Shellac

1 Nonproprietary Names 7 Applications in Pharmaceutical Formulation or

BP: Shellac Technology
JP: Purified Shellac, JP: White Shellac Shellac is widely used as a moisture barrier coating for tablets and
pellets due to its low water vapor and oxygen permeability. It has
PhEur: Shellac
usually been applied in the form of alcoholic or aqueous solutions
USP-NF: Shellac (pharmaceutical glazes). However, due to stability problems with
alcoholic shellac solutions, it has had limited use in the pharma-
2 Synonyms ceutical industry for modified-release or enteric coatings; see also
Section 18.
Blonde; Bulls Eye Shellac; CertiSeal FC 300A; Crystalac; E904; Shellac, particularly novel aqueous shellac solutions, is mainly
Excelacs 3-Circles; Excelacs 3-Stars; Gifu Shellac GBN-PH; Gifu used in food products and nutritional supplements. Recent research
Shellac Pearl-811; lac; lacca; Mantrolac R-49; Mantrolac R-52; results indicate good application properties and chemical stability
Marcoat 125; Opaglos R; Sepifilm SN; SSB Aquagold; SSB 55 of shellac films from aqueous shellac solutions.(1,2) Aqueous
Pharma; SSB 56 Pharma; SSB 57 Pharma; Swanlac. ammonium shellac solutions, based on dewaxed orange shellac,
do not show the problems exhibited by alcoholic shellac solutions
and are used as an enteric coating for pellets, tablets, soft and hard
3 Chemical Name and CAS Registry Number gelatine capsules, primarily in nutritional supplements.(3)
Shellac [9000-59-3] Shellac is a primary ingredient of pharmaceutical printing inks
for capsules and tablets, and can be applied as a 40% w/v alcoholic
solution. It has also been used to apply one or two sealing coats to
4 Empirical Formula and Molecular Weight tablet cores to protect them from moisture before being film- or
Shellac is the general term for the refined form of lac, a natural sugar-coated.
polyester resin secreted by insects. Other applications of shellac are the coating or encapsulation of
PhEur 6.2 and USP32–NF27 define four types of shellac powders or granules, e.g. in probiotics. Prior to the introduction of
depending on the refining method, and JP XV mentions only two film coating, a combination of shellac, cetostearyl alcohol and
types; see Section 13. stearic acid was used as an enteric coating. In cosmetics, shellac is
Elementary analysis reveals that shellac contains carbon, used in hairsprays, mascara and lipstick formulations.(4) Aqueous
hydrogen, oxygen, and a negligible amount of ash. Orange shellac shellac solutions are also used for colonic drug delivery.(5)
contains approx. 68% carbon, 9% hydrogen and 23% oxygen, and
with a molecular weight of 1006 (bleached shellac is 949) the 8 Description
empirical formula for the average shellac molecule is C60H90O15. Shellac is a natural resin that may be obtained in a variety of colors
Even with this relatively low molecular weight, shellac has excellent ranging from light yellow to dark red in the form of hard, brittle
film-forming properties. flakes with or without wax, depending on the refining process; see
Lac is a complex mixture of aliphatic and alicyclic acids. The Sections 4 and 13. The different types of shellac include bleached
major components are aleuritic, jalaric and shellolic acids, as well as shellac, bleached dewaxed shellac, dewaxed and decolorized
butolic and kerrolic acids. Seed lac and orange shellac contain shellac, dewaxed flake shellac, dewaxed orange shellac, dewaxed
S approximately 5–6% wax and two coloring components, the water
soluble laccaic acid and the water insoluble erythrolaccin.
shellac, orange shellac, purified shellac, refined bleached shellac,
regular bleached shellac, regular waxy shellac, wax-containing
shellac, and white shellac. The flakes may be crushed or milled to a
coarse or fine powder. Bleached shellac is supplied as a coarse off-
5 Structural Formula white powder.
Shellac is tasteless and may have a faint odor. The typical odor of
shellac is the result of a complex fragrance system.(6)

9 Pharmacopeial Specifications
See Table I.

10 Typical Properties
The properties of shellac depend on the insect strain and host tree as
well as the method used for refining the crude lac (seed lac).
Density 1.035–1.140 g/cm3
Dissociation constant pKa value = 5.60–6.59(7)
Glass transition temperature 33–528C;(7) the wide range in
temperature is a result of the process used in refining and the
type of seed lac used as a starting material.
Hydroxyl value 230–280
Iodine number 10–18
Melting point 77–908C
6 Functional Category Refractive index n20 D = 1.514–1.524
Coating agent; encapsulating agent; film-forming agent; matrix- Saponification value 185–260
forming agent; modified-release agent. Solubility see Table II.

