The document discusses the structure elucidation of quinine through analysis of its properties and reactions. Quinine was found to contain a quinoline nucleus joined at position 4 to a quinolizidine ring at position 8, with a methoxy group at position 6 and a secondary alcohol group joining the two rings. This structure was determined based on analysis of oxidation and other reaction products of quinine like quininic acid and meroquinene.
Reserpine(Structure Elucidation, Extraction and Isolation)Mohammad Khalid
Reserpine(Structure Elucidation, Extraction and Isolation)
Introduction
Constitution of reserpine
Structure of Reserpic acid
Structure of Yobyrine
Synthesis of Yobyrine
Structure of Reserpine
Synthesis of Reserpine
Classification
Extraction
Isolation:
Identification test
Mode of Action
Introduction, classification, isolation, purification, biological activity of alkaloids, general methods of structural determination of alkaloids, structural elucidation of Morphine, Reserpine and Emetine
Reserpine(Structure Elucidation, Extraction and Isolation)Mohammad Khalid
Reserpine(Structure Elucidation, Extraction and Isolation)
Introduction
Constitution of reserpine
Structure of Reserpic acid
Structure of Yobyrine
Synthesis of Yobyrine
Structure of Reserpine
Synthesis of Reserpine
Classification
Extraction
Isolation:
Identification test
Mode of Action
Introduction, classification, isolation, purification, biological activity of alkaloids, general methods of structural determination of alkaloids, structural elucidation of Morphine, Reserpine and Emetine
This slides discusses about Isoquinoline nucleus (fused heterocyclic compound). this ring contain benzene ring fused with pyridine nucleus with nitrogen atom
THIS SLIDE HAVE GOOD CONTENT. THIS SLIDE CONTAIN INTRODUCTION, STRUCTURE, RESONANCE, AROMATICITY, PHYSICAL AND CHEMICAL PROPERTIES, SYNTHESIS AND APPLICATION OF QUINOLINE.
Extraction, isolation and structure elucidation of flavonoids: QuercetinMohammad Khalid
Extraction, isolation and structure elucidation of- Flavonoids Quercetin
Introduction
FLAVONOIDS & THEIR EXAMPLES
Quercetin
general isolation method
Extraction and isolation
Extraction from neem leaves
Isolation of Quercetin Methanolic Extract of Azadirachta indica leaves
Structure elucidation of Quercetin
Health benefits
Side Effects of Quercetin
Presented by Shikha Popali and Harshpal singh Wahi students from Gurunanak college of pharmacy, Nagpur in Department of pharmaceutical Chemistry. The explained topic is seful for every chemistry student and for others too
STEREOSPECIFIC REACTION, STEREOSELECTIVE REACTION, OPTICAL PURITY, ENANTIOMERIC EXCESS.. all these topics are explained in this slide with examples and formula.
Alkaloids are a group of naturally occurring chemical compounds that mostly contain basic nitrogen atoms.
The term alkaloid was coined by Meissner, a German pharmacist, in 1819.
Alkaloids are cyclic organic compounds containing nitrogen in a negative state of oxidation with limited distribution among living organisms.
Most alkaloids contain oxygen in their molecular structure; those compounds are usually colorless crystals at ambient conditions.
Some alkaloids are colored, like berberine (yellow) and sanguinarine (orange).
Most alkaloids are weak bases, but some, such as theobromine and theophylline, are amphoteric.
Many alkaloids dissolve poorly in water but readily dissolve in organic solvents.
Most alkaloids have a bitter taste or are poisonous when ingested.
Study material for chemistry UG and PG students
Chapter No 05 Terpenoids, Study of natural product Chemistry of natural products, Pharmaceutical chemistry.
MORPHINE AS A LEAD DRUG MOLECULE COMPOUNDShikha Popali
THE ADDICTED DRUG MORPHINE AN ALKALOID USED TO TREAT SOME DISEASE , HERE WE HAVE ATTEMPT ALL DATA ITS STURECTURE MECHANISM OF ACTION, SAR AND APPLICATIONS.
