Phamacognosy Compiled by I.

K Laroco, RPh, MPH 17/03/2023

Lipids

LIPIDS
Ian Kenneth B.Laroco, RPh, MPH

Lipids Triglycerides

Fixed Oils Esters of Fatty Liquid at room Plants

Acid (Unsaturated) temp except
+ Glycerol THEOBROMA
OILS

Fats Esters of Fatty Solid at room temp Animals

Acid + Saturated except COD
fatty acid + LIVER OIL
Glycerol
Waxes Esters of Fatty Solid, Semi-solid, Plants & Animals
Acid + High MW Liquid
straight chain
acids
Phamacognosy Compiled by I.K Laroco, RPh, MPH 17/03/2023

Lipids Lipids

These are esters of long chain fatty acid and alcohol, or of  These are heterogenous group of  Biomedical importance
closely related derivatives. compounds related more by their  Cell differentiation and growth
physical than by their chemical  Cell membrane structure
properties containing C, H, and O,  Signal transmission
FORMS: sometimes N and P.  Hormone synthesis
 Fixed oils –glycerol combines with unsaturated fatty acid  They have common property of  Bile acid synthesis

 Fats –glycerol combines with saturated fatty acid being:

Insoluble in water
 Waxes –esters from alcohol which has a higher M.W.


 Soluble in non-polar solvents

 Prostaglandins –C20 lipid metabolites formed in the body from
 On hydrolysis, they give fatty acids
essential, unsaturated fatty acids

USP Tests USP Tests

1. Acid Value/Acid No. 4. Hydroxyl Value

--# of mg of KOH req’d to neutralize the free fatty acid in 1 g of the subs. --# of mg of KOH equivalent to the OH content of 1 g of a subs.
--indicates the amount of free fatty acid present in the oil.
2. Ester Value 5. Iodine Value
--# of mg of KOH req’d to saponify esters in 1 g of the subs.
--# of grams of iodine absorbed by 100 g of the subs.
--aka KOETTSDORFER No.
--indicates the degree of unsaturation
3. Saponification Value
--# of mg of KOH req’d to neutralize free fatty acid and saponify esters in
1 g of the subs.
Phamacognosy Compiled by I.K Laroco, RPh, MPH 17/03/2023

Fatty Acids Fatty Acids

 Fatty acids are the building  Saturated Fatty Acids  Unsaturated Fatty Acids
blocks of lipids; they are  Structure of Fatty acids  Contain no double bonds and  Monounsaturated: contain one

 Fatty acids consist of one are based on acetic acid as double bond
straight-chain organic acids.
carboxyl group (-COOH) the first member of the series  Polyunsaturated: contain two or
 Fatty acids are important attached to a non-polar in which –CH2 is more double bonds
sources of fuel because, hydrocarbon tail. progressively added between
 Eicosanoids: these compounds
metabolized, they yield large the terminal CH3- and COOH derived from eicosa-(20 carbon)
 General Formula:
quantities of ATP. groups
 CH3(CH2)n-COO- polyunsaturated FA, comprise the
prostanoids and leukotrienes (LTs)
and Lipoxins

SATURATED FATTY ACIDS – NO DOUBLE BONDS

# of C Common Name Systematic Name Formula
1 Formic Acid Methanoic Acid HCOOH
2
11 Acetic Acid Ethanoic Acid CH3COOH 12

3 Proprionic Acid Propanoic Acid CH3CH2COOH UNSATURATED FATTY ACIDS – NO DOUBLE BONDS
4 Butyric Acid Butanoic Acid CH3(CH2)2COOH # of C Common Name Position of the Double Formula
5 Valeric Acid Pentanoic Acid ? Bond
6 Caproic Acid Hexanoic Acid ? Monounsaturated Fatty Acids
8 Caprylic acid Octanoic Acid ? 16 Palmitoleic Acid C9 CH3(CH2)5CH=CH(CH2)7COOH
10 Capric acid Decanoic Acid ? 18 Oleic Acid C9
12 Lauric acid Dodecanoic Acid ? 18 Elaidic Acid C9
14 Myristic acid Tetradecanoic Acid ? 20 Nervonic Acid C15
16 Palmitic acid Hexadecanoic Acid ? Polyunsaturated Fatty Acids
18 Stearic acid Octadecanoic Acid ? 18 Linoleic Acid C9, C12
20 Arachidic acid Eicosanoic Acid ? 18 Linolenic Acid C9, C12, C15
22 Behemic acid Docosanoic Acid ? 20 Arachidonic Acid C5, C8, C11, C14
24 Lignoceric acid Tetracosanoic Acid ?
Phamacognosy Compiled by I.K Laroco, RPh, MPH 17/03/2023

Fatty Acids Stearates

Stearate Use
1. Stearic acid
Calcium stearate Tablet lubricant
C: stearic and palmitic acid (purified stearic acid
Magnesium stearate Tablet lubricant
contains NLT 90% stearic acid)
Sodium stearate Emulsifying and stiffening
U: emulsion adjunct and tablet lubricant agent
Aluminum monostearate Suspending agent
Glyceryl monostearate
Propylene glycol Emulsifying agent and
monostearate emollient

