Chemical and physical properties of vitamin D

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Chemical and physical properties of vitamin D Domina Petric, MD

Essential features of the chemical structure are: Side-chain-substituted, open-ring steroid Cis-Triene structure Open positions on carbon atoms at positions 1 (ring) and 25 (side chain) November 20, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008.

Chemical structures of the vitamin D group are: Vitamin D2: ergocalciferol Vitamin D3: cholecalciferol 25-OH-Vitamin D3 1,25-(OH)2-Vitamin D3 November 20, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008.

Vitamin D nomenclature Vitamin D is the generic descriptor for all steroids exhibiting qualitatively the biological activity of cholecalciferol. These compounds contain the intact A, C and D steroid rings, being ultimately derived in vivo by photolysis of the B ring of 7-dehydrocholesterol. That process frees the A ring from the rigid structure of the C and D rings, yielding conformational mobility in which the A ring undergoes rapid interconversion between two chair configurations. November 20, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008.

Ergocalciferol Vitamin D-active compounds also have either of two types of isoprenoid side chains attached to the steroid nucleus at C-17 of the D ring. One side chain contains nine carbons and a single double bond. Vitamin D-active compounds with that structure are derivatives of ergocalciferol (vitamin D2). November 20, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008.

Medicineonline.com November 20, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008.

Ergocalciferol This vitamer can be produced synthetically by the photolysis of plant sterols. November 20, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008.

Cholecalciferol The other type of side chain consists of eight carbons and contains no double bonds. Vitamin D-active compounds with that structure are derivatives of cholecalciferol (vitamin D3). Vitamin D3 is produced metabolically through a natural process of photolysis of 7-dehydrocholesterol on the surface of skin exposed to ultraviolet irradiation (sunlight). November 20, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008.

www.newdruginfo.com November 20, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008.

Active forms The metabolically active forms of vitamin D are ring- (at C-1) and side chain-hydroxylated derivatives of vitamins D2 and D3. November 20, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008.

Vitamin D chemistry Vitamin D-active compounds tend to exist in extended conformations due to the 180° rotation of the A ring about the 6,7 single bond. The hydroxyl group on C-3 is thus in the β position (above the plane of the A ring) in the closed forms and in the α position (below the plane of the A ring) in the stretched forms. November 20, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008.

Vitamin D chemistry Rotation about the 5,6 double bond can also occur by the action of light or iodine to interconvert the biologically active 5,6-cis compounds to 5,6-trans compounds, which show little or no vitamin D activity. November 20, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008.

Physical properties Vitamins D2 and D3 are white to yellowish powders that are: insoluble in water moderately soluble in fats, oils and ethanol freely soluble in acetone, ether and petroleum ether November 20, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008.

Solubility of D2 and D3 WATER FATS, OILS, ETHANOL Freely soluble in Insoluble in WATER insoluble Moderately soluble in FATS, OILS, ETHANOL soluble Freely soluble in soluble ACETONE, ETHER, PETROLEUM ETHER November 20, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008.

Physical properties Both vitamin D2 and D3 show strong ultraviolet (UV) absorption, with a maximum at 264 nm. Vitamin D is sensitive to oxygen, light and iodine. Heating or mild acidity can convert it to the 5,6-trans and other inactive forms. November 20, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008.

Physical properties In solution, both vitamins D2 and D3 undergo reversible, temperature-dependent isomerization to pre-vitamin D, forming an equilibrium mixture with the parent vitamin. November 20, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008.

Vitamin D biopotency Those vitamers that require metabolic activation (cholecalciferol and ergocalciferol) are less biopotent than those that are more proximal to the points of metabolic functioning (25-OH-vitamin D). November 20, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008.

Vitamin D biopotency Compound Relative biopotency Vitamin D2 (ergocalciferol) 100 Vitamin D3 (cholecalciferol) Dihydrotachysterol 5-10 25-OH-cholecalciferol 200-500 1,25-(OH)2-cholecalciferol 500-1000 1α-OH-cholecalciferol November 20, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008.

Literature Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008. November 20, 2018 Combs GF. The Vitamins. Fundamental Aspects in Nutrition and Health. Elsevier Inc. 2008.