undecylenic acids


Summary: Salts and derivatives of undecylenic acid.

Top Publications

  1. Moy T, Ferguson P, Grange A, Matchett W, Kelliher V, Brumley W, et al. Development of separation systems for polynuclear aromatic hydrocarbon environmental contaminants using micellar electrokinetic chromatography with molecular micelles and free zone electrophoresis. Electrophoresis. 1998;19:2090-4 pubmed
    ..These additional classes of analytes are separated by capillary zone electrophoresis/laser-induced fluorescence detection using a frequency-doubled laser operated at 257 nm. ..
  2. Ho I, Yang S, Chiu W, Huang S. Structure and polymer form of poly-3-hydroxyalkanoates produced by Pseudomonas oleovorans grown with mixture of sodium octanoate/undecylenic acid and sodium octanoate/5-phenylvaleric acid. Int J Biol Macromol. 2007;40:112-8 pubmed
    ..T(g) of the products fell between those of pure PHO and pure PHPV. By means of DSC analysis and fractionation method, the PHA obtained was regarded as a random copolymer...
  3. González Paz R, Lligadas G, Ronda J, Galià M, Ferreira A, Boccafoschi F, et al. Enhancement of fatty acid-based polyurethanes cytocompatibility by non-covalent anchoring of chondroitin sulfate. Macromol Biosci. 2012;12:1697-705 pubmed publisher
    ..Cytotoxicity and cell morphology analysis using osteoblast cell line MG63 showed that PU-CS films are suitable materials for cell growth, spreading, and differentiation. ..
  4. Lens J, Terlingen J, Engbers G, Feijen J. Preparation of heparin-like surfaces by introducing sulfate and carboxylate groups on poly(ethylene) using an argon plasma treatment. J Biomater Sci Polym Ed. 1998;9:357-72 pubmed
    ..The ratio of carboxylate/sulfate groups at the plasma treated surfaces was dependent on the composition of the precoated surfaces. The minimum surface density of these groups on the resulting samples was about one group per 40 A2. ..
  5. Yadav M, Kavadia M, Vadgama R, Odaneth A, Lali A. Green enzymatic production of glyceryl monoundecylenate using immobilized Candida antarctica lipase B. Prep Biochem Biotechnol. 2017;47:1050-1058 pubmed publisher
    ..Optimized GMU synthesis in the present study can be used as a useful reference for industrial synthesis of fatty acid esters of glycerol by the enzymatic route. ..
  6. Horrocks A. Prontosan wound irrigation and gel: management of chronic wounds. Br J Nurs. 2006;15:1222, 1224-8 pubmed
    ..This article discusses the cause of chronicity within a wound and discusses in depth three of the ten patients in the evaluation. ..
  7. McLain N, Ascanio R, Baker C, Strohaver R, Dolan J. Undecylenic acid inhibits morphogenesis of Candida albicans. Antimicrob Agents Chemother. 2000;44:2873-5 pubmed
    ..Of 10 liners tested, 2 were found to inhibit the switch from the yeast form to hyphae and a third was found to stimulate this switch. The inhibitor was determined to be undecylenic acid. ..
  8. Chen X, Su Z, Horner J, Newcomb M. Oxidation of 10-undecenoic acid by cytochrome P450(BM-3) and its Compound I transient. Org Biomol Chem. 2011;9:7427-33 pubmed publisher
    ..The kinetic parameters for oxidation of the substrate by P450(BM-3) under turnover conditions were similar to those of the Compound I transient even though the products differed. ..
  9. Feugmo C, Champagne B, Caudano Y, Cecchet F, Chabal Y, Liégeois V. Towards modelling the vibrational signatures of functionalized surfaces: carboxylic acids on H-Si(111) surfaces. J Phys Condens Matter. 2012;24:124111 pubmed publisher
    ..Two exceptions to this are the two ?(Si-H) modes which are active in both spectroscopies. Finally, we compare our simulated spectra with some experimental measurements and we find an overall good agreement. ..

More Information


  1. Lin M, Wu H, Kou H, Wu S. Simple fluorimetric liquid chromatographic method for the analysis of undecylenic acid and zinc undecylenate in pharmaceutical preparations. J Chromatogr A. 2006;1119:264-9 pubmed
    ..Application of the method to the analysis of undecylenic acid and zinc undecylenate in ointment, powder and solution preparations proved feasible. ..
