RESINS AND RESIN COMBINATION

Chapter Outline
Introduction
Properties

Difference between Oleoresins, Oleo-gum resins, Glycoresins and Balsams

Detailed study of;
• Resins: Rosin, Cannabis
• Oleoresins: Turpentine, Capsicum, Ginger
• Oleo-gum resins: Asafoetida, Myrrh
• Glycoresins: Podophyllum, Jalap, Ipomoea, Colocynth
• Balsams: Storax, Peruvian balsam, Tolu balsam, Benzoin

Introduction and Properties

Resins are amorphous products with a complex chemical nature
They are usually formed in schizogenous or in schizolysigenous ducts or cavities
These are end products of metabolism
Physically resins are usually hard, transparent or translucent
On heating they soften and finally melt
These are insoluble in water but dissolve more or less completely in alcohol, chloroform and ether
Chemically resins are complex mixtures of resin acids, resin alcohols (resinols), resin
phenols
(resinotannols), esters and chemically inert compounds known as resenes
Some investigators believe resins are oxidation products of the terpenes
Resenes: These are complex natural substances devoid of characteristic chemical properties
• They don’t form salts or esters and resist hydrolysis by alkalies
Pharmaceutical resin
The resin which has undergone any process of purification is called pharmaceutic resin
These processes can be evaporation, extraction, distillation etc.
Examples: Colophony, podophyllin
Pathological resin
The resin which is produced by giving stimuli to the tree e.g. cut, is called pathological resin
Examples: Levant storax, Peruvian balsam, Benzoin
Physiological resin
The resin which don’t require any stimuli for its production is called physiological resin
Their yield can be increased by giving stimuli

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 Examples: Ginger, capsicum

Oleoresins, Oleo-gum resins, Glycoresins and Balsams

Oleoresins
Oleoresins are homogenous mixtures of resins and volatile oils
Crude drugs containing oleoresins: Turpentine, capsicum, ginger
Volatile oils from oleoresins can be separated by distillation process because resins don’t evaporate
Oleogum resins
Oleogum resins are homogenous mixtures of resin, gum and volatile oil
Crude drugs containing oleogum resins: Asafoetida, myrrh
Gums are water soluble, so these can be easily separated from oleoresin
No hard and fast distinction can be made between these groups because small amounts of volatile oil are
often present in resins and small amounts of gum are often present in oleoresins
Glycoresins
Glycoresins are complex mixtures yielding sugars and complex resin acids on hydrolysis
Crude drugs containing glycoresins: Podophyllum, jalap
Balsams
Balsams are resinous mixtures that contain cinnamic acid, benzoic acid or both or esters of these acids
Crude drugs containing balsams: Tolu balsam, Peru balsam, storax, benzoin
‘Balsam of copaiba’ is an oleoresin; not balsam

Resins: Rosin, Cannabis

Rosin/Colophony
Rosin is the solid resin material obtained from Pinus palustris and from other species of Pinus (Fam.
Pinaceae)
Pinus palustris (Fam. Pinaceae)

Bark of the plant is chipped by using a ‘bark hack’

Turpentine (Oleoresin)
(Turpentine is a thick liquid, secreted from chipped bark)
Steam distillation

Turpentine oil Rosin

(Volatile oil) (Hot filtered residue left after distillation)
Collection and Preparation

Bark of the plant is chipped by using a ‘bark hack’

A thick liquid (oleoresin), secreted from chipped bark, is obtained
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 This thick liquid (oleoresin) is steam distilled; yields volatile oil (turpentine oil), and a residue is left
behind CH3
This hot filtered residue left after distillation is ‘rosin’
CH3
CH3
Constituents
80-90% of anhydrides of abietic acid
Abietic acid
• On treatment with alcohol changes to crystalline abietic acid H3 C COOH

