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Lipids Notes

The document discusses various fixed oils, fats, and waxes that are used pharmaceutically. It describes the source, composition, properties and uses of oils like olive oil, peanut oil, and soybean oil. It also covers cocoa butter and lanolin obtained from sheep's wool. Various fatty acids and their derivatives that are used as emulsifying agents, tablet lubricants, and topical treatments are outlined. Finally, it discusses natural waxes like beeswax, carnauba wax, and their uses in ointments and cosmetics.
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100% found this document useful (1 vote)
195 views3 pages

Lipids Notes

The document discusses various fixed oils, fats, and waxes that are used pharmaceutically. It describes the source, composition, properties and uses of oils like olive oil, peanut oil, and soybean oil. It also covers cocoa butter and lanolin obtained from sheep's wool. Various fatty acids and their derivatives that are used as emulsifying agents, tablet lubricants, and topical treatments are outlined. Finally, it discusses natural waxes like beeswax, carnauba wax, and their uses in ointments and cosmetics.
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as DOCX, PDF, TXT or read online on Scribd
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FIXED OILS

SUNFLOWER OIL

CASTOR OIL

ETHIODIZED OIL INJECTION

USE: stimulant cathartic, plasticizer


(in flexible collodion)
USUAL DOSE: 15 60 mL

OLIVE OIL
-

USE: pharmaceutic aid; setting


retardant (for dental cements);
preparation of soaps, plasters, and
liniments; demulcent; emollient;
laxative; nutrient; used as a salad oil

PEANUT OIL
-

USE: solvent for intramuscular


injections

SOYBEAN OIL
COTTONSEED OIL
-

USE: solvent for a number of


injections
- Hydrogenated: substitute for lard,
large amount used for a manufacture
of soap.

SESAME OIL
-

USE: pharmaceutic aid, solvent for


intramuscular injections, nutritive,
laxative, demulcent, emollient

ALMOND OIL
-

USE: (Expressed almond oil)


emollient, ingredient in cosmetics

PERSIC OIL
-

USE: vehicle, pharmaceutic necessity

COCONUT OIL
CORN OIL
SAFFLOWER OIL

FATS AND RELATED COMPOUNDS


THEOBROMA OIL
-

CACAO SEEDS OR CACAO BEANS


- seeds
- Theobroma cacao
- fam: sterculiaceae
- seeds are separated from the pod
and allowed to ferment (change from
white to dark reddish brown
- then roasted (not above 140C) to
remove water and develop
characteristic odor and taste
- passed through nibbling machine
to crack the seed coats (cacao shells)
-> separated from kernels by
winnowing
- nibs: broken kernels
- when ground between hot rollers
->
yields a paste (containing
up to 50% of fat, cacao butter)
- paste congeals @ room temp to
form bitter chocolate
- sweet chocolate: bitter chocolate
+ sugar and vanilla/ other flavoring
substances have been added
- After expressing cocoa butter, marc
(which retains some oil) is powdered.
Then called PREPARED CACAO OR
BREAKFAST COCOA
- Contain alkali to render it soluble
- ofc it is not soluble but the alkali
partially saponifies the fat at the
surface of each minute particle
- results to a smoother and more
complete suspension of the cocoa in
water or milk
- contains:
> 35 to 50% of fixed oil
> 15% of starch
> 15% of proteins
> 1 to 4% of theobromine
> 0.07 to 0.36% of caffeine
- red color is due to cacao red
- when the seeds are roasted, the
theobromine in the kernel passes into
the shell
- commercial source of xanthine
derivative

COCOA
- aka breakfast cocoa
- popular beverage
- usually contains more than 22% of
fat
- powder
- from roasted, cured kernels
- ripe seed
- Theobroma cacao
- color: wake reddish to purplish
brown to moderate brown powder
- odor: chocolate like
- taste: not sweet
- USE: employed in making cocoa
syrup
- cocoa syrup: flavored vehicle
NOTE: cocoa not containing more
than 12% of non volatile ether soluble
extractive (preferred for cocoa syrup)
- yields a syrup that has a minimum
tendency to separate
THEOBROMA OIL/ COCOA BUTTER
- fat obtained from the roasted seed
- T. cacao
- melts between 30-35 deg Celsius
- consists of:
- oleic 37%
- stearic 34%
- palmitic 26%
- linoleic 2%
- sharp melting point, comparative
brittleness, nongreasiness due to
peculiar glyceride structure
- MAJOR CONSTITUENTS:
- mono-oleodisaturated glycerides
- oleopalmitostearin (chiefly)
COCOA BUTTER
- use: suppository base