  2. van der Steen M, Stevens C. Undecylenic acid: a valuable and physiologically active renewable building block from castor oil. ChemSusChem. 2009;2:692-713 pubmed publisher
    ..2 10-Undecenoic acid or undecylenic acid is a fatty acid derived from castor oil that, owing to its bifunctional nature, has many possibilities to develop sustainable applications. ..
  3. Guo J, Wang W, Hu J, Xie D, Gerhard E, Nisic M, et al. Synthesis and characterization of anti-bacterial and anti-fungal citrate-based mussel-inspired bioadhesives. Biomaterials. 2016;85:204-17 pubmed publisher
  4. Yin H, Brown T, Wilkinson J, Eason R, Melvin T. Submicron patterning of DNA oligonucleotides on silicon. Nucleic Acids Res. 2004;32:e118 pubmed
    ..The method will offer much potential for the creation of nano- and micro-scale DNA biosensor devices in silicon. ..
  5. Raku T, Kitagawa M, Shimakawa H, Tokiwa Y. Enzymatic synthesis of hydrophilic undecylenic acid sugar esters and their biodegradability. Biotechnol Lett. 2003;25:161-6 pubmed
    ..6-O-(10-Undecylenoyl) D-glucose, 6-O-(10-undecylenoyl) trehalose and 1'-O-(10-undecylenoyl) sucrose were obtained. The influence of structural variation by changing the sugar moiety was analyzed the surface tension and biodegradability. ..
  6. DaSilva J, van Lier J. Synthesis and structure-affinity of a series of 7 alpha-undecylestradiol derivatives: a potential vector for therapy and imaging of estrogen-receptor-positive cancers. J Med Chem. 1990;33:430-4 pubmed
    ..The potential to use the 7 alpha-undecylestradiol as a vector for site-selective delivery of diagnostic and therapeutic moieties to estrogen-receptor-positive human cancers is discussed. ..
  7. Gleeson J, Heade J, Ryan S, Brayden D. Stability, toxicity and intestinal permeation enhancement of two food-derived antihypertensive tripeptides, Ile-Pro-Pro and Leu-Lys-Pro. Peptides. 2015;71:1-7 pubmed publisher
    ..There is potential to make on oral dosage form once in vivo pharmacology is confirmed. ..
  8. Hao J, Granowski P, Stefan M. Zinc undecylenate catalyst for the ring-opening polymerization of caprolactone monomers. Macromol Rapid Commun. 2012;33:1294-9 pubmed publisher
  9. McDonough V, Stukey J, Cavanagh T. Mutations in erg4 affect the sensitivity of Saccharomyces cerevisiae to medium-chain fatty acids. Biochim Biophys Acta. 2002;1581:109-18 pubmed
    ..These results indicate that yeast require ergosterol for optimal growth on certain MCFAs. We discuss the role ergosterol may have in cells responding to exogenous MCFAs and in supporting optimal cell growth. ..
  10. Lluch C, Ronda J, Galià M, Lligadas G, Cadiz V. Rapid approach to biobased telechelics through two one-pot thiol-ene click reactions. Biomacromolecules. 2010;11:1646-53 pubmed publisher
    ..UDA-based thelechelic diol prepared using this methodology was reacted with 4,4'-methylenebis(phenylisocyanate) and 1,4-butanediol as the chain extender to obtain multiblock poly(ester urethane). ..
  11. Ahlstrom D, Hoyos Y, Arslan H, Akbay C. Binary mixed micelles of chiral sodium undecenyl leucinate and achiral sodium undecenyl sulfate: I. Characterization and application as pseudostationary phases in micellar electrokinetic chromatography. J Chromatogr A. 2010;1217:375-85 pubmed publisher
    ..Free energies of transfer of selected functional groups in each surfactant systems were also calculated and found to be in good agreement with the LSER data. ..
  12. Rehder P, Nguyen T. A new concept in the topical treatment of onychomycosis with cyanoacrylate, undecylenic acid, and hydroquinone. Foot Ankle Spec. 2008;1:93-6 pubmed publisher
    ..Negative mycologic cultures in these 3 groups were 100%, 65%, and 35%, respectively. All patients reported subjective improvement in the first 3 months. ..