6 16
 Shellac 61 7

Table I: Pharmacopeial specifications for shellac. which is secreted through the surface of their body. The resin forms
thick encrustations on the smaller branches and twigs, which are
Test JP XV PhEur 6.2 USP32–NF27 then scraped off the twigs and further processed to produce seed lac,
Identification — þ þ as it is known at this stage. Seed lac is then refined to become
Characters — þ — shellac.
Chloride 40.14%(a) — — The chemical composition, properties and the color of shellac
Sulfate 40.11%(a) — — depend on the insect or insect strain, and thus the host tree, as well
Heavy metals 410 ppm 410 ppm 40.001% as the process used for refining.(7) Three very different processes are
Arsenic 45 ppm 43 ppm — used for refining the seed lac to shellac (bleaching, melting, and
Ethanol-insoluble substances 42.0% — — solvent extraction),(7–9) resulting in products with different char-
Rosin þ þ þ
Total ash 41.0% — — acteristics and properties.
Acid value (on dried basis) þ þ þ Bleaching process Refined bleached or white shellac is obtained
Dewaxed orange shellac 60–80 65–95 71–79 by dissolving seed lac in an aqueous alkaline solution, which is
Orange shellac — 65–95 68–76 then filtered, dewaxed, and bleached with sodium hypochlorite
Refined bleached shellac 65–90 65–95 75–91 to completely remove the color. However, changes in the
Regular bleached shellac — 65–95 73–89 molecular structure and the addition of chlorine substituents
Loss on drying þ þ þ may lead to self-crosslinking and polymerization.
Dewaxed orange shellac 42.0% 42.0% 42.0%
Melting process After melting the seed lac, the highly viscous
Orange shellac — 42.0% 42.0%
Refined bleached shellac 46.0% 46.0% 46.0% molten lac is pressed through a filter and drawn to a thin film.
Regular bleached shellac — 46.0% 46.0% Once cooled, the film breaks into thin flakes. The shellac wax is
Wax þ þ(b) þ not removed by this process and the color depends on the type of
Dewaxed orange shellac 420 mg — 40.2% seed lac used.
Orange shellac — — 45.5% Solvent extraction process Solvent extraction is a very gentle
Refined bleached shellac 420 mg — 40.2% process for refining shellac. The seed lac is dissolved in ethanol,
Regular bleached shellac — — 45.5%
and wax and impurities are removed by filtration. Activated
(a) For white shellac. carbon is used to produce light-colored grades. After a further
(b) Refer to Identification test B. filtration step and the removal of ethanol, the resin is drawn to a
thin film, which breaks into flakes after cooling. The properties
of the final product depend on the type of seed lac used and are
Table II: Solubility of shellac. influenced by the processing parameters and the grade of
activated carbon.
Solvent Solubility at 208C PhEur 6.2 and USP32–NF27 define four types of shellac
depending on the refining method, and the JP XV mentions two
Alkalis Soluble
Benzene 1 in 10 types; see Table III.
Ethanol 1 in 2
Ethanol (95%) 1 in 1.2 (very slowly soluble) Table III: Types of shellac according to the refining process.
Ether 1 in 8
Hexane Practically insoluble Refining process JP XV PhEur 6.2 USP32–NF27
Propylene glycol 1 in 10
Bleaching — Bleached shellac Regular
Water Practically insoluble
bleached
shellac
Bleaching and White shellac Bleached Refined
11 Stability and Storage Conditions
After long periods of storage, shellac becomes less readily soluble in
dewaxing

