Anarcadic acids from cashew nut shell liquid: preparation of ester derivatives and evaluation of toxicity against dog ticks (Rhipicephalus sanguineus)

Date

4-2007

Degree

Bachelor of Science in Chemistry

College

College of Arts and Sciences (CAS)

Adviser/Committee Chair

Hidelisa P. Hernandez

Abstract

The cashew out shell liquid (CNSL) was extracted from the cashew shells through mechanical expulsion using a Carver press and an improvised mechanical oil expeller from FPRDI. The extracted CNSL for both batches of extraction was brown color and slightly viscous. A higher % yield was obtained in the extraction using the mechanical oil expeller (24.1%) than using a Carver press (10.4%). The anacardic acid was isolated from the cashcw nut shell liquid using the modified method of Paramashivappa and co-workers (2001). The average %yicld of crude anacardic acid was 52.1% The natural CNSL and anacardic acid M. subjected to TLC on silica gel G using chloroform-ethyl acct.-formic acid (95:5'2, v/v/v) and visualized using iodine vapor. The chromatogram of natural CNSL showed 3 spots (cardol, anacardic acid and cardanol) while only one spot for the isolated anacardic acid with the components in the origin_ The zinacudic acid in the natural CNSL and isolate have sundae Rf values (0.52). The anacardic esters were prepared by the Fischer justification method. The average % yield for crude ethylene glycol and crude glycerol esters were about 740% and 75.5% respectively. Both derivatives wort subjected to TLC. The Rf values of crude ethylene glycol and glycerol esters were 0.60 and 0.39 respectively. The enidc anacardic acid and its ester derivatives Were characterized using chemical tests and IR and NMR spectroscopy. The IR data were consistent with the expected structural features of the compounds Weak OH absorption peak was observed for anacardic acid probably due to intra-molecular H-bonding and dimcniation of anacardic acid. In the Ill-NMR data of the derivatives, new peaks observed at 3.3 to 4.5 ppm suggests the presence of the ester (C=0) groups, ester (C-O-C) groups The amount of ester produced in the sample is minimal and the data also suggests the pram= of unreacted anacardic acid and possible side products The ferric chloride-pyridine test confirmed the presence of phenolic group of crude antarctic acid and its ester derivatives The NaHCO, test indicated the presence of the carboxylic group for anacardic acid. Thc cxperimental molecular weights of anacardic acid (336.3 g/mol), crude ethylene glycol ester (390.2 g/mol) and chide glycerol cater (452.2 g/tnol) wore close to the theoretical molecular weigths and confirmed the formation of monocsters. The octoparasiticidal activities of natural CNSL, anacardic acid, sodium anacardate and the chide anacardic esters wore evaluated on brown dog ticks Analysis of Vanancc for 2-Factor Factoral Experiment and Painvise Mean Comparison or Duncan's Multiple Range Test showed significant differences in percent mortality at 15 minutes exposure time. Natural CNSL (10000 ppm) and sodium. anacardate (10000 ppm) when the most active. Natural CNSL (1000 and 500 ppm) and both erode ester derivatives (10000 ppm) were more active than the carbarnate (5000 ppm). The assay suggests that that these substances arc potential octoparasticidal agents against dog ticks.

Language

Filipino

Location

UPLB Main Library Special Collections Section (USCS)

Call Number

Thesis

Document Type

Thesis

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