1alpha-Hydroxycholecalciferol
Structural Formula Vector Image
Title: 1a-Hydroxycholecalciferol
CAS Registry Number: 41294-56-8
CAS Name: (1a,3b,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-1,3-diol
Additional Names: 1a-hydroxyvitamin D3; 1a-OH-CC; alfacalcidol
Trademarks: Alfarol (Chugai); Alpha D3 (Teva); EinsAlpha (Thomae); Etalpha (Leo Pharm); One-Alpha (Leo Pharm); Vetalpha (A.T.I.)
Molecular Formula: C27H44O2
Molecular Weight: 400.64
Percent Composition: C 80.94%, H 11.07%, O 7.99%
Literature References: Synthetic analog of calcitriol, q.v., the hormonal form of vitamin D3, which shows identical potency with respect to stimulation of intestinal calcium absorption and bone mineral mobilization. This common activity is thought to be due either to the presence in both of a 1a hydroxy group or more likely, to the conversion of the 1a-OH-CC in vivo to 1a,25-dihydroxycholecalciferol: Haussler et al., Proc. Natl. Acad. Sci. USA 70, 2248 (1973). Synthesis from cholesterol: Holick et al., Science 180, 190 (1973); Barton et al., J. Am. Chem. Soc. 95, 2748 (1973); Fürst et al., Helv. Chim. Acta 56, 1708 (1973); M. Morisaki et al., Chem. Pharm. Bull. 23, 3272 (1975); T. Sato et al., ibid. 26, 2933 (1979). Total synthesis: R. G. Harrison et al., Tetrahedron Lett. 1973, 3649; eidem, J. Chem. Soc. Perkin Trans. 1 1974, 2654; P. J. Kocienski, B. Lythgoe, ibid. 1980, 1400. Synthesis of the 1b-epimer from the 1a-form and biological properties: H. E. Paaren et al., Chem. Commun. 1977, 890.
Properties: mp 134-136° (Harrison); also reported as mp 138-139.5° (Fürst). [a]D25 +28° (ether). uv max (ether): 264 nm (e 18000) (Harrison); also reported as e 20200 (Barton).
Melting point: mp 134-136° (Harrison); mp 138-139.5° (Fürst)
Optical Rotation: [a]D25 +28° (ether)
Absorption maximum: uv max (ether): 264 nm (e 18000) (Harrison); also reported as e 20200 (Barton)
 
Derivative Type: 1b-Epimer
Additional Names: 1b-Hydroxycholecalciferol; 1b-hydroxyvitamin D3
 
Therap-Cat: Vitamin D source.
Therap-Cat-Vet: Vitamin D source.
Keywords: Vitamin/Vitamin Source; Vitamin D.

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