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Vitamin D


DATA No : VVD0030 INFORMANT : Sachiko Yamada

NAME : (5Z,7E)-(1S,3R)-21-nor-20-oxa-9,10-seco-5,7,10(19)-cholestatriene-1,3,25-triol

COMMON NAME: 1a,25-dihydroxy-21-nor-20-oxavitamin D3 / 1a,25-dihydroxy-21-nor-20-oxacholecalciferol
SYMBOL: 1a,25-(OH)2-20-oxa-21-nor-D3
FORMULA: C25H40O4 MOL.WT (average) : 404.583


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BIOLOGICAL ACTIVITY
Differentiation inducing activity of HL-60 (ED50): 4.0 times 10-8 M (1,25-(OH)2D3, 8.3 times 10-9 M); Binding affinity for chick intestinal receptor: 1/1000 of 1,25-(OH)2D3. Calcemic activity at a dose of 500mg/kg in normal mice, 8.96 pm 0.13 (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:[a]d-24 -44.6 deg (c = 0.56 in EtOH) (Ref. 0207)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (EtOH) (nm) 262, lmin (nm) 227 (Ref. 0207)

IR SPECTRA:

NMR SPECTRA:1H-NMR (d, CDCl3) 0.63 (3H, s), 1.23 (6H, s), 3.51 (3H, m), 4.17-4.29 (1H, m), 4.34-4.49 (1H, m), 4.98 (1H, t, J = 1.6 Hz), 5.31 (1H, t, J = 1.6 Hz), 5.99 (1H, d, J = 12.0 Hz), 6.36 (1H, d, J = 12.0 Hz) (Ref. 0207)

MASS SPECTRA:m/z 404 (M+), 83 (100%) (Ref. 0207)

OTHER SPECTRA:Colorless crystals (Ref. 0207)
CHROMATOGRAM DATA

SOURCE

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

GENETIC INFORMATION

NOTE

REFERENCES
[0207]
AUTHOR:Kubodera, N.; Miyamoto, K.; Ochi, K.; Matsunaga, I.
TITLE:Synthetic Studies of Vitamin D Analogues. VII. Synthesis of 20-oxa-21-norvitamin D3 analogues.
JOURNAL:Chem. Pharm. Bull.
VOL:34 PAGE : 2286 -2289 (1986)
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[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.