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Terpenoids

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Terpenoids
S.RAVIKUMAR M.Sc
TERPENOIDS
• 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 which give plants
and flowers their fragrance.
• They occur widely in the leaves and fruits of higher
plants, conifers, citrus and eucalyptus.
S.RAVIKUMAR M.Sc
TERPENOIDS
• The term ‘terpene’ was given to the compounds
isolated from terpentine, a volatile liquid isolated
from pine trees.
• The simpler mono and sesqui terpenes are chief
constituent of the essential oils obtained from sap
and tissues of certain plant and trees. The di and
tri terpenoids are not steam volatile.
• They are obtained from plant and tree gums and
resins. Tertraterpenoids form a separate group of
compounds called ‘Carotenoids’ .
S.RAVIKUMAR M.Sc
TERPENOIDS
• 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 include hydrocarbons and
their oxygenated derivatives.
• However the term terpene is being used these
days by some authors to represent terpenoids.
S.RAVIKUMAR M.Sc
THE MODERN DEFINITION
• “Terpenoids are the hydrocarbons of
plant origin of the general formula
(C5H8)n as well as their oxygenated,
hydrogenated and dehydrogenated
derivatives.”
S.RAVIKUMAR M.Sc

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Terpenoids

  • 3. TERPENOIDS • 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 which give plants and flowers their fragrance. • They occur widely in the leaves and fruits of higher plants, conifers, citrus and eucalyptus. S.RAVIKUMAR M.Sc
  • 4. TERPENOIDS • The term ‘terpene’ was given to the compounds isolated from terpentine, a volatile liquid isolated from pine trees. • The simpler mono and sesqui terpenes are chief constituent of the essential oils obtained from sap and tissues of certain plant and trees. The di and tri terpenoids are not steam volatile. • They are obtained from plant and tree gums and resins. Tertraterpenoids form a separate group of compounds called ‘Carotenoids’ . S.RAVIKUMAR M.Sc
  • 5. TERPENOIDS • 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 include hydrocarbons and their oxygenated derivatives. • However the term terpene is being used these days by some authors to represent terpenoids. S.RAVIKUMAR M.Sc
  • 6. THE MODERN DEFINITION • “Terpenoids are the hydrocarbons of plant origin of the general formula (C5H8)n as well as their oxygenated, hydrogenated and dehydrogenated derivatives.” S.RAVIKUMAR M.Sc
  • 7. Isoprene Rule • Thermal decomposition of terpenoids give isoprene as one of the product. • Otto Wallach pointed out that skeleton structure of all naturally occuring terpenoids can be built up of isoprene unit, this is called Isoprene rule. • Isoprene rule stats that the terpenoid molecules are constructed from two or more isoprene unit. S.RAVIKUMAR M.Sc CH3 CH2 CH2
  • 8. Special Isoprene Rule • Ingold suggested that ‘the terpenoid molecule are constructed of two or more isoprene units joined in a ‘head to tail’ fashion’. S.RAVIKUMAR M.Sc CH3 CH2 CH2 tailhead CH2 C CH3 CH2 CH2 CH C CH CH3 CH2 head tail head tail
  • 9. Examples open chain monoterpenoids, • But this rule can only be used as guiding principle and not as a fixed rule. • For example carotenoids are joined tail to tail at their central and there are also some terpenoids whose carbon content is not a multiple of five. CH2 CH3CH3 CH2 Mycene CH3CH3 CH3 CHO citral CH3CH3 CH3 CH2OH geraniol head head head head head head tail tail tail tail tail tail S.RAVIKUMAR M.Sc
  • 10. ‘Gem Dialkyl Rule’ • Ingold pointed that a gem alkyl group affects the stability of terpenoids. He summarized these results in the form of a rule called ‘gem dialkyl rule’, • which may be stated as "Gem dialkyl group tends to render the cyclohexane ring unstable where as it stabilizes the three, four and five member rings.” • This rule limits the number of possible structure in closing the open chain to ring structure. • Thus the monoterpenoid open chain give rise to only one possibility for a monocyclic monoterpenoid i.e the p- cymene structure. • Most of the monoterpenoids are derivative of p-cymene. S.RAVIKUMAR M.Sc CH3 CH3 CH3 p-cymene
