PHA 040 Volatile Oils (SAS 5) PDF

Course Code: PHA 040 (Pharmacognosy and Plant Chemistry) Student Activity Sheet SAS #5...

Course Code: PHA 040 (Pharmacognosy and Plant Chemistry) Student Activity Sheet SAS #5 Name: _____________________________________________________________ Class number: _______ Section: ____________ Schedule: ______________________________________ Date: ______________ Lesson title: Volatile oils Materials: 1. Student activity sheet Lesson Objectives: 2. Pen At the end of this module, you are expected to; 1. Identify the Pharmaceutical and Pharmacological uses of Volatile References: oils related Crude drugs -Shah, biren. (latest ed.). Textbook of 2. Identify the sources of the Volatile oil related Crude drugs pharmacognosy and phytochemistry. India : elsevier. -Tyler, varro. Pharmacognosy, , phila. : 1. lea & febiger, latest ed. Productivity Tip: For this session we will try to learn another concept, please take note that we have already reached the half way marker for the course, so just hang in, you can finish all of this. A. LESSON PREVIEW/REVIEW Introduction (5 mins) Volatile oils are odorous volatile principles of plant and animal sources, evaporate when exposed to air at ordinary temperature, and are hence known as volatile or etheral oils. These represent the essence of active constituents of the plant and are hence also known as essential oils. In most instances, the volatile oil preexists in the plant and is usually contained in some special secretory tissues, for example, the oil ducts of umbelliferous fruits, the oil cells, or oil glands occurring in the sub-epidermal tissue of the lemon and orange, mesophyll of eucalyptus leaves, trichome of several plants, etc. Figure 1. Products that contain Volatile oils Activity 1: What I Know Chart, part 1 (5 mins) Complete the contents of the table, for the first part answer only the “What I Know” part of the table, then once you end the given module return to this table then answer the “What I Learned” cells. This document is the property of PHINMA EDUCATION  Course Code: PHA 040 (Pharmacognosy and Plant Chemistry) Student Activity Sheet SAS #5 What I Know Questions: What I Learned (Activity 4) 1. Why Volatile oils are also called as Etherial oils 2. What is the correct storage condition of Volatile oils 3. What is the Primary Pharmacologic effect of Volatile oils? B.MAIN LESSON Activity 2: Content Notes (90 mins) Volatile oils are Odorous plant principles found in various plant parts, Because they evaporate when exposed to the air at ordinary temperatures, they are also called ethereal oils or essential oils, it has a lot of uses however it presents Problems such as; Volatilization, Auto-oxidation & Photosensitive. Therefore, the proper Storage for volatile oils should be in – a dry, cold place preferably in a full amber glass that is tightly stoppered. Volatile oils may act as insect repellents or attractants. In a few cases, the volatile oil does not preexist but is formed by the decomposition of a glycoside. For example, whole black mustard seeds are odorless, but upon crushing the seeds and adding water to it a strong odor evolved. This is due to allyl isothiocyanate (the main constituent of the essential oil of mustard) formed by the decomposition of a glycoside, sinigrin, by an enzyme, myrosin. Glycoside and enzyme are contained in different cells of the seed tissue and are unable to react until the seeds are crushed with water present so that the cell contents can intermingle. Volatile oils are freely soluble in ether and in chloroform and fairly soluble in alcohol; they are insoluble in water. The volatile oils dissolve many of the proximate principles of plant and animal tissues, such as the fixed oils and fats, resins, camphor, and many of the alkaloids when in the free state. These are chemically derived from terpenes (mainly mono and sesqui terpenes) and their oxygenated derivatives. These are soluble in alcohol and other organic solvents, practically insoluble in water, lighter than water (Clove oil heavier), possess characteristic odor, have high refraction index, and most of them are optically active. Volatile oils are colorless liquids, but when exposed to air and direct sunlight these become darker due to oxidation. Unlike fixed oils, volatile oils neither leave permanent grease spots on filter paper nor are saponified with alkalis. Volatile oils are classified according to the functional groups present such as Hydrocarbons, Alcohols, Aldehydes, Ketones, Phenols, Phenolic