Other constituents: Sylvic acid (decomposition product of abietic acid), sapinic acid, pimaric acid and other
acids and resenes
Anhydrides are used to dehydrate the substances or solutions
Uses
Used as stiffening agent in ointments, plasters and cerates
Used in cosmetics
As diuretic in veterinary medicine
Used in varnishes, paints, soaps, printing inks, sealing wax, floor coverings
As an adulterant of other resinous products (because it is cheap) [Misuse]
Cannabis
Cannabis consists of the dried flowering tops of the pistillate plants of Cannabis sativa (Fam. Moraceae)
The Indian hemp or ganja of the Indian Pharmacopoeia (1955) is required to contain ‘not more than 10%
of its fruits, large foliage leaves and stems over 3 mm’. This is the flat– or Bombay–ganja, which was
formerly official in many pharmacopoeias
Round– or Bengal–ganja is prepared by rolling the wilted tops between the hands
Bhang (Hindustani) or Hashish (Arabic) consists of the larger leaves and twigs of both male and female
plants
It is used in India for smoking, either with or without tobacco and drugs such as opium or datura, or is
taken in the form of an electuary made by digestion with melted butter
Charas or churrus is the crude resin, obtained from Cannabis sativa, by;
• Rubbing the tops between the hands
• Beating them on cloths or carpets
• By natives who wear leather aprons walking among the growing plants
• The resin is scraped off and forms an ingredient of numerous smoking mixture
• Like bhang, it is also used with butter
The product used by addicts is known;
• In America and Europe as marihuana
• In North Africa as kief
• In South Africa as dagga

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 • In Arabia and Egypt as hashish
Constituents
15-20 % resin; containing major active constituent (-) ∆9–trans tetrahydrocannabinol (∆9 THC)
Other constituents: Cannabinol, cannbidiol, cannabidiolic acid, ∆8 THC, cannnabichromene
and cannabigerol
CH3
Uses 9
8 OH
Hypnotic
1
7
Anticonvulsant 2
H3 C 6
Anxiolytic
O 3 C5H11
4
Antitussive CH3 5

THC
∆8 THC and ∆9 THC possess euphoric activity
∆9 THC more potent when smoked than orally
∆9 THC used to control nausea and vomiting of cancer chemotherapy
Cannabidiolic acid is sedative

Oleoresins: Turpentine, Capsicum, Ginger

Turpentine/Gum turpentine/Gum thu
Turpentine is a concrete oleoresin obtained from Pinus palustris and from other species of Pinus (Fam.
Pinaceae)
Collection and Preparation
Large trees measuring 45-50 cm in diameter are preferred
If skillfully worked, trees yield product about 15-20 years
The oleoresin is secreted in ducts located directly beneath the cambium in the sapwood
During spring, bark is chipped using ‘bark hack’
A spray of 50% solution of H2SO4 is applied to the freshly cut surface
Sap (oleoresin) flow is guided by metal gutters into containers attached to the tree trunk
Thick liquid that collects is removed periodically and taken to the turpentine still
Acid treatment collapses thin walled parenchyma cells that line the resin ducts, allowing the duct channels
to become larger, providing more rapid flow of oleoresin and reducing the chances of hardened secretions
blocking the outlets
The acid does not stimulate greater production of oleoresin, but enables more oleoresin to escape from the
ducts
The usual turpentining season lasts about 32 weeks
The product of first year’s cutting is superior and is known as ‘virgin turpentine’; on steam distillation,
yields 15-30% volatile oil (turpentine oil)

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 Product of second and third year may yield not more than 10% of oil
The hot filtered residue left after distillation is ‘rosin’
The US is the world’s largest producer of rosin and turpentine, accounting for
about 70% of the supply
Cup and gutter method for collection of turpentine
This method with different modifications, is used in America, France and other
European countries, India and Pakistan
The longitudinal groove is cut with a suitable instrument
It is at first only a few feet long, but it is enlarged at intervals, and in about 4 years
is some 4 m long
As the length of the groove is increased, the instrument may be replaced by one
having a longer handle
The metal or earthenware cups are attached to the trunk by nails and one or two
strips (gutters) of galvanized iron are placed above each to direct the flow
of oleoresin
As the grooves are lengthened, the cups are moved higher up the tree and new
grooves are started when the old ones become exhausted, or collection is too difficult
The cups are emptied at intervals and the oleoresin sent to the distillery
Trees can be tapped by this method for about 40 years, commencing when the tree is about 20-30 years
old
Physical properties of turpentine
Yellowish opaque massed, lighter internally, more or less glossy
Sticky when warm, brittle in the cold
Its odor and taste are characteristic
Freely soluble in alcohol, ether, chloroform and glacial acetic acid
Constituents
Volatile oil
• α-pinene (65%), β-pinene (30%), Other terpenes (5%)
-pinene -pinene
Resin (Rosin, detail is given above)
Contains not more than 2% of foreign organic matter
Uses
Used externally as counter irritant