  • 11. • Bicyclic monoterpenodis contain a six member and a three member ring. • Ingold also find out that cyclopropane and cyclobutane ring have gem-dimethyl group to render them sufficiently stable. • Thus closure of the ten carbon open chain monoterpenoid gives three possible bicyclic structures. S.RAVIKUMAR M.Sc O camphor (6+5)system pinane (6+4)system carane (6+3)system
  • 12. CLASSIFICATION OF TERPENOIDS • Most natural terpenoid hydrocarbon have the general formula (C5H8)n. They can be classified on the basis of value of ‘n’ or ‘number of carbon atoms’ present in the structure. S.No . Number of carbon atoms Value of ‘n’ Class 1 10 2 Monoterpenoids (C10H16) 2 15 3 Sesquiterpenoinds (C15H24) 3 20 4 Diterpenoids (C20H32) 4 25 5 Sesterpenoids (C25H40) 5 30 6 Triterpenoids (C30H48) 6 40 8 Tetraterpenoids (C40H64)(carotenoids) 7 >40 >8 Polyterpenoids (C5H8)n S.RAVIKUMAR M.Sc
  • 13. Classification, According to the Number of Rings • Each class can be further subdivided into subclasses according to the number of rings present in the structure. i) Acyclic Terpenoids: They contain open structure. ii) Monocyclic Terpenoids: They contain one ring in the structure. iii) Bicyclic Terpenoids: They contain two rings in the structure. iv) Tricyclic Terpenoids: They contain three rings in the structure. v) Tetracyclic Terpenoids: They contain four rings in the structure. S.RAVIKUMAR M.Sc
  • 14. Mono Terpenoids i) Acyclic Monoterpenoids ii) Monocyclic monoterpenoids CH2 CH3CH3 CH2 Mycene CH3CH3 CH3 CHO citral CH3CH3 CH3 CH2OH geraniol CH2CH3 CH3 CH3CH3 CH3 OH limonene alpha-terpineol CH3CH3 CH3 OH menthol S.RAVIKUMAR M.Sc
  • 15. Mono Terpenoids iii) Bicyclic monoterpenoids: These are further divided into three classes. CH3CH3 Thujane Carane pinane Bornane (Camphane) NON-Bornane (iso-Camphane) 6+3 membered ring 6+4 membered ring 6+5 membered ring Some bicyclic monoterpenes are: O champhor alpha-pinene S.RAVIKUMAR M.Sc
  • 17. Diterpenoids: i) Acyclic diterpenoids ii) Mono cyclic diterpenoids CH CH2OH CH3CH3CH3 CH3 CH3 phytol CH2OH vitamin A1 (retinol) S.RAVIKUMAR M.Sc
  • 18. ISOLATION OF MONO AND SESQUITERPENOIDS • Both mono and sesquiterpenoids have common source i.e essential oils. Their isolation is carried out in two steps: i) Isolation of essential oils from plant parts ii)Separation of Terpenoids from essential oils. S.RAVIKUMAR M.Sc
  • 19. • The plants having essential oils generally have the highest concentration at some particular time. Therefore better yield of essential oil plant material have to be collected at this particular time. e.g. From jasmine at sunset. There are four methods of extractions of oils. 1. Expression method 2. Steam distillation method 3. Extraction by means of volatile solvents 4. Adsorption in purified fats • Steam distillation is most widely used method. In this method macerated plant material is steam distilled to get essential oils into the distillate form these are extracted by using pure organic volatile solvents. If compound decomposes during steam distillation, it may be extracted with petrol at 50oC. After extraction solvent is removed under reduced pressure. S.RAVIKUMAR M.Sc
  • 20. • A number of terpenoids are present in essential oil obtained from the extraction. • Definite physical and chemical methods can be used for the separation of terpenoids. • They are separated by fractional distillation. • The terpenoid hydrocarbons distill over first followed by the oxygenated derivatives. • More recently different chromatographic techniques have been used both for isolation and separation of terpenoids. S.RAVIKUMAR M.Sc
