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Environmental Chemistry Letters

, Volume 16, Issue 4, pp 1493–1499 | Cite as

An efficient synthesis of bisenols in water extract of waste onion peel ash

  • Poh Wai ChiaEmail author
  • Ban Soon Lim
  • Fu Siong Julius Yong
  • Seng-Chee Poh
  • Su-Yin Kan
Original Paper
  • 139 Downloads

Abstract

Bisenols and its derivatives are attractive heterocyclic compounds exhibiting a wide range of biological properties, including anticancer, antipyretic and antimicrobial characteristics. Many catalytic systems have been reported to enhance the synthesis of bisenols, but these catalytic systems suffer from several drawbacks, such as the use of external metals, expensive and toxic chemicals. Thus, the development of a greener and efficient catalyst for the synthesis of bisenols is highly sought after. Herein, an improved protocol for the synthesis of bisenols in the water extract of burned-ash of onion peel waste (ash-water extract) as an efficient catalytic system is reported. Upon completion of the reaction, the crude mixture was extracted with ethyl acetate and the ash-water extract was successfully reused for several times in the synthesis of a variety of bisenols. Bisenols were obtained in good to excellent yields (62–94%) by using various benzaldehyde and 4-hydroxycoumarin catalyzed by the ash-water extract. Moreover, all pure products were obtained by precipitation without the need of column purification.

Keywords

Ash-water extract Onion peel Heterocyclic compounds Bisenols Recyclable catalytic system Bio-waste 

Notes

Acknowledgements

The author would like to acknowledge the talent and publication enhancement-research Grant (TAPE-RG) Universiti Malaysia Terengganu for its research Grant (Vot. No. 55111) and the Universiti Malaysia Terengganu for its research facilities.

