Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Patent
1999-04-01
2000-11-28
Carr, Deborah D.
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
554191, C11B 700
Patent
active
061537748
ABSTRACT:
A method for providing a purified conjugated linoleic acid (CLA) is disclosed. The purified conjugated linoleic acid (CLA) is formed by separating by liquid chromatography a 9-cis, 11-trans octadecadienoic acid formed by a novel synthesis of reacting an ester of ricinoleic acid with a tosyl chloride or a mesyl chloride to form a tosylate or mesylate of an ester of ricinoleic acid, and reacting the tosylate or mesylate of an ester of ricinoleic acid with diazabicyclo-undecene. Reacting an ester of ricinoleic acid with a tosyl chloride or a mesyl chloride to form a tosylate or mesylate of an ester of ricinoleic acid, and reacting the tosylate or mesylate of an ester of ricinoleic acid with diazabicyclo-undecene forms a 9-cis, 11-trans octadecadienoic acid having a purity greater than 50%, and separating by liquid chromatography forms a 9-cis, 11-trans octadecadienoic acid having a purity greater than 90%. In one aspect, the liquid chromatography uses a strong acid macroreticular ion exchange resin. In one aspect, the liquid chromatography includes silver ion liquid chromatography.
REFERENCES:
patent: 5554646 (1996-09-01), Cook et al.
A. Cesano et al., "Opposite Effects of Linoleic Acid and Conjugated Linoleic Acid on Human Prostatic Cancer in SCID Mice," Anticancer Research, vol. 18, No. 833-838 (1998) pp. 1429-1434.
M. Sugano et al., "Conjugated Linoleic Acid Modulates Tissue Levels of Chemical Mediators and Immunoglobins in Rats," Lipids vol. 33, No. 5 (1998) pp 521-527.
Y. Li et al, "Conjugated Linoleic Acids Alter Bone Fatty Acid Composition and Reduce ex vivo Prostglandin E2 Biosynthesis in Rats Fed n-6 or n-3 Fatty Acids," Lipids vol. 33, No. 4 (1998) pp 417-425.
N. Sehat et al., "Silver Ion High-Performance Liquid Chromatographic Separation and Identification of Conjugated Linoleic Acid Isomers," Lipids vol. 33, No. 2 (1998) pp 217-221.
K. Houseknecht et al., "Dietary Conjugated Linoleic Acid Normalizes Impaired Glucose Tolerance in the Zucker Diabetic Fatty fa/fa Rat," Biochemical and Biophysical Research Communications 244 (1998) pp. 678-682.
Berdeaux et al, "Large-Scale Synthesis of Methyl cis-9, trans-11-Octadecadienoate from Methyl Ricinoleate," JAOCS, vol. 74, No. 8, pp. 1011-1015 (1997).
S. Visonneau et al., "Conjugated Linoleic Acid Suppresses the Growth of Human Breast Adenocarcinoma Cells in SCID Mice," Anticancer Research, vol. 17, No. 969-974 (1997) pp. 969-974.
H. Frykman et al, "Enrichment of Lesquerolic and Auricolic Acids from Hydrolyzed Lesquerella fendleri and L. gordoni Oil by Crystallization," JAOCS, vol. 74, No. 6, pp. 699-701 (1997).
"Status of lesquerella as an industrial crop," Inform, vol. 8, No. 11 (Nov. 1997) pp. 1169-1175.
J. Kramer et al., "Evaluating Acid and Base Catalysts in the Methylation of Milk and Rumen Fatty Acids with Special Emphasis on Conjugated Dienes and Total trans Fatty Acids," Lipids vol. 32, No. 11 (1997) pp 1219-1228.
"Conjugated linoleic acid offers research promise," Inform, vol. 7, No. 2 (Feb. 1996) pp. 152, 153, 156-159.
K.N. Lee et al, "Conjugated linoleic acid and atherosclerosis in rabbits," Atherosclerosis 108 (1994) pp 19-25.
C. Ip et al., "Conjugated Linoleic Acid Suppresses Mammary Carcinogenesis and Proliferative Activity of the Mammary Gland in the Rat," Cancer Research 54 (Mar. 1, 1994) pp. 1212-1215.
C. Ip et al., "Mammary Cancer Prevention by Conjugated Dienoic Derivative of Linoleic Acid," Cancer Research 51 (Nov. 15, 1991) pp. 6118-6123.
Y. L. Ha et al., "Inhibition of Benzo(a)pyrene-induced Mouse Forestomach Neoplasia by Conjugated Dienoic Derivatives of Linoleic Acid," Cancer Research 50 (Feb. 15, 1990) pp. 1097-1101.
R. O. Adlof et al., "Partial Argentation Resin Chromatography (PARC): I. Effect of Percent Silver on Elution and Separation of Methyl Octadecadienoate Isomers," JAOCS (Sep. 1980) pp. 273-274.
Gunstone et al, "Fatty Acids, Part 29 Methyl 12-Mesyloxyoleate as a Source of Cyclopropane Esters and Conjugated Octadecadienotes," Chem. Phys. Lipids, 6, 147, pp. 121-134 (1971).
Carr Deborah D.
Glantz Douglas G.
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