  13. Ferreira M, Ranjan S, Correia A, Mäkilä E, Kinnunen S, Zhang H, et al. In vitro and in vivo assessment of heart-homing porous silicon nanoparticles. Biomaterials. 2016;94:93-104 pubmed publisher
    ..0-fold, at 10 min. This study highlights the potential of these peptide-modified nanosystems for future applications in heart diseases. ..
  14. Gao W, Li N, Zong M. Highly regioselective synthesis of undecylenic acid esters of purine nucleosides catalyzed by Candida antarctica lipase B. Biotechnol Lett. 2011;33:2233-40 pubmed publisher
    ..In addition, the lipase displayed excellent operational stability in THF, and retained 96% of its initial activity after reused for five batches. ..
  15. Petrović M, Bonvin D, Hofmann H, Mionić Ebersold M. Fungicidal PMMA-Undecylenic Acid Composites. Int J Mol Sci. 2018;19: pubmed publisher
    ..0125% UA. Furthermore, the embedded filamentation test after 24 h and 48 h showed complete inhibition of the Candida growth at 0.4% UA. ..
  16. Sam S, Touahir L, Salvador Andresa J, Allongue P, Chazalviel J, Gouget Laemmel A, et al. Semiquantitative study of the EDC/NHS activation of acid terminal groups at modified porous silicon surfaces. Langmuir. 2010;26:809-14 pubmed publisher
    ..Results are accounted for by NHS surface adsorption and a kinetic competition between the various EDC-induced surface reactions. ..
  17. Kim M, Shim K, Lee S, Kim Y, Min Y, Kim S. Stimulatory effect of undecylenic acid on mouse osteoblast differentiation. Phytother Res. 2010;24:559-64 pubmed publisher
  18. Mionić Ebersold M, Petrović M, Fong W, Bonvin D, Hofmann H, Milošević I. Hexosomes with Undecylenic Acid Efficient against Candida albicans. Nanomaterials (Basel). 2018;8: pubmed publisher
    ..All these render the here-developed hexosomes with UA efficient and promising anti-Candida agents. ..
  19. Shafran S, Sacks S, Aoki F, Tyrrell D, Schlech W, Mendelson J, et al. Topical undecylenic acid for herpes simplex labialis: a multicenter, placebo-controlled trial. J Infect Dis. 1997;176:78-83 pubmed
    ..Undecylenic acid 15% cream reduces viral shedding in recurrent herpes labialis, but clinical benefits are minimal and largely restricted to patients initiating therapy during the prodrome. ..
  20. Tokiwa Y, Kitagawa M, Raku T. Enzymatic synthesis of arbutin undecylenic acid ester and its inhibitory effect on mushroom tyrosinase. Biotechnol Lett. 2007;29:481-6 pubmed
    ..These results suggest that the arbutin ester inhibits the latter part of the tyrosinase reaction, which consists of hydroxylation and oxidation. ..
  21. Difonzo E, Scarfì F, Galeone M. New formulation for topical treatment of onychomycoses. G Ital Dermatol Venereol. 2017;152:432-435 pubmed publisher
    ..If used alone in the cases that meet inclusion criteria for topical treatment, it allowed us to achieve a complete healing just with a 5-month treatment in 60% of cases, data that reached 76% on the follow-up visit. ..
  22. Chong K, Loh K, Vedula S, Lim C, Sternschulte H, Steinmüller D, et al. Cell adhesion properties on photochemically functionalized diamond. Langmuir. 2007;23:5615-21 pubmed
    ..Finally, using capillary injection, a surface gradient of polyethylene glycol could be assembled on top of the diamond surface for the construction of a cell gradient. ..
  23. Chung C, Kim H, Kim Y, Rhee Y. Poly(ethylene glycol)-grafted poly(3-hydroxyundecenoate) networks for enhanced blood compatibility. Int J Biol Macromol. 2003;32:17-22 pubmed
    ..Blood compatibility of polymer networks increased as the fraction of grafted PEG increased. The results of this study suggest that PEG-g-PHU networks might be useful for blood-compatible biomedical applications. ..
