Resins and Resin Combination

Dr. Harish Kakrani

Purvi Kakrani

Resins and Resin Combination

04/09/23 1Dr. Harish Kakrani & Purvi Kakrani

Definitions

Resins are solid or semisolid substances of complex chemical nature

They are secretion or exudation of plant tissues, produced either normally or due to pathogenic conditions

N.B.N.B. Artificial resins: are polymeric products formed through certain condensation reactions


Chemical Composition

They are formed of compounds rich in carbon, low in oxygen & free from nitrogen

They are complex mixtures of

Resin acids e.g. resinolic acid

Resin alcohols e.g.

resinotannol & resinol

Resin esters (of resin alcohols with aromatic acids)

Resenes (neutral

compounds)

Glycoresins: certain resin

alcohol linked to sugars


Resin Combinations

Resins occur frequently in homogenous mixtures with either

volatile oil, gums or both to form :

1. Oleoresin: mixture with V.O. e.g. Turpentine

2. Gum-resin: mixture with gum e.g. Gamboge

3. Oleogum-resin: Mixture with gum & V.O. e.g. Myrrh

4. Glycoresins: resis in glycosidal form e.g Jalap

5. Balsams: resinous substances with variable amounts of

aromatic acids e.g. benzoic or cinnamic or both or their esters

e.g. Copaipa


Occurrence in Plants

They are produced in the normal different secretory structures such as: Resin cells (e.g. ginger) Schizogenous or schizolysigenous ducts

(e.g. pinus) Glandular hairs (e.g. cannabis)

They are also formed as a result of incision of certain trees e.g. benzoin & balsam Tolu (i.e pathological)


Preparation of Resin

1. Natural resin: occurs as exudates from plants normally or

as result of pathogenic conditions (as artificial punctures,

e.g. mastic) or (deep cuts in the wood of plant e.g.

turpentine) or (hammering and scorching, e.g. Balsam of

Peru)

2. Prepared: obtained by different methods, as extraction with

alcohol then conc. alc. extract is either evaporated or poured

into water and the precipitated resin is collected, washed and

carefully dried, e.g. podophyllum, jalap and scammony resins


Physical Properties

1. Hard or brittle, translucent, transparent (when pure) & become opaque when they contain water

2. Uncrystallizable & have little taste

3. Heavier than water

4. On heating, they soften forming a sticky fluid & burns with a smoky flame

5. Insoluble in water and Pet. ether (except colophony and mastic) & soluble in alcohol, ether and chloroform. They are also soluble in volatile oils.


Representative ExamplesI- Resins

E.g.1 Colophony:

Source It is the solid left after steam distillation of

V.O. from oleoresin of Pinus spp.

especially Pinus palustris (Fam. Pinaceae)

Properties Shiny, angular, translucent yellow masses

with brittle fracture, soluble in alcohol &

organic solvents

Uses In preparation of adhesive plasters,

ointments, manufacturing of varnishes,

soap, sealing wax & printing ink.04/09/23 8Dr. Harish Kakrani & Purvi Kakrani

Cont. Colophony

Composition: mainly resin acids

(90%), in the form of isomeric

diterpene acids

N.B. Before distillation, the resin

contains large amounts of d- & l-

pimaric acid & during distillation

l-pimaric acid isomerizes to give

abietic acid. On heating to 300

ºC further rearrangement

produces neo-abietic acid

COOH COOH

300Co

Abietic acid L-Pimaric acid

Neo-abietic acid

Distillation


Tests for identity: Copper acetate test (test for abietic acid): Extract the powder with pet. ether and

filter Shake the filtrate with twice its volume

of Cu acetate The pet. ether layer turns emerald greenemerald green

colour (bluish-greenbluish-green)) due to formation of copper salt of abietic acid

Cont. Colophony


e.g.2 Scammony resin

e.g.3 Jalap Resine.g.3 Jalap Resin

PreparationPreparation::They are obtained by precipitating with water the alcoholic extract of the dried roots of these plants

Ipomea orizabensis & Convolvulus scammonia Fam. Convolvulaceae

Ipomoea purga Fam. Convolvulaceae.

ConstituentsConstituents:: Glycosides of jalapinolic acid, and its methyl esterOther glycosides including jalapin, Ipuranol, ipurganol,

Scammonin (ether soluble fraction), “jalapin” (ether-insoluble resin) & ipurganol

Use:Use:hydragogue cathartic


II- Oleoresins

Origin:Origin: It is the oleoresin of Dryopteris filix-mas (Fam.

Polypodiaceae)

Preparation:Preparation: extract the male fern rhizome with ether

& evaporate → oleoresin

Constituents:Constituents: 5% of filmarone (ester of filicic acid &

aspidinol), flavaspidinol & flavaspidic acid

Identification:Identification: dil. alc. solution + FeCl3→ green green

colourcolour

Uses:Uses: anthelmintic especially as taenifuge (due to

filmarone)

N.B.N.B. Its use requires care, since it may be absorbed

and cause blindness. So, it should be preceded and

followed by saline purgative

CH3

H3CO

OH O

Aspidinol

OH

E.g.1 Male Fern Oleoresin, Aspidium


II- Oleo-Gum-ResinsII- Oleo-Gum-Resins

OriginOrigin:: by incision of root & rhizome of Ferula foetida (Fam.

