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Lecture № 11

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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. - PowerPoint PPT Presentation
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Lecture Lecture 11 11 Chemical analysis of MPM Chemical analysis of MPM containing essential oils. containing essential oils. Herbs and MPM that contain Herbs and MPM that contain monoterpenes and monoterpenes and sesquiterpenes sesquiterpenes
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Page 1: Lecture  № 11

Lecture Lecture №№1111

Chemical analysis of MPM containing Chemical analysis of MPM containing essential oils. Herbs and MPM that essential oils. Herbs and MPM that

contain monoterpenes and contain monoterpenes and sesquiterpenessesquiterpenes

Page 2: Lecture  № 11

Volatile oils (VO) are miscellaneous Volatile oils (VO) are miscellaneous volatile organic compounds which are volatile organic compounds which are

produced in plants and cause their produced in plants and cause their specific odourspecific odour

They differ entirely in both chemical and physical They differ entirely in both chemical and physical properties from fixed oils. VO can be distilled from properties from fixed oils. VO can be distilled from their natural sources; they do not consist of their natural sources; they do not consist of glyceryl esters of fatty acids. Henceglyceryl esters of fatty acids. Hence,, they do not they do not leave a permanent grease spot on paper. VO do leave a permanent grease spot on paper. VO do not become rancid as do the fixed oils, but not become rancid as do the fixed oils, but instead, on exposure to light and air, they oxidize instead, on exposure to light and air, they oxidize and resinify. and resinify.

Page 3: Lecture  № 11

VO can be divided into 3 main groups:VO can be divided into 3 main groups: monoterpenoids (acyclic, monocyclic monoterpenoids (acyclic, monocyclic

and bicyclic);and bicyclic); sesquiterpenoids (acyclic, sesquiterpenoids (acyclic,

monocyclic, bicyclic, tricyclic);monocyclic, bicyclic, tricyclic); aromatic compounds (derivatives of aromatic compounds (derivatives of

n-cimen, benzol and phenilpropan).n-cimen, benzol and phenilpropan).

Page 5: Lecture  № 11

МоМоnoterpenoids noterpenoids (C10H16)(C10H16)

ААcycliccyclic

Linalool2,6-Dimethyloctan

Citronellal

Page 6: Lecture  № 11

•Monocyclic monoterpenoidsMonocyclic monoterpenoids

Menthol N-menthan 1 methyl,4-Isopropilhexan

Carvone 1,4-Cineol 1,8-Cineol

Page 7: Lecture  № 11

•Bicyclic monoterpenesBicyclic monoterpenes ( (types of types of caranecarane, , pinanepinane, , camphanecamphane, , thujanethujane))

