Synthesis of conjugated eicosadienoic acid

Details Synthesis of conjugated eicosadienoic acid Synthesis of conjugated eicosadienoic acid

1999-04-01

2000-12-12

Carr, Deborah D.

Organic compounds -- part of the class 532-570 series

Organic compounds

Fatty compounds having an acid moiety which contains the...

554154, C07C 51347

Patent

active

061601411

ABSTRACT:
A synthesis process for producing 11-cis, 13-trans eicosadienoic acid at room temperature in high yield is disclosed, including providing a tosylate or mesylate of a methyl lesquerolate and 11-cis, 13-trans eicosadienoic acid formed when the tosylate or mesylate reacts with diazabicyclo-undecene. In one aspect, the tosylate of the methyl lesquerolate is formed with tosyl chloride in a pyridine solvent. In one aspect, the mesylate of the methyl lesquerolate is formed with mesyl chloride in acetonitrile and triethyl amine. In one aspect, the tosylate or mesylate is reacted with diazabicyclo-undecene in a polar, non-hydroxylic solvent of acetonitrile to form the preferred isomer of 11-cis, 13-trans eicosadienoic acid at room temperature in high yield.

REFERENCES:
patent: 5554646 (1996-09-01), Cook et al.
patent: 5855917 (1999-01-01), 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 from Hydrolyzed Lesquerella fendeleri 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 atheroslerosis 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 od 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. Adolf et al., "Partial Argentation Resin Chromatography (PARC): I. Effects 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 of Conjugated Octadecadienotes," Chem. Phys. Lipids, 6, 147, pp. 121-134 (1971).

Affiliated with

Also associated with

Rating

Synthesis of conjugated eicosadienoic acid does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Synthesis of conjugated eicosadienoic acid, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis of conjugated eicosadienoic acid will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-219444