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Vitamin D


DATA No : VVD0003 INFORMANT : Sachiko Yamada

NAME : (5Z,7E)-(1S,3R)-1,3-dihydroxy-9,10-seco-5,7,10(19)-pregnatrien-20-one

COMMON NAME: 1a-hydroxy-20-oxo-22,23,24,25,26,27-hexanorvitamin D3 / 1a-hydroxy-20-oxo-22,23,24,25,26,27-hexanorcholecalciferol
SYMBOL: 1a-OH-20-oxo-22,23,24,25,26,27-hexanor-D3
FORMULA: C21H30O3 MOL.WT (average) : 330.461


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BIOLOGICAL ACTIVITY
Had no affinity for progesterone receptor in MCF-7. (Ref. 0304)
Effects of the compound given at the doses of 0.2 or 1.0mg/kg on the primary immune response in BALB/C mice immunized with 1 times 107 sheep red blood cells were shown in comparison with 1a-hydroxyvitamin D3 (0.2mg/kg). The binding affinity with chick intestinal cytosolic receptor was 1/10,000 compared to 1a,25-(OH)2D3. no calcemic activity of the compound (125mg/kg, times 5, i.v.) was observed. (Ref. 0211)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-23 9.20 deg (c = 1.00 in EtOH) (Ref. 0211)

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), 3.95 (1H, m, 3a-H), 4.81 (1H, br s, 19E-H), 5.06 (1H, br s, 19Z-H), 6.06 (1H, d, J = 11.2 Hz, 7-H), 6.22 (1H, d, J = 11.2 Hz, 6-H) (Ref. 0304)
1H-NMR (d, CDCl3) 0.51 (3H, s), 2.13 (3H, s), 2.23-2.37 (1H, m), 2.52-2.73 (3H, m), 2.84 (1H, br d, J = 12.8 Hz), 3.26 (2H, br s), 4.15-4.28 (1H, br), 4.36-4.47 (1H, br), 4.99 (1H, t, J = 1.4 Hz), 5.33 (1H, t, J = 1.4 Hz), 6.04 (1H, d, J = 11.4 Hz), 6.36 (1H, d, J = 11.4 Hz) (Ref. 0211)

MASS SPECTRA:m/z 314 (M+, 23), 296 (2.4), 281 (15), 271 (1.5) 253 (4.6), 136 (33), 118 (73), 43 (100) (Ref. 0304)

OTHER SPECTRA:HRMS Calcd 330.2195, Found 330.2176 (Ref. 0211)
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS
From corresponding C-22 aldehyde via oxidative decarbonylation. (Ref. 0304)
Synthesis from dehydroepiandrostertone via 5,7-diene compound by photochemical method. (Ref. 0211)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0211]
AUTHOR:Murayama, E.; Miyamoto, K.; Ochi, K.; Kubodera, N.
TITLE:Synthesis and Immunoregulating Activity of Vitamin D Analogues Bearing Pregnane Side Chain.
JOURNAL:Bioorg. Med. Chem. Lett.
VOL:2 PAGE : 1289 -1292 (1992)
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[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.