Abstract
Ten capsaicin analogues were synthesized and their pungency degrees were determined through Scoville Organoleptic Test. The relationship between the structure and pungency degree of these capsaicin analogues was discussed. Then four of these capsaicin analogues with higher pungency degree were picked out and added to anti-biofouling paints as repellents to study their anti-biofouling performance by shallow sea buoyant raft hung-plate experimentation. The results showed that capsaicin and dihydrocapsaicin exhibited equally good anti-biofouling performance while nordihydrocapsaicin and N-vanillylnonanamide had poor anti-biofouling performance. Experimental results also showed that the paints with only 0.1% capsaicin or dihydrocapsaicin as repellent without any other biocides had also exhibited good anti-biofouling performance, which provided a new idea for developing novel, more environment-friendly and Cu2O-free antifouling paints.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Peng BX. A report on the survey and investigation on the international and domestic development trends of the antifouling paints used for oceanic ships. A review report on the workshop of “alternative to DDT usage in the production of antifouling paint” organized by SEPA. Beijing, 2006
Zhou SZ, Peng BX. A comparative study of the antifouling performance of four different capsaicinoids as expellers in antifouling paints. The 14th International Congress on Marine Corrosion and Fouling. Japan, 2008
Peng BX. Some progress of anti-biofouling paints which used capsaicin as expeller. Conference of screening standard and method of the substitution technology for DDT antifouling paint of alternatives to DDT usage in the production of antifouling paint. Organized by SEPA. Qingdao, 2008
Watts JL. Anti-fouling coating composition containing capsaicin. US patent 5397385, 1995
Xu QW, Barrios CA, Cutright T, Newby BMZ. Evaluation of toxicity of capsaicin and zosteric acid and their potential application as antifoulants. Environ Toxicol, 2005, 20(5): 467–474
Xu QW, Barrios CA, Cutright T, Newby BMZ. Assessment of antifouling effectiveness of two natural product antifoulants by attachment study with freshwater bacteria. Environ Sci Pollut Res, 2005, 12(5): 278–284
Shi H, Wang LM. Discussion on nontoxic sodium silicate antifouling paint used in the netting of marine cage. Marine fisheries, 2004, 26(3): 239–242
Cope WG, Bartsch MR, Marking LL. Efficacy of candidate chemicals for preventing attachment of zebra mussels (Dreissena polymorpha). Environ Toxicol Chem, 1997, 16(9): 1930–1934
Angarano MB, McMahon RF, Hawkins DL, Schetz JA. Exploration of structure-antifouling relationships of capsaicin-like compounds that inhibit zebra mussel (Dreissena polymorpha) macrofouling. Biofouling, 2007, 23(5):295–305
Gannett PM, Nagel DL, Reilly PJ, Lawson T, Sharpe J, Toth B. The capsaicinoids — their separation, synthesis, and mutagenicity. J Org Chem, 1988, 53(5):1064–1071
Kaga H, Miura M and Orito K. A facile procedure for synthesis of capsaicin. J Org Chem, 1989, 54(14): 3477–3478
Torsten H, Einar B. Capsaicin derivatives and their synthetic methods and applications. CN patent 1849 068A, 2006
Du WN. Studies on the application of synthesized capsaicin in antifouling paints. Shanghai coatings, 2009, 47(8): 1–4
Zhou SZ, Zhou XF, Peng BX. Synthetic methods of capsaicin analogues. Application No. 2009100877050
Zhan JX, Zhou XZ, Zou LP, Wu WJ. Synthesis of 4-hydroxy-3-methoxyphenyl oxime. J Nat Univ defense technol 2002, 24(2): 17–18, 26
Ramirez FA and Burger A. The reduction of phenolic beta-nitrostyrenes by lithium aluminum hydride. J Am Chem.= Soc, 1950, 72(6): 2781–2782
Milhazes N, Calheiros R, Marques MPM, Garrido J, Cordeiro MNDS, Rodrigues C, Quinteira S, Novais C, Peixe L, Borges F. Beta-nitrostyrene derivatives as potential antibacterial agents: A structure-property-activity relationship study. Bioorg Med Chem, 2006, 14(12): 4078–4088
McNulty J, Steere JA, Wolf S. The ultrasound promoted Knoevenagel condensation of aromatic aldehydes. Tetrahedron Lett, 1998, 39(44): 8013–8016
Ouk S, Thiebaud S, Borredon E, Legars P, Lecomte L. O-methylation of phenolic compounds with dimethyl carbonate under solid/liquid phase transfer system. Tetrahedron Lett, 2002, 43(14): 2661–2663
Paluch G, Bartholomay L, Coats J. Mosquito repellents: A review of chemical structure diversity and olfaction. Pest Management Sci, 2010, 66(9): 925–935
Wang JL, Wang FQ, Yu J, Zhuang Y, Zhou XF, Zhang XB, Peng BX. A survey analysis of heavy metals bio-accumulation in internal organs of sea shell animals affected by the sustainable pollution of antifouling paints used for ships anchored at some domestic maritime spaces. China Sci Bull, 2008. 53(16): 2471–2475
Huang ZG. Marine fouling organisms and their control (Part II). Beijing: China Ocean Press, 2008
Zhou XJ, Qian PY. Ginestein and its derivatives against larval settlement of the barnacles balanus amphitrite. The 14-th International Congress on Marine Corrosion and Fouling. Japan, 2008
Wang JX, Zhou SZ, Peng ZH, Zhou XF, Zhang XB, Peng BX. Synthesis and characterization of new members of capsaicinoids and preliminary research on the relationship between the strcture and pungency. Chinese J Org Chem, 2011, in press
Walpole CSJ, Wrigglesworth R, Bevan S, Campbell EA, Dray A, James IF, Perkins MN, Reid DJ, Winter J. Analogs of capsaicin with agonist activity as novel analgesic agents-structure activity studies. 1. The aromatic A-region. J Med Chem, 1993, 36(16): 2362–237
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Peng, B., Wang, J., Peng, Z. et al. Studies on the synthesis, pungency and anti-biofouling performance of capsaicin analogues. Sci. China Chem. 55, 435–442 (2012). https://doi.org/10.1007/s11426-011-4307-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11426-011-4307-x