HYDROGENATED VEGETABLE OIL


-

Consists mainly of triglycerides of


stearic and palmitic acids
Fine, white powder at room temp
Melting point: 61-66 deg Celsius
- gives a pale yellow oily liquid
- USE: tablet lubricant

LANOLIN
-

Wool of the sheep


Ovis aries
Fam: bovidae

Contains: 25 and 30% water


- therefore it is commonly called
HYDROUS WOOL FAT
Heated -> separates into 2 layers ->
continue with stirring = drives off the
water that comprises the lower layer
CHIEF CONSTITUENTS:
- cholesterol and isocholesterol
Contains:
- esters of lanopalmitic, lanoceric,
carnaubic, oleic, myristic and other FA
USE: water absorbable ointment base,
ingredient in many skin creams and
cosmetics

ANHYDROUS LANOLIN
-

Aka wool fat


Contains not more than 0.25% of
water
USE: Water absorbable ointment
base, base for therapeutic agents ,
emollient
More readily absorbed through the
skin than any other known fat

LANOLIN ALCOHOLS
-

Mixture of aliphatic alcohols,


triterpenoid alcohols, and sterols,
obtained by the hydrolysis of lanolin
Contains not less than 30%
cholesterol
USE: emulsifying agent (in ointment
formulations)

FATTY ACIDS
-

Usually obtained by hydrolysis of fats


or oils
Used in topical antifungal
preparations
Sodium morrhuate: sclerosing agent
-Sclerosing agents are used to treat
varicose veins.
Linoleic and linolenic acid: dietary
supplement

STEARIC ACID
-

Contains not less than 40% of stearic


acid and not less than 40% of palmitic
acid
Sum of these acids is not less than
90%

PURIFIED STEARIC ACID


- not less than 90% stearic acid
- total content of stearic and palmitic
acids is not less than 96%
- practically insoluble in water
- USE: emulsion adjunct, tablet
lubricant
CALCIUM STEARATE and MAGNESIUM
STEARATE
- USE: tablet lubricants
ZINC STEARATE
- USE: dusting powders
SODIUM STEARATE
- USE: emulsifying and stiffening
agent
ALUMINUM MONOSTEARATE
- USE: suspending agent
GLYCERYL MONOSTEARATE AND
PROPYLENE GLYCOL
MONOSTEARATE
- USE: emulsifying agent
*these esters have EMOLLIENT
properties and CONTRIBUTE TO THE
STABILITY OF EMULSIONS
ISOPROPYL MYRISTATE AND
ISOPROPYL PALMITATE
- consisting of the esters of isopropyl
alcohol and saturated high molecular
weight fatty acids
- semisynthetic
- contain not less than 90% of the
designated esters
- USE: ingredients in topical emollient
creams and ointments
- ADVANTAGE OVER VEGETABLE OIL:
- freedom from oxidation and
rancidity
- less oleaginous(greasy)
- lack persensitization potential
(encountered with lanolin)

OLEIC ACID
-

From edible fats


Obtained as a by product in the
production of stearic acid
CHIEF CONSTITUENT:
- cis-9-octadecenoic acid
Insoluble in water
Soluble in alcohol
Gradually absorbs oxygen then
darkens
USE: emulsion adjunct

ETHYL OLEATE
- USE: pharmaceutic vehicle
- less viscous
- more rapidly absorbed by the tissues
OLEYL ALCOHOL emollient and
emulsifying agent

LINOLEIC AND LINOLENIC ACID


-

Aka Vitamin F
From soybean oil and other suitable
vegetable oils
Polyunsaturated octadecenoic acid
Essential for human nutrition
USE: dietary supplement

UNDECYLENIC ACID
-

10 undecenoic acid
USE: antifungal, ingredient in
ointments and powders for topical
application to treat athletes foot
CALCIUM UNDECYLENATE
- USE: for diaper rash and similar skin
irritations
CAPRYLATE AND PROPIONATE SALTS
- USE: (topical) control of fungal
infections
Glyceryl triacetate is related to the
gradual release of acetic acid

SODIUM MORRHUATE
-

Sodium salts of the fatty acids of cod


liver oil
(sterile solution) used as a sclerosing
agent
- to obliterate varicose veins
USUAL DOSE: 1 mL of a 5% solution
to a localized area
Should not be used if any such
material does not dissolve completely
when warmed.

