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Chemical Compound Review

Ricinolic acid     (Z)-12-hydroxyoctadec-9-enoic acid

Synonyms: Ricinic acid, HSDB 5634, NSC-281242, NSC281242, LS-143811, ...
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Disease relevance of AI3-17956


Psychiatry related information on AI3-17956

  • These structural and functional alterations may contribute to intraluminal accumulation of fluid and catharsis that can result from administration of ricinoleic acid (castor oil) [6].
  • Ricinoleic acid and castor oil poduced a brief initial stimulation followed by polonged inhibition of small bowel motor activity [7].

High impact information on AI3-17956


Chemical compound and disease context of AI3-17956


Biological context of AI3-17956


Anatomical context of AI3-17956


Associations of AI3-17956 with other chemical compounds


Gene context of AI3-17956

  • Evidence for cytochrome b5 as an electron donor in ricinoleic acid biosynthesis in microsomal preparations from developing castor bean (Ricinus communis L.) [13].
  • These include protein disulphide isomerase (PDI), calreticulin and developing-ER-specific oleate-12-hydroxylase involved in the biosynthesis of ricinoleic acid [24].
  • Of the various low HLB primary surfactants tested, only cethyl dimethicone copolyol (Abil EM90), A-B-A block copolymer (Arlacel P135), and polyglycerol ester of ricinoleic acid (Grinstead PGR-90) yielded a stable W/O emulsion [25].
  • Sixteen Pseudomonas aeruginosa strains, including patent strain NRRL B-18602, three recent isolates from composted materials amended with ricinoleic acid, and 12 randomly selected from the holdings of the ARS Culture Collection, were examined for their fatty acid converting abilities [26].
  • TO (10 and 30 mmol/l), BSA (3%), and RA (5 mmol/l) had no inhibitory effect on the ileal absorption of TCA [27].

