PHARMACOGNOSY

TERPENOIDS AND CHEMISTRY OF VOLATILE OILS

Terpene hydrocarbons are summarized

PERFUME below:

GROUP EMPERICAL ISOPRENE EXAMPLES

FORM UNITS
EXTRACTION TECHNIQUE

 Yield varies form plant to plant, Hemiterpene C3H3 01 Isoprene

species to species and even depends
Monoterpene C10H16
on the isolation method.
 Most common is hydrodistillation Acyclic C5H8 02 Myrcene
using a Clevenger type apparatus. Monocyclic 02 Limonene
TERPENES Bicyclic 02 a-pinene
 Are large group of organic compound Sesquiterpene C15H24 03 (15 santalone
which are simple hydrocarbons carbon)
 Simple hydrogen compounds
 Hemiterpene, monoterpene,
BIOSYNTHESIS
diterpene, sesquiterpene,etc.
 Used in the food industry,cosmetic BUILDING UNITS NO. OF CARBON
industry, pharmaceutical industry & IPP- Isophenyl 5 (building block of
biotechnology pyrophosphate isoprene unit)
GPP- Geranyl 10 ( building block
TERPENOIDS pyrophosphate of monoterpenoids)
 Aka isoprenoids FPP- Farsenyl 15 ( building block
pyrophosphate of sesquiterpene)
 Made up isoprene with 5c C5H8
GGPP- Geranyl- 20 ( building block
 Large group of organic compounds geranyl of diterpenoids)
that are derived from isoprene pyrophosphate
 Hydrocarbon compound with oxygen
containing functional groups
 Important in traditional herbal GPP + IPP = FPP
remedies FPP + IPP = GPP

GPP= 25 C

NO. NO.
ISOPRENE CARBON
UNITS ATOMS
Monoterpene 2 10
Sesquiterpene 3 15
Diterpene 4 20
Sesterterpene 5 25
Triterpenes 6 30
Tetraterpenes 8 40
Polyterpenes >8 >40
MONOTERPENOIDS  Supposed to release a continuous
pleasant fragrance that will provide a
 Camphor
long lasting feeling of freshness
 Eucalyptol
 Only used for religious purpose.
 Menthol
 Terpinol HISTORY OF PERFUME:
 Thymol
EGYPTIANS
SESQUITERPENOID
 First who used perfume for personal
 Arteminisinin- antimalarial / Artemisia enjoyment, but the production of
annue ( CN: Qinghaosu) perfume was reserved for the prists &
 Chamomile – carminative / they used it in religious purpose
spasmolytic
GREEK
 Feverfew – antipyretic
 Valerian- anti- anxiety  Used an extraordinary amount of
perfume & for each part of the body
DITERPENOIDS they used a different fragrance for
 Forskolin hygiene and cult of the body.
 Gingko ARABS
 Taxol ( anti- cancer)
 Fusion of art and science
TRITERPENOIDS  2 talented Arabian chemists (Jabir ibn
 Cucurbitacins ( bitter principles) hayyan and Al- kindi) established the
 Quassinoids ( bitter principle) perfume industry.
 Saponins ROMANS
 Limonoids ( neon plant – anti feed
ant)  Used perfume as part of industry
 Phytoedcysone NOTE:
TETRATERPENOIDS Oldest perfume was discovered on the island
 Vitamin A of Cyprus 4000 years ago indicating that
 Beta- carotene perfume manufacturing was an industrial
( precursor of vitamin a) scale.

HUNGARIANS

 The first modern perfume

PERFUME  Made scented oils blended in an
alcohol solution at the command of
queen Elizabeth of hungry

 Mixture of fragrant essential oils or

aromatic compounds, fixatives &
solvent used to give to human body,
animal, food objects & living spaces a
pleasant scent
FRANCE IS THE BIRTHPLACE OF  Bottom or dry notes appear while
middles notes are fading
MODERN PERFUME  The base and the middle notes
together are the main theme of a
perfume
FRANCE  Bring depth & solidity to a perfume
 Provided to grow aromatic plants for Common fragrance:
perfume industry with raw materials
 Remains the centre of the European  Lemon, orange, bergamot
perfume design and trade  Rose, jasmine, iris
 Sandalwood, oakmoss, musk
ENGLAND & GERMANY

 Also contributed a lot in

modernization of perfumery. CLASSIFICATION OF PERFUMES

NOTES IN PERFUME: CLASS % OF ESSENTIAL

OILS
 Described in a musical metaphor as Extrait de perfum 20-40
having 3 sets of notes, making Eau de perfum 15-20
harmonious scent accord. Eau de toilette 5-15
Eau de cologne 2-4
Eau traiche 1-3
1. TOP NOTES
 The lightest of all notes PARFUM OR EXTRAIT / EXTRAIT DE PERFUM
 Consist small, light molecule with high
volatility that evaporate quickly  Contains high concentration of
fragrance, typically the most
Common fragrance: expensive
Citrus ( lemon, orange zest)  Usually a heavier,oiler product that
the other types of perfume & tends to
High fruits ( grapes & berries) be used more sparingly
Herbs ( clary sage & lavender)  Smell is long lasting ( 8-24hrs)

2. MIDDLE NOTES 1. BRIGHT FLORAL

 The heart notes  Fragrance from one or several flowers
 Make an appearance once top notes EX: Estee lauders beautiful
evaporate
 From the ‘heart’ or main body of a 2. GREEN
perfume  Fragrance from cut grass or leaf
 Act to mask often unpleasant initial EX: Calvin klein’s eternity
impression of base notes which
become more pleasant with time. 3. AQUATIC
 A clean smell reminiscent of ocean

EX: David off cool water

3. BASE NOTES
4. CITRUS
  Has freshening effect b. SOLVENT DISTILLATION
 Flower parts are dissolved in benzene
EX: Faberge brut
or petroleum that retains the
5. FRUITY fragrance of the flower
 Aromas of fruits other than citrus  Alcohol is used to dissolve the
fragrance & heated to obtain it after
EX: Ginestet botrytis evaporation of alcohol.
6. GOURMAND
 Scent with edible or dessert like
qualities c. ENFLEURAGE
 Flowers are kept in glass sheet with
EX: Thierny mugler’s angel grease that absorb the fragrance of
flowers

AROMATIC SOURCES
d. EXPRESSION
PLANT SOURCE  Citrus fruits or plants are manually or
mechanically pressed until all the oil is
 Barks, flowers, blossoms, fruits, resin,
squeezed out.
roots, seeds, woods, etc.
BLENDING
ANIMAL SOURCE
 Known as a ‘nose’
 Musk,civet honey comb, etc.
 It is mixed with alcohol
SYNTHETIC SOURCE  full perfumes are made out about 10-
20 % perfume oils are dissolved in
 Calone, synthetic terpenes, etc.
alcohol & trace of water.

AGING
MANUFACTURING PROCESS:
 aged for several months or even years
COLLECTION  ensure that the correct scent has
been achieved.
 Sources of suitable fragrance are
collected in the manufacturing centre. PERFUMES ARE MAINLY COMPOSED OF:

EXTRACTION 1. ESSENTIAL OIL

 Derived from natural aromatic plant
 Oils are extracted from plants & other
extracts or synthetic aromatic
substances by several methods.
chemicals.

EX: limonene, linalool, geranoil, eitral

a. STEAM DISTILLATION
2. FIXATIVES
 Passed through plant materials held in
 Natural or synthetic substances used
a still, whereby the essential oil turn
to reduce the evaporation rate.
to gas.
 This gas passed through tubes, EX: benzyl benzoate, benzyl alcohol
cooled, liquefied and collected.
 3. SOLVENTS
 The liquid in which the perfume oil is
dissolved and it usually 98% ethanol &
2 % water
 Allows alcohol fragrance to spread
along with it & does not permit
microbial growth in the perfume.

INGREDIENT CAUSING ALLERGIC REACTION.

INGREDIENT USES SIDE EFFECT

Limonene Slightly Irritates the
astringent skin
smell
Sandal fragrance Hypersensitivity
wood
Benzyl fixative Skin irritant
alcohol causing pain
Benzyl Fixative, Blister itching,
benzoate sweet scaling, redness
balsamic to skin.
odor
Acetone solvent Inhalation
cause dryness
of mouth and
throat
Ethyl solvent Defatting effect
acetate on skin & may
cause drying &
cracking.