Volume 4, Number 3 (2019)
Year Launched: 2016
Journal Menu
Previous Issues
Why Us
-  Open Access
-  Peer-reviewed
-  Rapid publication
-  Lifetime hosting
-  Free indexing service
-  Free promotion service
-  More citations
-  Search engine friendly
Contact Us
Email:   service@scirea.org
Home > Journals > SCIREA Journal of Chemistry > Archive > Paper Information

The Practical Synthesis and Purification of cis-11-Octadecenoic Acid: A Component of Inhibition of Endotoxin Response

Volume 4, Issue 3, June 2019    |    PP. 106-112    |PDF (232 K)|    Pub. Date: August 9, 2019
45 Downloads     1321 Views  

Yoshifumi Yuasa, Kasai Chemical Laboratory, 7-7-402 Akashicho, Hiratsuka, Kanagawa, 254-0042, Japan
Akiko Horizoe, Kasai Chemical Laboratory, 7-7-402 Akashicho, Hiratsuka, Kanagawa, 254-0042, Japan

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.

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. Vol. 4 , No. 3 , 2019 , pp. 106 - 112 .


[ 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.

Submit A Manuscript
Review Manuscripts
Join As An Editorial Member
Most Views
by Sergey M. Afonin
2935 Downloads 44132 Views
by Syed Adil Hussain, Taha Hasan Associate Professor
2295 Downloads 20097 Views
by Omprakash Sikhwal, Yashwant Vyas
2366 Downloads 16771 Views
by Munmun Nath, Bijan Nath, Santanu Roy
2263 Downloads 16675 Views
Upcoming Conferences