ethers, Oxides, and Esters. Volatile oils can be prepared or isolated by different means such as. Method Description Extraction by The distillation is carried out either by water or steam. The volatile oils from fresh materials are Distillation separated by hydrodistillation, and volatile oils from air dried parts are separated by steam distillation. However, it is better to use fresh materials in either case. This method is used for the preparation of the oil of lemon, oil of orange, and oil of bergamot. These oils are found in large oil glands just below the surface of the peel of the fruit. The two principal methods of scarification are the sponge and the ecuelle method. Sponge Process: In this process, the contents of the fruit are removed after making longitudinal or transverse cuts, and the peel has been immersed in water for a short period of time. Then it is ready for expression. The operator takes a sponge in one hand and with the Extraction by other presses the softener peel against the sponge so that the oil glands burst open, and the Scarification sponge absorbs the exuded oil, which is transferred to a collecting vessel. The turbid liquid consisting of oil and water is allowed to stand for a short time, whereupon the oil separates from the water and is collected. The whole of the above process is carried out in cool, darkened rooms to minimize the harmful effects of heat and light on the oil. Ecuelle Process: In this process, the rinds are ruptured mechanically using numerous pointed projections with a rotary movement and the oil is collected. Extraction by Non- A nonvolatile solvent, for example, a fine quality of either lard or olive oil, is used in this Volatile Solvent process. After saturation with the floral oil the lard or olive oil is sometimes used as a flavouring base for the preparation of pomades, brilliantine, etc., or converted to a triple extract. In the This document is the property of PHINMA EDUCATION  Course Code: PHA 040 (Pharmacognosy and Plant Chemistry) Student Activity Sheet SAS #5 latter instance the lard or oil is agitated with two or three successive portions of alcohol, which dissolve the odorous substances. The mixed alcoholic solutions so obtained constitute the ‘triple extract’ of commerce. Enfleurage: In this a fatty layer is prepared using lard and the flower petals are spreaded over it, after the imbibitions is over the fatty layer is replaced with fresh petals. After the saturation of fatty layer, the odorous principles are removed by treating with alcohol and a triple extract then prepared. When oil is used as a solvent the flowers are placed on an oil-soaked cloth supported by a metal grid enclosed in a frame. Fresh flowers are added as required, and finally the oil is expressed from the cloths. It may then be used as perfumed oil or extracted with alcohol to produce a triple extract. Maceration: This is also used to extract the volatile matters of flowers. The lard or oil is heated over a water bath, a charge of flowers added, and the mixture stirred continuously for some time. The exhausted flowers are removed, pressed, the expressed fluid returned to the hot fat, fresh flowers, added and the process continued until defined weights of flowers and solvent have been used. Again, a triple extract is prepared by extracting the perfumed lard or oil with alcohol. Spraying: In this process a current of warm air is sprayed through a column of the flowers. Then oil or melted fat is sprayed over this oil-laden air which absorbs and dissolves most of the perfume, the collected oil or fat is then extracted with alcohol as described above. Extraction by Volatile In this the flowers are extracted by using the solvent light petroleum and the latter is distilled off Solvent at a low temperature, leaving behind the volatile oil. There are many different classes of naturally occurring compounds. Terpenoids also form a group of naturally occurring compounds majority of which occur in plants, a few of them have also been obtained from other sources. Terpenoids are volatile substances that give plants and flowers their fragrance. They occur widely in the leaves and fruits of higher plants, conifers, citrus, and eucalyptus. The term ‘terpene’ was given to the compounds isolated from terpentine, a volatile liquid isolated from pine trees. The simpler mono and sesquiterpenes is the chief constituent of the essential oils obtained from sap and tissues of certain plant and trees. The di- and triterpenoids are not steam volatile. They are obtained from plant