Fatty Acids Fatty Acids

2. Oleic acid 4. Undecylenic acid

--often obtained as a by-product in the production of stearic acids --10-undecenoic acid
C: cis-9-octadecenoic acid --prepared by pyrolysis of ricinoleic acid, obtained from ______
U: emulsion adjunct U: antifungal
3. Linoleic and linolenic acids
--polyunsaturated octadecenoic acids 5. Sodium morrhuate
--“vitamin F” --sodium salts of fatty acids of _______
--obtained mostly in soybean and others U: sclerosing agent (to obliterate varicose veins)
U: dietary supplement
Phamacognosy Compiled by I.K Laroco, RPh, MPH 17/03/2023

Cis & Trans Configuration of Fats Omega End

18

Omega End Fixed Oils

 Have a higher proportion of liquid glycerides or polyunsaturated

glycerides
 Official Fixed Oils
 Peanut Oil

 Sesame Oil

 Corn Oil

 Cottonseed Oil
Phamacognosy Compiled by I.K Laroco, RPh, MPH 17/03/2023

Biosynthesis of Fixed Oils Extraction of Fixed Oils & Fats

1. via degradation reactions: By expression:

a. hydrolysis of the glycerol-fatty acid esters by the a. Cold expression –product is called “_______” or “cold-pressed
enzyme_______ oil”;without aid of heat
b. Heat expression –product is called “hot-pressed oil”;with heat
b. subsequent removal of 2-carbon units as acetyl-CoA from
the fatty acid chain by _______ OCCURENCES:
 seeds
2. via Malonyl-Acetate Pathway  pericarp

Classification of Fixed Oils General Uses of Fixed Oils

1. Drying  Emollient, lubricant

-120 Iodine (linseed and cod liver oil)
 Manufacture of soaps, paints, and varnishes
2. Semi-drying
-100-120 (sesame and cottonseed oil)  Parenteral solvents/nutrients in hyperalimentation

3. Non-drying
-100 (olive and almond oil)
Phamacognosy Compiled by I.K Laroco, RPh, MPH 17/03/2023

Fixed Oils Fixed Oils

2. Olive oil
1. Castor oil
-“sweet oil”, “salad oil”
SN: Ricinus communis
SN: Olea europaea
FN: Euphorbiaceae
FN: Oleaceae
C: Ricin, triricinolein, ricinine
C: 75% Oleic acid (Turkish var), 65% Oleic acid
Use: stimulant cathartic, plasticizer in flexible
(Italian var)
collodion, manufacture of soaps and lubricant for
internal combustion U: for dental cements, preparation of soaps, plasters
and liniments as setting retardant, as nutrient and
salad oil

Fixed Oils Fixed Oils

3. Peanut oil
Grades of Olive Oil:
-“So oil”
1. Virgin –cold-pressed, gentle pressure
SN:Arachis hypogaea
2. Technical oil –hot-pressed (mixing oil with hot water)
FN: Fabaceae
3. Sulfur olive oil –pulp is extracted with Carbon disulfide
C: oleic acid
solvent
U: lubricant, solvent for IM inj, manufacture of WHITE
4. Tournant oil –low grade olive oil obtained from fallen,
SOAP
decomposed or refused olives; contains large amounts of
free fatty acid
Phamacognosy Compiled by I.K Laroco, RPh, MPH 17/03/2023

Fixed Oils Fixed Oils

4. Cottenseed oil 5. Corn oil

SN: Gossypium hirsutum SN: Zea mays
FN: Malvaceae FN: Poaceae
C: Gossypol C: linoleic acid
U: solvent for inj, manufacture of soaps U: sovent for inj, solvent for irradiated ergosterol

Fixed Oils Fixed Oils

6. Sesame oil 7. Soybean oil

-“teel oil” or “benne oil” SN: Glycine soja
SN: Sesamum indicum FN: Fabaceae
FN: Pedaliaceae C: linoleic acid
C: sesamol U: parenteral solvent
U: solvent for inj, synergist for pyrethrum insecticides
Phamacognosy Compiled by I.K Laroco, RPh, MPH 17/03/2023

Fixed Oils Fixed Oils

8. Almond oil 9. Persic oil

-“expressed almond oil”, “sweet almond oil” -“apricot kernel oil”, “peach kernel oil”
SN: Prunus amygdalus SN: Prunus armeniaca, P. persica
FN: Rosaceae FN: Rosaceae
C: oleic acid U: vehicle, pharmaceutic necessity
U: emollient, ingredient in cosmetics

Fixed Oils Fixed Oils

10. Coconut oil

SN: Cocos nucifera 11. Safflower oil
FN: Palmae SN: Carthamus tinctorius
C: lauric and myristic acid FN: Compositae
U: high saponification value yielding quality soaps and shampoos
C: linoleic acid
U: high-calorie dietary supplement
Phamacognosy Compiled by I.K Laroco, RPh, MPH 17/03/2023