This slides discusses about Isoquinoline nucleus (fused heterocyclic compound). this ring contain benzene ring fused with pyridine nucleus with nitrogen atom
THIS SLIDE HAVE GOOD CONTENT. THIS SLIDE CONTAIN INTRODUCTION, STRUCTURE, RESONANCE, AROMATICITY, PHYSICAL AND CHEMICAL PROPERTIES, SYNTHESIS AND APPLICATION OF QUINOLINE.
Extraction, isolation and structure elucidation of flavonoids: QuercetinMohammad Khalid
Extraction, isolation and structure elucidation of- Flavonoids Quercetin
Introduction
FLAVONOIDS & THEIR EXAMPLES
Quercetin
general isolation method
Extraction and isolation
Extraction from neem leaves
Isolation of Quercetin Methanolic Extract of Azadirachta indica leaves
Structure elucidation of Quercetin
Health benefits
Side Effects of Quercetin
Presented by Shikha Popali and Harshpal singh Wahi students from Gurunanak college of pharmacy, Nagpur in Department of pharmaceutical Chemistry. The explained topic is seful for every chemistry student and for others too
STEREOSPECIFIC REACTION, STEREOSELECTIVE REACTION, OPTICAL PURITY, ENANTIOMERIC EXCESS.. all these topics are explained in this slide with examples and formula.
Alkaloids are a group of naturally occurring chemical compounds that mostly contain basic nitrogen atoms.
The term alkaloid was coined by Meissner, a German pharmacist, in 1819.
Alkaloids are cyclic organic compounds containing nitrogen in a negative state of oxidation with limited distribution among living organisms.
Most alkaloids contain oxygen in their molecular structure; those compounds are usually colorless crystals at ambient conditions.
Some alkaloids are colored, like berberine (yellow) and sanguinarine (orange).
Most alkaloids are weak bases, but some, such as theobromine and theophylline, are amphoteric.
Many alkaloids dissolve poorly in water but readily dissolve in organic solvents.
Most alkaloids have a bitter taste or are poisonous when ingested.
Study material for chemistry UG and PG students
Chapter No 05 Terpenoids, Study of natural product Chemistry of natural products, Pharmaceutical chemistry.
MORPHINE AS A LEAD DRUG MOLECULE COMPOUNDShikha Popali
THE ADDICTED DRUG MORPHINE AN ALKALOID USED TO TREAT SOME DISEASE , HERE WE HAVE ATTEMPT ALL DATA ITS STURECTURE MECHANISM OF ACTION, SAR AND APPLICATIONS.
What is a Heterocyclic Compound?
A heterocyclic compound has at least two different elements as a member of its ring.
The most common hetero atoms found on a cyclic ring are Oxygen (O), Nitrogen (N) and Sulphur (S).
Example:
Nucleic Acid that is present in the body responsible for storing and expressing genetic information, is an example of a Heterocyclic compound.
Essential micronutrient, Vitamins is also an example of a heterocyclic compound.
The majority of drugs, pesticides, dyes, and plastics are examples of heterocyclic compounds.
Classification of Heterocyclic Compounds
Based on the electronic arrangement, we can classify Heterocyclic compounds into two types:
Aliphatic Heterocyclic Compounds
Aromatic Heterocyclic Compounds
Aliphatic Heterocyclic Compounds
Aliphatic heterocyclic compounds are those cyclic heterocycles that do not contain any double bond.
The properties of aliphatic heterocyclic compounds are mainly affected due to ring strain.
Examples of aliphatic heterocyclic compounds are Aziridine, Ethylene Oxide, Thiirane, Oxetane, Azetidine, Thietane, Tetrahydrofuran (THF), Dioxane, Pyrrolidine, Piperidine, etc.
Aromatic Heterocyclic Compound
Aromatic heterocyclic compounds, as the name suggests, are cyclic aromatic compounds.
Aromatic Heterocyclic compounds obey Huckels Rule, i.e.
It should be cyclic.
It should be planar.
It should not contain any sp3 hybridised atoms.
It must have (4n+2) 𝛑 electrons.
Aromatic Heterocyclic compounds are analogous to Benzene.
Examples: Furan, Pyrrole, Thiophene, Indole, Benzofuran, Carbazole, Quinoline, Isoquinoline, Imidazole, Oxazole, Pyrazole, Pyridazine, Pyrimidine, Purine, etc.
