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ISOLATION OF ALEURITIC ACID WITH THE TREATMENT OF DIFFERENT

PERCENTAGES OF SODIUM HYDROXIDE SOLUTION FROM LOCAL VARIETIES
OF LAC

Article · October 2013

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 BANGLADESH RESEARCH PUBLICATIONS JOURNAL
ISSN: 1998-2003, Volume: 9, Issue: 1, Page: 39-43, September - October, 2013

Review Paper
ISOLATION OF ALEURITIC ACID WITH THE TREATMENT OF DIFFERENT
PERCENTAGES OF SODIUM HYDROXIDE SOLUTION FROM LOCAL
VARIETIES OF LAC
S. Khatun, A. M. Khan, M.Z. Rahman, M.B Islam, M.J. Islam, M.L. Rahman and K. Hossain1

S. Khatun, A. M. Khan, M.Z. Rahman, M.B Islam, M.J. Islam, M.L. Rahman and K. Hossain (2013).
Isolation of Aleuritic acid with the treatment of different percentages of Sodium hydroxide
Solution from local varieties of lac. Bangladesh Res. Pub. J. 9(1): 39-43. Retrieve from
http://www.bdresearchpublications.com/admin/journal/upload/1309106/1309106.pdf

Abstract
Aleuritic (9, 10, 16-trihydroxy palmitic acid) a unique acid containing three
hydroxyl groups of which two are attached to adjacent carbon atoms,
isolated from local varieties of seed lac, shellac and de-waxed shellac
respectively with the treatment of different percentages (10%, 15%. 20%,
25%, 30%) of sodium hydroxide solution. From the experiment, it was
observed that at optimum condition, the use of 20% sodium hydroxide
solution permitted the best isolation of aleuritic acid. The isolated aleuritic
acid was confirmed by Fourier Transform Infrared Spectroscopy (FTIR).
Key words: Seed lac, Shellac, De-waxed shellac, Aleuritic acid, Saponification, Comparative
study.
Introduction
Seed lac, Shellac and De-waxed shellac are an important source of aleuritic acid.
They contain about 30% aleuritic acid which is present in the respective lac in the form
of their lactides or lactones (Harris, et al., 1928). Aleuritic acid is the first crystalline
compound isolated from lac. It is a white crystalline solid melting at 101.5 °C which is
an attractive material for the preparation of microcylic musk -like lactones and
ketones (Bose, et al., 1963).

Fig. 1: Aleuritic acid (9, 10, 16-trihydroxy, palmitic acid).

It is also a valuable starting material for the preparation of transparent water clear
adhesive, plasticisers and resins in combination with other chemicals (Sen, et al.1948).
Aleuritic acids are useful in compounding up to 60% with cellulose ethers and esters for the
preparation of lacquers, plastics and fibres (Sartort, 1945). Aleuritic acid is soluble in hot
water and in alcohol, acetone and ammonia in the cold (Tschirch, et al., 1999). It is also
dissolved on warming in ethyl acetate, benzene, toluene, chloroform and potassium
hydroxide but not in ether and carbon disulphide (Bhattacharya, 1935). Aleuritic acid
condensed with equimolecular portion of phthalic anhydride and glycerol at 180-190°C
gives a clear, flexible transparent product called glass-clear cement (Sen, et al.,1959).
Glass clear cement shows very good adhesive property specially in glass to glass bonding.

*Corresponding Author: E-mail: [email protected]

