Chemical and physical properties of pantothenic acid

Chemical and physical properties of pantothenic acid or vitamin B5

1. Chemical and physical
properties of pantothenic acid
Domina Petric, MD

2. Essential features of the chemical
structure:
Formal derivative of
pantoic acid and alanine
Optically active
April 17, 2018
Combs GF. The Vitamins. Fundamental Aspects in
Nutrition and Health. Elsevier Inc. 2008.
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3. Panthenol is a provitamin.
Comptox.epa.gov
April 17, 2018
Combs GF. The Vitamins. Fundamental Aspects in
Nutrition and Health. Elsevier Inc. 2008.
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4. Pantothenic acid or B5
April 17, 2018
Combs GF. The Vitamins. Fundamental Aspects in
Nutrition and Health. Elsevier Inc. 2008.
4
Studyandexam.com

5. Nomenclature
•Pantothenic acid is the trivial designation for
thecompound
dihydroxy-β,β-dimethylbutyryl-β-alanine.
Ithas two metabolically active forms:
•coenzyme A,in which the vitamin is linked
via a phosphodiestergroup with adenosine-
3′,5′-diphosphate
•acyl-carrierprotein, in which it is linked
via a phosphodiester to aserinylresidue of
the protein
April 17, 2018
Combs GF. The Vitamins. Fundamental Aspects in
Nutrition and Health. Elsevier Inc. 2008.
5

6. Chemical and physical properties
•Pantothenic acid is composed of
β-alanine joined to2,4-dihydroxy-
3,3-dimethylbutyric acid via an amide
linkage.
•The molecule has an asymmetric center
and only the R-enantiomer,usually called
D-(+)pantothenic acid, biologically active
and occurs naturally.
•Pantothenic acid is a yellow, viscous oil.
April 17, 2018
Combs GF. The Vitamins. Fundamental Aspects in
Nutrition and Health. Elsevier Inc. 2008.
6

7. Chemical and physical properties
Itscalcium and other saltsare colorless
crystalline substances.
Calciumpantothenateis the mainproduct
of commerce.
Neither form is soluble inorganic solvents,
but each is soluble in water and ethanol.
April 17, 2018
Combs GF. The Vitamins. Fundamental Aspects in
Nutrition and Health. Elsevier Inc. 2008.
7

8. Chemical and physical properties
•Aqueous solutions of
pantothenic acid are unstable to
heating under acidic or alkaline
conditions,resulting in the
hydrolytic cleavage of the
moleculeto yield β-alanine and
2,4-dihydroxy-3,3-
dimethylbutyrate.
April 17, 2018
Combs GF. The Vitamins. Fundamental Aspects in
Nutrition and Health. Elsevier Inc. 2008.
8

9. Chemical and physical properties
The analog panthenol (in which
the carboxyl group is replaced
by anhydroxymethyl group)is
fairly stable in solution.
In dry form, the salts arestable
to air and light, but they
(particularly sodium
pantothenate) are hygroscopic.
April 17, 2018
Combs GF. The Vitamins. Fundamental Aspects in
Nutrition and Health. Elsevier Inc. 2008.
9

10. Literature
•Combs GF. The Vitamins. Fundamental Aspects in
Nutrition and Health. Elsevier Inc. 2008.
April 17, 2018 10