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Vitamin D


DATA No : VVD0041 INFORMANT : Sachiko Yamada

NAME : (5Z,7E)-(1S,3R)-1,3,25-trihydroxy-22-oxa-9,10-seco-5,7,10(19)-cholestatrien-24-one

COMMON NAME: 1a,25-dihydroxy-24-oxo-22-oxavitamin D3 / 1a,25-dihydroxy-24-oxo-22-oxacholecalciferol
SYMBOL: 1a,25-(OH)2-24-oxo-22-oxa-D3
FORMULA: C26H40O5 MOL.WT (average) : 432.593


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BIOLOGICAL ACTIVITY
Antiproliferative activity (HL-60) was the same as that of 22-oxacalcitriol (OCT). The binding affinity for bovine thymus vitamin D receptor was 1/2 of OCT. (Ref. 0213)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (EtOH) (nm) 263, lmin (nm) 227 (Ref. 0213)

IR SPECTRA:

NMR SPECTRA:1H-NMR (d, CDCl3) 0.53 (3H, s), 1.21 (3H, d, J = 6.3 Hz), 1.40 (6H, s), 4.18-4.27 (1H, m), 4.22 and 4.43 (each 1H, d, J = 16.3 Hz), 4.39-4.48 (1H, m), 5.00 (1H, s), 5.33 (1H, s), 6.03 (1H, d, J = 12.0 Hz), 6.37 (1H, d, J = 12.0 Hz) (Ref. 0213)

MASS SPECTRA:m/z 432 (M+), 59 (100%) (Ref. 0213)

OTHER SPECTRA:Colorless oil. (Ref. 0213)
CHROMATOGRAM DATA
Preparative TLC developed with AcOEt. (Ref. 0213)
SOURCE

CHEMICAL SYNTHESIS
Synthesis from dehydroepiandrostertone via the 5,7-diene by photochemical method. (Ref. 0213)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0213]
AUTHOR:Watanabe, H., Hatakeyama, S., Tazumi, K., Takano, S., Masuda, S., Okano, T., Kobayashi, T., and Kubodera, N.
TITLE:Synthetic studies of vitamin D analogs. XXII. Synthesis and antiproliferation activity of putative metabolites of 1 alpha, 25-dihydroxy-22-oxavitamin D3 PubMed ID:8996858
JOURNAL:Chem Pharm Bull (Tokyo).
VOL:44 PAGE : 2280-2286 (1996)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.