Title: Vitamin D2
CAS Registry Number: 50-14-6
CAS Name: (3b,5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-ol
Additional Names: calciferol; ergocalciferol; oleovitamin D2; activated ergosterol; viosterol
Trademarks: Condol; Decaps; Dee-Ron; Deltalin (Lilly); De-Rat Concentrate (Rentokil); Deratol (Brewer); Detalup (Bayer); Diactol; Divit Urto; Drisdol (Winthrop); D-Tracetten; Ergorone; Ertron; Fortodyl; Hi-Deratol; Infron (Whittier); Metadee; Mina D2; Mulsiferol; Mykostin; Ostelin; Radiostol; Radsterin; Shock-Ferol; Sterogyl (Roussel Diamant); Uvesterol-D (Crinex); Vio-D (Rowell)
Molecular Formula: C28H44O
Molecular Weight: 396.65
Percent Composition: C 84.78%, H 11.18%, O 4.03%
Literature References: The synthetic form of vitamin D. Prepd from ergosterol by uv irradiation in a suitable solvent: Askew et al., Proc. Roy. Soc. London B109, 488 (1931/32). The best wavelengths for production of vitamin D2 seem to be from 275 to 300 nm: Knudson, Benford, J. Biol. Chem. 124, 287 (1938); Bunker et al., J. Am. Chem. Soc. 62, 508 (1940). Prepn by electron bombardment of ergosterol using longer waves: AT 119210. Manuf: US 1902785 (1933); US 2030792 (1936); US 1680818 (1928); US 1871136 (1932). Direct total synthesis: B. Lythgoe et al., Tetrahedron Lett. 1977, 3685. Discussion of structural problems: Papers by Askew and Windaus et al., beginning in 1930. Stereochemistry: Crowfoot, Dunitz, Nature 162, 608 (1948); Chem. Ind. (London) 1957, 1149. General review: Inhoffen, Angew. Chem. 72, 875 (1960). A polar, biologically active metabolite of vitamin D2, 25-hydroxyergocalciferol, which is ~1.5 times more active in curing rickets in rats, has been isolated from pig plasma. See Suda et al., Biochem. Biophys. Res. Commun. 35, 182 (1969); eidem, Biochemistry 8, 3515 (1969).
Properties: Prisms from acetone, mp 115-118°. Sublimes in very high vacuum (0.0006 mm) without dec. [a]D25 +82.6° (c = 3 in acetone); [a]D20 +102.5° (alcohol); [a]D20 +52° (CHCl3). uv max (hexane): 264.5 nm (E1%1cm 458.9 ± 7.5). Not precipitated by digitonin (diff from ergosterol). Insol in water. Sol in the usual organic solvents. 1 ml acetone dissolves 0.0695 g at 7°. Slightly sol in vegetable oils. Commercial solns are usually made with propylene glycol or sesame oil. Vitamin D2 crystals have a potency of 40 units of vitamin D (U.S.P.) per mg. The behavior in storage is described under vitamin D3. See also Huber, Barlow, J. Biol. Chem. 149, 125 (1943) for stability information.
Melting point: mp 115-118°
Optical Rotation: [a]D25 +82.6° (c = 3 in acetone); [a]D20 +102.5° (alcohol); [a]D20 +52° (CHCl3)
Absorption maximum: uv max (hexane): 264.5 nm (E1%1cm 458.9 ± 7.5)
Use: Rodenticide.
Therap-Cat: Vitamin (antirachitic).
Therap-Cat-Vet: Nutritional factor (antirachitic). Low activity in poultry.
Keywords: Vitamin/Vitamin Source; Vitamin D. |