Synthesis of the isofatty acid 13-methyl-tetradecanoic acid and its triglyceride


  • S. Zlatanos Chemical Engineering Department , Aristotle University of Thessaloniki
  • K. Laskaridis Chemical Engineering Department , Aristotle University of Thessaloniki
  • E. Koliokota Chemical Engineering Department , Aristotle University of Thessaloniki
  • A. Sagredos Chemical Engineering Department , Aristotle University of Thessaloniki



Isofatty acid, 13-methyl-tetradecanoic acid (iso 15, 0), Isofatty acid 13- methyl-11cis-tetradecenoic acid (iso 15, 1, ω3 c), Triglyceride of 13-methyl-tetradecanoic acid


A new and more convenient synthesis of the isofatty acid 13-methyl-tetradecanoic acid and its triglyceride is described here. This isofatty acid is prepared through elongation of the undecanoic acid chain with isobutyraldehyde according to Wittig by the reaction between bromo-undecanoic acid ethyl ester-triphenylphosphonium salt and sodium methoxide followed by the addition of isobutyraldehyde. Its triglyceride is formed by the esterification of the free isofatty acid with glycerin without catalyst. Its purity was over 99% after high refining over activated silica gel. Total yield was estimated to be 22,8%.


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Bergelson LD, Schemjakin MM 1964 Synthesis of Naturally Occurring Unsaturated Fatty Acids by Sterically Controlled Carbonyl Olefination. Chem. Intl. Ed. Engl. 3, 250-260.

Bergelson LD, Shemyakin MM 1963 Control of the Steric Course of the Wittig Reaction, Stereochemical Studies and Synthetic Applications. Tetrahedron 19, 149-159.

Bergelson LD. Vaver VA, Barsukov LI, Shemyakin MM 1963 Unsaturated Acids and Macrocyclic Lactones, Communication 11. Total Synthesis of cis-8-Hexadecenoic, cis-11-Hexadecenoic (Palmitovaccenic), cis-7-Octadecenoic, and cis-9-Hexacosenoic Acids. Institute for the Chemistry of NaturaI Products, Academy of Sciences, USSR, 8, 1417-1421.

Constantinou-Kokotou V, Kokotos G 1999 Synthesis of optically active lipidic a-amino acids and lipidic 2-amino alcohols. Amino Acids 16, 273-285. PMid:10399016

DGF-Einheitsmethoden, Methode: C-V- 11d - (02). Iodine value according to Wijs. DGF standard methods, 2006.

DGF-Einheitsmethoden, Methode: C-V-2- (06). Determination of acid value and free fatty acid content (acidity). DGF standard methods, 2006. Klein RA, Halliday D, Pittet PG 1980 The use of 13-Methyltetradecanoic Acid As an Indicator of Adipose Tissue Turnover. Lipids 15, 572-579.

Pohnert G, Adolph S, Wichard T 2004 Short synthesis of labeled and unlabeled 6Z,9Z,12Z,15-hexadecatetraenoic acid as metabolic probes for biosynthetic studies on diatoms. Chemistry and Physics of Lipids 131, 159–166. PMid:15351268

Sagredos A.N., Inventor, DE Patent 3643848 C2 1986 Verfahren zur Herstellung hochraffinierter essbarer Glyceridöle mit einem Anteil an ungesättigten Fettsäuren im Triglyceridverband und ihre Verwendung, Proprietor: Natec Institut, Hamburg(DE).

Schroder U, Berger S 2000 The Wittig Reaction with Pyridylphosphoranes. Eur. J. Org. Chem. 2601-2604.<2601::AID-EJOC2601>3.0.CO;2-L

Silk MH, Hahn HH 1954 The isolation and structure of a hexadecatetraenoic acid from South African Pichard oil. Biochem. J. 57, 582–587. PMid:13198806    PMCid:1269807

Sommermeyer K, Weidler B, Sagredos A.N., Remse K., Inventors, EU Patent 0298293 B1, 1998, Fettemulsion, Verfahren zu ihrer Herstellung und ihre Anwendung, Proprietor: Fresenius AG, Oberursel(DE).

Thurnhofer S, Vetter W 2006 Synthesis of (S) - (1) - enantiomers of food relavant (n-5) monoenoic and saturated an teiso – fatty acids by a Wittig reaction. Tetrahedron 63, 1140-1145.

Unbehend M, Scharmann H, Strauss HJ, Billek G 1973 Anwendung der Gelpermeationschromatographie auf die Untersuchung thermisch-oxydativ. Fette Seifen Anstrichmittel 75, 689-696.

Wittig G, Geisler G 1953 Liebigs Ann. Chem. 580, 44-57.

Yang Zhenhua, inventor US Patent 6,214,875b, 1998, Anticancer effects of specific branched-chain fatty acids and related production process, West Covina, CA (USA).




How to Cite

Zlatanos S, Laskaridis K, Koliokota E, Sagredos A. Synthesis of the isofatty acid 13-methyl-tetradecanoic acid and its triglyceride. grasasaceites [Internet]. 2011Dec.30 [cited 2022Dec.6];62(4):462-6. Available from: