Transcript 11_Chem. anal. of VO. Monoterpenoids and sesquiterpenoids.pp

Lecture №11
Chemical analysis of MPM containing
essential oils. Herbs and MPM that
contain monoterpenes and
sesquiterpenes
Volatile oils (VO) are miscellaneous
volatile organic compounds which are
produced in plants and cause their
specific odour
 They differ entirely in both chemical and physical
properties from fixed oils. VO can be distilled from
their natural sources; they do not consist of
glyceryl esters of fatty acids. Hence, they do not
leave a permanent grease spot on paper. VO do
not become rancid as do the fixed oils, but
instead, on exposure to light and air, they oxidize
and resinify.
VO can be divided into 3 main groups:
 monoterpenoids (acyclic, monocyclic
and bicyclic);
 sesquiterpenoids (acyclic,
monocyclic, bicyclic, tricyclic);
 aromatic compounds (derivatives of
n-cimen, benzol and phenilpropan).
Terpene hydrocarbons
Monoterpene hydrocarbons
Sesquiterpenes
Oxygenated compounds
Phenols
Alcohols
Monoterpene alcohols
Sesquiterpene alcohols
Aldehydes
Ketones
Esters
Lactones
Coumarins
Ethers
Oxides
Моnoterpenoids (C10H16)
 Аcyclic
2,6-Dimethyloctan
Linalool
Citronellal
•Monocyclic monoterpenoids
N-menthan
1 methyl,4-I
sopropilhexan
Carvone
1,4-Cineol
Menthol
1,8-Cineol
•Bicyclic monoterpenes (types of carane,
pinane, camphane, thujane)
Carane type
Carane
Carane
Carane
Pinane type
Pinane
α-pinane
β-pinane
Camphane type
Camphane Camphene
Thujane type
Thujane
Sabinen
Borneol
(-) Camphor
Thujol
Thujone
Bornil isovalerianate
Sesquiterpenoids (C15H24)
 Аcyclic
Farnesane
Farnesene
Farnesol
Bisabolone
Bisabolol
 Monocyclic
Bisabolane
•Bicyclic
1. Alkilnaphthalene type
Cadinane
Cadinene
Selinane (evdesmane)
Cadinol
α-Selinene
β-Selinene
2. Alkilazulene type
Guaiane type
Chamazulene type
Guaiane
S-Guaiazylene
Se-Guaiazylene
Chamazulane
Chamazulene
Azulane
3. Bicyclic sesquiterpenoids of other structure
Akorane
Tricyclic sesquiterpenoids
Sesquiterpene lactone
Eudesmanolide type
Alantolactone
Santonine
Guaianolide type
Mathrycyne
Aromadendrane
Aromatic compounds
p-Cymene type
p-Cymene
Thymol
Carvacrol
Phenylpropan type
Anetole
Evgenole
Azarone
Vanillin
Phenylehylic alcohol
Benzene type
Anise aldehyde
Occurrence
Essential oils are of wide occurrence in
Nature. More than 2500 of plants can
accumulate them. Tropical plants are rich in
VO. Usually they occur in such families as
Lamiaceae, Apiaceae, Asteraceae and
Rosaceae. The content may rich up to 20%
(Citrus fruits). Ether oils are produced by
special exo- and endogenic organs.
Glands (fam. Lamiaceae)
Essential oil reservoir
(Eucalyptus globulus)
Essential oil cells
(Acoruc calamus)
Glands (fam. Asteraceae)
Essential oil tubes (ducts)
(Foeniculum vulgare)
Methods of obtaining of
volatile oils
1. Distillation in water and steam
2. Scarification and expression
(pressing)
3. Extraction with solvents
(Extraction with volatile
solvents and the enfleurage)
4. Enzymatic hydrolysis
(according to WHO, EuPh\
Xylen
Clavenger apparatus
(according to Sovet pharmacopeia XI)
1. A round bottom pyrex distillation
2. A receiver (trap)
3. A cork
4. A condenser
Allspice
Aniseed
Basil
Bay
Benzoin
Bergamot
Black pepper
Cajuput
Camomile
Camphor
Caraway
Carrot seed
Cassia
Cedarwood
Chamomile
Cinnamon
Citronella
Clary sage
Clove
ESSENTIAL OILS
Coriander
Mandarin
Cypress
Marjoram
Dill
Melissa
Eucalyptus Myrrh
Fennel
Neroli
Frankincense Niaouli
Geranium
Nutmeg
Ginger
Orange
Grapefruit
Palma rosa
Helichrysum Patchouli
Hyssop
Peppermint
Jasmine
Petitgrain
Juniper
Pimento
Lavandin
Pine
Lavender
Rose
Lemon
Rose geranium
Lemongrass Rosemary
Lemon verbena Rosewood
Lime
Sandalwood
Sage
Spearmint
Tagetes
Tangerine
Thyme
Tea tree
Vetiver
Ylang-ylang
ESSENTIAL OILS
NOT SOLD BY US
Angelica
Birch
Bitter almond
Boldo
Buchu
Calamus
Cardamom
Cumin
Elemi
Mugwort
Mustard
Oregano
Pennyroyal
Rose otto
Rue
Sassafras
Spikenard
Tansy
Tarragon
Savin
Thuja
Tuberose
Vanilla
Wintergreen
Wormseed
Wormwood
Yarrow
PRE-BLENDED
FORMULAS
Muscle & Joint
Relaxation
Sensual
Anti-cellulite
Circulation
Hair & Scalp
Dry & Mature Skin
Insomnia
Baby
Vein & Artery
Sunburn
OTHER OILS
Rosehip oil
Baobab oil
Marula oil
Neem oil
CARRIER OILS
Almond oil
Aloe vera oil
Apricot kernel oil
Avocado oil
Calendula oil
Evening primrose
oil
Grape seed oil
Hazelnut oil
Jojoba oil
Macadamia oil
Sesame oil
Walnut oil
Wheatgerm oil
CARRIER OILS
NOT SOLD BY US
Olive oil
Pumpkin seed oil
Safflower oil
Sunflower
MP and MPM containing
monoterpenoids
Menthae piperitae folia
Mentha piperita- Peppermint, Lamb
mint, American mint, Brandy mint
Lamiaceae
 Constituents. Leaves contain up to
3.5% of ether oil and menthol is the
main part- up to 80%; resin, tannins,
acetic acid, etc.