and tree gums and resins. Tetraterpenoids form a separate group of compounds called ‘Carotenoids’. The term ‘terpene’ was originally employed to describe a mixture of isomeric hydrocarbons of the molecular formula C10H16 occurring in the essential oils obtained from sap and tissue of plants and trees. But there is a tendency to use more general term ‘terpenoids’, which includes hydrocarbons and their oxygenated derivatives. However, the term terpene is being used these days by some authors to represent terpenoids. According to modern definition, ‘Terpenoids are the hydrocarbons of plant origin of the general formula (C5H8)n as well as their oxygenated, hydrogenated, and dehydrogenated derivatives.’ Figure 2. Structure of an isoprene Further, these isoprene units are further classified into classes, wherein theu differ in number of isoprene units found in their structure. This document is the property of PHINMA EDUCATION  Course Code: PHA 040 (Pharmacognosy and Plant Chemistry) Student Activity Sheet SAS #5 Figure 3. Example of Ioprenoids Each class can be further subdivided into subclasses according to the number of rings present in the structure. 1. Acyclic Terpenoids: They contain open structure. 2. Monocyclic Terpenoids: They contain one ring in the structure. 3. Bicyclic Terpenoids: They contain two rings in the structure. 4. Tricyclic Terpenoids: They contain three rings in the structure. 5. Tetracyclic Terpenoids: They contain four rings in the structure. Product from different manufacturers varies considerably since it is inherently difficult to control all the factors that affect a plants chemical composition. Environmental conditions such as sunlight and rainfall, as well as the manufacturing process, can create substantial variability in essential oil quality. Various procedures are given for the evaluation of essential oils. Preliminary examinations like odor, taste, and color. Physical measurements include optical rotation, relative density, and refractive index. Chromatographic techniques are used to determine the proportions of individual components of certain oils. The ketone and aldehyde content of oils is determined by reaction with hydroxylamine hydrochloride (oxime formation) and titration of the liberated acid. The oil, which passes the above examinations, would be having good quality and therapeutic value. Natural drugs containing volatile oils can be tested by following chemical tests: 1. Thin section of the drug on treatment with an alcoholic solution of Sudan III develops red color in the presence of volatile oils. 2. Thin section of the drug is treated with a tincture of alkana, which produces red color that indicates the presence of volatile oils in natural drugs. Volatile oils are used as flavoring agent, and perfuming agents in pharmaceutical formulations, foods, beverages, and in cosmetic industries. These are also used as an important medicinal agent for therapeutic purposes like: This document is the property of PHINMA EDUCATION  Course Code: PHA 040 (Pharmacognosy and Plant Chemistry) Student Activity Sheet SAS #5 1. Carminative (e.g. Umbilliferous fruits) 2. Anthelmintic (e.g. Chenopodium oil) 3. Diuretics (e.g. Juniper) 4. Antiseptic (e.g. Eucalyptus) 5. Counter irritant (e.g. Oil of wintergreen) 6. Local anesthetic (e.g. Clove) 7. Sedative (e.g. Jatamansi) 8. Local irritant (e.g. Turpentine) 9. Insect repellent (e.g. Citronella) 10. Source of vitamin A (e.g. Lemongrass) + HYDROCARBON VOLATILE OIL Limonene – the most widely distributed of the monocyclic terpenes. It occurs in citrus, myristica, caraway, thyme, cardamom, coriander, and many other oils. Pinene – a dicyclic monoterpene, is also widely distributed. It is found in many conifer oils as well as in lemon, anise, eucalyptus, thyme, fennel, coriander, orange flower, and myristica oils. Sabinene- a dicyclic monoterpene of thujane class, is distributed in cardamom and lemon oils. Cadiene – occurs in juniper tar, and is a typical sesquiterpene hydrocarbon. 