The Practical Synthesis and Purification of cis-11-Octadecenoic Acid: A Component of Inhibition of Endotoxin Response
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Author(s)
Abstract
cis-11-Octadecenoic acid 1, which is known to be a useful chemical for the component of drugs, has been synthesized by Wittig reaction with n-heptanal and 10-methoxycarbonyldecyltriphenylphosphonium bromide using potassium t-butoxide at –50 °C to give methyl cis-11-octadecenoate 2 in 79% yield with 95% cis-selectivity, followed by hydrolysis and then recrystallizated by MeOH at –20 °C to give a high purity of 1 in 33% yield.
Keywords
cis-11-Octadecenoic acid; Asclepic acid; Wittig reaction; Potassium t-butoxide; cis-Selectivity.
Cite this paper
Yoshifumi Yuasa, Akiko Horizoe,
The Practical Synthesis and Purification of cis-11-Octadecenoic Acid: A Component of Inhibition of Endotoxin Response
, SCIREA Journal of Chemistry.
Volume 4, Issue 3, June 2019 | PP. 106-112.
References
[ 1 ] | I. D. Morton and A. Todd, “The Haemolytic Acid present in Horse Brain” R. Biochem. J., Vol. 47, pp. 327-330, 1950. |
[ 2 ] | K. Hofmann, R. A. Lucas and S. M. Sax, “The Chemical Nature of The Fatty Acids of Lactobacilus Arabinosus” J. Biol. Chem., Vol. 195, pp. 473-485, 1952. |
[ 3 ] | K. Hofmann and S. Sax, “The Chemical Nature of the Fatty Acids of Lactobacilus Casei” J. Biol. Chem., Vol. 205, pp. 55-66, 1953. |
[ 4 ] | M. Mullarkey, J. R. Rose, J. Bristol, T. Kawata, A. Kimura, S. Kobayashi, M. Przetak, J. Chow, F. Gusovsky, J. William,. W. J. Christ, P. Daniel and D. P. Rossignol, “Inhibition of Endotoxin Response by E5564, a Novel Toll-Like Receptor 4-Directed Endotoxin Antagonist” J. Pharmacol. Exp. Ther., Vol. 304, pp. 1093-1102, 2003, W. J. Christ, D. P. Rossignol, S. Kobayashi and T. Kawata, US Patent 5935938, 1999. |
[ 5 ] | K. Ahmad, F. M. Bumpus and F. M. Strong, “Synthesis of cis-11-Octadecenoic and trans-11-ctadecenoic (Vaccenic) Acids” J. Amer. Chem. Soc., Vol. 70, pp. 3391-3394, 1948. |
[ 6 ] | S. A. Fusari, K. W. Greenlee and J. B. Brown, “Synthesis of Cis- and Trans-7- and 8-Octadecenoic Acids: Comparison of the Properities of Cis- and Trans-6-, 7-, 8-, 9-, and 11-Octadecenoic Acids” J. Amer. Oil. Chem., Vol. 28, pp. 416-420, 1951. |
[ 7 ] | W. F. Huber, “A Study of n-Octadecenoic Acids. Synthesis of cis- and trans-7- through 12- and of 17-Octadecenoic Acids” J. Amer. Chem. Soc., Vol. 73, pp. 2730-2735, 1951. |
[ 8 ] | D. G. Bounds; R. P. Linstead, and B. C. L. Weedon, “Anodic Synthesis. Part XII. Synthesis of cis- and trans-Octadec-11-enoic Acid, with a Note on the Nature of Vaccenic Acid.” J. Chem. Soc., pp. 4219-4224, 1954. |
[ 9 ] | G. Pattenden and B. C. L. Weedon, “Carotenoids and Related Compounds. Part XVIII. Synthesis of cis- and Di-cis-Polyenes by Reactions of the Wittig Type” J. Chem. Soc. (C), pp. 1984-1992, 1968. |
[ 10 ] | S. Ranganathan, V. Maniktala, R. Kumar and G. P. Singh,”Metamorphosis of Gastor Oil to Inset Sex-pheromones & Useful Synthons ” Indian J. Chem., Vol. 23B, pp. 1197-1207, 1984. |
[ 11 ] | A. Maercker, “The Wittig Reaction”Organic Reaction, Vol. 14, pp. 270-490, 1965. |
[ 12 ] | U. M. Dzhemilev, G. G. Balezina, L. A. Volkova, V. P. Krivonogov and G. A. Tolstikov, “Insect Pheromones and Their Analogs III. Synthesis of the Sex Attractants of Some Lepidoptera” Chemistry of Natural Compounds, Vol. 16, pp. 82-85, 1980, Khimiya Prirodnykh Soedinenii, Vol. 16, pp. 97-102, 1980. |