Capsicum
Capsicum is the dried ripe fruit of Capsicum frutescens, C. annuum var. conoides, C. annuum var.
longum
(Fam. Solanaceae)

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Constituents
Capsaicin (0.02%) [it is of phenolic nature]
• Extremely pungent principle
• 1 part diluted with 11 million parts of water, even then gives pungent taste
Other constituents: Volatile oils (1.5%), fixed oils, ascorbic acid (0.2%), carotenoids
Uses H CH(CH3)2
Carminative CH2NHCO(CH2)4 C C
Stimulant H
Capsaicin
Condiment
OCH3
Counter irritant (increases local blood flow)
OH
Rubefacient (this character depends on pungency)
Ginger/Zingiber

Ginger is the dried rhizome of Zingiber officinale (Fam. Zingiberaceae)

The outer cortical layers are often either partially or completely removed
Constituents
Volatile oil (1-3%)
• Containing zingiberene, zingiberol, bisabolene (sesquiterpenes)
• This volatile oil is responsible for characteristic aroma of ginger
Oleoresin
• Containing zingerone and shogaol (aromatic ketones)
• This oleoresin is responsible for characteristic pungency of ginger
Starch (more than 50%)
Uses O
CH3
Ginger is used as; CH2 CH2 C CH3
• Flavoring agent Zingerone
• Carminative H3 C
• Anti-emetic OCH3 Zingiberene
OH H3C CH3
• Diaphoretic (sweat inducing)
• Aromatic stimulant
• Condiment
Ginger oleoresin has same properties as that of ginger

Much of the ginger consumed in the present day market is used in the manufacture of ginger ale (ginger
flavored soft drinks)

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Oleo-gum Resins: Asafoetida, Myrrh
Asafoetida/Asafetida
 Asafoetida is the oleo-gum resin obtained by incising the living rhizomes and roots of Ferula asafoetida
and other species of Ferula (Fam. Umbelliferae)
Asafoetida is ill smelling, has offensive odor
It is also called ‘devil’s drug’
Physical properties of asafoetida
Soft, sometimes semiliquid mass
Irregular masses of agglutinated tears or as separate ovoid tears that range 1-4 cm in diameter
When fresh are tough, yellowish white and translucent
These tears change in color gradually to pinkish, violet-streaked and finally reddish brown
When dry, are hard and brittle
Internally the tears are milky white and opaque
Odor is persistently alliaceous
Taste is bitter, alliaceous and acrid
Asafoetida should be kept in closed bottles
Constituents
Volatile oil (4-20%)
• Main constituent of oil is isobutylpropanyl disulfide that is accompanied by a number of
related organic sulfides
Resin (40-65%)
• Consists of asaresinotannol, both free and combined with ferulic acid
Gum (25%)
Some terpenes
Umbelliferone (in combined form)
Uses
Carminative
Expectorant
Laxative
Antispasmodic
Myrrh/Gum myrrh
It is an oleogum resin obtained from Commiphora molmol, C. abyssinica and from other species
of
Commiphora (Fam. Burseraceae)
The plants are small trees, sometimes attain the height of 10 meters
Found growing on the Arabian Peninsula and in Ethiopia and Somalia
Physical properties of myrrh
Exudes naturally or from incisions made on the bark

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 At first of yellowish color, soon hardens in the intense heat of these countries, becomes darker and is then
collected
Varieties of myrrh
A. Africa or Somalia myrrh B. Arabian or Yemen myrrh
‘Africa or Somalia myrrh’ is considered better of the two
Practically all of the commercial supply comes from Somalia
Constituents
Resin (25-40%)
• Composed of several constituents, among which are resin acids (α-, β- and γ-commiphoric
acid), resenes and phenolic compounds (one of which yields protocatechuic acid and pyrocatechin)
Volatile oil (2.5-8%)
• Yellow or yellowish green, has characteristic odor of myrrh
Gum (60%)
• Consisting of soluble and insoluble portions)
A bitter principle (sparingly soluble in water but soluble in alcohol)
Uses
Protective
Stimulant
Stomachic (historic term for a medicine that serves to tone the stomach, improving its function
and increase appetite)
In mouth washes as astringent