Melting —
dewaxed
shellac
Wax-containing
bleached
shellac
Orange shellac
S
alcohol, less fluid on heating, and darker in color; see also Section shellac
18. Solvent Purified shellac Dewaxed shellac Dewaxed
extraction orange shellac
Shellac should be stored in a well-closed container at tempera-
tures below 158C. Wax-containing grades should be mixed before
use to ensure uniform distribution of the wax. Orange and dewaxed The use of the term ‘pharmaceutical grade’ as well as the quality
orange shellac have a shelf-life of 1 to 2 years. The shelf-life of of the shellac depends on the manufacturer.
bleached shellac is approximately 6 months. Seed lac is mainly produced in India, Thailand and China.
Orange shellac, refined by the melting process, is manufactured by
12 Incompatibilities several companies in India, Thailand and South-East Asia. Bleached
shellac is produced in the USA, Canada, Japan, India, Thailand and
Shellac is chemically reactive with aqueous alkalis, organic bases,
South China. Dewaxed orange shellac is refined by the solvent
alcohols, and agents that esterify carboxyl groups. Therefore,
extraction process in Germany, Japan and India.
shellac should be used with caution in the presence of such
compounds.
14 Safety
13 Method of Manufacture Shellac is used in oral pharmaceutical formulations, food products,
and cosmetics. It is generally regarded as an essentially nonirritant
Shellac or lac is cultivated and refined from lacca, a resinous
and nontoxic material at the levels employed as an excipient.
secretion produced by the tiny insect Kerria lacca (Kerr) Lindinger
(Coccideae), formerly Laccifer lacca (Kerr). The insects are parasitic
on certain trees, mainly in India. In Thailand and South China, the 15 Handling Precautions
resin is secreted by another species, Laccifer chinensis (Madihassan) Observe normal precautions appropriate to the circumstances and
on different trees.(7,8) The insects pierce through the bark of the tree quantity of material handled. Shellac can be irritating to the eyes,
and transform the sap into a natural polyester resin, called stick lac, and to the respiratory system if inhaled as dust. Eye protection,
 6 18 Shellac

gloves, and a dust respirator are recommended. Shellac should be limited use as enteric coatings in the pharmaceutical industry
handled in a well-ventilated environment. today.(3,11,12) Problems are due to an esterification of the carboxyl
groups of shellac with alcohol and a polymerization due to trapped
16 Regulatory Status alcohol residues in the dry film. The use of bleached shellac, where
the molecular structure is partly changed by the treatment with
Accepted as a food additive in the USA, Europe, and Japan.
sodium hypochlorite, increases the polymerization problems.
Included in the FDA Inactive Ingredients Database (oral capsules
Shellac films from ammoniated aqueous shellac solutions using
and tablets). Included in nonparenteral medicines (oral tablets and
dewaxed orange shellac do not have these problems and have very
capsules, often in printing ink formulations) licensed in the UK.
stable release characteristics even after extended storage times.
Included in the Canadian List of Acceptable Non-medicinal
Furthermore, they can be formulated in combination with other
Ingredients.
polymers such as HPMC or modified starch together with
plasticizers to meet the disintegration requirements of the USP,
17 Related Substances PhEur and JP.(2,3,8,9)
Aleuritic acid; aqueous shellac solution; laccaic acid B; pharma- A specification for bleached shellac is contained in the Food
ceutical glaze. Chemicals Codex (FCC).(13) The EINECS number for shellac is 232-
Aleuritic acid 549-9.
Empirical formula C16H32O5
Molecular weight 304.42 19 Specific References
CAS number [533-87-9] 1 Freed P et al. Moisture vapor transmission comparison between acrylic,
Synonyms DL-erythro-9,10,16,-Trihydroxyhexadecanoic acid; aqueous shellac, and HPMC coating systems. Proc AAPS Annual
9,10,16-trihydroxypalmitic acid; 8,9,15-trihydroxypenta- Meeting 2007.
decane-1-carboxylic acid. 2 Pearnchop N et al. Shellac used as coating material for solid
Melting point 100–1018C pharmaceutical dosage forms. STP Pharma Sci 2003; 13: 387–396.
3 Signorino C. Shellac film coatings providing release at selected pH and
Solubility Soluble in hot water and lower alcohols.
method. US Patent 6,620,431; 2003.
Comments Main component of shellac. Isolated by saponifica- 4 Tannert U. Shellac – a natural polymer for hair care products. Seifen Öle
tion, and the starting material for the synthesis of macrocyclic Fette Wachse 1992; 17: 1079–1083.
musk compounds for fragrances and pheromones.(10) 5 Roda A et al. A new oral formulation for the release of sodium butyrate
The EINECS number for aleuritic acid is 208-578-8. in the ileo-cecal region and colon. World J Gastroenterol 2007; 13:
1079–1084.
Aqueous shellac solution 6 Buchbauer G et al. Headspace constituents of shellac. Zeitschr
CAS number [68308-35-0] Naturforsch 1993; 48b: 247–248.
Synonyms Shellac ammonium salt 7 Buch K et al. Investigations of various shellac grades: additional
Comments Aqueous solution of shellac with 20-25 % solids at a analysis for identity. Drug Dev Ind Pharm 2009; 35(6): 639–648.
pH of 7–7.5. The EINECS number is 269-647-6. Used as a 8 Penning M. Aqueous shellac solutions for controlled release coatings.
coating material for granules, pellets, tablets, hard and soft Karsa DR, Stephenson RA, eds. Chemical Aspects of Drug Delivery
gelatine capsules. Suitable for sustained-release and enteric Systems. London: Royal Society of Chemistry, 1996; 146–154.
coatings, as moisture barrier and as encapsulation agent.(3,8,9) 9 Specht F et al. The application of shellac acidic polymer for enteric
coating. Pharm Technol Eur 1998; 10(9): 20–28.
Laccaic acid B 10 Subramanian GB, Bushan KH. Aleuritic acid in perfumery and
Empirical formula C24H16O12 pheromones. Perfumer Flavorist 1993; 18: 41–44.
Molecular weight 496 11 Luce GT. Disintegration of tablets enteric coated with CAP. Manuf
Synonyms Lac dye; natural red 25; 9,10-dihydro-3,5,6,8-tetra- Chem Aerosol News 1978; 49(7): 50–67.
hydroxy-7-[2-hydroxy-5-(2-hydroxyethyl)phenyl]-9,10-dioxo- 12 Chambliss WG. The forgotten dosage form: enteric-coated tablets.

