Isolation of anacardic acid from cashew (Anacardium occidentale L.) nut shell liquid and synthesis of 2- hydroxyethyl anacardate

Date

6-2008

Degree

Bachelor of Science in Chemistry

College

College of Arts and Sciences (CAS)

Adviser/Committee Chair

Hidelisa P. Hernandez

Co-adviser

Maria Amelita C. Estacio

Committee Member

Ernesto J. Del Rosario

Abstract

Natural cashew nut shell liquid (CNSL) was extracted from the cashew nut shells through mechanical expulsion. The CNSL obtained was viscous and brown with percentage yield of 23% (g/g air-dried shell). The TLC profile of the extract on silica gel G using the solvent system CH2C12:HCOOH (2:0.01 v/v) showed three spots which correspond to cardanol, anacardic acid and cardol having Rf values of 0.68, 0.38 and 0.13, respectively. Anacardic acid was extracted from CNSL by precipitation of calcium anacardate. The percent yield of crude anacardic acid was 76.05%. The TLC profile of the isolate on silica gel G using the solvent system CH2C12:HCOOH (2:0.01 v/v) showed one highly colored elongated spot with an Rf of 0.40 which is nearly similar to the Rf value of anacardic acid spot in the profile of natural CNSL. The isolate was purified using preparative TLC on silica gel G with CH2C12:HCOOH (2:0.01 v/v) as solvent. The percent recovery was 82.34%. The isolate was characterized by 1H-NMR and '3C-NMR spectroscopy. Prominent peaks in the spectra agree with the known structure of anacardic acid with its monoene, dime and triene side chain. Ethylene glycol (2-hydroxyethyl anacardate) ester derivative of anacardic acid was prepared via Fischer esterification. The crude 2-hydroxyethyl anacardate (2-HEA) obtained was a dark yellow orange viscous liquid with percent yield of 75.70%. Analytical TLC profile of this crude ester showed two spots: 2-hydroxyethyl anacardate I (2-HEA-I) with Rf4).39 and 2- hydroxyethyl anacardate II (2-FEEA-II) with Rf=0.57. The two components were purified by preparative TLC using CH2C12:HCOOH (2:0.01 v/v) yielding two viscous yellow orange liquids. 2-HEA-II makes up 32.01% while 2-FLEA-I makes up 27.21 % of the crude ester. Analysis of the 'H-NMR and "C-NMR spectra showed that both components are esters. However, it was also found that 2-HEA-I probably has a hydrated side chain while 2-HEA-II has traces of cardanol.

Language

English

Location

UPLB Main Library Special Collections Section (USCS)

Call Number

LG 993.5 2008 C4 M34

Document Type

Thesis

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