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Chemistry of Flavonoids

Flavonoids are a group of organic compounds found in plants that include flavones and isoflavones. They are yellow pigments that occur naturally in plants and provide antioxidant and other protective health effects. Flavones lack hydroxyl groups and can be identified through fusion with potassium hydroxide and boiling with alcoholic potassium hydroxide. Isoflavones have a phenyl group replacing a hydrogen on carbon 3 of the benzo-γ-pyrone ring. Isoflavones contain hydroxyl and methoxyl groups and can be identified through chemical tests and fusion with potassium hydroxide.

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139 views15 pages

Chemistry of Flavonoids

Flavonoids are a group of organic compounds found in plants that include flavones and isoflavones. They are yellow pigments that occur naturally in plants and provide antioxidant and other protective health effects. Flavones lack hydroxyl groups and can be identified through fusion with potassium hydroxide and boiling with alcoholic potassium hydroxide. Isoflavones have a phenyl group replacing a hydrogen on carbon 3 of the benzo-γ-pyrone ring. Isoflavones contain hydroxyl and methoxyl groups and can be identified through chemical tests and fusion with potassium hydroxide.

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Sathish Sizzy
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CHEMISTRY OF FLAVONOIDS

• Introduction
• Identification test
• Chemistry of flavones & Isoflavones
• Flavonoids are a group of organic compounds which
include flavones, isoflavones, flavonols etc.
• They are yellow pigments, also called anthoxanthins,
occurring in plants either in free state or as glycosides
or associated with tannins.
• Significant quantities of flavonoids are consumed every
day in our vegetable diet, providing protective effects
to the body which includes
 antioxidant protection of DNA and low-density
lipoprotein
 Inhibition of platelet platelet aggregation
 Modulation of inflammation
 Oestrogenic effects
Flavones
Structural elucidation:
1. Molecular formula: C15H10O2

2. Absence of hydroxyl groups:


Usual standard chemical reactions (Acetylation,
oxidation) revealed that flavone does not
possess any hydroxyl group.
3. Structure of flavone
a) Fusion with KOH:

b) Boiling with alcoholic KOH:


c) By assuming the structure (I) for flavones, formation of the above
products can be explained.

d) Due to opening of the pyrone ring of flavones (I), α-


hydroxydibenzoylmethane (IA) is formed which then undergoes
cleavage in two different ways to yield two pairs of products i.e. (A)
and (B), & (C) and (D).
4. Robinson’s synthesis
ISOFLAVONES
• If a hydrogen atom from C3 in benzo-γ-pyrone ring is replaced by
a phenyl group, isoflavone is formed.

• Like other pigments isoflavones are also found either free or as


glycosides.

• Glycosides on hydrolysis yield sugar free isoflavones.

• Isoflavones are more susceptible than flavones to alkali hydrolysis


Examples of isoflavonoids
Structural elucidation of Isoflavones
1. Presence of hydroxyl and methoxyl group:

Standard chemical tests – the number of hydroxyl and methoxyl


groups present in isoflavones are estimated.

o Acetylation

o Oxidation

o Zerewitnoff’s reaction

o Zeisel reaction
2.Fusion of isoflavones with KOH
• Oxidation of isoflavones with alkaline hydrogen peroxide
employed for degrading isoflavones. It is useful in knowing the
substituents in the 3-phenyl nucleus.

Spath synthesis (Spath, 1930)

• General method for synthesizing isoflavones

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