  • 21. 1. Most of the terpenoids are colourless, 2. Fragrant liquids which are lighter than water and volatile with steam. few of them are solids e.g. camphor. 3. All are soluble in organic solvent and usually insoluble in water. 4. Most of them are optically active. 5. Open chain or cyclic unsaturated compounds having one or more double bonds. Consequently they undergo addition reaction with hydrogen, halogen, acids, etc. A number of addition products have antiseptic properties. 6. They undergo polymerization and dehydrogenation 7. They are easily oxidized nearly by all the oxidizing agents. 8. On thermal decomposition, most of the terpenoids yields isoprene as one of the product. S.RAVIKUMAR M.Sc
  • 22. 1. Molecular formula: molecular formula is determined by usual quantitative analysis and mol.wt determination methods and by means of mass spectrometry. If terpenoid is optically active, its specific rotation can be measured. 2. Nature of oxygen atom present: If oxygen is present in terpenoids its functional nature is generally as • alcohol • aledhyde, • ketone or carboxylic groups. S.RAVIKUMAR M.Sc
  • 23. Presence of –OH Group • Presence of –OH group can be determined by the formation of acetates with acetic anhydride and benzoyate with 3.5-dinitirobenzoyl chloride. • Primary alcoholic group undergo esterification more readily than secondary and tertiary alcohols. R OH + (CH3CO)2O R O C CH3 O + CH3COOH R OH + O2N NO2 OCl O2N NO2 OOR 3,5-dinitrobenzoyl chloride S.RAVIKUMAR M.Sc
  • 24. Presence of >C=O group • Terpenoids containing carbonyl function form crystalline addition products like oxime, phenyl hydrazone and bisulphite etc. • If carbonyl function is in the form of aldehyde it gives carboxylic acid on oxidation without loss of any carbon atom whereas the ketone on oxidation yields a mixture of lesser number of carbon atoms. R C R 1 O + R C R 1 O + R C R 1 O + H2NOH H2N.NHC6H5 NaHSO 4 R C R 1 NOH + OH2 R C R 1 N.NHC 6H5 + OH2 R C R 1 OH SO3Na oxime phenyl hydrazone sodium bisulphate derivatives S.RAVIKUMAR M.Sc
  • 25. • The presence of olefinic double bond is confirmed by means of bromine, and number of double bond determination by analysis of the bromide or by quantitative hydrogenation or by titration with monoperpthalic acid. • Presence of double bond also confirmed by means of catalytic hydrogenation or addition of halogen acids. • Number of moles of HX absorbed by one molecule is equal to number of double bonds present. C C + H2 C C + HX CATALYST C C H X C C H H S.RAVIKUMAR M.Sc
  • 26. • Addition of nitrosyl chloride(NOCl) (Tilden’s reagent) • Epoxide formation with per acid • Gives idea about double bonds present in terpenoid molecule. C C + NOCl C C ON Cl C C + C C O CH3COOOH + CH3COOH S.RAVIKUMAR M.Sc
  • 27. • Dehydrogenation give carbone skelton • On dehydrogenation with sulphur, selenium, polonium or palladium terpenoids converted to aromatic compounds. • Examination of these products the skelton structure and position of side chain in the original terpenoids can be determined. • For example α-terpenol on Se-dehydrogenation yields p-cymene. OH Se dehydrogenation α-terpenol p-cymene S.RAVIKUMAR M.Sc
  • 28. • Thus the carbon Skelton of terpenol is as follows. • Oxidative degradation has been the parallel tool for elucidating the structure of terpenoids. • Reagents for degradative oxidation are ozone, acid, neutral or alkaline potassium permanganate, chromic acid, sodium hypobromide, osmium tetroxide, nitric acid, lead tetra acetate and peroxy acids. • Since oxidizing agents are selective, depending on a particular group to be oxidized, the oxidizing agent is chosen with the help of structure of degradation products. S.RAVIKUMAR M.Sc
  • 29. 6. Number of the rings present • With the help of general formula of corresponding parent saturated hydrocarbon, number of rings present in that molecule can be determined. • For example limonene (mol. formula. C10H16) absorbs 2 moles of hydrogen to give tetrahydro limonene (mol. Formula C10H20) corresponding to the general formula. CnH2n. It means limonoene has monocyclic structure. Relation between general formula of compound and type of compounds General formula of parent saturated Hydrocarbon Type of structure CnH2n+2 acyclic CnH2n monocyclic CnH2n-2 bicyclic CnH2n-4 tricyclic CnH2n-6 tetracyclic S.RAVIKUMAR M.Sc
