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Vitamin D


DATA No : VVD0002 INFORMANT : Sachiko Yamada

NAME : (5Z,7E)-(3S)-3-dihydroxy-9,10-seco-5,7,10(19)-pregnatrien-20-one

COMMON NAME: 20-oxo-22,23,24,25,26,27-hexanorvitamin D3 / 20-oxo-22,23,24,25,26,27-hexanorcholecalciferol
SYMBOL: 20-oxo-22,23,24,25,26,27-hexanor-D3
FORMULA: C21H30O2 MOL.WT (average) : 314.462


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BIOLOGICAL ACTIVITY
Had significant affinity for progesterone receptor in MCF-7. (Ref. 0304)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (EtOH) (nm) 264, lmin (nm) 228 (Ref. 0304)

IR SPECTRA:

NMR SPECTRA:1H-NMR (d, CDCl3) 0.51 (3H, s, 18-CH3), 2.13 (3H, s, 21-CH3), 4.20 (1H, m, 3a-H), 4.45 (1H, m, 1b-H), 4.98 (1H, br s, 19E-H), 5.33 (1H, br s, 19Z-H), 6.04 (1H, d, J = 11.3 Hz, 7-H), 6.36 (1H, d, J = 11.3 Hz, 6-H) (Ref. 0304)

MASS SPECTRA:m/z 330 (M+, 31), 312 (21), 183 (95), 134 (100) (Ref. 0304)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS
From corresponding C-22 aldehyde via oxidative decarbonylation. (Ref. 0304)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0304]
AUTHOR:Perlman, K. L.; Darwish, H. M.; DeLuca, H. F.
TITLE:20-Oxopregnacalciferols : Vitamin D Compounds That Bind The Progesterone Receptor.
JOURNAL:Tetrahedron Lett.
VOL:35 PAGE : 2295 -2298 (1994)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.