Malaysian
Journal of Analytical Sciences Vol 22 No 2 (2018): 339 - 345
DOI:
10.17576/mjas-2018-2202-21
SELF-ASSEMBLIES BEHAVIOUR OF PALM OIL-BASED
GALACTOSIDE
(Sifat Swapenyusunan Galaktosida Berasaskan Minyak
Sawit)
Marina Yusoff , Nurul Fadhilah Kamalul Aripin*, Nurfatin Inani Aznan, Ruzitah Mohd Salleh
School
of Chemical Engineering,
Universiti
Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia
*Corresponding
author: fadhilah9413@salam.uitm.edu.my
Received: 25
February 2017; Accepted: 2 January 2018
Abstract
Analyses
of palm kernel oil-based galactosides self-assemblies are important to
determine their applications in pharmaceutical products. The palm kernel
oil-based galactosides (GalPKO) are synthesized by adopting Fischer
glycosylation method with minor modification. A birefringent fan-shaped texture
was observed upon cooling using optical polarizing microscope (OPM) indicates
formation of a smectic phase. The galactosides form isotropic phase completely
at 137 °C. Water contact penetration showed that GalPKO does not form other
lyotropic system except hydrated smectic phase. Based on its lyotropic behavior,
critical aggregation concentration (CAC) is determined at value 0.11 mM
indicating low solubility of the galactosides in water. Based on finding,
galactoside can form a special class of liquid crystal mesophases and give a
variety interesting application.
Keywords: galactoside, thermotropic, lyotropic, liquid
crystal, mesophase
Abstrak
Analisa swapenyusunan
galaktosida berasaskan minyak kernel sawit penting bagi menentukan aplikasinya
dalam produk farmaseutikal. Galaktosida berasaskan minyak kernel sawit (GalPKO)
disintesis menggunakan kaedah Fischer glikosilasi yang diubahsuai. Tekstur
birefringen berbentuk seperti kipas diperhatikan menggunakan mikroskop
polarisasi optik (OPM) semasa proses penyejukan sampel, menunjukkan pembentukan
fasa smektik. Galaktosida membentuk fasa isotropik sepenuhnya pada 137 °C. Penyerapan
air menunjukkan bahawa GalPKO hanya membentuk sistem liatropik fasa smektik
terhidrat. Berdasarkan sifat liotropik itu, kepekatan gumpalan kritikal (CAC)
ditentukan pada 0.11 mM menunjukkan keterlarutan galaktosida dalam air yang
memuaskan. Hasil penyelidikan menunjukkan galatoksida ini bakal membentuk satu
kelas khas fasameso cecair hablur serta kemungkinan dalam pelbagai aplikasi
menarik.
Kata kunci: galaktosida, termotropik, liotropik, cecair hablur,
fasameso
References
1.
Rodzi, N. Z. B. M., Heidelberg,
T., Hashim, R., Sugimura, A. and Minamikawa, H. (2011). Synthesis and liquid
crystals properties of α-methylated galactosides. Physics Procedia, 14: 91–95.
2.
Jeffrey, G. A. and Wingert, L.W.
(1992). Carbohydrate liquid crystal. Liquid
Crystal, 12: 179–202.
3.
Allen, H. J. and Kisailus, E.C.
(1992). Glycoconjugates: composition, structure and function. Marcel Dekker Inc
USA.
4.
Kwong, W. L., Gan, W. C., Abd.
Majid, W. H., Hashim, R. and Heidelberg, T. (2010). Pyroelectric detection in
glycolipid thin film. Thin Solid Films,
518: 4412–4416.
5.
Long, F. A. (1975). The Priestley
heritage: Prospects for chemistry in its third 100 years. Journal of Chemistry Education, 52 (1): 12-14.
6.
De Vries, R. J. (1984). Utilization
of Malaysian palm oil and palm kernel oil for fatty acids and derivatives. Journal of American Oil Chemical Society,
61: 404–407.
7.
Wakao, M. and Suda, Y. (2008).
Synthesis of glycolipids. Glycoscience. Berlin Heidelberg: Springer-Verlag
Berlin Heidelberg.
8.
Van Boeckel, C. A. A. and van Boom,
J. H. (1980). Synthesis of phosphatidyl-α-glucosyl-diacylglycerol containing
palmitic and oleic acid esters. Tetrahedron
Letters, 21: 3705–3708.
9.
Ruiz, C. C. (2008). Sugar-Based
Surfactants: Fundamentals and Applications. Paper presented at the CRC Press.
10.
Tyman, J. H. P. (1992).
Surfactants in lipid chemistry: Recent synthetic, physical, and biodegradative studies.
Royal Society of Chemistry.
11.
Holmberg, K. (2001). Natural
surfactants. Current Opinion in Colloid
Interface Science, 6: 148-159.
12.
Fischer, E. (1895). Ber. Dtsch. Chemische Berichte, 28: 1973–1974.
13.
Ahmadi, S., Achari, V. M., Nguan,
H. S. and Hashim, R. (2014). Atomistic simulation studies of the α/β-glucoside
and galactoside in anhydrous bilayers: Effect of the anomeric and epimeric
configurations. Journal of Molecular Modelling,
20: 1-12.
14.
Hashim, R., Abdalla Hashim, H. H.,
Mohd. Rodzi, N. Z., Duali Hussen, R. S. and Heidelberg, T. (2006). Branched
chain glycosides: Enhanced diversity for phase behavior of easily accessible
synthetic glycolipids. Thin Solid Films,
509: 27–35.
15.
Nystrom, R. F. and Brown, W. G. (1947).
Reduction of organic compounds by lithium aluminum hydride. I. aldehydes,
ketones, esters, acid chlorides and acid anhydrides. Journal of American Chemical Society, 69: 1197–1199.
16.
Vogel, A. (1989). Textbook of quantitative
chemical analysis (5th edition). New York: Longman and John Wiley
and Sons.
17.
Ferrer, F., Comelles, F., Plou,
F. J., Cruces, M. A., Fuentes, G., Parra, J. L. and Ballesteros, A. (2002). Comparative
surface activities of di- and trisaccharide fatty acid esters. Langmuir, 47(6): 1517-1520.
18.
Aripin, N. F. K., Park, J. W. and
Park, H. J. (2012). Preparation of vesicle drug carrier from palm oil- and palm
kernel oil-based glycosides. Colloids
Surface B, 95: 144-153.
19.
Vill, V., von Minden, H. M., Koch,
M. H. J., Seydel, U. and Brandesburg, K. (2000). Thermotropic and lyotropic
properties of long chain alkyl glycopyranosides. Part I: Monosaccharide
headgroups. Chemistry and Physics of Lipids,
104: 75–91.
20.
Von Minden, H. M., Brandenburg, K.,
Seydel, U., Koch, M. H. J., Garamus, V., Willumeit, R. and Vill, V. (2000).
Thermotropic and lyotropic properties of long chain alkyl glycopyranosides.
Part II. Disaccharide headgroups. Chemistry
and Physics of Lipids, 106: 157–179.
21.
Ducret, A., Giroux, A., Trani, M.
and Lortie, R. (1996). Characterization of enzymatically prepared
biosurfactants. Journal of American Oil Chemistry Society, 73: 109-113.
22.
Garofalakis, G., Murray, B. S.
and Sarney, D. B. (2000). Surface activity and critical aggregation
concentration of pure sugar esters with different sugar headgroups. Journal of Colloid Interface Science,
229: 391-398.