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Synthesis of stigmasteryl oleate, palmitate and stearate applying ethyl chloroformate as activator
Tofiana F.A.a, Immaculata I. M.b, Elfahmib, Kartasasmita R.E.b
a Directorate of Standardization of Traditional Medicine Cosmetic and Complementary Product, National Agency of Drug and Food Control, Republic of Indonesia, Jakarta, Indonesia
b School of Pharmacy, Institut Teknologi Bandung, Indonesia
[vc_row][vc_column][vc_row_inner][vc_column_inner][vc_separator css=”.vc_custom_1624529070653{padding-top: 30px !important;padding-bottom: 30px !important;}”][/vc_column_inner][/vc_row_inner][vc_row_inner layout=”boxed”][vc_column_inner width=”3/4″ css=”.vc_custom_1624695412187{border-right-width: 1px !important;border-right-color: #dddddd !important;border-right-style: solid !important;border-radius: 1px !important;}”][vc_empty_space][megatron_heading title=”Abstract” size=”size-sm” text_align=”text-left”][vc_column_text]© 2016, Journal of Chemical and Pharmaceutical Research. All rights reserved.Ethyl chloroformate as activator was investigated for esterification of long chain carboxylic acids (oleic, palmitate, and stearate) with stigmasterol at mild temperatures. Optimal conditions for ethyl chloroformate activity were found under anhydrous and basic conditions at 4°C to room temperature. Esterification products were isolated and purified using preparative radial chromatography and characterized by GC-MS and 1H-NMR spectroscopy. The GC-MS analysis results showed a fragment of (m/z) = 676.8, 650.5, and 679.8, which are correlated with the molecular weights of stigmasteryl oleate, stigmasteryl palmitate, and stigmasteryl stearate, respectively. Another confirmation was done by 1H-NMR, showing a change of chemical shift of 3.5 ppm given by the stigmasterol’s third carbon atom (C-OH) was deshielded to 4.6 ppm as it turned into (C-OR). GC-MS and 1H-NMR spectra indicated that stigmasteryl oleate, stigmasteryl palmitate, and stigmasteryl stearate have been successfully synthesized, suggesting that ethyl chloroformate is a worthy alternative activator for stigmasterylester synthesis.[/vc_column_text][vc_empty_space][vc_separator css=”.vc_custom_1624528584150{padding-top: 25px !important;padding-bottom: 25px !important;}”][vc_empty_space][megatron_heading title=”Author keywords” size=”size-sm” text_align=”text-left”][vc_column_text]1H-NMR spectra,Basic conditions,Ethyl chloroformate,GC-MS analysis,Long chain carboxylic acids,Mild temperatures,Optimal conditions,Radial chromatography[/vc_column_text][vc_empty_space][vc_separator css=”.vc_custom_1624528584150{padding-top: 25px !important;padding-bottom: 25px !important;}”][vc_empty_space][megatron_heading title=”Indexed keywords” size=”size-sm” text_align=”text-left”][vc_column_text]Ethyl chloroformate,Oleic acid,Palmitic acid,Stearic acid,Stigmasterylesters synthesis[/vc_column_text][vc_empty_space][vc_separator css=”.vc_custom_1624528584150{padding-top: 25px !important;padding-bottom: 25px !important;}”][vc_empty_space][megatron_heading title=”Funding details” size=”size-sm” text_align=”text-left”][vc_column_text][/vc_column_text][vc_empty_space][vc_separator css=”.vc_custom_1624528584150{padding-top: 25px !important;padding-bottom: 25px !important;}”][vc_empty_space][megatron_heading title=”DOI” size=”size-sm” text_align=”text-left”][vc_column_text][/vc_column_text][/vc_column_inner][vc_column_inner width=”1/4″][vc_column_text]Widget Plumx[/vc_column_text][/vc_column_inner][/vc_row_inner][/vc_column][/vc_row][vc_row][vc_column][vc_separator css=”.vc_custom_1624528584150{padding-top: 25px !important;padding-bottom: 25px !important;}”][/vc_column][/vc_row]