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Vitamin D


DATA No : VVD0045 INFORMANT : Sachiko Yamada

NAME : (5Z,7E)-(1R)-9,10-seco-3-thia-5,7,10(19)-cholestatriene-1,25-diol

COMMON NAME: (5Z)-1,25-dihydroxy-3-thiavitamin D3 / (5Z)-1,25-dihydroxy-3-thiacholecalciferol
SYMBOL: (5Z)-3-thia-1,25-(OH)2D3
FORMULA: C26H42O2S MOL.WT (average) : 418.676


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BIOLOGICAL ACTIVITY
Affinity for chicken intestinal recepto : 0.1% of 1,25-(OH)2D3 effect. Inhibitory effect of a series of 3-thiavitamin D derivatives on 25-OHD3 1a-hydroxylase was evaluated. (Ref. 0306)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:(100% EtOH) lmax (nm) (emax) 268 (18300) (Ref. 0306)

IR SPECTRA:

NMR SPECTRA:1H-NMR (d, CDCl3, 300MHz) 0.56 (3H, s, 18C-CH3), 0.94 (3H, d, J = 6.3 Hz, 21C-CH3), 1.22 (6H, s, 26C- and 27C-CH3), 2.75-2.90 (2H, m, 2- and 9b-H), 3.08 (1H, dd, J = 13.2, 2.3 Hz, 2-H), 3.25 and 3.44 (2H, AB pattern, J = 13.5 Hz, 4-H2), 4.39 (1H, m, 1-H), 4.99 (1H, s, 19-H), 5.01 (1H, distorted d, J = 1.8 Hz, 19-H), 5.79 and 6.41 (2H, AB pattern, J = 11.5 Hz, 6- and 7-H) (Ref. 0306)

MASS SPECTRA:m/z 418 (34, M+), 400 (7, M+-H2O), 385 (20), 372 (10), 354 (5), 342 (2), 318 (4), 289 (7), 271 (15), 246 (14), 213 (7), 189 (9), 175 (14), 154 (base, A-ring portion due to C7- and C8-cleavage), 135 (68), 121 (12), 108 (66), 95 (31), 81 (22), 69 (13), 59 (16) (Ref. 0306)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS
From corresponding 5E-vitamin D (1a,25-dihydroxy-3-deoxy-3-thiavitamin D3) by iodine catalyzed isomerization followed by HPLC separation. (Ref. 0306)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0306]
AUTHOR:Muralidharan, K. R., Rowland-Goldsmith, M., Lee, A. S., Park, G., Norman, A. W., Henry, H. L., and Okamura, W. H.
TITLE:Inhibitors of 25-hydroxyvitamin D3-1alpha-hydroxylase: thiavitamin D analogs and biological evaluation PubMed ID:9366500
JOURNAL:J Steroid Biochem Mol Biol.
VOL:62 PAGE : 73-78 (1997)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.