S
1,2-anthracenedicarboxylic acid. Pharm Technol 1983; 7: 124–140.
CAS number [17249-00-2] 13 Food Chemicals Codex, 6th edn. Bethesda, MD: United States
Pharmacopeia, 2008; 869.
Solubility Water soluble
Comments Laccaic acid consists of 5 compounds, laccaic acid A,
B, C, D and E. Laccaic acid B is used as a food color in Japan. 20 General References
The color is pH dependent: orange at pH 3 to reddish purple at Bose PK et al. Chemistry of Lac. Ranchi, India: Indian Lac Research
above pH 7. Institute, 1962.
Cockeram HS, Levine SA. The physical and chemical properties of shellac. J
Pharmaceutical glaze Soc Cosmet Chem 1961; 12: 316–323.
Synonyms Confectionary glaze, alcoholic shellac solution Martin J. Shellac. Kirk-Othmer RE, ed. Encyclopedia of Chemical
Comments Pharmaceutical glaze is a specially denatured alcoholic Technology, 3rd edn. NJ: John Wiley, 1982; , vol. 20: 737–747.
solution of shellac containing between 20% and 57% of shellac. Misra GS, Sengupta SC. Shellac.Encyclopedia of Polymer Science and
It may be prepared using either ethanol or ethanol (95%), and Technology. NJ: John Wiley, 1970; , vol. 12: 419–440.
may contain waxes and titanium dioxide as an opacifying agent. Mukhopadhyay B, Muthana MS. A Monograph on Lac. Ranchi, India:
Indian Lac Research Institute, 1962.
Stroever Schellack Bremen. Product Data Sheets: SSB (Shellac). http://
18 Comments www.stroever.de/shellac/shop/products.html (accessed 19 February
Under the general term shellac, many grades are available. The 2009).
pharmacopeial specifications are very narrow with regard to purity;
however, they allow a wide range for the acid value. 21 Authors
Shellac in the form of its alcoholic solution (pharmaceutical
BR Jasti, CS Leopold, X Li, M Penning.
glaze) has been used for many years as an enteric coating for
pharmaceutical applications. However, due to significant problems
with delayed disintegration and changes in release profiles of the 22 Date of Revision
coated dosage forms after storage, alcoholic shellac solutions have 19 February 2009.
 Simethicone