Based on structure, we can classify Heterocyclic compounds into five types:
Three-Membered Heterocyclic Compounds
Four-Membered Heterocyclic Compounds
Five-Membered Heterocyclic Compounds
Six-Membered Heterocyclic Compounds
Condensed or Fused Heterocyclic Compounds
Three-Membered Heterocyclic Compounds
These heterocyclic compounds contain three atoms which may be saturated or unsaturated.
Based on the number of heteroatoms present, we can further classify them into two categories:
5 Production Methods of Benzene cyclic hydrocarbon first isolated by Faraday a natural component of crude oil can be produced using different methods Pyrolysis gasoline, coal tar, Catalytic Reforming, Toluene hydrodealkylation, Toluene disproportionation
Vitamin A or Retinol
It is monocyclic diterpenoid.
Molecular formula of retinol is C20H30O.
It is optically inactive and sensitive to light and air. It is destroyed by UV light.
Vitamin A has multiple functions: It is important for growth and development, for the maintenance of the immune system and good vision.
The deficiency of vitamin A causes night blindness, as well as dry eye and skin.
CONSTITUTION OF RETINOL
Molecular formula of Retinol
Presence of primary alcoholic group
Presence of five double bonds
Presence of β ionone nucleus
Presence of group
Position of c-methyl groups
Number of isoprene unit
Structure of Retinol
Confirmation of structure
Synthesis of Retinol
Molecular formula of Retinol
The molecular formula of retinol has been found to be C20H30O.
Presence of primary alcoholic group
As vitamin A forms an ester with p- nitrobenzoic acid, it follows that vitamin A contains a hydroxyl group.
C20H30O
Moreover ,the oxidation of vitamin A yields an aldehyde indicating that the hydroxyl group is primary alcoholic one.
Presence of five double bonds and one ring
When Vitamin A catalytically reduced in the presence of platinum or aluminum amalgam, Vitamin A react with five moles of hydrogen forming perhydroretinol (C20H40O).
The reaction indicates the presence of five double bonds in vitamin A.
Vitamin A forms adduct with maleic anhydride it indicating that vitamin A contains conjugated double bonds.
The formula of deoxygenated parent saturated hydrocarbon of Vitamin A is C20H40 which corresponds to CnH2n molecular formula which is the general formula for compounds having one ring. Hence, Vitamin A is a monocyclic compound.
Presence of β -ionone nucleus
Ozonolysis of vitamin A yields geronic acid per molecule of the vitamin.
Therefor vitamin A may contain one β ionone unit, since β –ionone also gives geronic acid on oxidation.
Presence of 2-methyl propene groups
Retinol is oxidized with alkaline KMnO4 at high temperature yields two molecules of acetic acid per molecule of Vitamin.
It indicates the presence of two 2-methyl propene groups in the side chain.
Position of C-Methyl group
The position of C-methyl group in the side chain has been assumed from the fact that most of the carotenoids contain isoprene units.
Number of Isoprene units
Treatment of vitamin A with alcoholic hydrogen chloride yields an anhydro form which on selenium dehydrogenation yields 1,6-dimethyl naphthalene. The formation of this product can only be explained if there are two isoprene units in the vitamin A.
When vitamin A is oxidized with alkaline KMnO4 at high temperature, it yields two moles of CH3COOH indicating the presence of two isoprene units.
Structure of Retinol
Confirmation of structure
Structure of Vitamin A was confirmed by the synthesis of per hydro retinol A from β-ionone that had been found to be identical with the product obtained by the reduction of vitamin A.
Van dorp and Tishler’s synthesis
Aldehydes and ketones contain the carbonyl group. Aldehydes are considered the most important functional group. Ketones A carbon double bonded to an oxygen is called a carbonyl group. Compounds in which the carbon of a carbonyl group is bonded to two other carbons
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2. Quinine:-
• It is a well known bitter antimalarial drug
occurring among the alkaloids of cinchona
bark and Ramijia.
• Cinchona bark contains about thirty• Cinchona bark contains about thirty
alkaloids, but its antimalarial activity is mainly
due to quinine, quinidine, cinchonine and
cinchonidine.