BCSIR Laboratories, Binodpur Bazar, Rajshahi-6206.
Khatun et al. 40

Several studies were carried out by Gidvani (1944), Puntumbekar (1956), and Hossain et
al.(1987) for the isolation of aleuritic acid from de-waxed shellac, hard resin portion of lac
and from seed lac respectively. But none of the methods were found to be suitable for
the isolation of aleuritic acid. So, the present investigation was carried out with a view to
finding out a suitable method for the isolation of aleuritic acid from the local varieties of
lac.
Materials and Methods
Seed lac and shellac were collected from local lac industry of Baliapukur, Rajshahi and
de-waxed shellac was collected from natural products Research Division, BCSIR,
Laboratories, Rajshahi for conducting the isolation of aleuritic acid. Sodium hydroxide,
sulphuric acid and methyl alcohol were purchased from a local market and used without
further purification. Aleuritic acid was isolated from seed lac, shellac and de-waxed
shellac in percentage of alkali are essentially same, only a representative method has
been described here.
Seed lac from local varieties 'Baisaki' and 'katki' was used; Each variety was dissolved in
100 ml different concentrations (10%, 15%, 20%, 25% and 30%) of Sodium hydroxide
solution. 100 g of seed lac was added to the solution with slow and constant stirring and
boiled until the lac saponifies. After saponification, the mixture was allowed to stand at
room temperature for 24 hours while the crystal of sodium aleuritate was separated out. It
was then diluted with 100 ml of 25% Sodium hydroxide solution to facilitate the filtration.
The mixture was then filtered through Buckner funnel using sand as a filtering aid. The
residue was collected and washed with 25% NaCl solution to remove alkali from the
solution. The residual crude sodium aleuritate was then dissolved in 100 ml of boiling water
and suction filtered under hot condition. The filtrate was then acidified with 20-30 ml of
10% H2S04. Here the aleuritic acid was left undissolved while all other acid went into
solution (Bose et al., 1963). Then it was filtered through a filter paper. The waxy residue on
crystallization from aqueous alcohol yielded aleuritic acid m. p. 101 - 103° C (Harris et al.,
1922) at methyl ester being 70 - 72° C (Shamsuzzaman et al., 1963). The precipitated
aleuritic acid was collected and purified and nearly 25% aleuritic acid was yielded.
Aleuritic acid was also isolated from shellac and de-waxed shellac following the same
method. IR spectra of aleuritic acid were recorded on a Simadzu, Model-8900, FTIR
spectrophotometer as KBr pellets.
Results and Discussion
Aleuritic acid was isolated from seedlac, shellac and de-waxed shellac and its yield of
percentages are shown in Table-I, 2 and 3 respectively. The differences between the yield
of aleuritic acid obtained from the varieties 'baisaki' and 'katki' is negligible.
In the first set of experiments, maximum yield of aleuritic acid from seed lac was
optimized. It was observed that with the concentration of 10% of sodium hydroxide
solution the yield of aleuritic acid was 15.8%, whereas 15% sodium hydroxide yielded 18.5%
aleuritic acid. However, 20% sodium hydroxide yielded highest 25.5% aleuritic acid. But
when the percentage of sodium hydroxide solution was further increased to 25% the yield
of aleuritic acid was decreased to 20.3% and In 30% sodium hydroxide solution only 18.5%
aleuritic acid was produced. It has been, however, concluded that the yield of aleuritic
acid was depended on the percentage variation of sodium hydroxide solution.
Respective data has been presented in Table 1 and figure 1.
In another set of experiment, 20% sodium hydroxide has yielded maximum aleuritic acid
(27.2%) from both varieties of seed. Respective data has been shown in Table 2 and figure
3.
In de-waxed shellac, 20% sodium hydroxide again proved best for maximum yield of
aleuritic acid. From the Table - 3, it was also found that the maximum yield of aleuritic acid
(28.7%) was obtained from de-waxed shellac variety corresponding the same sodium
hydroxide solution (20%).
Among the three different sources, highest yield of aleuritic acid obtained from de-waxed
shellac (28.7%) whereas minimum yield was from seed lac (25.5%). Intermediate result from
shellac variety depending on the percentage variation of sodium hydroxide solution.

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Isolation of Aleuritic acid 41
Infrared spectra
The IR spectra provide valuable information regarding the nature of functional group
attached to the aleuritic acid molecule. The appearance of a broad strong band in the
IR spectra of the molecule in 3402cm-1 is assigned to the O-H stretching vibration of
hydroxyl group of the molecule. The spectrum of the molecule shows –C=O bands in the
region (1708-1651) cm-1, which is assigned for the carbonyl group of the carboxylic group
of the molecule. The C–O stretch appears in the region (1311-1130) cm-1, and the O–H
bend is in the region 1406 cm-1 and 1057 cm-1. The FTIR spectrum of the aleuritic acid
shows the band related to aliphatic C-H stretching in the range (2924-2856) cm-1. The
characteristics FTIR bands of the isolated aleuritic acid are shown in Table 4.
Table 1. Yield of aleuritic acid from seed lac
No. of Expt. Percentage of sodium hydroxide Yield of aleuritic acid from seed lac
(%) (%)
1 10 15.8
2 15 18.5
3 20 25.5
4 25 20.3
5 30 18.3
Yield of aleuritic acid from seed lac

