Isoprene unit

Chemistry VITAMIN D (Calciferol)

This comprises a group of fat soluble sterol founds naturally in few foods.
The two major physiolgically relevant forms of vitamin D are D2 (ergocalciferol) and D3
(cholecalciferol).
Chemistry
• It is also called sunshine vitamins.
• Its active forms are vitamin D2 (ergo calciferol) and vitamin D3
 Vitamin A (Retinol) is a cyclic polyene alcohol which resembles the structure of Diterpenoid. (cholecalciferol).
 They are composed of β- ionone ring (methyl substituted cyclohexenyl ring) and side chain containing two • Calcitriol is the most active form of vitamin D that acts as
isoprene units with four conjugated double bonds. steroid hormone.
 Due to the presence of double bonds in isoprenoid side chain, vitamin A exhibits cis-trans (geometric) isomerism. • They are formed from provitamins which are sterols.
 Four conjugated double bonds in the side chain of vitamin A. Absorption, transport and storage
 Due to the presence of 4 double bonds, vitamin A can be oxidized by air or light slowly. • Dietary vitamin D2 and vitamin D3 are absorbed in the small
 They are in trans arrangement. intestine in presence of bile salts.
 Synthetic retinol is a trans isomer. • Absorbed Vit D is incorporated into chylomicrons and enters
 β- ionone ring and conjugated double bonds are essential for the biological activity of vitamin A. circulation via lymph.
• Vitamin D is stored in liver and adipose tissue.

VITAMIN E
Chemistry
• Chemically they are tocopherol
• They are derivatives of tocol or 6-hydroxy chromane ring with
phytyl side chain.

• Tocopherols are alkaline sensitive and their vitamin activity is

destroyed by oxidation.
• Among all tocopherols α-tocopherol is most potent and widely
distributed in nature.
• Cooking and food processing may destroy vitamin E to some
extent.

Synthesis of Phytonadione
Synthesis of Menadione

Metabolism

Vitamin K are absorbed from intestine via lymph and require bile salts for
absorption. Vitamin K1 is absorbed by simple diffusion. It is metabolized in liver by
side chain cleavage and glucuronide conjugation. Metabolites are excreted in bile
and urine.
 Chemistry Synthesis of Vit. B1
Thiamine is rather synthesized than being isolated/extracted from the food sources. It is
synthesized by the direct condensation of 2-methyl-4amino-5-chloromethylpyrimidine
hydrochloride and 4-methyl-5-(β-hydroxymethyl) thiazole.

Vitamin B2 (Riboflavin)
Biochemical functions
Riboflavin, also known as vitamin B2 is a water-soluble vitamin occurring widely in
Thiamine functions as a coenzyme in the oxidative decarboxylation of alpha-ketoacids animal and plant foodstuff. It is converted into FAD (flavin adenosine dinucleotide) and
Biochemical functions:
(involved in energy production) and in the transketolase reaction of the pentose necessary for metabolic processes.
phosphate pathway (involved in carbohydrate metabolism).
The enzyme thiamine pyrophosphate or co-carboxylase is intimately connected with the
energy releasing reactions in the carbohydrate metabolism.

TPP also plays an important role in the transmission of nerve impulse. This is because
TPP is required for acetylcholine synthesis and the ion translocation of neural tissue.
 Biochemical function of Vitamin B2 (Riboflavin) Synthesis:
Esterification of nicotinic acid affords ethyl nicotinate. Amidation of that with
ammonia in ethanol results in niacinamide (nicotinamide).
Riboflavin functions as a component of two flavin coenzymes– flavin
mononucleotide (FMN) and flavin adenine dinucleotide (FAD). Riboflavin through
its coenzymes Flavin mononucleotide (FMN) and Flavin adenine dinucleotide
(FAD) takes part in a variety of cellular oxidation-reduction reactions and in energy
production.
Examples include the oxidation of glucose, certain amino acids and fatty acids;
reactions with several intermediaries of the Krebs cycle; conversion of pyridoxine
to its active coenzyme; and conversion of tryptophan to niacin.
Riboflavin has a role as an antioxidant. It may be involved in maintaining the
integrity of erythrocytes.

Vitamin B6 (Pyridoxine) Vitamin C

 Vitamin C is a water soluble vitamin.
 The use of vitamin C in megadoses to cure everything from common cold
to cancer.

Synthesis Chemistry of vitamin C

 It is water soluble and is easily destroyed by heat, alkali and
storage.
 In the process of cooking, 70% of vitamin C is lost.
 The structural formula of ascorbic acid closely resembles that of
carbohydrates.
 It has strong reducing property.
 It’s a heterocyclic furan-2-one detivative.
 Ascorbic acid is a hexose derivative and closely resembles
monosaccharide’s in structure.

Synthesis Vit C

The synthesis of vitamin C is done from D-glucose. It is a semi-synthesis.

In this process D-glucose is hydrogenated to D-sorbitol which by oxidation
with Acetobactor suboxydans (fermentation) yields L-so rbo se. When
L-sorbose is treated with acetone in presence of conc. H 2 SO 4 and the
catalyst (used in dehydrogenation) diacetone sorbose is formed.

When it is oxidized with KMnO 4 in strong alkaline medium diacetone

sorburonic acid is formed which upon heating with conc. HCl gives 2-keto-
L-gulonic acid. This when treated with a solution of aqueous HCl in ethanol-
chloroform solvent leads to ascorbic acid.

Dosage:
Prophylactic dose → 45-60 mg/per day via oral or IM routes, during
pregnancy and lactation an additional 20-40 mg is required.
Therapeutic dose:
– Treatment of scurvy → 100 mg three times daily for several weeks
– For severe burns → 200-500 mg daily