Synthesis of 6-hydroxy δ-lactones and 5,6-dihydroxy eicosanoic/docosanoic acids from meadowfoam fatty acids via a lipase-mediated self-epoxidation

JAOCS, Journal of the American Oil Chemists' Society

Volumn 74, Issue 6, 1997, Pages 719-722

  Frykman, Hans B ^a   Isbell, Terry A ^a  

^a NATIONAL CENTER FOR AGRICULTURAL UTILIZATION RESEARCH   (United States)

Author keywords

5, 13 docosadienoic acid; 5,6 13, 14 Diepoxydocosanoic acid; 5,6 epoxyeicosanoic acid; 5 eicosenoic acid; 6 hydroxy lactones; Dihydroxy eicosanoic acid; Epoxidation; Formic acid; Hydrogen peroxide; Lactonization; Lipase; eicosanolactone

Indexed keywords

LIMNANTHES;

CATALYSIS; CROPS; ENZYMES; ESTERS; HYDROGEN PEROXIDE; SULFURIC ACID; SYNTHESIS (CHEMICAL);

DOCOSANOIC ACIDS; EPOXIDATION; LACTONES; LACTONIZATION; LIPASE; MEADOWFOAM FATTY ACIDS; PERFORMIC ACID;

FATTY ACIDS;

EID: 0031162607     PISSN: 0003021X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11746-997-0207-9     Document Type: Article

References (7)

1. Erhan, S.M., R. Kleiman, and T. Isbell, Estolides from Meadowfoam Oil Fatty Acids and Other Monounsaturated Fatty Acids, J. Am. Oil Chem. Soc. 70:461-465 (1993).
2. Isbell, T.A., and R. Kleiman, Mineral Acid Catalyzed Condensation of Meadowfoam Fatty Acids to Estolides, Ibid. 73: 1091-1107 (1996).
3. Isbell, T.A., and B.A. Plattner, A Highly Regioselective Synthesis of δ-Lactones from Meadowfoam Fatty Acids, Ibid. 74: 153-158 (1997).
4. Fore, S.P., and G. Sumrell, Some Derivatives of 5-Eicosenoic Acid, Ibid. 43:581-584 (1966).
5. Isbell, T.A., and M.S. Mund, Preparation of Secondary Ether Fatty Acids and Esters from Their Hydroxy Fatty Acid Equivalents, U.S. Patent Application 08/654654 (1996).
6. Björkling, F., H.B. Frykman, S.-E. Godfredsen, and O. Kirk, Lipase Catalysed Synthesis of Peroxycarboxylic Acids and Lipase Mediated Oxidations. Tetrahedron 22:4587-4592 (1992).
7. Warwel, S., and M.R. Klaas, Chemo-Enzymatic Epoxidation of Unsaturated Carboxylic Acids, J. Mol. Catal. B: enz. 29-35 (1995).