𝛼-pinene Limonene Camphene Figure 4- Structure of Hydrocarbon Volatile oils Turpentine oil/ spirits of turpentine. Volatile oil distilled from the oleoresin from Pine tree – Pinus palustris, It is a colorless liquid having a characteristic odor and taste, both of which become stronger and more disagreeable as the oil ages or is exposed to air. It is the largest volume essential oil in commerce, This Crude drug contains Alpha-pinene wherein it is used as a counterirritant and is present in Vicks VapoRub. Other Preparation that contains this crude drug are; Rectified Turpentine Oil- distillation of an aqueous solution of NaOH: it is dispensed when turpentine oil is required internally. It has been used as an expectorant. Terpine hydrate / Terpinol- formed by the action of Nitric acid on rectified turpentine oil in the presence of alcohol. It is a stimulant to mucous membranes; therefore, it is used as an expectorant in the form of terpin hydrate elixir. + ALCOHOL VOLATILE OIL Alcohols found in volatile oils may be classified into (1) acyclic alcohol, (2) monocyclic alcohol, and (3) dicyclic alcohol. Many natural oils contain acyclic alcohols that are terpene derivatives. Among the more important of these are geraniol, linalool and citronellol. Among the more important monocyclic alcohol are menthol (peppermint) and α-terpineol. Borneol is a dicyclic terpene alcohol from Borneo camphor. Sesquiterpene alcohols include zingiberol. Peppermint oil- Consists of the dried leaf and flowering top of Mentha piperita or Mentha arvensis – japanese peppermint oil. Is a colorless or pale-yellow liquid that has a strong, penetrating odor of peppermint and a pungent taste that is followed by a sensation of cold when air is drawn into the mouth. Peppermint contains volatile oil, resin, and tannin. Peppermint oil is a pharmaceutical aid (flavor). It has been used as a carminative, a stimulant, and a counterirritant. Its chief commercial importance is as a flavour for confections, especially for chewing gums (Listerin R ). This document is the property of PHINMA EDUCATION  Course Code: PHA 040 (Pharmacognosy and Plant Chemistry) Student Activity Sheet SAS #5 Figure 5 – Image of M. piperita & structures of Isoprenes found in the crude drug Japanese peppermint oil / Mentha arvensis oil – This is an oil Obtained by steam distillation from Mentha arvensis. This oil is considerably higher in menthol content but is inferior in flavor to peppermint oil. Therefore, it is solely employed as a source of menthol. Menthol or menthan-3-ol – is an alcohol obtained from diverse mint oils or prepared synthetically. And maybe levorotatory, (-)-menthol, from a natural or synthetic source. Menthol is usually prepared to form Japanese peppermint oil by refrigeration (-22C), during which the menthol crystallizes. The liquid portion is poured off, and the crystallized menthol is pressed between filter papers and subsequently purified by re-crystallization. Synthetic racemic menthol is produced by the hydrogenation of thymol. Menthol may also be prepared by pinene. This crude drug contains menthol and is a topical antipruritic. It has been used on the skin or mucous membrane as a counterirritant, an antiseptic, and a stimulant.; internally, menthol has a depressant effect on the heart. Menthol is topically applied as 0.1 to 2% preparations for use on the skin. Products: Burn or sun burn preparations: solarcaine R , and UngentineR. Treatment of Ivy Poisoning: Rhulicream. Douce preparations: Zonite Preparations for athlete’s Foot: NP27 powder. Analgesic preparation: absorbine R , Ben-GayR , Vicks-VaporubR Figure 6- Products that contains Menthol Cardamom oil - From the dried, ripe, seed of Elletaria cardamom, This crude drug contains Cineole – primary, important constituents (26%-40%), Wherein it is used as Flavor and Carminative. Figure 7- Secondary metabolites found in Cardamom oil This document is the property of PHINMA EDUCATION  Course Code: PHA 040 (Pharmacognosy and Plant Chemistry) Student Activity Sheet SAS #5 Coriander oil - Volatile oil distilled with steam from, dried, ripe fruit of Coriandrum sativum, Wherein it contains Linalool - primary, important constituent (60%-70%) and is used as flavorant and carminative, Rose oil/ otto of rose –is Volatile oil distilled with steam from the fresh flowers of Rosa gallica. The plant contains primarily;Geraniol, citronellol, Nerol. The practical application of the plant is in the perfume industry. Figure 8- Secondary metabolites found in coriander. Orange Flower/ Neroli oil - is a volatile oil from the fresh flowers of Citrus aurantium. Generally, the plant contains linalool, α-terpinol, and geraniol. Geranyl acetate and limonene were also isolated. The plant is employed in the perfume industry for its odor, and sometimes, as a pharmaceutical aide wherein it gives its flavor. Figure 9 – Structure of the Secondary metabolite found in Orange Juniper oil is a volatile oil that is distilled with steam from the dried ripe fruit of Juniperus communis. Its constituents is mainly composed of Borneol and