Sains Malaysiana 45(4)(2016): 621–625

Synthesis, Characterization and Antibacterial Activity of mono-, di- and tri-tosylate of Glycerol

(Sintesis, Pencirian dan Aktiviti Antibakteria Gliserol mono-, di- dan tri-tosilat)

 

 

YUSRABBIL AMIYATI YUSOF^1,2 & AZHAR ARIFFIN¹*  

 

¹University of Malaya, Lembah Pantai, 50603 Kuala Lumpur, Malaysia

 

²Consumer Product Development Unit, Advanced Oleochemical Technology Division, Malaysian Palm Oil Board, 6, Persiaran Institusi, Bandar Baru Bangi, 43000 Kajang, Selangor Darul Ehsan

Malaysia

 

Received: 19 November 2014/Accepted: 16 November 2015

 

ABSTRACT

Glycerol is a valuable co-product from oleochemical industry such as from fatty acid and biodiesel production. By having three hydroxyl groups in its molecule, glycerol can undergo chemical modifications that lead to many possible applications. This paper reports the tosylation process of glycerol with para-toluenesulfonyl chloride (p-TsCl). Reaction of glycerol with p-TsCl in the presence of a base produced mono-, di- and tri-tosylate of glycerol even though the reaction was carried out at the mole ratio of 1.2:1.0 of glycerol to p-TsCl. The compounds were successfully isolated and characterized. Mono-, di- and tri-tosylate of glycerol exhibited inhibitory activity against Staphylococcus aureus (gram positive bacteria) and Pseudomonas aeruginosa (gram negative bacteria).

 

Keywords: Antibacterial activity; glycerol; tosylate

 

ABSTRAK

Gliserol merupakan produk sampingan berharga yang diperoleh daripada industri oleokimia seperti daripada pengeluaran asid lemak dan biodiesel. Dengan mempunyai tiga kumpulan hidroksil dalam molekulnya, gliserol boleh menjalani pengubahsuaian kimia yang membawa kepada banyak aplikasi yang mungkin. Kertas ini melaporkan proses pentosilan gliserol dengan para-toluenesulfonil klorida (p-TsCl). Tindak balas gliserol dengan p-TsCl menghasilkan gliserol mono, di- dan tri-tosilat walaupun ia telah dijalankan pada nisbah mol 1.2: 1.0 gliserol kepada p-TsCl. Sebatian tersebut berjaya dipisah dan dicirikan. Gliserol mono-, di-dan tri-tosilat mempamerkan aktiviti antibakteria terhadap Staphylococcus aureus (bakteria gram positif) dan Pseudomonas aeruginosa (bakteria gram negatif).

 

Kata kunci: Aktiviti antibakteria; gliserol; tosilat

REFERENCES

Adlington, R.M., Barret, A.G.M., Quayle, P., Walker, A. & Betts, M.J. 1981. Novel syntheses of 3-methyleneazetidin-2-one derivatives and related systems. Chem. Comm. 9: 404-405.

Brown, H.C., Bernheimer, R., Kim, C.J. & Scheppele, S.E. 1967. Structural effects in solvolytic reactions. II. Nature of the intermediates involved in the solvolysis of symmetrically substituted β-anisylethyl derivatives. J. Am. Chem. Soc. 89: 370-378.

Ding, R., He, Y., Wang, X., Xu, J.L., Chen, Y., Feng, M. & Qi, C. 2011. Treatment of alcohols with tosyl chloride does not always lead to the formation of tosylates. Molecules 16: 5665-5673.

Holand, S. & Epsztein, R. 1977. Preparation of oxiranes from vic-diols. Synthesis 10: 706-708.

Hung, L.C., Ismail, R., Basri, M., Nang, H.L.L., Tejo, B.A., Hassan, H.A. & May, C.Y. 2010. Testing of glyceryl monoesters for their anti-microbial susceptibility and their influence in emulsions. Journal of Oil Palm Research 22: 846-855.

Jung, M.E. & Shaw, T.J. 1980. Total synthesis of (R)-glycerol acetonide and the antiepileptic and hypertensive drug (-)-γ-amino-β-hydroxybutyric acid (GABOB): Use of vitamin C as a chiral starting material. J. Am. Chem. Soc. 102: 6304-6311.

Jungermann, E. & Sonntag, N.O.V. 1991. Cosmetic Science and Technology Series. Vol 11. Glycerine: A Key Cosmetic Ingredient. New York: Marcel Decker, Inc.

Kabalka, G.W., Varma, M., Varma, R.S., Srivastava, P.C. & Knapp, Jr. F.F. 1986. Tosylation of alcohols. J. Org. Chem. 51: 2386-2388.

Kazemi, F., Massah, A.R. & Javaherian, M. 2007. Chemoselective and scalable preparation of alkyl tosylates under solvent-free conditions. Tetrahedron 63: 5083-5087.

Knothe, G., Gerpen, J.V. & Krahl, J. 2005. The Biodiesel Handbook. Urbana, Illinois: AOCS Press.

Lee, C.H., Yoh, S.D., Cheong, D.Y., Kim, S.H. & Park, J.H. 2000. Products analysis in the reaction of substituted 1-phenylethyl alcohols with p-toluenesulfonyl chloride. Bull. Korean Chem. Soc. 21: 1049-1051.

Razieh, F., Shahram, T. & Hamid, A. 2006. Solvent-free and selective tosylation of alcohols and phenols with p-toluenesulfonyl chloride by heteropolyacids as highly efficient catalysts. Canadian Journal of Chemistry 84: 812-818.

Tipson, R.S. 1944. On esters of p-toluenesulfonic acid. J. Org. Chem. 9: 235-241.

Wang, K., Hawley, M.C. & DeAthos, S.J. 2003. Conversion of glycerol to 1,3-propanediol via selective dehydroxylation. Ind. Eng. Chem. Res. 42: 2913-2923.

Yusof, Y.A., Ariffin, A., Hassan, H.A., Ng, S.W. & Tiekink, E.R.T. 2012. 1,3-bis{[(4-methylphenyl) sulfonyl] oxy}propan-2-yl 4-methylbenzenesulfonate. Acta Cryst. E68: O909- O910.

 

 

*Corresponding author email: azhar70@um.edu.my