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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Letter Article

Di[(R)-2-ethylhexyl] Phthalate, a Bioactive Metabolite First Isolated from Three Different Bacillus Species, and its Synthesis

Author(s): Miriam Castro, Jacqueline Jiménez, Aurelio Ortiz* and Estibaliz Sansinenea*

Volume 17, Issue 2, 2020

Page: [90 - 95] Pages: 6

DOI: 10.2174/1570178616666190718125617

Price: $65

Abstract

Di(2-ethylhexyl) phthalate (DEHP) is the most common phthalate ester, which has been used as a plasticizer for the production of numerous polymers, particularly polyvinyl chloride (PVC). Many other groups have synthesized meso-DEHP indicating interest in this molecule, but we are the first to synthesize enantiomerically pure di[(R)-2-ethylhexyl] phthalate. We report herein, for the first time, the isolation - from the cultures of Bacillus thuringiensis, B. subtilis, and B. velezensis strains - of di[(R)-2-ethylhexyl] phthalate, enantiomerically pure and in good yields: its biological activity against bacteria and fungi was probed and for the first time its synthesis was done.

Keywords: Di(2-ethylhexyl) phthalate, plasticizer, secondary metabolites, synthesis of enantiomers.

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[1]
Ortiz, A.; Sansinenea, E.J. Chem., 2018, 6040814/1-6040814/7.
[2]
Habib, M.R.; Karim, M.R. Acta Pharm., 2012, 62(4), 607-615.
[http://dx.doi.org/10.2478/v10007-012-0035-9] [PMID: 23333892]
[3]
Jassbi, A.R.; Zare, M.; Jamebozorgi, F.H. Open Bioactive Compd. J., 2017, 5, 16-22.
[http://dx.doi.org/10.2174/1874847301005010016]
[4]
El-Sayed, O.H.; Asker, M.M.S.; Shash, S.M.; Hamed, S.R. Int. J. Chemtech Res., 2015, 8, 58-66.
[5]
Smaoui, S.; Mathieu, F.; Elleuch, L.; Coppel, Y.; Merlina, G.; Karray-Rebai, I.; Mellouli, L. World J. Microbiol. Biotechnol., 2012, 28(3), 793-804.
[http://dx.doi.org/10.1007/s11274-011-0872-6] [PMID: 22805798]
[6]
El-Sayed, M.H. World Appl. Sci. J., 2012, 20, 1202-1212.
[7]
Sansinenea, E.; Ortiz, A. Biotechnol. Lett., 2011, 33(8), 1523-1538.
[http://dx.doi.org/10.1007/s10529-011-0617-5] [PMID: 21528405]
[8]
Sansinenea, E., Ed.; Springer; Netherlands, 2012.
[http://dx.doi.org/10.1007/978-94-007-3021-2]
[9]
Sansinenea, E.; Salazar, F.; Ramírez, M.; Ortiz, A. Jundishapur J. Microbiol., 2015, 8(7)e20910
[http://dx.doi.org/10.5812/jjm.20910v2] [PMID: 26421136]
[10]
Sansinenea, E.; Salazar, F.; Jiménez, J.; Mendoza, A.; Ortiz, A. Tetrahedron Lett., 2016, 57, 2604-2607.
[http://dx.doi.org/10.1016/j.tetlet.2016.04.117]
[11]
Semenov, A.A.; Enikeev, A.G.; Snetkova, L.V.; Permyakov, A.V.; Sokolova, N.A.; Dudareva, L.V. Dokl. Biochem. Biophys., 2016, 471(1), 421-422.
[http://dx.doi.org/10.1134/S1607672916060120] [PMID: 28058694]
[12]
Ostrowski, K.A.; Lichte, D.; Stuck, M.; Vorholt, A.J. Tetrahedron, 2016, 72, 592-598.
[http://dx.doi.org/10.1016/j.tet.2015.11.069]
[13]
Chakraborty, D.; Gowda, R.R.; Malik, P. Tetrahedron Lett., 2009, 50, 6553-6556.
[http://dx.doi.org/10.1016/j.tetlet.2009.09.044]
[14]
a) Dalcanale, E.; Montanari, F. J. Org. Chem., 1986, 51, 567-569.
[http://dx.doi.org/10.1021/jo00354a037]
b) Babu, B.R.; Balasubramaniam, K.K. Org. Prep. Proced. Int., 1994, 26, 123-125.
[http://dx.doi.org/10.1080/00304949409458021]
[15]
Davies, S.G.; Elend, D.L.; Jones, S.; Roberts, P.M.; Savory, E.D.; Smith, A.D.; Thomson, J.E. Tetrahedron, 2009, 65, 7837-7851.
[http://dx.doi.org/10.1016/j.tet.2009.07.004]
[16]
Jiménez, J.; Lopez, M.; Carranza, V.; Mendoza, A.; Varela, J.; Sansinenea, E.; Ortiz, A. Tetrahedron Lett., 2017, 58, 235-239.
[http://dx.doi.org/10.1016/j.tetlet.2016.12.017]
[17]
Prashad, M.; Har, D.; Kim, H-Y.; Repic, O. Tetrahedron Lett., 1998, 39, 7067-7070.
[http://dx.doi.org/10.1016/S0040-4039(98)01521-4]
[18]
For the complete characterization of alcohols 9 and 10 see reference 19.. Both compounds are commercially available (CAS registry numbers 50373-29-0 and 128821-84-1 respectively),
[http://dx.doi.org/10.1016/S0040-4039(98)01521-4]
[19]
Hodgson, D.M.; Kaka, N.S. Angew. Chem. Int. Ed., 2008, 47, 9958-9960.
[http://dx.doi.org/10.1002/anie.200804369]
[20]
Ding, L.; Li, Z-H.; Lu, X-W.; Wu, Y.; Li, Y. Synthesis, 2012, 44, 3296-3300.
[http://dx.doi.org/10.1055/s-0032-1316776]
[21]
Sejidov, F.T.; Mansoori, Y.; Goodarzi, N. J. Mol. Catal. Chem., 2005, 240, 186-190.

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