α-pinene. The plant is primarily used as a flavoring agent and a diuretic in the OTC drug Odrinil R Pine oil – This is a volatile oil obtained by extraction and by fractionation or by steam distillation of the wood from the tree Pinus palustris. The primary constituent found in the plant is Alpha terpineol (65%). The plant is generally used as a disinfectant and a deodorant. + ALDEHYDE VOLATILE OIL Aldehydes occurring in volatile oils may be divided into acyclic and cyclic. Biosynthesis of such aromatic aldehydes as benzaldehyde and vanillin takes place from phenylpropanoid precursors. Because these compounds constitute the aglycones of certain glycosides. The terpene aldehydes derive from acetate metabolism. Among the important drugs in this class are cinnamom, cinnamon oil, orange oil, lemon peel, lemon oil, hamamelis water, and citronella oil. Cinnamon (Saigon Cinnamon – dried bark of cinnamomum laureirii, Ceylon Cinnamon – dried inner shoots of cinnamomum zeylancium, Cassia Cinnamon – dried bark of cinnamomum cassia) - Cinnamon oil is the Volatile oil distilled from the twigs of Cinnamomum cassia and rectified by distillation. Cinnamon is named as a spice in the books of moses, by ancient greek and latin historians, and chinese herbals as early as 2700BC. The principal constituent of the oil is cinamic aldehyde, 80%-95% Cinnamaldehyde, cinnamic aldehyde, or cannamyl aldehyde is obtained naturally from cassia oil or synthetically from a mixture of benzaldehyde and acetaldehyde by the action of NaOH. Use : Saigon, Ceylon, and Cassia cinnamon are carminatives and flavors. Figure 10- Plant source of cinnamon and the chemical constituent found in the crude drug This document is the property of PHINMA EDUCATION  Course Code: PHA 040 (Pharmacognosy and Plant Chemistry) Student Activity Sheet SAS #5 Lemon peel - This is the fruit of Citrus limon. Lemon Peel is the outer yellow rind of the fresh ripe fruit of C. limon, contains a volatile oil a small quantity of heseridin, bitter principles, a tannin-like principle, and calcium oxalate. The crude drug contains Citral (neral +geraniol), as a secondary metabolite. Lemon peel is a flavoring agent, stimulant, and stomachic. Lemon oil is the Volatile oil obtained by expression, without the aid of heat, from the fresh peel of the fruit of C. limon, with or without the previous separation of the pulp or peel. Contains 90% of terpenes. Consisting of (+)- limonene. Sweet orange oil/orange oil - is a Volatile oil obtained by expression from the fresh peel of the fruit Citrus sinnensis. The crude drug contains Limonene (more than 90%) and decanal (1%-2%). and pharmaceutically used as a flavoring agent. Citronella oil- is a volatile oil distilled with steam from the freshly cut or dried leaves of Cymbopogon nardus[ (Tanglad – Cymbopogon citratus) a relative of Citronella]. The crude drug contains citronellal 5-55% acts as an insect repellant, Gerianol 25-40%, and (+)- citronellol 11-15%. Figure 11- Chemical Constituents found in Citronella Figure 12- Chemical constituents found in Lemongrass + KETONE VOLATILE OIL Ketones occurring in volatile oils may be divided into (1) monocyclic terpene ketones, including methone, carvone, piritone, pulegone, and diosphenol (a crystalline ketone in buchu); and (2) dicyclic ketones, including camphor, fechone, and thujone. The more important drugs in this category are camphor, spearmint, and caraway. Camphor - is a Ketone Volatile oil Obtained From Cinnamomum camphora. Camphora is from the Arabic Kafur meaning chalk. Natural camphor occurs as a crystalline product in clefts in the woody stems and roots and, to a greater extent, dissolved in the volatile oil. Synthetic camphor is made from pinene, the principal constituent of turpentine oil. The starting point is the stumps of felled pine trees previously used in turpentining. A number of complex methods have been used for used in producing synthetic camphor, but all are based on (1) converting pinene into bornyl esters, which are (2) hydrolyzed to isoborneol, and finally (3) oxidized to camphor. The specific rotation of natural camphor is between +410 and +430. Synthetic camphor is the optically inactive racemic form. Camphor is a topical antipruritic, rubefacient, and anti- infective employed at 1-3%. Figure 13- Chemical constituent found in Camphor Spearmint (Spearmint, Garden mint, Mackerel mint, Our lady’s mint, Green mint, Sage of Bethlehem.) - Consists of the dried leaf and flowering top of Mentha spicata. Mint is mentioned in all early mediaeval lists