  • 30. 7. Spectroscopic studies • All the spectroscopic methods are very helpful for the confirmation of structure of natural terpenoids and also structure of degradation products. The various methods for elucidating the structure of terpenoids are, 1. UV spectroscopy 2. IR spectroscopy 3. NMR spectroscopy 4. Mass spectroscopy 5. X-ray analysis S.RAVIKUMAR M.Sc
  • 31. UV spectroscopy • In terpenes containing conjugated dienes or α,β-unsaturated ketones, UV spectroscopy is very useful tool for detection of the conjugation. • The values of λmax for various types of terpenoids have been calculated by applying Woodward’s empirical rules. Parent system is butadiene means BASIS BASIC VALUES Acyclic diene 217nm Homo annular dienes 253nm Hetroannular dienes 214nm Increment for each C- substituents 5nm for exocyclic double bond 5nm for double bond extends 30nm S.RAVIKUMAR M.Sc
  • 32. UV spectroscopy • Parent system is α,β-unsaturated ketones means 1. Example; myrcene • Acyclic diene = 217nm • C-substituent = 5nm • Total λmax = 222nm BASIS BASIC VALUE Acyclic enone 215nm Increment for C-sub., at α 10nm At β 12nm At gama 18nm Exo cyclic double bond 5nm Extends conjugation 30nm CH2 CH3CH3 CH2 S.RAVIKUMAR M.Sc
  • 33. IR spectroscopy • IR spectroscopy is useful in detecting functional groups such as hydroxyl group (~3400cm-1) or an oxo group (saturated 1750-1700cm-1). Isopropyl group, cis and trans also have characteristic absorption peaks in IR region. S.RAVIKUMAR M.Sc
  • 34. NMR spectroscopy • This technique is useful to detect and identify double bonds, to determine the nature of end group and also the number of rings present, and also to reveal the orientation of methyl group in the relative Position of double bonds. Mass spectroscopy • It is now being widely used as a means of elucidating structure of terpenoids. Used for Determining mol. Wt., Mol. Formula, nature of functional groups present and relative positions of double bonds. X-ray analysis • This is very helpful technique for elucidating structure and Stereochemistry of terpenoids. S.RAVIKUMAR M.Sc
  • 35. 8. Synthesis • Proposed structure is finally confirmed by synthesis. • In terpenoid chemistry, many of the synthesis are ambiguous and in such cases analytical evidences are used in conjunction with the synthesis. S.RAVIKUMAR M.Sc
  • 39. • Camphor occurs in of Formosa and Japan. • It is optically active; the (+) and (-) forms occur in nature. • It is solid • Having . • It is obtained by steam distillation of wood, leaves or bark of camphor tree. • It S.RAVIKUMAR M.Sc
  • 40. • It is used in pharmaceutical preparation because of its analgesic, • Stimulant for heart muscles, • Expectorant and antiseptic properties. • It is used in manufacture of celluloid, smokeless powder and explosives. • It is also used as moth repellent. S.RAVIKUMAR M.Sc
  • 42. 1. MOLECULAR FORMULA: • Molecular formula is C10H16O found by molecular weight determination methods (mass spectroscopy). 2. SATURATED NATURE: • Formation of mono substituted products in the reaction. i.e., monobromo, monochloro camphor and molecular refraction show that it is saturated. S.RAVIKUMAR M.Sc
  • 43. 3. NATURE OF OXYGEN ATOM PRESENT: • Nature of Oxygen atom in camphor is ketone form.It is found by formation of oxime, phenyl hydrozone with hydroxyl amine, phenyl hydrazine respectively. C10H16O + H2NOH C10H16O + H2NNHC6H5 C10H16=NOH C10H16=NNHC6H5 Hydroxyl amine Phenyl hydrazine oxime Phenyl hydrazone -H2O -H2O S.RAVIKUMAR M.Sc
  • 44. 4. NATURE OF OXYGEN ATOM PRESENT: • Camphor oxidised with nitric acid yields a dicarboxylic acid called camphoric acid (C10H16O4 ) (with out loss of carbon atom) • Further oxidation give camphoronic acid (C9H14O6) Camphor reduced with Na/Hg it gives secondary alcohol Borneol. • It confirms that the oxygen in the camphor is cyclic ketone. S.RAVIKUMAR M.Sc
  • 45. 5. PRESENCE OF BICYCLIC SYSTEM: • The parent compound of camphor having molecular formula and corresponds C10H8. • Molecular formula of saturated hydrocarbon of camphor (C10H16O) corresponds to the general formula of a bicyclic compound (CnH2n-2). • It is bicyclic system. S.RAVIKUMAR M.Sc