 Uses. Infusion stimulates the
secretion of digestive glands, has
sedative, spasmolitic, cholagogue
and light pain-killing action. Volatile
oil is part of Inhalipt, Corvaldin, Mint
tablets, Tooth drops, Urolesan,
Pinosol. Menthol is applied externally
in solutions for the relief of neuralgic
pains, and as antiseptic and cooling
agent in certain skin diseases.
Internally it is an antiseptic. It is part
of Alorom, Boromentol, Gevkamen,
Cameton, Camphomen, Zelenin’s
Drops, Menovasin, Pectussin.
Salviae Folia
Salvia officinalis- Sage
Lamiaceae
 Constituents. Up to 2.5% of a
greyish-yellow volatile oil
containing borneol, pinene,
thujone and cineol, bitter
principles, resin and tannins.
 Uses. Sage is used chiefly as a
condiment but is also employed
as a carminative in dyspepsia,
also has antiseptic, astringent
action. Salvin works as plant
antibiotic due to the content of
diterpenes; is used in treatment
of gingivitis and stomatitis.
Eucalypti Folia
Folia Eucalypti viminalis
Oleum Eucalypti
Eucalyptus globulus, Eucalyptus cinerea, Eucalyptus viminalis
English names: Eucalyptus, Blue Gum leaves, Australian Fever
Tree, Iron Bark Tree
Myrtaceae
Coriandri Fructus
Coriandrum sativum- Coriander
Apiaceae
 Constituents. Up to 1% of volatile
oil containing coriandrol (d-linalool)
and d-pinene, etc.; fixed oil, calcium
oxalate, tannins.
 Uses. Aromatic stimulant, has
spasmolitic and antibacterial
properties. It is part of appetising,
cholagogue, expectorant and antihaemorrhoidal species, infusionpart of Flora, ether oil is part of
Espol (anti-inflammation and painkilling drug).
Carvi Fructus
Carum carvi L.
Caraway
Apiaceae
 Constituents. Volatile oil (57%), fixed oils, tannins, etc.
The volatile oil contains
carvone, limonene,
dihydrocarvone, caryeol, and a
small quantity of a base having
a narcotic odour.
 Uses. Stimulant, carminative,
condiment, diuretic, diaphoretic
and flavouring agent; source of
oil of caraway. It is used in the
food industry for flavouring
bread, cheese and candy.
Juniperi Fructus
Juniperus communisJuniper, Horse Savin Berries
Cupressaceae
 Constituents. From 0.3 to 1.5% of a
VO containing the terpenes camphene
and x-pinene, a sesquiterpene called
cadinene; terpene alcohols borneol,
one of which is terpineol; resin, fixed
oils, up to 30% of dextrose, etc. A
crystalline substance deposits in the
oil at low temperatures known as
juniper camphor.
 Uses. Juniper berries are used for the
preparation of juniper oil. The juniper
oil has diuretic, antireumatic and
antiseptic properties. Used as
stimulating diuretic in chronic genitourinary disorders.
Valerianae radix
Valeriana officinalis- Valerian, Wild,
Great Wild, Cat’s Valerian
Valerianaceae
 Constituents. Volatile oil (up to
2%) containing bornyl
isovalerianate, bornyl formiate,
bornyl acetate and bornyl
butyrate, camphene, borneol and
pinene; two alkaloids- chatinine
and valerianine, a glucoside,
resin, α-methylpyrryl ketone,
stated to be narcotic, valeric,
formic and acetic acids, tannins,
sugar, etc.
 Uses. Valerian is used as a
calmative in nervousness and
hysteria and as a carminative.
Preparations- Valerian fluid
extract, Valerian tincture,
Valocordinum, Corvalolum, as
ingredient of Species Sedativae.
Lavandulae Flores
Lavandula angustifolia L.
Lamiaceae
 Constituents. Up to 3%
of VO containing esters,
also linalool, geraniol,
limonene and
sesquiterpene; resin,
tannins, etc.
 Uses. Lavender flowers
are chiefly used as a
perfume. Livian has antiinflammatory and painkilling action and used to
treat burns.
MP and MPM containing
sesquiterpenoids
Calami Rhizomata
Acorus calamus- Sweet Flag,
Sweet Root
Araceae
 Constituents. Vo (1.5to
3.5%) containing asaryl
aldehyde, eugenol and
asarone; a bitter glucoside
called acorin; soft resin,
starch, inulin, etc.
 Uses. Carminative, aromatic
bitter and stimulant;
flavouring agent. Used in
atonic dyspepsia and colic.
Vicalin, Vicair and
Herbogastrin are used for the
treatment of ulcers.
Betulae Gemmae
Betulae Folia
Betula pendula, Betula pubescens
English name- Birch
Betulaceae
 Constituents. VO 5-8% with
balsamic odour, contained
bicyclical sesquiterpenoid
betulen and alcohol betulenol.
 Uses. Medicines have diuretic,
diaphoretic, cholagogue,
spasmolytic, anti-inflammation,
anti-viral, wound-heeling and
antihelmintic actions.
Medicines- infusion, tincture,
Propobesan.