References

  1. Ariyama K, Aoyama Y, Mochizuki A, Homura Y, Kadokura M, Yasui A (2007) Determination of the geographic origin of onions between three main production areas in Japan and other countries by mineral composition. J Agric Food Chem 55:347–354.  https://doi.org/10.1021/jf062613m CrossRefGoogle Scholar
  2. Bhowmick S, Mondal A, Ghosh A, Bhowmick KC (2015) Water: the most versatile and nature’s friendly media in asymmetric organocatalyzed direct aldol reactions. Tetrahedron Assym 26:1215–1244.  https://doi.org/10.1016/j.tetasy.2015.09.009 CrossRefGoogle Scholar
  3. Boruah PR, Ali AA, Chetia M, Saikia B, Sarma D (2015) Pd(OAc)2 in WERSA: a novel green catalytic system for Suzuki–Miyaura cross-coupling reactions at room temperature. Chem Commun 51:11489–11492.  https://doi.org/10.1039/C5CC04561D CrossRefGoogle Scholar
  4. Choi IS, Cho EJ, Moon JH, Bae HJ (2015) Onion skin waste as a valorization resource for the by-products quercetin and biosugar. Food Chem 188:537–541.  https://doi.org/10.1016/j.foodchem.2015.05.028 CrossRefGoogle Scholar
  5. Dewan A, Sarmah M, Bora U, Thakur AJ (2016) A green protocol for ligand, copper and base free Sonogashira cross-coupling reaction. Tetrahedron Lett 57:3760–3763.  https://doi.org/10.1016/j.tetlet.2016.07.021 CrossRefGoogle Scholar
  6. Fiorito S, Taddeo VA, Genovese S, Epifano F (2016) A green chemical synthesis of coumarin-3-carboxylic and cinnamic acids using crop-derived products and waste waters as solvents. Tetrahedron Lett 57:4795–4798.  https://doi.org/10.1016/j.tetlet.2016.09.023 CrossRefGoogle Scholar
  7. Gao S, Li L, Geng K, Wei X, Zhang S (2015) Recycling the biowaste to produce nitrogen and sulfur self-doped porous carbon as an efficient catalyst for oxygen reduction reaction. Nano Energy 16:408–418.  https://doi.org/10.1016/j.nanoen.2015.07.009 CrossRefGoogle Scholar
  8. Jafari AA, Ghadami M (2016) Efficient synthesis of α, β-unsaturated ketones with trans-selective Horner–Wadsworth–Emmons reaction in water. Environ Chem Lett 14:223–228.  https://doi.org/10.1007/s10311-016-0552-8 CrossRefGoogle Scholar
  9. Karmakar B, Nayak A, Banerji J (2012) Sulfated titania catalyzed water mediated efficient synthesis of dicoumarols—a green approach. Tetrahedron Lett 53:4343–4346.  https://doi.org/10.1016/j.tetlet.2012.06.024 CrossRefGoogle Scholar
  10. Khurana JM, Kumar S (2009) Tetrabutylammonium bromide (TBAB): a neutral and efficient catalyst for the synthesis of biscoumarin and 3,4-dihydropyrano[c]chromene derivatives in water and solvent-free conditions. Tetrahedron Lett 50:4125–4127.  https://doi.org/10.1016/j.tetlet.2009.04.125 CrossRefGoogle Scholar
  11. Li CJ, Chen L (2006) Organic chemistry in water. Chem Soc Rev 35:68–82.  https://doi.org/10.1039/B507207G CrossRefGoogle Scholar
  12. Liu DX, Li FL, Li HX, Gong WJ, Gao J, Lang JP (2014) Efficient and reusable CuI/1, 10-phenanthroline-catalyzed oxidative decarboxylative homocoupling of arylpropiolic acids in aqueous DMF. Eur J Org Chem 2014:4817–4822.  https://doi.org/10.1002/ejoc.201402416 CrossRefGoogle Scholar
  13. Maresca A, Scozzafava A, Supuran CT (2010) 7,8-Disubstituted- but not 6,7-disubstituted coumarins selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II in the low nanomolar/subnanomolar range. Bioorg Med Chem Lett 20:7255–7258.  https://doi.org/10.1016/j.bmcl.2010.10.094 CrossRefGoogle Scholar
  14. Marshall RE, Farahbakhsh K (2013) Systems approaches to integrated solid waste management in developing countries. Waste Manag 33:988–1003.  https://doi.org/10.1016/j.wasman.2012.12.023 CrossRefGoogle Scholar
  15. Miklós F, Fülöp F (2016) A simple green protocol for the condensation of anthranilic hydrazide with cyclohexanone and N-benzylpiperidinone in water. J Heterocycl Chem 53:32–37.  https://doi.org/10.1002/jhet.1844 CrossRefGoogle Scholar
  16. Nile SH, Park SW (2013) Total phenolics, antioxidant and xanthine oxidase inhibitory activity of three colored onions (Allium cepa L.). Front Life Sci 7:224–228.  https://doi.org/10.1080/21553769.2014.901926 CrossRefGoogle Scholar
  17. Patil SK, Awale DV, Vadiyar MM, Patil SA, Bhise SC, Kolekar SS (2017) Simple protic ionic liquid [Et3NH][HSO4] as a proficient catalyst for facile synthesis of biscoumarins. Res Chem Intermed 43:5365–5376.  https://doi.org/10.1007/s11164-017-2932-5 CrossRefGoogle Scholar
  18. Qu D, Li J, Yang XH, Zhang ZD, Luo XX, Li MK, Li X (2014) New biscoumarin derivatives: synthesis, crystal structure, theoretical study and antibacterial activity against Staphylococcus aureus. Molecules 19:19868–19879.  https://doi.org/10.3390/molecules191219868 CrossRefGoogle Scholar