WAXES
-

Mixtures of different molecular weight


acids and alcohols
May also contain paraffins
Found on the outer cell walls of
epidermal tissue of plants for
protection and loss of water

VEGETABLE WAXES
- EX. Carnauba wax, bayberry wax
INSECT WAXES
- EX. Lac wax, beeswax
USE: harden ointments and cosmetic
creams, used in the preparation of
cerates
- (industry) used for protective
coatings

SYNTHETIC SPERMACETI
-

Head of the spermwhale


Physeter macrocephalus
Fam physeteridae
USE: quality emollient, ingredient in
cold creams and other cosmetics
No longer avail (cause the whales are
endangered)
Substitute: synthetic spermaceti/
jojoba oil
Consists of a mixture of hexadecyl
esters of FA.
Consititutes of at least 85% of the
total esters:
- hexadecyl dodecanoate (cetyl
laurate)
- hexadecyl tetradecanoate (cetyl
myristate)
- hexadecyl hexadecanoate (cetyl
palmitate)
- hexadecyl octadecanoate (cetyl
stearate)

- SYNTHETIC SPERMACETI/ CETYL ESTERS


WAX
- Mixture consisting of primarily esters
of:
- saturated fatty alcohols (C14 to
C18)
- saturated fatty acids (C14 to C18)
- CETYL ALCOHOL
- mixture of solid alcohols
- chiefly (not less than 90%) of cetyl
alcohol or 1-hexadecanol
- Use: emulsifying aid, stiffening
agent
- STEARYL ALCOHOL
- mixture of solid alcohols
- chiefly (not less than 90%) of stearyl
alcohol or 1-octadecanol
- USE: alternative to cetyl alcohol, as
is cetostearyl alcohol

- CETOSTEARYL ALCOHOL
- not less than 40% of stearyl alcohol
- not less than 90% of cetyl and
stearyl alcohols
JOJOBA OIL
-

Liquid wax
Seeds
Simmondsia chinensis
Fam buxaceae
Contain 45 to 55% of an ester mixture
(liquid at ambient temperature)
MAJOR COMPONENTS:
- 35% of eicosenoic acid (C20
unsaturated acid)
- 22% of eicosenol (C20 unsaturated
alcohol)
- 21% of docosenol (C22 unsaturated
alcohol)
Hydrogenation -> crystalline wax
(appearance and properties similar to
spermaceti)
USE: emollient, agents of
pharmaceutic necessity

BEESWAX
-

Aka. Yellow wax or beeswax


Purified wax
Honeycomb of the bee
Apis mellifera
Fam apidae
Color: yellow to grayish brown
When cold = brittle, dull, granular,
non crystalline fracture
CONSISTS:
- alkyl esters of fatty and wax acids
(about 72%)
- (chiefly) myricyl palmitate
- free wax acids (about 14%)
- esp cerotic acid and its homologs
- hydrocarbons (12%)
Minor constituents
-moisture,pollen, and propolis (bee
glue)
The latter 2 materials : responsible for
most of the color of the wax
USE: stiffening agent, ingredient in
yellow ointment, base for cerates and
plasters
- COMMERCIALLY: contained in a
number of polishes

WHITE WAX

Bleached, purified wax


Honeycomb of the bee
Apis mellifera
Apidae
Aka. Bleached beeswax
Saponification cloud test rapid,
reliable, and inexpensive method of
detecting the presence of certain
adulterants of natural beeswax
USE: in ointments and in cold creams

CARNAUBA WAX
-

Leaves
Copernicia prunifera, C. cerifera
(arruda da camara)
Consists of:
- alkyl esters of wax acids 80%
- myricyl cerotate (chiefly)
- free monohydric alcohols 10%
- a lactone
- resin
- other minor constituents
USE: manufacture of candles, wax
varnishes, leather and furniture
polishes, polish for coated peanuts