of plants; it was grown in English gardens and cultivated in the Convent gardens during the ninth century. The Ancients believed that mint would prevent the coagulation of milk, to scent their bath water and as a restorative, as we use smelling salts today. Mint was so universally esteemed, that it was found wild in nearly all the countries to which civilization has extended. In America for 200 years, the mint was known as an escape from gardens, growing in all moist soils and proving on occasion troublesome like a weed. In the fourteenth century, mint was used for whitening the teeth, and its distilled oil is still used to flavor toothpastes, and in America, it is used especially to flavor chewing gums, confectionery, and perfume soap. Spicata is from the Latin spica, meaning a spike, and refers t the arrangement of the flowers. Spearmint is composed of resin, tannin, and a volatile oil (0.5%) that co tains (-)carvone. Spearmint oil is distilled with steam from the fresh, overground This document is the property of PHINMA EDUCATION  Course Code: PHA 040 (Pharmacognosy and Plant Chemistry) Student Activity Sheet SAS #5 parts of the flowering plant. Spearmint oil is a colorless/ yellow/greenish-yellow liquid that has the characteristic odor and taste of spearmint. Spearmint oil is a flavor. It possesses carminative properties and is used to a considerable extent in the chewing gum industry. And they are also employed in toothpaste, mouthwash, etc. Caraway - Is a crude drug from the dried ripe fruit Carum carvi, it contains (+) carvone 50-85% as a secondary metabolite and is used as a flavoring agent. Buchu - Is a crude drug from the dried leaf of Barosma betulina, it contains 30% Diosphenol , and pharmacologically used as a diuretic, urinary antiseptic (FluidexR ) Wormwood oil (Absinthe oil) is a Volatile oil distilled with steam from the dried leaves and flowering tops of Artemisia absinthum, it contains Thujone, camphene, phellandrene, and B-cary-ophyllene and is pharmacologically used as counterirritant in OTC drug Absorbine Jr. R Cedar leaf – Is an oil from the fresh leaves of Thuja occidentalis, it contains Thujone, (-) fenchone &, α-pinene and is Used as counterirritant in OTC drug, Vicks + PHENOL VOLATILE OIL Two kinds of phenols occur in volatile oils: those are present naturally and those that are produced as the result of destructive distillation of certain products. Eugenol, thymol, and carvacol are the most important phenols occurring in volatile oils. Eugenol occurs in clove oil, myricia oil and other oils. Thymol and carvacol occur in thyme oil. Creosol and guaiacol occur in creosote and pine tar. Thymol A phenol obtained from thyme oil (Thymus vulgaris), horsemint oil (Monarda punctata) and ajowan oil (Carum copticum). The oil may be treated in 2 ways to obtain thymol crystals: (1) it may be subjected to freezing temperatures (2) it may be treated with NaOH solution, the aqueous solution of sodium thymol being separated and decomposed with acid, thus liberating the thymol. Thymol occurs as large colorless crystals or as a white crystalline powder. It has aromatic thyme-like odor and a pungent taste. Use: thymol is an antifungal and antibacterial agent. It is employed topically in lotions, creams, and ointments in concentrations from 0.1-1% Preparations: Listerine mouthwashR, Vicks vaporubR. Clove or Cloves (Clove buds. Love flowers) - is the dried flower bud of Eugenia caryophilus. Cloves contain volatile oil, 14-20% gallotanic acid, 10-13%; oleanolic acid; vanillin; and chromone, eugenin. Clove oil is a volatile oil distilled with steam from the dried flower buds. It is a colorless or pale-yellow liquid that becomes darker and thicker by age or exposure to air and has the characteristic odor and taste of clove. Clove contains 14%-21% of volatile oil. Eugenol Caryophyllene Figure 14 – (Chemical constituents found in Clove (Eugenol and Caryophyllene) Clove is used as an antiseptic, stimulant, carminative, aromatic, and as flavoring agent. It is also used as an anodyne, and antiemetic. Dentists use clove oil as an oral anesthetic and to disinfect the root canals. Clove kills intestinal parasites and exhibits broad antimicrobial properties against fungi and bacteria and so it is used in the treatment of diarrhea, intestinal worms, and other digestive ailments. Clove oil can stop toothache. A few drops of the oil in water will stop vomiting, eating cloves is said to be an aphrodisiac. Eugenol is also used as a local anesthetic in small doses. The oil This document