  24. Flores Perez R, Zemlyanov D, Ivanisevic A. DNA molecules on GaP (100) surfaces: spectroscopic characterization and biospecificity assessment. Chemphyschem. 2008;9:1528-30 pubmed publisher
  25. Zhong Y, Chong K, May P, Chen Z, Loh K. Optimizing biosensing properties on undecylenic Acid-functionalized diamond. Langmuir. 2007;23:5824-30 pubmed
    ..Non-faradic impedimetric DNA sensing revealed that lightly doped diamond gives better signal transduction sensitivity compared to highly doped diamond. ..
  26. Lu W, Shamsi S, McCarley T, Warner I. On-line capillary electrophoresis-electrospray ionization mass spectrometry using a polymerized anionic surfactant. Electrophoresis. 1998;19:2193-9 pubmed
    ..When a low concentration of this poly-SUS surfactant was added to a volatile EKC buffer, these structurally similar cationic drugs were EKC separated and on-line detected by ESI-MS...
  27. Kim H, Chung C, Kim Y, Rhee Y. Preparation and hydrolytic degradation of semi-interpenetrating networks of poly(3-hydroxyundecenoate) and poly(lactide-co-glycolide). Int J Biol Macromol. 2005;37:221-6 pubmed
    ..These results showed that hydrolysis of PHA could be enhanced by incorporating a second component that lowered the pH of the hydrolysis system. ..
  28. Lluch C, Lligadas G, Ronda J, Galià M, Cadiz V. Thermoplastic polyurethanes from undecylenic acid-based soft segments: structural features and release properties. Macromol Biosci. 2013;13:614-22 pubmed publisher
    ..In addition, given the potential use of these materials for biomedical applications, hydrolytic degradation, their biocompatibility using a human fibroblast cell line, and performance as drug delivery carriers are evaluated. ..
  29. Hashem M, Jun K, Lee E, Lim S, Choo H, Kwon Y. A rapid and sensitive screening system for human type I collagen with the aim of discovering potent anti-aging or anti-fibrotic compounds. Mol Cells. 2008;26:625-30 pubmed
    ..Lactic acid, EGCG, resveratrol, and retinol that can inhibit collagen synthesis effectively in a dose-dependent manner may be used for anti-fibrosis treatment purposes. ..
  30. Lee E, Eom J, Kim H, Kang D, Jun K, Jung D, et al. Neuroprotective effect of undecylenic acid extracted from Ricinus communis L. through inhibition of ?-calpain. Eur J Pharm Sci. 2012;46:17-25 pubmed publisher
    ..These results suggest that UDA is a novel non-peptide-like ?-calpain inhibitor with good cell permeability and potent neuroprotective effect...
  31. Saatchi K, Tod S, Leung D, Nicholson K, Andreu I, Buchwalder C, et al. Characterization of alendronic- and undecylenic acid coated magnetic nanoparticles for the targeted delivery of rosiglitazone to subcutaneous adipose tissue. Nanomedicine. 2017;13:559-568 pubmed publisher
    ..We propose MNPs for targeted delivery of anti-diabetic agents to superficially located subcutaneous adipose tissue. ..
  32. Tabasi O, Falamaki C, Khalaj Z. Functionalized mesoporous silicon for targeted-drug-delivery. Colloids Surf B Biointerfaces. 2012;98:18-25 pubmed publisher
    ..Accordingly this new functionalized PSi may be considered a proper candidate for targeted drug delivery. ..
  33. Piotrowski M, Jantas D, Szczepanowicz K, Łukasiewicz S, Lasoń W, Warszyński P. Polyelectrolyte-coated nanocapsules containing undecylenic acid: Synthesis, biocompatibility and neuroprotective properties. Colloids Surf B Biointerfaces. 2015;135:8-17 pubmed publisher
    ..These data suggest that designed nanocapsules might serve as novel, promising delivery systems for neuroprotective agents. ..
  34. Anguita J, Escutia B, Marí J, Rodriguez M, De La Cuadra J, Aliaga A. Allergic contact dermatitis from undecylenic acid in a commercial antifungal nail solution. Contact Dermatitis. 2002;46:109 pubmed
  35. Ahmed H, Ahlstrom D, Arslan H, Guzel M, Akbay C. Study of chemical selectivity of molecular binary mixed micelles of sodium 10-undecenyl sulfate and sodium N-undecenyl leucinate using linear solvation energy relationships model. J Chromatogr A. 2012;1236:207-14 pubmed publisher
    ..Selectivity differences between pseudostationary phases were also compared by plotting the log k values against each other and were found to agree well with LSER results. ..