  19. Saeed A, Larik FA (2016) Metal-free synthesis of isocoumarins (microreview). Chem Heterocycl Compd 52:450–452.  https://doi.org/10.1007/s10593-016-1911-x CrossRefGoogle Scholar
  20. Safaei-Ghomi J, Eshteghal F, Ghasemzadeh MA (2014) Solvent-free synthesis of dihydropyrano[3, 2-c]chromene and biscoumarin derivatives using magnesium oxide nanoparticles as a recyclable catalyst. Acta Chim Slov 61:703–708Google Scholar
  21. Saikia B, Borah P (2015) A new avenue to the Dakin reaction in H2O2–WERSA. RSC Adv 5:105583–105586.  https://doi.org/10.1039/c5ra20133k CrossRefGoogle Scholar
  22. Sangshetti JN, Kokare ND, Shinde DB (2009) Water mediated efficient one-pot synthesis of bis-(4-hydroxycoumarin)methanes. Green Chem Lett Rev 2:233–235.  https://doi.org/10.1080/17518250903393874 CrossRefGoogle Scholar
  23. Sarmah M, Mondal M, Utpal B (2017) Agro-waste extract based solvents: emergence of novel green solvent for the design of sustainable processes in catalysis and organic chemistry. ChemistrySelect 2:5180–5188.  https://doi.org/10.1002/slct.201700580 CrossRefGoogle Scholar
  24. Sharma K, Mahato N, Nile SH, Leeb ET, Lee YR (2016) Economical and environmentally-friendly approaches for usage of onion (Allium cepa L.) waste. Food Funct 7:3354–3369.  https://doi.org/10.1039/C6FO00251J CrossRefGoogle Scholar
  25. Siddiqui ZN, Farooq F (2011) Zn(Proline)2: a novel catalyst for the synthesis of dicoumarols. Catal Sci Technol 1:810–816.  https://doi.org/10.1039/c1cy00110h CrossRefGoogle Scholar
  26. Simon MO, Li CJ (2012) Green chemistry oriented organic synthesis in water. Chem Soc Rev 41:1415–1427.  https://doi.org/10.1039/C1CS15222J CrossRefGoogle Scholar
  27. Singh P, Kumar P, Katyal A, Kalra R, Dass SK, Prakash S, Chandra R (2010) Phosphotungstic acid: an efficient catalyst for the aqueous phase synthesis of bis-(4-hydroxycoumarin-3-yl)methanes. Catal Lett 134:303–308.  https://doi.org/10.1007/s10562-009-0239-x CrossRefGoogle Scholar
  28. Singh LK, Priyanka Singh V, Katiyar D (2015) Design, synthesis and biological evaluation of some new coumarin derivatives as potential antimicrobial agents. Med Chem 11:128–134.  https://doi.org/10.2174/1573406410666140902110452 CrossRefGoogle Scholar
  29. Su CX, Mouscadet JF, Chiang CC, Tsai HJ, Hsu LY (2006) HIV-1 integrase inhibition of biscoumarin analogues. Chem Pharm Bull 54:682–686.  https://doi.org/10.1248/cpb.54.682 CrossRefGoogle Scholar
  30. Surnenia N, Baruaa NC, Saikia B (2016) Application of natural feedstock extract: the Henry reaction. Tetrahedron Lett 57:2814–2817.  https://doi.org/10.1016/j.tetlet.2016.05.048 CrossRefGoogle Scholar
  31. Vamisetti GB, Chowdhury R, Kumar M, Ghosh SK (2017) ‘On water’ organocatalyzed enantioselective synthesis of highly functionalized cyclohexanones with an all-carbon quaternary centre from allylidene malononitriles and enones. Tetrahedron Assym 28:317–323.  https://doi.org/10.1016/j.tetasy.2016.12.012 CrossRefGoogle Scholar
  32. Wagare DS, Netankar PD, Shaikh M, Farooqui M, Durrani A (2017) Highly efficient microwave-assisted one-pot synthesis of 4-aryl-2-aminothiazoles in aqueous medium. Environ Chem Lett 15:475–479.  https://doi.org/10.1007/s10311-017-0619-1 CrossRefGoogle Scholar
  33. Wang Q, Chan Chan TR, Hilgraf R, Fokin VV, Sharpless KB, Finn MG (2003) Bioconjugation by copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition. J Am Chem Soc 125:3192–3193.  https://doi.org/10.1021/ja021381e CrossRefGoogle Scholar
  34. Yang C, Su W-Q, Xu D-Z (2016a) Ionic liquid [Dabco-H][AcO] as a highly efficient and recyclable catalyst for the synthesis of various bisenol derivatives via domino Knoevenagel–Michael reaction in aqueous media. RSC Adv 6:99656–99663.  https://doi.org/10.1039/C6RA23018K CrossRefGoogle Scholar
  35. Yang Y, Zhang S, Tang L, Hu Y, Zha Z, Wang Z (2016b) Catalyst free thiolation of indoles with sulfonyl hydrazides for the synthesis of 3-sulfenylindoles in water. Green Chem 18:2609–2613.  https://doi.org/10.1039/C6GC00313C CrossRefGoogle Scholar
  36. Yorulmaz T, Aydogan F, Yolacan C (2017) New and effective proline-based catalysts for asymmetric aldol reaction in water. Synth Commun 47:78–85.  https://doi.org/10.1080/00397911.2016.1252988 CrossRefGoogle Scholar

Copyright information

© Springer International Publishing AG, part of Springer Nature 2018

Authors and Affiliations

  1. 1.School of Marine and Environmental SciencesUniversiti Malaysia TerengganuKuala TerengganuMalaysia
  2. 2.Institute of Marine BiotechnologyUniversiti Malaysia TerengganuKuala TerengganuMalaysia
  3. 3.Faculty of Health SciencesUniversiti Sultan Zainal AbidinKuala NerusMalaysia

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