Thujane Sabinen Thujol Thujone

Thujane typeCamphane Camphene Borneol (-) Camphor

Camphane type Pinane α-pinane β-pinane

Pinane typeCarane Carane Carane

Carane type

Page 8: Lecture  № 11

Bornil isovalerianate

Page 9: Lecture  № 11

Sesquiterpenoids (C15H24)Sesquiterpenoids (C15H24) ААcyclic cyclic

MonocyclicMonocyclic

Farnesane Farnesene Farnesol

Bisabolane Bisabolone Bisabolol

Page 10: Lecture  № 11

•BicyclicBicyclic1. 1. Alkilnaphthalene typeAlkilnaphthalene type

2. 2. Alkilazulene typeAlkilazulene type

Cadinane Cadinene Cadinol

Selinane (evdesmane) α-Selinene β-Selinene

Guaiane type

Guaiane S-Guaiazylene Se-Guaiazylene

Chamazulene type

Chamazulane Chamazulene

Page 11: Lecture  № 11

3. Bicyclic sesquiterpenoids of other structure

Azulane

Akorane

Page 12: Lecture  № 11

Tricyclic sesquiterpenoidsTricyclic sesquiterpenoids

Sesquiterpene lactoneSesquiterpene lactoneEudesmanolide typeEudesmanolide type

Guaianolide typeGuaianolide type

Aromadendrane

Alantolactone Santonine

Mathrycyne

Page 13: Lecture  № 11

Aromatic compoundsAromatic compoundsp-Cymene type

p-Cymene Thymol CarvacrolPhenylpropan type

Anetole Evgenole Azarone Benzene type

Anise aldehyde Vanillin Phenylehylic alcohol

Page 14: Lecture  № 11

Occurrence Occurrence

Essential oils are of wide occurrence in Essential oils are of wide occurrence in Nature. More than 2500 of plants can Nature. More than 2500 of plants can accumulate them. Tropical plants are rich in accumulate them. Tropical plants are rich in VO. Usually they occur in such families as VO. Usually they occur in such families as Lamiaceae, Apiaceae, Asteraceae and Lamiaceae, Apiaceae, Asteraceae and Rosaceae. The content may rich up to 20% Rosaceae. The content may rich up to 20% (Citrus fruits). Ether oils are produced by (Citrus fruits). Ether oils are produced by special exo- and endogenic organs. special exo- and endogenic organs.

Page 15: Lecture  № 11

Glands (fam. Lamiaceae)

Essential oil reservoir (Eucalyptus globulus)

Essential oil cells (Acoruc calamus)

Glands (fam. Asteraceae)

Essential oil tubes (ducts) (Foeniculum vulgare)

Page 16: Lecture  № 11

Methods of obtaining of Methods of obtaining of volatile oilsvolatile oils

1.1. Distillation in water and steamDistillation in water and steam2.2. Scarification and expression Scarification and expression

(pressing)(pressing)3.3. Extraction with solvents (Extraction Extraction with solvents (Extraction

with volatile solvents and the with volatile solvents and the enfleurage)enfleurage)

4.4. Enzymatic hydrolysis Enzymatic hydrolysis

Page 17: Lecture  № 11

Clavenger apparatus(according to Sovet pharmacopeia XI)1.A round bottom pyrex distillation2.A receiver (trap)3.A cork4.A condenser

(according to WHO, EuPh\Xylen

Page 18: Lecture  № 11

ESSENTIAL OILSAllspiceAniseedBasilBayBenzoinBergamotBlack pepperCajuputCamomileCamphorCarawayCarrot seedCassiaCedarwoodChamomileCinnamonCitronellaClary sageClove

CorianderCypressDillEucalyptus

FennelFrankincense

GeraniumGingerGrapefruit

HelichrysumHyssopJasmine

JuniperLavandinLavenderLemon

LemongrassLemon verbena

Lime

Mandarin SandalwoodMarjoram SageMelissa SpearmintMyrrh TagetesNeroli TangerineNiaouli ThymeNutmeg Tea treeOrange VetiverPalma rosa Ylang-ylangPatchouliPeppermintPetitgrainPimentoPineRoseRose geraniumRosemaryRosewood

Page 19: Lecture  № 11

ESSENTIAL OILS NOT SOLD BY US

AngelicaBirchBitter almondBoldo

BuchuCalamusCardamomCumin

ElemiMugwortMustardOregano

PennyroyalRose ottoRueSassafras

SpikenardTansyTarragonSavinThuja

TuberoseVanillaWintergreenWormseedWormwoodYarrow

PRE-BLENDED FORMULAS

Muscle & JointRelaxationSensualAnti-celluliteCirculationHair & ScalpDry & Mature SkinInsomniaBabyVein & ArterySunburn

OTHER OILSRosehip oil

Baobab oilMarula oilNeem oil

CARRIER OILSAlmond oil

Aloe vera oilApricot kernel oil

Avocado oilCalendula oil

Evening primrose oil

Grape seed oilHazelnut oil

Jojoba oilMacadamia oil

Sesame oilWalnut oil

Wheatgerm oil CARRIER OILS

NOT SOLD BY USOlive oilPumpkin seed oilSafflower oilSunflower

Page 20: Lecture  № 11

MP and MPM containing MP and MPM containing monoterpenoidsmonoterpenoids

Page 21: Lecture  № 11

Menthae piperitae folia Menthae piperitae folia Mentha piperita- Peppermint, Lamb Mentha piperita- Peppermint, Lamb mint, American mint, Brandy mintmint, American mint, Brandy mintLamiaceaeLamiaceae

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.

Page 22: Lecture  № 11
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Salviae Folia Salviae Folia Salvia officinalis- SageSalvia officinalis- SageLamiaceaeLamiaceae Constituents.Constituents. Up to 2.5% of a Up to 2.5% of a

greyish-yellow volatile oil greyish-yellow volatile oil containing borneol, pinene, containing borneol, pinene, thujone and cineol, bitter thujone and cineol, bitter principles, resin and tannins.principles, resin and tannins.

