PHA6117: Resins

Oxidation products of terpenes

Resins are what products of terpenes?

smoky flame

resins characteristic when burned?

soften and melt

What happens to resins when heated?

volatile oil

Resins are products of _______ oxidation

petroleum spirit;

alcohol, chloroform and ether

Usually insoluble in _______ but dissolve more or less completely in ______, ______, and ______

schizogenous or lysigenous ducts (resin ducts)

resins are contained in what ducts?

increased

Yield is usually ______ (decreased/increased) by injury

• use of alcohol (ex. Jalap, podophyllotoxin)

• distillation (ex. copaiba, turpentine),

• punctures (ex. mastic)

Resins can be isolated by

use of alcohol

What is used to isolate resins from Jalap, podophyllotoxin?

distillation

What is done to isolate resins from copaiba, turpentine?

punctures

What is done to isolate resins from mastic?

Resin acids

Resin alcohols

Resenes

Glycoresins

CLASSIFICATIONS OF RESINS

Resin acids

CLASSIFICATIONS OF RESINS:

contain oxyacids, and form metallic salts known as resinates; used in soaps and varnishes

resinates

metallic salts formed from Resin acids

abietic acid in rosin, commiphoric acid in myrrh, and copaivic acid in copaiba

Resin acids examples

Resin alcohols

CLASSIFICATIONS OF RESINS

occur in free state and ester forms

- aloeresinotannol (aloe)

- peruresinotannol and toluresinotannol (balsams)

- siaresinotannol and sumaresinotannol (benzoins)

Examples of resin alcohols

Resenes

CLASSIFICATIONS OF RESINS

neutral, do not form salts

Glycoresins

CLASSIFICATIONS OF RESINS

contain sugars

jalap

Example of glycoresins

Mastic, jalap, guaiac, cannabis, kava, eriodictyon

NOTES AND EXAMPLES

Resins

Capsicum, ginger, copaiba

NOTES AND EXAMPLES

Oleoresins

VOLATILE oils (not fixed)

Oleo in oleoresins means

Gamboge

NOTES AND EXAMPLES

Gum Resins

Myrrh, frankincense, asafetida

NOTES AND EXAMPLES

Oleogum Resins

Peruvian balsam, tolu balsam, benzoin, storax

NOTES AND EXAMPLES

Balsams

Balsams

Contain balsamic acids (major: benzoic and cinnamic acids)

Rubber, gutta percha, chico

NOTES AND EXAMPLES

Latex

oleoresins

Balsam of Copaiba classification

oleoresins

Canada turpentine classification

Latex

Consists of polyisoprenes

- Light amber is fine grade

- darker colors of lesser quality

What color of rosin is of fine grade? lesser quality?

(+) and (-) pimaric acids

Before distillation, resin of rosin contains large amounts of ______

(+)-pimaric acid

ROSIN/ COLOPHONY

During distillation, the _______ stays as is but the (-) isomer becomes abietic acid

abietic acid

ROSIN/ COLOPHONY

During distillation, the (+)-pimaric acid stays as is but the (-) isomer becomes ______

ROSIN/ COLOPHONY

Main adulterant of other resins

cis form of podophyllotoxin or picropodophyllin

What form of podophyllotoxin is inactive?

picropodophyllin

cis form of podophyllotoxin

etoposide and teniposide

Derivatives of podophyllotoxin

cupric acetate test

Guaiacum resin is differentiated from rosin by the

Colophony (Portugal)

Pine Resin

Agathis Philipinensis

Golden Copal Resin

Canarium sp.

Elemi Resin

gingerol

Pungency of ginger is due to

boiling with 2% KOH

How is gingerol destroyed?

Zingerone

constituent of ginger that is also pungent but with sweet odor

Shogaols

constituent of ginger that is from loss of water from gingerols

Cayenne Pepper

Cheapest source of resins

isobutylpropanyldisulfide

Sulfur compound in asafoetida

ASAFOETIDA

Has an "evil" smell and contains sulfur compounds

- Galbanum (Ferula galbaniflua)

- Ammoniacum (Dorema ammoniacum)