Umbelliferae)

ConstituentsConstituents:: volatile oil (sulfur compounds), resin, gum, combined

umbelliferone, ferulic & umbellic acids

Tests for identityTests for identity::

The freshly fractured surface + 1 drop H2SO4 → redred colorcolor → changing

to violetviolet on washing with water.

The freshly fractured surface + dil. HNO3 → green colorgreen color

Boil the extract with Dil. HCl & filter→ filterate + conc. NH4OH → blue blue

fluorescence fluorescence (due to umbelliferone)(due to umbelliferone)

UseUse:: Carminative, expectorant, antispasmodic and laxative specially

in veterinary O OHO

Umbelliferone

E.g.1 AsafoetidaE.g.1 Asafoetida


Origin:Origin: oleo-gum-resin obtained by incision of

stems of Ferula galbaniflua (Umbelliferae)

Constituents:Constituents: Free umbelliferone, volatile oil,

resin & gum

Test for identity:Test for identity: boil with alcohol, filter →

filtrate + conc. NH4OH→ blue fluorescence blue fluorescence (free (free

umbelliferone)umbelliferone)

Uses:Uses: Topical stimulant in plasters.

E.g.2 Galbanum


OriginOrigin:: oleo-gum-resin obtained by incision of stems of

Dorema ammoniacum (Umbelliferae)

Constituents:Constituents: volatile oil, resin, gum, ammoresinol & traces

of salicylic acid

N.B.N.B. Both free, combined umbelliferone & sulfur compounds

are absent

Test for identity:Test for identity: With water it forms a white emulsion,

colored deep orange-reddeep orange-red by chlorinated soda (due to

ammoresinol)

Uses:Uses: It is used as a disinfectant, expectorant in chronic

bronchitis

E.g.3 Ammoniacum


Origin:Origin: oleo-gum-resin obtained from stem & branches of Comphora molmol

(Fam. Burseraceae). Secreted by ducts in the phloem & exudes through

cracks present in the bark.

Properties:Properties: Reddish-brown tears with strong aromatic odour & bitter taste

Test for identity:Test for identity: Extract with ether, then divide in two dishes & evaporate:

a. To one add few drops of HNO3 → purplish violetpurplish violet

b. To the other pass Br2 vapour → violetviolet

Constituents:Constituents:

7-17 % Volatile oil cont. terpene esters, cuminic aldehyde & eugenol,

25-40 % Resin cont. commiphoric acid

Gum containing oxidase enzyme

Uses:Uses: Antibilharzial, antiseptic (in mouthwash),

E.g. 4 MyrrhE.g. 4 Myrrh


Origin:Origin: Benzoin is the balsamic resin obtained from the incised stems, of

Styrax benzoin (known in commerce as Sumatra benzoin) or of Styrax

tonkinensis (known in commerce as Siam benzoin) Fam. Styraceae

ConstituentsConstituents

A) Sumatra benzoin:

contains balsamic acids (cinnamic and benzoic) free or esters

Triterpenoid acids, such as siaresinolic acid & sumaresinolic acid

Traces of vanillin

B) Siam benzoin:

Coniferyl benzoate (75%)

Free benzoic acid, triterpenoid acids & vanillin.

III-BALSAMS

E.g.1 Benzoin


Cont. Benzoin

Tests of identityTests of identity

Powder + KMnO4/H2SO4 ,warm → faint odor of benzaldehyde only

with Sumatra benzoin (Siam benzoin contains insufficient

cinnamic acid to give an odour of benzaldehye)

Prepare ethereal solution → put in a porcelain dish containing 2 to

3 drops of H2SO4 → deep purplish red colordeep purplish red color is given with Siam

benzoin

UsesUses

Carminative, expectorant, diuretic, antiseptic, fumigant (inhaled in

steam as a treatment for bronchitis) & in skin care preparations.


Origin:Origin: It is the balsam obtained by incision of the trunks of Myroxylon toluifera (Fam.

Leguminosae)

Test for identityTest for identity

It is soluble in alcohol & the solution give green colorgreen color with FeCl3

It contains cinnamnic acid, so it yields odour of benzaldhyde when oxidized KMnO4

ConstituentsConstituents::

80 % of resin (resin alcohols combined with cinnamic & benzoic acids)

Free cinnamic & benzoic acids & little vanillin

Esters such as benzyl benzoate & benzyl cinnamate

UsesUses

Balsam of Tolu has antiseptic properties

It is a common pleasant ingredient of cough mixtures (added as syrup or tincture)

E.g.2 Balsam oF Tolu


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Resins and Resin Combination