• Pure quinine and cinchonine were first
isolated in 1820 by Pelletier and Caventou.
3. Isolation:-
• The bark is stripped and dried in the
sun.
• This is crushed to a fine powder and
then treated with lime and caustic
soda solution for several hours and
finally extracted with hot petroleum.finally extracted with hot petroleum.
• The solvent petroleum is drawn off
and the petroleum extract is washed
with dilute sulphuric acid in a lead
lined vessel provided with a powerful
stirrer.
4. • The acid aqueous layer, while still hot, is
neutralised and allowed to stand when the
neutral sulphates of the alkaloids (quinine,
cinchonine and cinchonidine) crystallise out.
• The mixtures of sulphates of three alkaloids
is recrystallised when quinine sulphate,
having minimum solubility crystallises out
first while the sulphates of cinchonine and
cinchonidine remain in the mother liquor.cinchonidine remain in the mother liquor.
• The crude quinine sulphate is redissolved in
water, decolorised with charcoal and
recrystallised until cinchonidine and
cinchonine are reduced to the required
percentage
• Quinine may be obtained from the sulphate
by precipitation with alkali, washing and
drying.
5. Properties:-
• Quinine is a white crystalline
Antipyretic
Analgesic
Anti-inflammatory Anti-inflammatory
Antimalarial
•Quinine is insoluble in water.
• It melts at 177 °C in anhydrous
condition.
• It is laevorotatory and has a bitter
taste.
6.
7.
8. Molecular formula
From elementary analysis and molecular
weight determination, it follow that the
molecular formula of quinine is C20H24N2O2
Presence of two tertiary N atoms
As quinine adds on two moles of methylAs quinine adds on two moles of methyl
iodide to form a diquaternary salt, it is a
ditertiary base.
9. Presence of a secondary alcoholic group
As quinine forms a monoacetate and a
monobenzoate, it means that quinine must
contain one –OH group.
However, this is a secondary alcoholic
group which is shown by the fact thatgroup which is shown by the fact that
quinine on oxidation gives a ketone,
quininone.
10. Presence of a methoxyl group
When quinine is heated with hydrochloric
acid, it eliminates one mole as methyl chloride,
indicating that a methoxyl group is present in
the quinine.
It means that the second oxygen atom inIt means that the second oxygen atom in
the quinine is found to be present as a methoxy
group.
11. Presence of an Olefinic linkage
As quinine adds on one molecule of
bromine, it indicates that quinine must contain
one ethylenic double bond.
The same is also proved by the fact that
quinine absorbs a molecule of hydrogen in the
presence of catalyst.
The presence of an olefinic linkage isThe presence of an olefinic linkage is
further proved by its formation of halogen
substituted compounds with halogen acids.
12. Presence of a Vinyl group
When controlled oxidation of quinine is done
with KMnO4 , it yields a monocarboxylic acid
along with formic acid. This reaction reveals
that a vinyl group is present in quinine.
13. Presence of a Quinoline nucleus
When quinine is fused with concentrated
potassium hydroxide, it yields a mixture of 6-
methoxyquinoline and lepidine (4-methoxyquinoline)
along with other products.
These products prove that a quinoline nucleus
is present in quinine.
Cinchonine when fused with potassium
hydroxide under the same conditions yields
quinoline and lepidine, indicating that quinine is
methoxycinchonine.
14. Presence of Meroquinene
When oxidation of quinine is done with
chromic acid, it produces, among other products,
quininic acid.
On the other hand, controlled oxidation of
quinine with chromic acid yields quininic acid
and the other component known as the “secondand the other component known as the “second
half” commonly known as meroquinene.
In order to establish the structure of
quinine, the structure of these two oxidation
products, i.e., of the quininic acid and
meroquinene should be established.
15. Structure of Quininic acid
When quininic acid is heated with
sodalime, it undergoes decarboxylation,
yielding 6-methoxy-quinoline.
The position 6 of the methoxyl group has
been confirmed by the conversion of quininic
acid to 6-hydroxyquinoline by heating with
hydrochloric acid.hydrochloric acid.