  36. Isard O, Leveque M, Knol A, Aries M, Khammari A, Nguyen J, et al. Anti-inflammatory properties of a new undecyl-rhamnoside (APRC11) against P. acnes. Arch Dermatol Res. 2011;303:707-13 pubmed publisher
    ..acnes, confirming its potential interest in inflammatory acne. ..
  37. Froner E, D Amato E, Adamo R, Prtljaga N, Larcheri S, Pavesi L, et al. Deoxycholate as an efficient coating agent for hydrophilic silicon nanocrystals. J Colloid Interface Sci. 2011;358:86-92 pubmed publisher
    ..Results indicate that deoxycholate is a stabilizer of luminescent silicon nanocrystals. Deoxycholate coated nanocrystals appear suitable for applications as multifunctional probes in biomedicine. ..
  38. Tellman K, Palmer C. Polymers of sodium-N-undec-10-ene-1-oyl taurate and sodium-N-undec-10-ene-1-oyl aminoethyl-2-phosphonate as pseudostationary phases for electrokinetic chromatography. Electrophoresis. 1999;20:152-61 pubmed
    ..The polymers do exhibit unique selectivity, but the differences in selectivity are not significant for the majority of compounds studied. ..
  39. Bourne N, Ireland J, Stanberry L, Bernstein D. Effect of undecylenic acid as a topical microbicide against genital herpes infection in mice and guinea pigs. Antiviral Res. 1999;40:139-44 pubmed
  40. Tokiwa Y, Kitagawa M, Raku T, Yanagitani S, Yoshino K. Enzymatic synthesis of arbutin undecylenic acid ester and its inhibitory effect on melanin synthesis. Bioorg Med Chem Lett. 2007;17:3105-8 pubmed
    ..9 M, the conversion rate was more than 90% under addition of 2 M undecylenic acid vinyl ester. The obtained arbutin ester significantly suppressed melanin production in murine B16 melanoma cells. ..
  41. Bousquet E, Spadaro A, Santagati N, Scalia S, Ronsisvalle G. Determination of undecylenic and sorbic acids in cosmetic preparations by high performance liquid chromatography with electrochemical detection. J Pharm Biomed Anal. 2002;30:947-54 pubmed
    ..45 V. The analytical method developed in this study is suitable for quality control assays of complex cosmetic formulations containing sorbic and/or UA. ..
  42. Simon Colin C, Gouin C, Lemechko P, Schmitt S, Senant A, Kervarec N, et al. Biosynthesis and characterization of polyhydroxyalkanoates by Pseudomonas guezennei from alkanoates and glucose. Int J Biol Macromol. 2012;51:1063-9 pubmed publisher
    ..Molecular weights determined by GPC ranged from 119000 and 530000 g/mol. The biosynthesis of natural polyesters with controlled ratio of vinyl-terminated side chains is of great interest for further chemical modifications. ..
  43. Goncalves L, Del Bel Cury A, Sartoratto A, Garcia Rehder V, Silva W. Effects of undecylenic acid released from denture liner on Candida biofilms. J Dent Res. 2012;91:985-9 pubmed
    ..05). Overall, UDA did not prevent Candida biofilm formation. ..
  44. Lee J, Danino D, Raghavan S. Polymerizable vesicles based on a single-tailed fatty acid surfactant: a simple route to robust nanocontainers. Langmuir. 2009;25:1566-71 pubmed publisher
    ..DVB-cross-linked UDA vesicles are very stable and cannot be disrupted by detergents like Triton X-100. ..
  45. Gonzalez Cabo J, Bárcena Asensio M, Gomez Rodriguez F, Amigot Lázaro J. An outbreak of dermatophytosis in pigs caused by Microsporum canis. Mycopathologia. 1995;129:79-80 pubmed
    ..The morbidity was 100% among sows, 95% among new-borns and 75% among feedlot animals. Microsporum canis was also isolated from walls and environmental air. ..