is the property of PHINMA EDUCATION  Course Code: PHA 040 (Pharmacognosy and Plant Chemistry) Student Activity Sheet SAS #5 stimulates peristalsis; it is a strong germicide, and also a stimulating expectorant in bronchial problems. The infusion and Clove water are good vehicles for alkalies and aromatics. Myrica oil / Bay oil – This is a Volatile oil distilled with steam from the leaves of Pimenta racemosa.. It contains 55-65% eugenol, myrcene, and chavicol and is used in the perfume industry. Creosote/beechwood creosote – This is a mixture of phenols obtained from wood tar produced by destructive distillation of wood of Fagus grandiflora. This crude drug contains Guiacol/creosol (Precursor to antitussive Guaifenesin ), and is used as a Disinfectant in the OTC drug Dewitt’s toothache dropsR. Juniper tar/cade oil is an Empyreumatic volatile oil distilled from the heartwood Juniper oxycedrus. It contains cardinene as a constituent. Juniper is also used as a local antieczematic in OTC drug PolytarR Pine tar Empyreumatic product obtained by destructive distillation of the wood of Pinus palustris Contains phenol and creosol Local anti-eczematic, anti-psoriasis. + PHENOLIC ETHER A number of phenolic ether occur in volatile oils. For example, anethole from anise and fennel, and safrole from sassafras and nutmeg. Biosynthesis of phenolic ether. Studies of anethole biosynthesis in Foeniculum vulgare have revealed that formation takes place from phenylalanine. A cell-free enzyme system capable of effecting the conversion has been prepared. Methionine serves as a methyl donor for the methylation reaction. Some of the drugs containing phenolic ether volatile oil are anise, fennel, and myristica. Nutmeg / myristica (Semen myristicae, Myristica, Nux moschata, Myristica aromata.)Is the dried seed of Myristica fragrans , Contains myristicin and safrole Nutmeg is a Hallucinogen commonly used by prison inmates. The oil is colorless or pale-yellow liquid that has the characteristic odor and taste of nutmeg. Nutmeg oil is a flavoring agent. It possesses carminative properties. Nutmeg contains of 5 to 15% volatile oil, lignin, stearin, starch, gum, colouring matter, and 0.08% of an acid substance. The volatile oil contains clemicine, myristicin, geraniol, borneol, pinene, camphene, and dipentene. It also contains eugenol, safrol, p-cymene and isoeugenol in small quantity. Nutmeg is aromatic, carminative, flavouring agent. Both nutmeg and mace are used for flatulence, in allay nausea and vomiting. Graded nutmeg along with lard is used in ointment for piles. It has narcotic action and peripherally it irritates and produces anesthetics action, since it irritates intestine and uterus it can cause abortion. Oil of Nutmeg is used to conceal the taste of various drugs and as a local stimulant to the gastrointestinal tract. Figure 15 – Nutmeg and Chemical constituents found in Nutmeg. Anise /aniseed – is the dried, ripe fruit of Pimpinella anisum. This contains 1-3% volatile oil (Trans-anethol ) and is used as Flavor Fennel oil - is a Volatile oil distilled with steam from the dried, ripe fruit Foeniculum vulgarae. It contains 50%-605 Trans-anethol, (+)-fenchone, (+)- α-pinene., and is used as Flavor, carminative Chinese star anise/star anise is the dried fruit of Ilicium verum. It contains 2.5%-3%Trans- anethole , wherein it is used as Flavor. This document is the property of PHINMA EDUCATION  Course Code: PHA 040 (Pharmacognosy and Plant Chemistry) Student Activity Sheet SAS #5 + OXIDATIVE VOLATILE OIL Cineole (eucalyptol) is found in eucalyptus and several other volatile-oil-yielding drugs. It is also called cajuptol because it occurs in cajuput. Eucalyptus oil is the dried, scythe-shaped leaf of the Eucalyptus globulus.. Eucalyptus contains volatile oil, 3%-6%, several resins, and tannic acid. The oil is a colorless/pale yellow liquid that has a characteristic, aromatic, somewhat camphoraceous odor and a pungent, spicy, cooling taste. Uses: Eucalyptus oil is classed as a flavor. It is frequently used as an antiseptic, diaphoretic, and expectorant. Eucalyptol/cineole is obtained from eucalyptus oil and from other sources. + ESTER VOLATILE OIL A wide variety of esters occurs in volatile oils. The most common are the acetates of terpineol, borneol, and geraniol. Biosynthesis of esters. Terpene esters are generally formed from respective alcohols by reaction with aliphatic acid moieties (commonly acetic acid), as was indicated for methyl acetate. Formation of aromatic esters, at least in the case of