids is possible byargentation thin-layer chromatography.[12]
References
[edit]- ^Fatope, Majekodunmi O., Oumar A. Adoum & Yoshio Takeda. (2000) C18 Acetylenic Fatty Acids ofXimenia americanawith Potential Pesticidal Activity.Journal of Agricultural and Food Chemistry48(5): 1872–1874doi:10.1021/jf990550k
- ^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.
- ^Arnaud A (1892). "Sur un novel acide gras non saturé de la sérieC
nH
2n–4O
2"[On a novel unsaturated fatty acid of the seriesC
nH
2n–4O
2].Comptes rendus de l'Académie des Sciences(in French).114:79. - ^Grützner B (1893). "Ueber einen krystallisirten Bestandtheil der Früchte vonPicramnia camboita"[On a crystallized component of the fruit ofPicramnia camboita].Chemiker Zeitung(in German).100:1851.
- ^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.
- ^Grimme C (1912)."Über das Fett vonPicramnia lindeniana"[On the fat ofPicramnia lindeniana].Chemische Revue über die Fett- und Harzindustrie(in German).19(3): 51.doi:10.1002/lipi.19120190305.
- ^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 ofMarrubium vulgareL. 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
- ^G. F. Spencer, R. Kleiman, F. R. Earle & I. A. Wolff. (1970) The trans-6 fatty acids ofPicramnia sellowiiseed oil.Lipids5:285
- ^M. B. Pearl, R. Kleiman & F. R. Earle. (1973) Acetylenic acids ofAlvaradoa amorphoidesseed oil.Lipids8:627
- ^R. Hänsel, 22. Lipide in: R. Hänsel, O. Sticher (Hrsg.)Pharmakognosie Phytopharmazie9. Auflage (2010) 673–674 Springer, HeidelbergISBN978-3-642-00962-4(Google Books)
- ^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.
- ^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.PMID3611285.