Uses. Uses. Sage is used chiefly as a Sage is used chiefly as a condiment but is also employed condiment but is also employed as a carminative in dyspepsia, as a carminative in dyspepsia, also has antiseptic, astringent also has antiseptic, astringent action. action. Salvin Salvin works as plant works as plant antibiotic due to the content of antibiotic due to the content of diterpenes; is used in treatment diterpenes; is used in treatment of gingivitis and stomatitis.of gingivitis and stomatitis.

Page 24: Lecture  № 11

Eucalypti Folia Eucalypti Folia Folia Eucalypti viminalisFolia Eucalypti viminalisOleum EucalyptiOleum EucalyptiEucalyptus globulus, Eucalyptus cinerea, Eucalyptus viminalisEucalyptus globulus, Eucalyptus cinerea, Eucalyptus viminalisEnglish names: Eucalyptus, Blue Gum leaves, Australian Fever English names: Eucalyptus, Blue Gum leaves, Australian Fever Tree, Iron Bark TreeTree, Iron Bark TreeMyrtaceaeMyrtaceae

Page 25: Lecture  № 11
Page 26: Lecture  № 11

Coriandri Fructus Coriandri Fructus Coriandrum sativum- CorianderCoriandrum sativum- CorianderApiaceaeApiaceae

Constituents. Constituents. Up to 1% of volatile Up to 1% of volatile oil containing coriandrol (d-linalool) oil containing coriandrol (d-linalool) and d-pinene, etc.; fixed oil, calcium and d-pinene, etc.; fixed oil, calcium oxalate, tannins.oxalate, tannins.

Uses. Uses. Aromatic stimulant, has Aromatic stimulant, has spasmolitic and antibacterial spasmolitic and antibacterial properties. It is part of appetising, properties. It is part of appetising, cholagogue, expectorant and anti-cholagogue, expectorant and anti-haemorrhoidal species, infusion- haemorrhoidal species, infusion- part of part of FloraFlora, ether oil is part of , ether oil is part of EspolEspol (anti-inflammation and pain- (anti-inflammation and pain-killing drug).killing drug).

Page 27: Lecture  № 11

Carvi Fructus Carvi Fructus Carum carvi L. Carum carvi L. CarawayCarawayApiaceaeApiaceae Constituents. Constituents. Volatile oil (5-Volatile oil (5-

7%), fixed oils, tannins, etc. 7%), fixed oils, tannins, etc. The volatile oil contains The volatile oil contains carvone, limonene, carvone, limonene, dihydrocarvone, caryeol, and a dihydrocarvone, caryeol, and a small quantity of a base having small quantity of a base having a narcotic odour.a narcotic odour.

Uses. Uses. Stimulant, carminative, Stimulant, carminative, condiment, diuretic, diaphoretic condiment, diuretic, diaphoretic and flavouring agent; source of and flavouring agent; source of oil of carawayoil of caraway. It is used in the . It is used in the food industry for flavouring food industry for flavouring bread, cheese and candy.bread, cheese and candy.

Page 28: Lecture  № 11

Juniperi Fructus Juniperi Fructus Juniperus communis- Juniperus communis- Juniper, Horse Savin BerriesJuniper, Horse Savin BerriesCupressaceaeCupressaceae Constituents. Constituents. From 0.3 to 1.5% of a From 0.3 to 1.5% of a

VO containing the terpenes camphene VO containing the terpenes camphene and x-pinene, a sesquiterpene called and x-pinene, a sesquiterpene called cadinene; terpene alcohols borneol, cadinene; terpene alcohols borneol, one of which is terpineol; resin, fixed one of which is terpineol; resin, fixed oils, up to 30% of dextrose, etc. A oils, up to 30% of dextrose, etc. A crystalline substance deposits in the crystalline substance deposits in the oil at low temperatures known as oil at low temperatures known as juniper camphor.juniper camphor.

Uses. Uses. Juniper berries are used for the Juniper berries are used for the preparation of juniper oil. The juniper preparation of juniper oil. The juniper oil has diuretic, antireumatic and oil has diuretic, antireumatic and antiseptic properties. Used as antiseptic properties. Used as stimulating diuretic in chronic genito-stimulating diuretic in chronic genito-urinary disorders.urinary disorders.

