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Vitamin D


DATA No : VVD0050 INFORMANT : Sachiko Yamada

NAME : (5Z,7E)-(1S,3R)-21-nor-9,10-seco-5,7,10(19)-cholestatriene-1,3,25-triol

COMMON NAME: 1a,25-dihydroxy-21-norvitamin D3 / 1a,25-dihydroxy-21-norcholecalciferol
SYMBOL: 1a,25-(OH)2-21-nor-D3
FORMULA: C26H42O3 MOL.WT (average) : 402.610


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BIOLOGICAL ACTIVITY
Differentiation inducing activity of HL-60 (ED50):2.9 times 10-8 M (1,25-(OH)2D3: 8.3 times 10-9 M). Binding affinity for chick intestinal receptor: 1/10 of 1a,25-(OH)2D3. Calcemic activity at the dose of 500 mg/kg in normal mice ; 9.68 pm 0.15 (1.25-(OH)2D3 ; 11.04 pm 0.12 at 10mg/kg). (Ref. 0209)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA: lmax (EtOH) (nm) 262, lmin (nm) 227 (Ref. 0209)

IR SPECTRA:(neat) 3380, 1470, 1450, 1375, 1060 cm-1 (Ref. 0209)

NMR SPECTRA:1H-NMR (d) 0.44 (3H, s), 1.21 (6H, s), 1.25 (3H, br s), 4.14-4.28 (1H, br), 4.34-4.47 (1H, br), 5.00 (1H, s), 5.33 (1H, s), 6.01 (1H, d, J = 11.0 Hz), 6.38 (1H, d, J = 11.0 Hz) (Ref. 0209)

MASS SPECTRA:m/z 402 (M+), 134 (100%) (Ref. 0209)

OTHER SPECTRA:
CHROMATOGRAM DATA
Preparative TLC devbeloped twice with CH2Cl2-EtOH (50 : 7) (Ref. 0209)
SOURCE

CHEMICAL SYNTHESIS
Synthesis from dehydroepiandrostertone via 5,7-diene compound by photochemical method. (Ref. 0209)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0209]
AUTHOR:Kubodera, N., Miyamoto, K., Matsumoto, M., Kawanishi, T., Ohkawa, H., and Mori, T.
TITLE:Synthetic studies of vitamin D analogues. X. Synthesis and biological activities of 1 alpha,25-dihydroxy-21-norvitamin D3 PubMed ID:1319286
JOURNAL:Chem Pharm Bull (Tokyo).
VOL:40 PAGE : 648-651 (1992)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.