  • 46. 6. PRESENCE OF A SIX MEMBERED RING: • When distilled with zinc Chloride or phosphorous peroxide, it yields p-cymene. • Formation of p-cymene confirms the presence of six-membered ring. C10H16O CH3 CH3 CH3 p-Cymene S.RAVIKUMAR M.Sc
  • 47. 7. NATURE OF CARBON FRAME: • Camphoric acid is saturated dicarboxylic acid with the same number of carbon atoms as camphor, • It suggest that keto group is present in one of ring and ring contain keto group is opened in the formation of camphoric acid . C10H16O C10H16O2 C9H14O6 camphor camphoric acid camphoronic acid HNO3 [O] HNO3 [O] S.RAVIKUMAR M.Sc
  • 48. 7. NATURE OF CARBON FRAME: • Thus camphoric acid should be a monocyclic compound. • Camphoronic acid is tricarboxylic acid. In order to determine the structure of camphor, • the structures of camphoric acid and camphoronic acid should be known. S.RAVIKUMAR M.Sc
  • 49. (C9H14O6 ) • Camphoronic acid is tricarboxylic acid. • Camphoronic acid under goes distillation at atm. pressure it gives • Isobutyric acid, trimethylsuccinic acid, carbon dioxide, carbon. • But it does not undergo decarboxylation under ordinary condition it shows that three carboxylic groups are attached to the different carbon atoms. S.RAVIKUMAR M.Sc
  • 50. (C9H14O6 ) • Camphoronic acid is a α,β- trimethyl tricarboxylic acid. CCH2 COOH CH3 CH(CH 3)2 COOH COOH  +2H CHCH3 COOH CH3 2 + CO2 Isobutyric acid CCH2 COOH CH3 CH(CH 3)2 COOH COOH  +2H CH COOH CH3 CH(CH 3)2 COOH + CO2 Trimethylsuccinic acid camphoronic acid camphoronic acid S.RAVIKUMAR M.Sc
  • 51. (C10H16O4 ) • Camphoric acid is saturated dicarboxylic acid • The saturated hydrocarbon of this (C5H10) corresponds to the general formula CnH2n. Thus camphoric acid is cyclopentene derivative and oxidation of camphoric acid to camphoronic acid may be written as; S.RAVIKUMAR M.Sc
  • 52. (C10H16O4 ) • So, the camphoric acid is contains above skekeleton + one carbon atom + 2COOH groups. • The camphoric anhydride gives that only one bromo derivatives. It shows that one alpha hydrogen is present. So, Carbon one is the COOH group. The cyclo pentane ring open on oxidation, it opens with loss of one carbon atom to give camphoronic acid. COOH COOH COOH COOH S.RAVIKUMAR M.Sc
  • 53. (C10H16O4 ) • So, we understand that the 2COOH of the camphoric acid produced from the CH2C=O group in camphor, from this the camphor contain a six membered ring with gem dimethyl group. CH2 C O [O] 2COOH S.RAVIKUMAR M.Sc
  • 55. • The structure of camphor • The structure 2 is rejected, due to on distillation with iodine it give carvacrol. It only possible for structure 1. O O (1) (2) S.RAVIKUMAR M.Sc
  • 56. O OH CAMPHOR CARVACROL Distillation O Distillation NO carvacrol S.RAVIKUMAR M.Sc
  • 57. • SO, the structure of the Camphor is O O O S.RAVIKUMAR M.Sc It will conformed by synthesis
  • 58. • Structure of camphor confirmed by the synthesis of camphoronic acid, camphoric acid and camphor. (i) Synthesis of camphoronic acid S.RAVIKUMAR M.Sc
  • 59. (i) Synthesis of camphoronic acid S.RAVIKUMAR M.Sc
  • 60. (ii) Synthesis of camphoric acid S.RAVIKUMAR M.Sc
  • 61. (ii) Synthesis of camphoric acid S.RAVIKUMAR M.Sc
  • 62. Camphoric acid exist in two geometrical isomeric forms (ci ans trans) S.RAVIKUMAR M.Sc
  • 63. (iii) Synthesis of camphor S.RAVIKUMAR M.Sc Na - Hg
  • 64. CONFORMATION OF CAMPHOR • The camphor has two dissimilar chiral centers only one pair of enantiomers Is possible, only cis fusion of the gem dimethyl methylene to cyclohexane ring is possible, • Boat conformation with cis fusion of gem dimethyl methylene is shown below, O S.RAVIKUMAR M.Sc
  • 65. • Commercially, camphor is prepared from α- pinene. • In this process the wagner-meerwin rearrangement is involved. α- pinene CAMPHOR S.RAVIKUMAR M.Sc
  • 68. REFERENCES • Chemistry of natural products and stereo chemistry vol:2 by I.L.FINAR. • Review of chemistry of natural products by Sameena Bano.