PROSTAGLANDINS
-

C20 lipid metabolites formed in the


body from essential, unsaturated fatty
acids of the diet
Occur in nearly all mammalian tissues
Present in low concentrations
MAJOR PROSTAGLANDINS (4 main
classes)
- prostaglandins A,B,E, and F
All havea cyclopentane ring with 2
aliphatic side chains.
Subscripts indicate the number of
double bonds in the side chains and
the stereochemistry of members of
each group
1930 constituents in human semen
could produce contraction and
relaxation of the human uterus
Appear to act at the level of the cell
membrane and they may modulate
the transmission of hormonal or other
extracellular stimuli into cyclic AMP
for the internal regulation of cellular
functions

PGE

PGE1

PGE2
PGA1
and
PGE2
PGF2
-

PHARMACOLOGIC EFFECTS:
- contraction or relaxation of smooth
mucles of the female reproductive
system, of the cardiovascular system,
of the intestinal tract and of the
bronchi
Influence gastric secretion and renal
function
KEY ACCOMPLISHMENTS
- development of an enzymatic
synthesis that uses prostaglandins
synthetase from sheep seminal
vesicles
- discovery of prostaglandin materials
in Plexaura homomalla (sea fan or sea
whip)
- development of several procedures
for total chemical synthesis
Have diverse pharmacologic effects
PGE2, PGF2, and 15-methyl PGF2
- USE: termination of second trimester
pregnancies
PGE1
- USE: palliative therapy to maintain
temporarily neonates with patent
ductus arteriosus and certain
congenital heart defects
POTENTIAL FOR THERAPEUTICS USE:
-prevent premature labor
-induce menstruation
-increase fertility in certain
conditions
- correct some defects in RBC
- inhibit gastric secretions in the
treatment of peptic ulcers
-exert antithrombogenic and
thrombolytic activity
- control asthmatic seizures
-induce labor
Manage some types of hypertension

Control certain cardiac arrhythmias


Multiple effects of prostaglandins and
the diverse response to individual
prostaglandins by various body
tissues
- factors that give above average
chances for undesirable side effects in

any therapeutic use of these


compounds
- full significance remains to be
evaluated
PROSTAGLANDIN F2
-

Prostaglandin F2 , PGF2 or Dinoprost


Tromethamine salt
USE: terminating second trimester
pregnancy
- stimulates contractions of the gravid
uterus
SIDE EFFECTS: related to the
contractile effect of PGF2 , it may
extend to smooth muscle of GI tract
(causing vomiting and/or diarrhea)
and smooth muscle of the vascular
system (causing elevation in blood
pressure
Rapidly inactivated (serum half life:
10 mins/ less) in the lungs and other
body tissues
Two metabolic processes in the
inactivation of this prostaglandin:
- reduction of the unsaturated bond at
position 13
- oxidation of the 15-hydroxyl group to
a keto function
Short duration of action is desirable
for oxytocic agents
USUAL DOSE: 40 mg by slow injection
into the amniotic sac
IF the abortion process has not been
established or completed with 24
hours. Additional dose may be
administered

15-methylprostaglandin F2
-

Aka 15- methyl PGF2 or carboprost


o 15 methyl analog of PCF2
15 methyl substituent precludes
metabolic inactivation via oxidation of
the 15-hydroxyl group and permits a
substantially different dosage
regimen
Avail as the tromethamine salt
- used in terminating second trimester
pregnancy

USUAL INITIAL DOSE: 200 microgram


(deep IM)
DOSE may be repeated at 1.5-3.5
hour intervals (depending on uterine
response)
Total dose shouldnt exceed 12 mg
Therapeutic duration shouldnt
exceed 2 days

PROSTAGLANDIN E2
-

AKA. PGE2 and dinoprostone


USE: uterine stimulant
Approved for termination of second
trimester pregnancy.
PGE2 differs from PGF2 only in that the
9-oxygen substituent is a keto group
Avail as vaginal suppository
Should be stored @ temp below -20
deg Celsius
20 mg suppository (intravaginally)
every 3 to 5 hours until abortion
Max dose should not exceed 240 mg
PGE2 have similar pharmacologic
effects PGF2 but there is a lack of
vasoconstriction
and
resulting
hypertension with high doses of PGE2
ADR:
N&V,
pyrexia,
diarrhea,
headache, chills

PROSTAGLANDIN E1

Derivations:
-

Ricinus tick/bug
Olea latin for oliva (olive)
Elaion oil
Sesamum (sesamon) original name
of the plant
Indicum habitat (india)
Prunus plum tree
Amygdalus almond tree
Amara bitter
Dulcis sweet
Theobroma food of the gods
Cacao tree

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