Fixed Oils Fixed Oils

12. Sunflower oil

13. Rapeseed oil
SN: Helianthus annuus
SN: Brassica campestris
FN: Compositae
FN: Brassicaceae
C: linoleic acid
C: erucic acid 50%
U: alternative to corn and safflower for culinary purposes
U: antinutritional
*canola oil

Fixed Oils Fixed Oils

14. Ethiodized Oil Inj 15. Cod liver oil

--an iodine addition product of the ethyl ester of the fatty acids of SN: Gadus morrhua
poppy seed oil FN: Gadidae
--radiopaque and used as diagnostic aid in hysterosalpingography C: oleovitamin A and D
and lymphography. U: source of oleovitamin A and D
Phamacognosy Compiled by I.K Laroco, RPh, MPH 17/03/2023

Fats and Related Compounds Fats and Related Compounds

1. Theobroma oil/Cocoa butter Cocoa products:

 --“food of the gods” 1. Cacao butter –paste formed from ground cacao kernels
 SN: Theobroma cacao containing up to 50% of fat
 FN: Sterculiaceae 2. Bitter chocolate –congealed cacao butter
 C: oleic acid, stearic acid, theobromine, oleopalmitostearin 3. Sweet chocolate –bitter chocolate to which sugar and vanilla
 U: suppository base, flavored vehicle or other flavoring have been added.
4. Prepared cacao or breakfast cocoa –powdered marc

Fats and Related Compounds Fats and Related Compounds

2. Hydrogenated vegetable oil 3. Lanolin

--refined, bleached, hydrogenated and decolorized vegetable oil -“hydrous wool fat”
stearins and consists mainly of trigycerides of stearic acid and --contains between 25-30% of water
palmitic acid SN: Ovis aries
--used as tablet lubricant FN: Bovidae
C: cholesterol and isocholesterol
U: water absorbable ointment base, ingredient in many skin creams
and cosmetics, allergenic contactant in hypersensitive persons
Phamacognosy Compiled by I.K Laroco, RPh, MPH 17/03/2023

Fats and Related Compounds Fats and Related Compounds

4. Anhydrous lanolin
5. Lanolin alcohols
-“wool fat”
--mixture of aliphatic alcohols, triterpenoid alcohols, and sterols,
-contains nmt 0.25% of water obtained by the hydrolysis of lanolin
U: water absorbable ointment base, emollient --contain NLT 30% cholesterol
U: emulsifying agent in ointments

Waxes Waxes

1. Spermaceti 2. Jojoba oil

--waxy subs. Obtained from the head of sperm whale --liquid wax which resembles spermaceti when hydrogenated
SN: Physeter macrocephalus
SN: Simmondsia chinensis
FN: Physeteridae
FN: Buxaceae
C: Cetyl laurate, myristate, palmitate, stearate
C: eicosanoic acid, eicosanol, docosenol
Synthetic spermaceti
U: emollient and pharmaceutic necessity
--“__________wax”
--mixture consisting primarily of saturated fatty alcohols and saturated fatty
acids
Phamacognosy Compiled by I.K Laroco, RPh, MPH 17/03/2023

Waxes Waxes
4. Carnauba wax
3. Beeswax
SN: Copernicia prunifera
-“yellow wax”
FN: Palmae
-purified wax obtained from the honeycomb of bees
C: myricyl _______
SN: Apis mellifera
U: manufacture of candles, wax, varnishes, leather polishes,
FN: Apidae
furniture polishes and floor polishes
C: myricyl _______ and ________ (bee glue)
U: stiffening agent, ingredient in yellow ointment, base for cerates
and plasters
White wax –bleached yellow wax

Prostaglandins Prostaglandins

 C20 Lipid metabolites from PROSTAGLANDINS

essential unsaturated fatty 1. Dinoprost
acids -“prostaglandin F2α”, “PGF2α”
 class of natural products - tromethamine salt for use in terminating trimester pregnancy; stimulates
with potent and diverse contraction of uterus
biological activities D: 40mg slow injection to the amniotic sac
involved in platelet
aggregation, pain and
inflammation
Phamacognosy Compiled by I.K Laroco, RPh, MPH 17/03/2023

Prostaglandins Prostaglandins

2. Carboprost 3. Dinoprostone
“15-methylprostaglandin F2α” “Prostaglandin E2”, PGE2
15 methyl analog of PGF2α Used in terminating 2nd trimester pregnancy
Used in terminating 2nd trimester pregnancy
Available as vaginal suppository
D: 200mcg by deep IM injection
D: 20mg

Prostaglandins

4. Alprostadil
“Prostaglandin E1”, PGE1
Produces vasodilation which stimulates uterine smooth muscle
contraction
Metabolized properly
D: 500mcg in 1-ml ampule