Percentage of NaOH

Fig. 1: The effect of different percentage of NaOH solution on

the yield of aleuritic acid from seed lac

Table 2. Yield of aleuritic acid from shellac (%)

No. of Expt. Percentage of sodium hydroxide Yield of aleuritic acid from shellac (%)
(%)
1 10 16.2
2 15 18.5
3 20 27.5
4 25 25.2
5 30 22.3

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Khatun et al. 42

Yield of aleuritic acid from shellac

Percentage of NaOH

Fig. 2: The effect of different percentage of NaOH solution

on the yield of aleuritic acid from shellac

Table 3. Yield of aleuritic acid from de-waxed shellac (%)

No. of Expt. Percentage of sodium hydroxide Yield of aleuritic acid from de-waxed
(%) lac (%)
1 10 18.2
2 15 20.5
3 20 28.7
4 25 25.2
5 30 22.4
Yield of aleuritic acid from de-waxed

Percentage of NaOH

Fig. 3: The effect of different percentage of NaOH

solution on the yield of aleuritic acid from de-waxed
shellac

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 Isolation of Aleuritic acid 43
Table 4. Characteristic FTIR bands of the compound Aleuritic acid
Sl. no. Peak cm-1 Intensity
1. 669.32 53.7235
2. 1057.03 50.1864
3. 1130.32 55.9355
4. 1311.64 43.7644
5. 1406.15 45.4159
6. 1651.12 42.7105
7. 1708.99 41.8397
8. 2349.38 43.7622
9. 2856.67 27.8553
10. 2924.18 21.6551
11. 3402.54 17.2908

Fig. 4: FTIR spectrum of aleuritic acid

Conclusion
Aleuritic acid which were isolated from the local varieties of seed Lac, shellac and de-
waxed shellac respectively with the treatment of different percentages (10%, 15%. 20%,
25%, 30%) of sodium hydroxide solutions has a continuous growing demand in the fields of
perfumery and pharmaceuticals due to it being an excellent starting material for the
synthesis of civetone, ambrettolide, isoambrettolide etc, which has the musk like odour.
Acknowledgement
The authors are thankful to the Director of BCSIR Laboratories Rajshahi for valuable
suggestions and co-operations during the research project.
References
Bhattacharya, R. (1935). Properties of aleuritic acid. J. Soc. Chem. Ind., 54
Bose, P. K., Sankaranarayanan, Y. & Sengupta, S.C. (1963) Chemistry of Lac, Indian Lac research
Institute, 1st edition, 71:107.
Gidvani, B.S. (1944) Preparation of aleuritic acid. J. Chem. Soc. 306.
Harries, C. D. & Nagel, W. (l928), Polymerization of shellac, Small Business Publisher, India 152.
Hossain, M.G., Ali M.H. & Chowdhury, F.K.N. (1987), Isolation of aleuritic acid from Lac, Bangladesh,
Acad. Sci, 2: 231-232.
Puntumbekar, S.V. (1956). An up-to-date picture of Lac resin, Report of the proceedings of the
symposium on Lac and Lac products, Johnmurry company, London, 72
Sartort, W.J.(1945) Aleuritic acid, U.S.P- 919.
Shamsuzzaman, L.A.M. & Khan, M.I.H. (1963). Pak. j. Biol. and Agric. Sci. 2(1): 68.
Sen, H. K. & Venugopalan (1948), Practical applications of recent Lac research, Orient Longmans
Publishers, Calcutta, 114.
Sen, H.K. & Ranganathan, S. (1959) Uses of Lac, Indian Lac research Institute, 35
Tschirch, A. & Farmer, A. (1999), Characteristics properties of aleuritic acid, Arch pharmacopia,
Longmanns publisher, 35.
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