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Course No.: CHM-3132/542

Course Title: Organic Chemistry-II

Class: BS-III/M.Sc.-I

Course In-charges: Dr. Najma Rasool/Dr. Farzana

Naz 2
INTERACTIVE CLASS WILL BE

ON ZOOM APP

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PHENOLIC COMPOUNDS

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i-INTRODUCTION

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Phenols, sometimes called phenolics, are a class of

chemical compounds consisting of one or more

hydroxyl groups (—OH) bonded directly to an

aromatic hydrocarbon group. The simplest is phenol,

C6H5OH. 6
 Phenol – the simplest of the phenols.

Phenols are both synthesized industrially and

produced by plants and microorganisms.

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 Phenols are more acidic than typical alcohols.

 The acidity of the hydroxyl group in phenols is

commonly intermediate between that of aliphatic

alcohols and carboxylic acids (their pKa is usually

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between 10 and 12).

 Deprotonation of a phenol forms a corresponding

negative phenolate ion or phenoxide ion, and the

corresponding salts are called phenolates or

phenoxides.
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 CONTENT OF THE LECTURE

i-Introduction

ii-Plant phenolics

iii-Classification of phenolics

iv-Examples of plant phenolics

v-References 10
 OBJECTIVES / LEARNING GOALS

At the end of lecture, In Sha ALLAH we will be able to

understand the chemistry of phenolics.

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 RELATION TO THE LAST LECTURE

I will start the topic chemistry of phenolics.

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 ii-PLANT PHENOLICS
 Phenolics are broadly distributed in the plant kingdom
and are the most abundant secondary metabolites of
plants.
 Phenolics are widespread constituents of plant foods
(fruits, vegetables, cereals, olive, legumes, chocolate,
etc.) and beverages (tea, coffee, beer, wine, etc.), and
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partially responsible for the overall organoleptic properties

of plant foods.

 Phenolics contribute to the bitterness and astringency of

fruit and fruit juices, because of the interaction between

phenolics and the glycoprotein in saliva.

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 Organoleptic properties

Organoleptic properties are the aspects of food, water

or other substances that create an individual

experience via the senses—including taste, sight,

smell, and touch.

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Inter-relationships between the primary and
secondary metabolism in plants.

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 iii-CLASSIFICATION OF PHENOLIC

COMPOUNDS

Phenolic compounds are classified as simple phenols

or polyphenols based on the number of phenol units in

the molecule.
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Main classes of phenolic compounds regarding to
their carbon chain.

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iv-EXAMPLES OF PLANT PHENOLICS

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 EXAMPLE OF HYDROXY BENZOIC ACID
GALLIC ACID
 Gallic acid is a phenolic compound also known as 3,4,5-

trihydroxy benzoic acid. It is classified as a phenolic acid.

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 It is found both as a free state and as a constituent

of tannins, namely, gallotannin.

Gallotannin 25
 Gallic acid is a well-known natural antioxidant.

 It is used as tea formulation, known as an

Ayurvedic herb.

 Gallic acid is found in gallnuts, sumac, witch hazel,

tea leaves, oak bark, and other plants. 26

 EXAMPLE OF HYDROXY CINNAMIC ACID
CAFFEIC ACID
 Caffeic acid (3,4-dihydroxy-cinnamic acid) is an
example of phenolic compound. It is classified as a
phenolic acid.

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 It is a potent antioxidant.

 The nutrient is claimed to have many health

benefits, including anti-inflammatory, anticancer,

and antiviral abilities.

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 The most common source of caffeic acid in the

human diet is from drinking coffee.

 It’s also found in certain vegetables, fruits, and

herbs.
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 EXAMPLE OF COUMARIN
SCOPOLETIN
 Scopoletin (7-Hydroxy-6-methoxy-2H-1-benzopyran-2-
one) belongs to coumarin.
 It found in the root of different plants.

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 It can also be found in fenugreek, vinegar, some

whiskies or in dandelion coffee.

 Scopoletin is highly fluorescent when dissolved in

dimethyl sulphoxide (DMSO) or water and is

regularly used as a fluorimetric assay for the

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peroxide in conjunction with horseradish peroxidase.

When oxidized, its fluorescence is strongly

suppressed.

 It was usually used for rheumatic arthritis therapy

in Traditional Chinese Medicine.

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 Horseradish peroxidase
The enzyme horseradish peroxidase, found in the roots of
horseradish, is used extensively in biochemistry applications.
It is a metalloenzyme with many isoforms, of which the most
studied type is C. It catalyzes the oxidation of various organic
substrates by hydrogen peroxide.
Isoform
A protein that has the same function as another protein but
which is encoded by a different gene and may have small
differences in its sequence.
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 NON-FLAVONOIDS
 Non-Flavonoids are phenolic compounds with

variable structures, that contribute to specific

characteristics in wine grapes.

 The non-flavonoids are found primarily in the flesh

of the grape berry. 34

 Non-flavonoids include tannins, stilbenes, and

lignans.
EXAMPLES OF TANNINS
GALLO TANNINS
 Gallotannins are natural polymers formed by the
subsequent esterification of hydroxyl groups of 35
D-glucose and gallic acid in polymeric chains.

 Gallotannin causes the contraction of body tissues,

typically used to reduce bleeding from minor
abrasions. 36
 Gallotannins are endogenous defense compounds, acting
as feeding deterrents or digestion reducing agents due to
protein precipitation and action as antioxidants.
Feeding deterrent
Feeding deterrent is a chemical agent that inhibits feeding
without killing the insect directly while the insect remains
near the treated foliage and dies through starvation.
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 EXAMPLES OF LIGNANS
PINORESINOL

 Pinoresinol is a lignan found in Styrax sp. and in

Forsythia suspensa.

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 It is also found in the caterpillar of the cabbage

butterfly, Pieris rapae where it serves as a defence

against ants.

 In food, Pinoresinol is found in sesame seed, in

Brassica vegetables and in olive oil.

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 EXAMPLES OF STILBENES
PINOSYLVIN
 Pinosylvin is a pre-infectious stilbenoid toxin that is
synthetized in plants during fungal infections, ozone
induced stress and physical damage for example.

Pinosylvin
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 It is a fungitoxin protecting the wood from fungal

infection.

 It is present in the heartwood of Pinaceae and also

found in Gnetum cleistostachyum.

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 v-REFERENCES

1-Dewick, P. M. Medicinal Natural Product, A

Biosynthatic approach, Willey John & Sons, 3rd

edition, (2009).

2-http://www.intech.open.com>books>phenolic

compounds 42
3-I. L. Finar, “Organic Chemistry,” Volume-2:

Stereochemistry and the Chemistry of Natural

Products, 5th edition, Pearson Education (2008).

4-V. Alagarsamy, “Pharmaceutical Chemistry of

Natural Products” Elsevier, (2012). 43

5-Jin Dai, Russell J. Mumper, “Plant Phenolics:

Extraction, Analysis and Their Antioxidant and

Anticancer Properties ,” Molecules, 2010, 15, 7313-

7352.

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6-http://www.intech.open.com>chapters

7-http://www.sciencedirect.com>topics>foodscience>phenolic

compounds

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