1 Nonproprietary Names not more than 7.0% of silicon dioxide. The PhEur 6.0 additionally
BP: Simeticone states that the degree of polymerization is between 20–400.
Simethicone occurs as a translucent, gray-colored, viscous fluid.
PhEur: Simeticone
It has a molecular weight of 14 000–21 000.
USP: Simethicone

2 Synonyms 9 Pharmacopeial Specifications

Dow Corning Q7-2243 LVA; Dow Corning Q7-2587; poly- See Table I.
dimethylsiloxane–silicon dioxide mixture; Sentry Simethicone;
simeticonum. Table I: Pharmacopeial specifications for simethicone.

Test PhEur 6.0 USP 32

3 Chemical Name and CAS Registry Number
Identification þ þ
a-(Trimethysilyl-o-methylpoly[oxy(dimethylsilylene)], mixture Characters þ —
with silicon dioxide [8050-81-5] Production þ —
Acidity þ —
4 Empirical Formula and Molecular Weight Defoaming activity 415 seconds 415 seconds
Loss on heating — 418%
See Section 8. Volatile matter 41.0% —
Heavy metals 45 ppm 45 mg/g
5 Structural Formula Mineral oils þ —
Phenylated compounds þ —
Assay (dimethicone) þ —
Assay (silicon dioxide) — 4.0–7.0%
Assay (silica) 47.0% —
Assay (polydimethylsiloxane) 90.5–99.0% 90.5–99.0%

10 Typical Properties
Boiling point 358C
Refractive index n20 D = 0.965–0.970
where n = 200–350 Solubility Practically insoluble in ethanol (95%) and water. The
liquid phase is soluble in benzene, chloroform, and ether, but
6 Functional Category silicon dioxide remains as a residue in these solvents.
Specific gravity 0.95–0.98 at 258C
Antifoaming agent; tablet diluent; water-repelling agent. Viscosity (kinematic) 370 mm2/s (370 cSt) at 258C for Dow

S
Corning Q7-2243 LVA.
7 Applications in Pharmaceutical Formulation or
Technology
11 Stability and Storage Conditions
The main use of simethicone as an excipient is as an antifoaming
agent in pharmaceutical manufacturing processes, for which Simethicone is generally regarded as a stable material when stored
1–50 ppm is used. in the original unopened container. A shelf-life of 18 months from
Therapeutically, simethicone is included in a number of oral the date of manufacture is typical. However, some simethicone
pharmaceutical formulations as an antiflatulent, although its products have a tendency for the silicon dioxide to settle slightly and
therapeutic benefit is questionable.(1,2) It is also included in antacid containers of simethicone should therefore be shaken thoroughly to
products such as tablets or capsules.(3–7) In some types of surgical or ensure uniformity of contents before sampling or use. Simethicone
gastroscopic procedures where gas is used to inflate the body cavity, should be stored in a cool, dry, location away from oxidizing
a defoaming preparation containing simethicone may be used in the materials.
area to control foaming of the fluids. Simethicone can be sterilized by dry heating or autoclaving. With
When simethicone is used in aqueous formulations, it should be dry heating, a minimum of 4 hours at 1608C is required.
emulsified to ensure compatibility with the aqueous system and
components.
In the USA, up to 10 ppm of simethicone may be used in food 12 Incompatibilities
products. Simethicone as supplied is not generally compatible with aqueous
systems and will float like an oil on a formulation unless it is first
8 Description emulsified. It should not be used in formulations or processing
The PhEur 6.0 and USP 32 describe simethicone as a mixture of conditions that are very acidic (below pH 3) or highly alkaline
fully methylated linear siloxane polymers containing repeating units (above pH 10), since these conditions may have some tendency to
of the formula [–(CH3)2SiO–]n, stabilized with trimethylsiloxy end- break the polydimethylsiloxane polymer. Simethicone cannot
blocking units of the formula [(CH3)3 SiO–], and silicon dioxide. It normally be mixed with polar solvents of any kind because it is
contains not less than 90.5% and not more than 99.0% of the very minimally soluble. Simethicone is incompatible with oxidizing
polydimethylsiloxane [–(CH3)2SiO–]n, and not less than 4.0% and agents.

61 9