16. When quininic acid is oxidised with chromic
acid, it yields pyridine-2, 3, 4- tricarboxylic acid, it
is evident that the benzene ring of the latter
(quininic acid) having the methoxy group is
oxidised.
The –COOH group at C4 reveals that in
quininic acid also, the –COOH group is present at
position 4.
17. When quininic acid is heated with
hydrochloric acid to yield the demethylated
product which on decarboxylation yields 6-
hydroxyquinoline. This reaction shows that the
methoxy group in quininic acid is present in the
6-position.
All these facts support structure (I) for quininic
acid.acid.
18. Structure of meroquinene
Its molecular formula has been found to be
C9H15NO2
As it forms a monosodium salt as well as an
ester, it reveals the presence of a (–COOH )
carboxylic group.
When meroquinene is reduced with hydrogen, it When meroquinene is reduced with hydrogen, it
takes up one molecule of hydrogen, suggesting
that a ethylenic double bond is present in it.
The presence of ethylenic double bond indicates
that –CH=CH2, i.e., side-chain is still present in
meroquinene.
19. When meroquinene is oxidised with cold
acidified KMnO4 , it yields a cincholoiponic
acid (a dicarboxylic acid) and formic acid.
The formation of formic acid reveals the
presence of –CH=CH2 (vinyl group) side-chain
in meroquinene.in meroquinene.
20. As meroquinene can be benzoylated, acetylated
and nitrosated (forms nitroso derivative with HNO2), it
means that a secondary amino group is present in
meroquinene.
When cicholoiponic acid is oxidised with acid
permanganate, it yields loiponic acid C7H11NO4.
As loiponic acid is a dicarboxylic acid and contains
one methylene group less than its precursor
cincholoiponic acid, this means that the latter
contains at least a side-chain –CH2COOH .
21. Loiponic acid has been somewhat less
stable and isomerises to more stable
hexahydrocinchomeronic acid, C7H11NO4
(piperidine -3,4- dicarboxylic acid) on treatment
with KOH at about 200°C; hence loiponic acid
should also be piperidine -3,4-dicarboxylic acid.
22. Loiponic acid contains one CH2 less than cincholoiponic acid
so chincholoiponic acid should be
on heating with HCl produces 2,4-dimethyl pyridine
or
on heating with HCl produces 2,4-dimethyl pyridine
on heating with con.H2SO4, it gives ϒ-picoline
23. • Meroquinene gives cincholopinic acid along
with HCOOH on oxidation so it should be
either structure A or B
• Structure A is found to be correct since
meroquinene forms 3-ethyl-4-methylpyridine
24. N
H
O
O H
CH 2
Zn / HI
N
H
CH 3
O
O H
Meroquinene Cincholoipon
Meroquinene on reduction with Zn/HI
gives cincholoipon which has a carboxyl
group and ethyl group.
Structure B cannot account for the
formation of cincholoipon so it should be A
25. we know that quinine forms quininic acid (which contains
quinoline nucleus) and meroquinene on oxidation
N
O
CH3
O OH
N
H
O
OH
CH2
Quinine
C20
H24
N2
O2
C
11
H
9
NO
3 C
9
H
15
NO
2
Quinine does not contains COOH groups, showing
that the two moieties are linked through those C atoms.
Quinine is a diteritary base, but meroquinene
contains a secondary N atom and a COOH group, showing
that during oxidation teritary N changes to secondary and a
COOH group is formed.
26. This is possible only when N atoms is a part
of condensed ring system like
N
CH2
N
CH2
N
CH2 CrO3
H2
SO4 N
H
CH2O
OH
N
H
O
OH
CH2
3-Vinylquinulidine Meroquinene
27. From the above facts we can conclude that in
quinine the quinoline nucleus is joined at position 4 and
the quinoclidine at position 8
The last thing to be fixed is the location of the
secondary alcoholic group
Rabe oxidized quinine to quininone by using CrO3.
Quininone on treatment with amyl nitrite and HCl gave
quinininc acid and an oxime. This shows that a methylene
group is present adjacent to a carbonyl group which is
formed from a CHOH group, linking the two moieties
OO H
CrO3
C5
H11
ONO
HCl
O
OH
+ N
O
H
N
O
H
Isomerization
NOH