Glycoresins: Podophyllum, Jalap, Ipomoea, Colocynth

Podophyllum/Mayapple
Podophyllum consists of the dried rhizome and roots of Podophyllum OH

peltatum (Fam. Berberidaceae) OO

O
Constituents Podophyllotoxin
Resin called ‘podophyllin’ (3.5-6%) O
H3CO
• Active principle of this resin are lignans;
Podophyllotoxin (20%) OCH3

α-peltatin (10%) OCH3

β-peltatin (5%)

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 A number of lignan glycosides are also present in the plant,
but because of their water solubility, they are lost during
the normal preparation of resin
Lignan: Dimer of phenyl propanoid, with β-β linkage
Neolignan: Dimer of phenyl propanoid, with no β-β Lignan Neolignan
linkage
Uses
Drastic purgative
Anticancer
Caustic (able to burn or corrode organic tissue by chemical action), used to remove warts

Jalap
Jalap is the dried tuberous root of Exogonium purga (Family Convolvulaceae)
Constituents
Resin (8-10%)
• Major constituent of this resin are;
A number of glycosides, such as ipurganol
A phytosterol glycoside
Jalapin (A mixture of acidic glycosides)
Other constituents: Volatile oil, starch, gum, sugar, β-methyl esculetin, palmitic acid and stearic acid
Uses
Used as cathartic

Ipomoea/Orizaba Jalap/Mexican scammony root

Ipomoea is the dried root of Ipomoea orizabensis (Fam. Convolvulaceae)
It yields not less than 15% resin
Constituents
Resin (10-20%)
Scopoletin (coumarin)
Volatile fatty acids
Sugars
β-sitosterol
Calcium oxalate
Uses
Cathartic
Colocynth
Colocynth is the dried pulp of the unripe but fully grown frit of Citrullus colocynthis (Fam.
Cucurbitaceae)

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Collection
The collected fruits are peeled to separate the pericarp and immediately dried under the sun
Morphology
The fruit is almost a globular berry
4-10 cm in diameter
Odorless
Taste is very bitter
Constituents
Resin
Citrullol
Pectin
Colocynthin
Albuminoids
Glycosides
Glycosides on hydrolysis form cucurbitacin E and cucurbitacin L
Uses
Very powerful cathartic
Cucurbitacin E is reported to possess anticancer activity

Balsams: Storax, Peruvian Balsam, Tolu Balsam, Benzoin

Storax/Styrax
Storax is a balsam obtained from the trunk of Liquidambar orientalis or of L. styraciflua (Fam.
Hammamelidaceae)
Drug obtained from L. orientalis is known in commerce as Levant storax
Drug obtained from L. styraciflua is known in commerce as American storax
L. orientalis is tree, attains a height of about 15 meters and grows in Asia Minor
L. styraciflua is tree, attains a height of about 40 meters and grows in Southern North America, Central
America and Northern America
Levant storax is a pathologic product
Physical properties of storax

Levant storax is viscid, grayish to grayish brown, more or less opaque, semisolid mass
• It deposits a heavier, dark brown, oleo-resinous stratum (layer) on standing
American storax is nearly clear, yellowish brown, semisolid
• It becomes hard, opaque and darker colored
Storax is transparent in thin layers

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 Storax is insoluble in water but almost completely soluble in warm alcohol
Its odor is agreeable and taste is balsamic
Constituents of Levant storax
Resin alcohols (50%) [α-storesin, β-storesin, partly free and partly in combination with cinnamic acid]
Storesin cinnamate (10-20%)
Styracin or cinnamyl cinnamate (5-10%) [in needle crystals which are colorless, odorless, tasteless]
Phenylpropyl cinnamate (10%) [a liquid with the odor and taste of styrax]
Volatile oil (0.5-1%)
Vanillin (in traces)
Free cinnamic acid (2-5%)
Free cinnamic acid may be obtained from storax by micro-sublimation with a yield of 20%
Constituents of American storax HC CH COOH