methyl salicylate, involves the reverse process; that is, the aromatic acid reacts with an aliphatic alcohol to form the ester. Wintergreen (Canada tea, Checker berry, Wintergreen oil. Gaultheria oil, betula oil, Checker berry, tea berry) Is the dried leaves of Gaultheria procumbens. It Can synthetically be produced by esterification giving a product named as methyl salicylate. The volatile oil contains 99% methyl salicylate, along with other components like Gaultherilene and an aldehyde or ketone, secondary alcohol, and an ester. The characteristic odour of the oil is due to the alcohol and ester. The oil does not occur crudely in the plant but is a non-odorous glucoside, produced by the fermentation of (between water and Gaultherin) leaves for twelve to twenty-four hours. It is used as tonic, stimulant, antiseptic, astringent, diuretic, emmenagogue, aromatic. Useful as a diuretic, it stimulate stomach, heart, and respiration; in chronic inflammatory rheumatism, rheumatic fever, skin diseases, sciatica; for dropsy, gonorrhea, stomach trouble, bladder troubles, and obstruction in the bowels. The oil is a flavouring agent for tooth powders, liquid dentrifices, pastes, etc., especially if combined with menthol and eucalyptus.. Fatal dose in children 10 ml Figure 16 – Gaultheria and the secondary metabolite found in the crude drug (Gualtherin) Lavender oil - is a Volatile oil distilled with steam from flowering tops of Lavandula angustifolia.. It contains 30%-60% (-) Linalyl acetate , (-)-linalool, cineole, terpinen-4-ol , and commonly used as a Perfume. Pine needle oil/dwarf pine needle oil is a Volatile oil distilled with steam from fresh leaf Pinus strobus. It contains 3%- 10% Bornyl acetate, α-pinene, β-pinene, and camphene, and is used as a Perfume & flavoring agent. Mustard oil is a Volatile oil obtained by maceration with water of the dried, ripe seed with the subsequent steam distillation of Brasica nigra/B. alba. It contains different volatile oils depending on the type of mustard used as a source. Allyl/ acrinyl isothiocyanate It is used as Rubefacient in the OTC drug musteroleR This document is the property of PHINMA EDUCATION  Course Code: PHA 040 (Pharmacognosy and Plant Chemistry) Student Activity Sheet SAS #5 Activity 3: Skill-building Activities (30 mins) Instruction. Create a concept map that shows the flow of each class of volatile oil. You may include three (3) examples of each class of volatile oils. VOATILE OILS Activity 4: What I Know Chart, part 2 (5 mins) Instruction: Please go back to the What I Know table which is placed in Activity 1. Please do read again the question and answer the question allotted for activity 4 “What I learned” This document is the property of PHINMA EDUCATION  Course Code: PHA 040 (Pharmacognosy and Plant Chemistry) Student Activity Sheet SAS #5 Activity 5: Check for Understanding (30 mins) TRUE or FALSE _____1. Enfleurage is a type of extraction method for volatile oils that uses non-volatile solvents. _____2. Turpentine oil is immiscible with water and acetic acid and miscible with ether, chloroform, and fixed oils. _____3. Cinnamon contains only 10 % volatile oil. _____4. Volatile oils have high refractive indices, most are optically active and are immiscible with water. _____5. Turpentine oil is composed chiefly of hydrocarbons. C. LESSON WRAP-UP Activity 6: Thinking about Learning (5 mins) A. Work Tracker You are done with this session! Let’s track your progress. Shade the session number you just completed. PHARMACOGNOSY AND PLANT CHEMISTRY P1 P2 P3 1 2 3 4 5 6 7 8 9 10 B. Think about your Learning. Today was a good start, it was quite hard but the important thing is that you learned new things. Please do tell me what is the highlight of the session for you and what are the thingsyou encountered in this session that inspired you to become The Best Pharmacist. _____________________________________________________________________ _____________________________________________________________________ _____________________________________________________________________ _____________________________________________________________________ _____________________________________________________________________ ________________. FAQ 1. What is the Common Pharmacological effect of Crude drugs that contains Volatile oils? The most common pharmacologic effect of Crude drugs that contains Volatile oils is Carminative, thus most of the crude drugs are delivered or prepared as an infusion. This document is the property of PHINMA EDUCATION