Page 29: Lecture  № 11

Valerianae radix Valerianae radix Valeriana officinalis- Valerian, Valeriana officinalis- Valerian, Wild, Great Wild, Cat’s ValerianWild, Great Wild, Cat’s ValerianValerianaceaeValerianaceae

Constituents. Constituents. Volatile oil (up to Volatile oil (up to 2%) containing bornyl 2%) containing bornyl isovalerianate, bornyl formiate, isovalerianate, bornyl formiate, bornyl acetate and bornyl butyrate, bornyl acetate and bornyl butyrate, camphene, borneol and pinene; camphene, borneol and pinene; two alkaloids- chatinine and two alkaloids- chatinine and valerianine, a glucoside, resin, α-valerianine, a glucoside, resin, α-methylpyrryl ketone, stated to be methylpyrryl ketone, stated to be narcotic, valeric, formic and acetic narcotic, valeric, formic and acetic acids, tannins, sugar, etc.acids, tannins, sugar, etc.

Uses. Uses. Valerian is used as a Valerian is used as a calmative in nervousness and calmative in nervousness and hysteria and as a carminative. hysteria and as a carminative. Preparations- Preparations- Valerian fluid Valerian fluid extract, Valerian tincture, extract, Valerian tincture, Valocordinum, Corvalolum, Valocordinum, Corvalolum, as as ingredient ofingredient of Species Sedativae. Species Sedativae.

Page 30: Lecture  № 11

Lavandulae Flores Lavandulae Flores Lavandula angustifolia L. Lavandula angustifolia L. LamiaceaeLamiaceae

Constituents. Constituents. Up to 3% Up to 3% of VO containing esters, of VO containing esters, also linalool, geraniol, also linalool, geraniol, limonene and limonene and sesquiterpene; resin, sesquiterpene; resin, tannins, etc.tannins, etc.

Uses. Uses. Lavender flowers Lavender flowers are chiefly used as a are chiefly used as a perfume. perfume. LivianLivian has anti- has anti-inflammatory and pain-inflammatory and pain-killing action and used to killing action and used to treat burns.treat burns.

Page 31: Lecture  № 11

MP and MPM containing MP and MPM containing sesquiterpenoidssesquiterpenoids

Page 32: Lecture  № 11

Calami Rhizomata Calami Rhizomata Acorus calamus- Sweet Acorus calamus- Sweet Flag, Sweet RootFlag, Sweet RootAraceaeAraceae

Constituents. Constituents. Vo (1.5to Vo (1.5to 3.5%) containing asaryl 3.5%) containing asaryl aldehyde, eugenol and aldehyde, eugenol and asarone; a bitter glucoside asarone; a bitter glucoside called acorin; soft resin, called acorin; soft resin, starch, inulin, etc.starch, inulin, etc.

Uses. Uses. Carminative, aromatic Carminative, aromatic bitter and stimulant; bitter and stimulant; flavouring agent. Used in flavouring agent. Used in atonic dyspepsia and colic. atonic dyspepsia and colic. Vicalin, VicairVicalin, Vicair and and HerbogastrinHerbogastrin are used for the are used for the treatment of ulcers.treatment of ulcers.

Page 33: Lecture  № 11

Betulae Gemmae Betulae Gemmae Betulae Folia Betulae Folia Betula pendula, Betula pubescensBetula pendula, Betula pubescensEnglish name- BirchEnglish name- BirchBetulaceaeBetulaceae

Constituents. Constituents. VO 5-8% with VO 5-8% with balsamic odour, contained balsamic odour, contained bicyclical sesquiterpenoid bicyclical sesquiterpenoid betulen and alcohol betulenol.betulen and alcohol betulenol.

Uses. Uses. Medicines have diuretic, Medicines have diuretic, diaphoretic, cholagogue, diaphoretic, cholagogue, spasmolytic, anti-inflammation, spasmolytic, anti-inflammation, anti-viral, wound-heeling and anti-viral, wound-heeling and antihelmintic actions. antihelmintic actions. Medicines- Medicines- infusion, tincture, infusion, tincture, Propobesan.Propobesan.


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