Contains almost same principles as Levant storax

Volatile oil (7%)
Cinnamic acid
Cinnamic acid (28%) HC CH COO H2C HC CH
Cinnamein (23%)
Resin esters (35%)
Resin acids (2%) Cinnamyl cinnamate
COOH
Uses
Pharmaceutic aid for compound benzoin tincture
Stimulant
Benzoic acid
Expectorant
Antiseptic when used internally

Peruvian balsam/Peru balsam

Peruvian balsam is a balsam obtained from Myroxylon pereirae (Fam. Leguminosae)

The balsam trees attain a height of about 25 meters
The balsam is a pathologic product
Physical properties of Peruvian balsam
Occurs as a dark brown, viscid liquid that appears reddish brown and transparent in thin layers
It is free from stringiness or stickiness
It has an empyreumatic, aromatic, vanilla like odor and bitter acrid persistent taste
Constituents
Volatile oil (60%) [consisting chiefly of benzyl cinnamate and a lesser amount of benzyl benzoate]
Resin esters (30-38%)
Vanillin

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 Free cinnamic acid
Peruviol
Uses
Local protectant and rubefacient
Parasiticide in certain skin diseases
Antiseptic
Vulnerary (capable of or used for healing wounds)
Due to astringent nature, in various preparations to treat hemorrhoids
Tolu balsam
Tolu balsam is a balsam obtained from Myroxylon balsamum (Fam. Leguminosae)
Tolu balsam is a pathologic product
Physical properties of Tolu balsam
Occurs as a plastic solid which gradually hardens, becoming brown or yellowish brown
It is transparent in thin layers
Brittle when old, dried or exposed to cold and show numerous crystals of cinnamic acid
Odor is agreeable aromatic, resembling that of vanilla
Taste is aromatic and slightly pungent
Constituents
Resin esters (75-80%) [chiefly toluresinotannol cinnamate with a small quantity of benzoate]
Volatile oil (7-8%) [chiefly benzyl benzoate]
Free cinnamic acid (12-15%)
Free benzoic acid (2-8%)
Vanillin
Uses
Pharmaceutic aid for compound benzoin tincture
Expectorant (Rarely)
Extensively used as pleasant flavoring agent in medicinal syrups, confectionary, chewing gum
and perfumery
Benzoin
Benzoin is the balsamic resin obtained from Styrax benzoin, S. paralleloneurus or S. tonkinensis (Fam.
Styraceae)
Drug obtained from S. benzoin, S. paralleloneurus is known in commerce as Sumatra benzoin
Drug obtained from S. tonkinensis is known in commerce as Siam benzoin
Sumatra benzoin: Used in pharmacy
Siam benzoin: Confined almost entirely to perfumery

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 The plant are trees of medium height
It is a pathologic product
Physical properties of Sumatra benzoin
Sumatra benzoin occurs as blocks or irregular masses composed of tears of variable size, embedded in a
translucent or opaque matrix
It is brittle
Internally tears are milky white, become soft when warmed and gritty when chewed
Matrix is reddish or greyish brown
Odor is agreeable, balsamic and resembles that of styrax
Taste is aromatic and resinous
Constituents of Sumatra benzoin
Free balsamic acids
• Cinnamic acid (10%)
• Benzoic acid (6%)
• Esters of these acids
Triterpene acids
• 19-hydroxyoleanolic acid
• 6-hydroxyoleanolic acid
Other constituents: Traces of vanillin, phenylpropyl cinnamate, cinnamyl cinnamate, phenyl-ethylene
Constituents of Siam benzoin
Coniferyl benzoate (60-70%)
Free benzoic acid (10%)
Siaresinol (6%)
Vanillin (in traces)
Sumatra benzoin: Yields not less than 75% of alcohol soluble extractive
Siam benzoin: Yields not less than 90% of alcohol soluble extractive
Uses
Antiseptic
Stimulant
Diuretic
Expectorant
Compound benzoin tincture: It contains benzoin, aloe, storax, Tolu balsam; topical protectant. Valuable
expectorant when vaporized.
Benzoic acid
Now a synthetic product but was first obtained by sublimation of Sumatra benzoin

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Benzoic acid and its sodium salt are extensively used as preservative of food, drinks,
pharmaceutic preparation and other substances
Used as antifungal agent
Read Books to be a Good Professional

Muhammad Soaib Said Lecturer Department of Pharmacy Uni. Of Poonch Rawalakot

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