Journal of Oil Palm Research Vol. 27  September 2015 p.  288-292
DOI:

INFLUENCE OF pH ON THE ACYLATION OF L-HYDROXYPROLINE WITH PALMITOYL CHLORIDE IN AN AQUEOUS ACETONE MEDIUM

Author(s): ZAINAB IDRIS*; MOHD AZMIL MOHD NOOR*; YEONG SHOOT KIAN*; HOONG SENG SOI*; ROSNAH ISMAIL* and HAZIMAH, A H*

Acylation reactions under Schotten-Bauman condition depend largely on the pH of the reaction medium. When the pH of the reaction medium was 9.0-10.0, the acylation of 0.1 mol of hydroxyproline with 2.5 mol of palmitoyl chloride in an aqueous acetone medium gave O-palmitoyl hydroxyproline and palmitic acid. In another reaction at a pH of 10.5-13.0, a small portion of the formed O-palmitoyl hydroxyproline was converted into N,O-di-palmitoyl hydroxyproline which is only between the range of 4.79% to 10.78%. However, at more higher pH values, the N-acylation reaction competed with hydrolysis of the formed O-palmitoyl hydroxyproline to regenerate palmitic acid and L-hydroxyproline which resulted in the reduction of percentage of N,O-di-palmitoyl hydroxyproline of 9.00%.

Keywords: , , , ,

Author Information
* Malaysian Palm Oil Board, 6 Persiaran Institusi, Bandar Baru Bangi, 43000 Kajang, Selangor, Malaysia. E-mail: zainab@mpob.gov.my


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