ASAFOETIDA Allied Drugs

Ferula galbaniflua

Galbanum SN

Dorema ammoniacum

Ammoniacum SN

TOLU BALSAM

Green color with ferric chloride

Green color

Tolu Balsam color with ferric chloride

TOLU BALSAM

Has the odor of benzaldehyde

benzaldehyde

TOLU BALSAM odor

PERUVIAN BALSAM

Only balsam not part of compound benzoin tincture

PERUVIAN BALSAM

Balsam is produced in the bark by boiling the bark in water

boiling the bark in water

PERUVIAN BALSAM is produced by

SIAM BENZOIN/ ASA DULCIS

Produced by incisions - the first secretion is very sticky and is

rejected, but the succeeding cuts yield harder secretions

SIAM BENZOIN/ ASA DULCIS

Has a vanillalike odor and is more expensive than Sumatra benzoin

vanilla-like

SIAM BENZOIN/ ASA DULCIS ODOR

SIAM BENZOIN/ ASA DULCIS

Ingredient of Friar's balsam

Cinnamic & benzoic, 2:1 ratio

Ratio of free balsamic acids in sumatra benzoin

KMnO4

On warming with _______, faint odor of benzaldehyde is noted with Sumatra but not Siamese

benzaldehyde

On warming with KMnO4, faint odor of _______ is noted with Sumatra but not Siamese

Sumatra but not Siamese

On warming with KMnO4, faint odor of benzaldehyde is noted with ______ but not ______

Ferric chloride

_______ gives green color to Siamese benzoin (not in Sumatra)

green

Ferric chloride gives _____ color to Siamese benzoin (not in Sumatra)

Siamese benzoin but not in Sumatra

Ferric chloride gives green color to ______ but not in ______

Liquidambar orientalis

Levant storax/ Oriental sweetgum SN

L. styraciflua

American storax/ sweetgum SN

alpha

storesins: amorphous but crystalline with potassium

beta

storesins: white flasks that do not crystallize with potassium

Compound Benzoin Tincture

topical protectant; "STAB" (Storax, Tolu Balsam, Aloe, Benzoin)

topical protectant

Compound Benzoin Tincture Use

Storax, Tolu Balsam, Aloe, Benzoin

Compound Benzoin Tincture Components

Benzoic acid

before: from sublimation of Sumatra Benzoin; now: synthetic

sublimation of Sumatra Benzoin

How is benzoic acid produced before?

antifungal, preservative of food, pharmaceutical preparations

Benzoic acid Use

for athlete's foot, ringworm; salicylic acid + benzoic acid

Whitfield's ointment uses, composition

by injuring the bark

How is rubber obtained?

Parthenium argentatum

Depletion of the natural sources of rubber led to use of ________ for limited production

vats

RUBBER/ CAOUTCHOUC:

Following initial cleaning of the latex in ____, it is coagulated and bleached by treatment with formic acid and bleaching agent

formic acid and bleaching agent

RUBBER/ CAOUTCHOUC:

Following initial cleaning of the latex in vats, it is coagulated and bleached by treatment with _______ and _____

Latex

RUBBER/ CAOUTCHOUC:

_____ emerges as blocks and passed through a mill 30x to give thin layers ready for further processing

mill 30x

RUBBER/ CAOUTCHOUC:

Latex emerges as blocks and passed through a ______ (__ & x) to give thin layers ready for further processing

proteolytic enzyme, papain is found in the latex of Carica.

Alkaloids are present in the latex of the Papaveraceae (enzyme, alkaloid, plant)

Hevea brasiliensis (Euphorbiaceae)

cultivated in Malaysia for commercial use.

Rubber (Ficus)

consists of linear chains of about 1500 to 60,000 C5- isoprenoid units linked by cis double bonds; can be vulcanized

1500 to 60,000 C5- isoprenoid

Rubber (Ficus) consists of linear chains of about ______ units linked by cis double bonds

cis

Rubber (Ficus) consists of linear chains of about 1500 to 60,000 C5- isoprenoid units linked by ____ double bonds

Ficus elastica

local source of rubber in the country

GUTTA PERCHA

Differs from rubber in being almost incapable of vulcanization and it becomes plastic when heated to about 45-60º C

becomes plastic

What happens to gutta percha when heated to about 45-60ºC?

GUTTA PERCHA

Should be preserved under water in well-closed containers protected from light

chloroformic solution

GUTTA PERCHA

Used in the form of ______ as means of applying drugs to the skin

CHICLE

Is a polyisoprenoid consisting of a mixture of cis and trans -C5 isoprenoids obtained from Manilkara zapota (Sapotaceae), the sapodilla plum

Manilkara zapota (Sapotaceae)

Chicle is a polyisoprenoid consisting of a mixture of cis and trans -C5 isoprenoids obtained from ________, the sapodilla plum