Chemical Properties
White Solid
Usage
A metabolite of Vitamin D. The principal circulating form of vitamin D3, formed in the liver by hydroxylation at C-25. Calcium regulator.
Originator
Dedrogyl,Roussel,France,1976
Uses
A metabolite of Vitamin D. The principal circulating form of vitamin D3, formed in the liver by hydroxylation at C-25. Calcium regulator.
Definition
ChEBI: A hydroxycalciol that is calciol in which the hydrogen at position 25 has been replaced by a hydroxy group. A prehormone resulting from the oxidation of calciol in the liver, it is further hydroxylated in the kidney to give calcitriol, the active form of v
tamin D3.
Manufacturing Process
A solution of 125 mg of cholesta-5,7-diene-3β,25-diol in 125 ml of benzene
and 10 ml of absolute ethanol is placed in a photo reactor equipped with a
quartz lamp well cooled with water and a nitrogen inlet. The reaction mixture
is cooled to about 16°C, and purged with N2. A Hanovia 8A36, 100-watt lamp,
centered in the lampwell 2.5 cm from the internal surface of the reaction
mixture, is turned on for 15 minutes, including the 5-6 minutes required for
the lamp to reach full brilliance. The lamp is a typical actinic energy source
suitable for the irradiation step in the known synthesis of Vitamin D, and can
be replaced by any such available lamp. The specific lamp used is a 100-watt
high-pressure quartz mercury-vapor lamp, producing approximately 11.5
watts total radiated energy distributed over the range of 220-1400 nm. A fast
stream of water is necessary to keep the outlet water temperature below
20°C. The reaction mixture is concentrated to dryness in a rotary evaporator
below room temperature. The semisolid residue is triturated with 5 ml of 35%
ethyl acetate-65% Skellysolve B hexanes mixture and filtered and another 5
ml of the same solvent is used for wash. The solid contains unreacted starting
material and the liquor contains the product. The liquor is poured onto a 40 g
column containing TLC grade Florisil, 150-200 mesh packed wet with 35%
ethyl acetate-Skellysolve B hexanes, and the products are eluted with the
same solvent mixture collecting 10 ml fractions. The fractions containing the
product, located by spotting on a TLC plate, are combined and evaporated to
dryness below room temperature to give an oily residue. A few drops of
absolute ether are added and removed under vacuum to give 25-
hydroxyprecholecalciferol as a fluffy foam; yield 60 mg.
A solution of about 300 mg of 25-hydroxyprecholecalciferol prepared as
described above in 5 ml of chloroform is heated for 3.5 hours at 70°-75°C
under N2 in a sealed flask. The solvent is evaporated and the residue is
chromatographed through a 60 g column containing TLC grade Florisil, 150-
200 mesh packed wet with 35% ethyl acetate in Skellysolve B hexanes. The
column is eluted with the same solvent mixture, collecting 10 ml fractions.
The fractions which crystallize on trituration with aqueous methanol are
combined and recrystallized twice from aqueous methanol to give 25-
hydroxycholecalciferol hydrate; yield 120 mg, MP 81°-83°C (sinters 75°C).
A solution of 20 mg of 25-hydroxycholecalciferol hydrate, prepared as
described above, in 20 ml of methylene chloride is dried with 200 mg of
anhydrous sodium sulfate. The solution is filtered and the filtrate is
evaporated to yield 25-hydroxycholecalciferol essentially anhydrous as an
amorphous oil.
Brand name
Calderol (Organon).
Therapeutic Function
Calcium regulator
General Description
25-Hydroxyvitamin D3 (calcifediol) is a prohormone produced via hydroxylation of vitamin D3 (cholecalciferol) in the liver. It is a precursor for the synthesis of calcitriol {1,25-dihydroxyvitamin D3 or [1,25(OH)2D3]}. It is used as a biomarker to determine the status of vitamin D in the body.
25-Hydroxyvitamin D3-23,24,25,26,27-13C5?is an isotope of vitamin D3 wherein C-23, C-24, C-25, C-26, C-27 carbons are replaced by 13C6 isotope.
Biochem/physiol Actions
Ergocalciferol (vitamin D2) and 25-Hydroxycholecalciferol (vitamin D3) are the two form of vitamin D which are activated in vivo by hydroxylation. Vitamin D2 and D3 may be used in a wide range of studies to assess their effects on function such as immune function and calcium homeostasis.