Analytical, diagnostic and therapeutic context of AI3-17956


  1. Production of conjugated linoleic acids through KOH-catalyzed dehydration of ricinoleic acid. Yang, L., Huang, Y., Wang, H.Q., Chen, Z.Y. Chem. Phys. Lipids (2002) [Pubmed]
  2. Relationship between intestinal microecology and the translocation of intestinal bacteria. Wells, C.L. Antonie Van Leeuwenhoek (1990) [Pubmed]
  3. Production of a novel compound, 7,10,12-trihydroxy-8(E)-octadecenoic acid from ricinoleic acid by Pseudomonas aeruginosa PR3. Kuo, T.M., Kim, H., Hou, C.T. Curr. Microbiol. (2001) [Pubmed]
  4. Pigmented contact cheilitis from ricinoleic acid in lipsticks. Leow, Y.H., Tan, S.H., Ng, S.K. Contact Derm. (2003) [Pubmed]
  5. Lipstick dermatitis caused by ricinoleic acid. Sai, S. Contact Derm. (1983) [Pubmed]
  6. Perfusion of rabbit colon with ricinoleic acid: dose-related mucosal injury, fluid secretion, and increased permeability. Gaginella, T.S., Chadwick, V.S., Debongnie, J.C., Lewis, J.C., Phillips, S.F. Gastroenterology (1977) [Pubmed]
  7. Effects of ricinoleic and oleic acids on the digestive contractile activity of the canine small and large bowel. Stewart, J.J., Bass, P. Gastroenterology (1976) [Pubmed]
  8. Ricinoleic acid stimulation of active anion secretion in colonic mucosa of the rat. Racusen, L.C., Binder, H.J. J. Clin. Invest. (1979) [Pubmed]
  9. Ricinoleic acid effect on the electrical activity of the small intestine in rabbits. Mathias, J.R., Martin, J.L., Burns, T.W., Carlson, G.M., Shields, R.P. J. Clin. Invest. (1978) [Pubmed]
  10. Translocation of indigenous bacteria from the gastrointestinal tract of mice after oral ricinoleic acid treatment. Morehouse, J.L., Specian, R.D., Stewart, J.J., Berg, R.D. Gastroenterology (1986) [Pubmed]
  11. Studies on the metabolism of unsaturated fatty acids. I. Synthesis and identification of 6-hydroxydodec-3-cis-enoic acid, the final metabolite of ricinoleic acid by Escherichia coli K-12. Mizugaki, M., Fukuyama, H., Sakamoto, T., Yamanaka, H. Chem. Pharm. Bull. (1978) [Pubmed]
  12. Allergic contact dermatitis from oleyl alcohol in lipstick cross-reacting with ricinoleic acid in castor oil and lanolin. Tan, B.B., Noble, A.L., Roberts, M.E., Lear, J.T., English, J.S. Contact Derm. (1997) [Pubmed]
  13. Evidence for cytochrome b5 as an electron donor in ricinoleic acid biosynthesis in microsomal preparations from developing castor bean (Ricinus communis L.). Smith, M.A., Jonsson, L., Stymne, S., Stobart, K. Biochem. J. (1992) [Pubmed]
  14. The direct effect of injectable cyclosporine and its vehicle, cremophor, on endothelial vascular cell adhesion molecule-1 expression. Ricinoleic acid inhibits coronary artery endothelial activation. De Caterina, R., Tanaka, H., Nakagawa, T., Hauptman, P.J., Libby, P. Transplantation (1995) [Pubmed]
  15. Lipase-catalyzed esterification of 2-monoricinolein for 1,2 (2,3)-diricinolein synthesis. Turner, C., Wani, S., Wong, R., Lin, J.T., McKeon, T. Lipids (2006) [Pubmed]
  16. Direct modulation of secretory chloride channels by arachidonic and other cis unsaturated fatty acids. Hwang, T.C., Guggino, S.E., Guggino, W.B. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  17. Increased cell loss in the human jejunum induced by laxatives (ricinoleic acid, dioctyl sodium sulphosuccinate, magnesium sulphate, bile salts). Bretagne, J.F., Vidon, N., L'Hirondel, C., Bernier, J.J. Gut (1981) [Pubmed]
  18. Actions of ricinoleic acid and structurally related fatty acids of the gastrointestinal tract. I. Effects on smooth muscle contractility in vitro. Stewart, J.J., Gaginella, T.S., Bass, P. J. Pharmacol. Exp. Ther. (1975) [Pubmed]
  19. Cytotoxicity of ricinoleic acid (castor oil) and other intestinal secretagogues on isolated intestinal epithelial cells. Gaginella, T.S., Haddad, A.C., Go, V.L., Phillips, S.F. J. Pharmacol. Exp. Ther. (1977) [Pubmed]
  20. Effect of propranolol on ricinoleic acid- and deoxycholic acid-induced changes of intestinal electrolyte movement and mucosal permeability. Evidence against the importance of altered permeability in the production of fluid and electrolyte accumulation. Binder, H.J., Dobbins, J.W., Racusen, L.C., Whiting, D.S. Gastroenterology (1978) [Pubmed]
  21. Accumulation of ricinoleic, lesquerolic, and densipolic acids in seeds of transgenic Arabidopsis plants that express a fatty acyl hydroxylase cDNA from castor bean. Broun, P., Somerville, C. Plant Physiol. (1997) [Pubmed]
  22. Inhibitory actions of laxatives on motility and water and electrolyte transport in the gastrointestinal tract. Stewart, J.J., Gaginella, T.S., Olsen, W.A., Bass, P. J. Pharmacol. Exp. Ther. (1975) [Pubmed]
  23. Polyamines are essential for the synthesis of 2-ricinoleoyl phosphatidic acid in developing seeds of castor. Tomosugi, M., Ichihara, K., Saito, K. Planta (2006) [Pubmed]
  24. Proteomic analysis of the endoplasmic reticulum from developing and germinating seed of castor (Ricinus communis). Maltman, D.J., Simon, W.J., Wheeler, C.H., Dunn, M.J., Wait, R., Slabas, A.R. Electrophoresis (2002) [Pubmed]
  25. Preparation of a stable double emulsion (W1/O/W2): role of the interfacial films on the stability of the system. Kanouni, M., Rosano, H.L., Naouli, N. Advances in colloid and interface science. (2002) [Pubmed]
  26. Diversity of oleic acid, ricinoleic acid and linoleic acid conversions among Pseudomonas aeruginosa strains. Kuo, T.M., Nakamura, L.K. Curr. Microbiol. (2004) [Pubmed]
  27. Intestinal bile salts in cystic fibrosis: studies in the patient and experimental animal. Harries, J.T., Muller, D.P., McCollum, J.P., Lipson, A., Roma, E., Norman, A.P. Arch. Dis. Child. (1979) [Pubmed]
  28. Antinociceptive activity of ricinoleic acid, a capsaicin-like compound devoid of pungent properties. Vieira, C., Evangelista, S., Cirillo, R., Terracciano, R., Lippi, A., Maggi, C.A., Manzini, S. Eur. J. Pharmacol. (2000) [Pubmed]
  29. Temporal effects of morphine on rat intestinal transit. Stewart, J.J. Pharmacology (1984) [Pubmed]
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