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Vitamin D


DATA No : VVD0031 INFORMANT : Sachiko Yamada

NAME : (5Z,7E)-(1S,3R)-24-nor-22-oxa-9,10-seco-5,7,10(19)-cholestatriene-1,3,25-triol

COMMON NAME: 1a,25-dihydroxy-24-nor-22-oxavitamin D3 / 1a,25-dihydroxy-24-nor-22-oxacholecalciferol
SYMBOL: 1a,25-(OH)2-22-oxa-24-nor-D3
FORMULA: C25H40O4 MOL.WT (average) : 404.583


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BIOLOGICAL ACTIVITY
The activity inducing differentiation of human myeloid leukemia cells (HL-60) into macrophases in vitro was compared with 1,25-(OH)2D3. Figure (Ref. 0203)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:(EtOH) lmax (nm) 263, lmin (nm) 227(Ref. 0203)

IR SPECTRA:

NMR SPECTRA:1H-NMR (d, CDCl3) 0.53 (3H, s), 1.16 (3H, d, J = 6.2 Hz), 1.19 (6H, s), 3.04 (1H, d, J = 8.4 Hz), 3.24-3.48 (1H, br), 3.39 (1H, d, J = 8.4 Hz), 4.20-4.32 (1H, br), 4.40-4.52 (1H, br), 4.99 (1H, s), 5.33 (1H, s), 6.03 (1H, d, J = 11.4 Hz), 6.37 (1H, d, J = 11.4 Hz) (Ref. 0203)

MASS SPECTRA:m/z 404 (M+), 72 (100%) (Ref. 0203)

OTHER SPECTRA:Colorless foam. (Ref. 0203)
CHROMATOGRAM DATA
1)Flash column chromatography with CH2Cl2/EtOH (12.5 : 1), 2)Flash column chromatography with AcOEt/n-hexane (6 : 1), 3)Preparative TLC developed four times with CH2Cl2/EtOH (12.5 : 1) (Ref. 0203)
SOURCE

CHEMICAL SYNTHESIS
Synthesis from dehydroepiandrostertone via 1a,3b-dihydroxy-20(S)-(2-hydroxy-2-methylpropyloxy)pregna-5,7-diene by photochemical method. (Ref. 0203)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0203]
AUTHOR:Kubodera, N., Watanabe, H., Kawanishi, T., and Matsumoto, M.
TITLE:Synthetic studies of vitamin D analogues. XI. Synthesis and differentiation-inducing activity of 1 alpha,25-dihydroxy-22-oxavitamin D3 analogues PubMed ID:1327561
JOURNAL:Chem Pharm Bull (Tokyo).
VOL:40 PAGE : 1494-1499 (1992)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.