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Vitamin D


DATA No : VVD0021 INFORMANT : Sachiko Yamada

NAME : (5Z,7E)-(1S,3R)-24-nor-9,10-seco-5,7,10(19)-cholatriene-1,3,23-triol

COMMON NAME: 1a,23-dihydroxy-24,25,26,27-tetranorvitamin D3 / 1a,23-dihydroxy-24,25,26,27-tetranorcholecalciferol
SYMBOL: 1a,23-(OH)2-24,25,26,27-tetranor-D3
FORMULA: C23H36O3 MOL.WT (average) : 360.530


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BIOLOGICAL ACTIVITY
HL-60 human promyelocytes differentiation : ED50 in nitro blue tetrazolium reduction, phagocytic activity, and nonspecific acid esterase activity are 3.0 times 10-6 M, 2.0 times 10-6 M and 2.0 times 10-6 M, respectively, when 1,25-(OH)2D3 shows the respective ED50 values of 1.0 times 10-8 M, 1.0 times 10-8 M and 1.1 times 10-8 M, respectively. (Ref. 0228)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (nm) 265, lmin (nm) 228 (Ref. 0069)

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:tris-TMS-ether: Spectrum (Ref. 0069)

OTHER SPECTRA:
CHROMATOGRAM DATA
HPLC : (Ref. 0069)
SOURCE

CHEMICAL SYNTHESIS
From 1,23,25-(OH)3-24-oxo-D3, which was produced enzymatically from 1,24,25-(OH)3D3, by NaIO4 oxidation followed by NaBH4 reduction. (Ref. 0069)
METABOLISM
1,23-(OH)2-Tetranor-D3 is metabolized to 1-OH-tetranor-D3 23-carboxylic acid (calcitroic acid). (Ref. 0070/0073)
GENETIC INFORMATION

NOTE

REFERENCES
[0069]
AUTHOR:Reddy, G. S., Tserng, K. Y., Thomas, B. R., Dayal, R., and Norman, A. W.
TITLE:Isolation and identification of 1,23-dihydroxy-24,25,26,27-tetranorvitamin D3, a new metabolite of 1,25-dihydroxyvitamin D3 produced in rat kidney PubMed ID:3828305
JOURNAL:Biochemistry.
VOL:26 PAGE : 324-331 (1987)
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[0070]
AUTHOR:Esvelt, R. P., Schnoes, H. K., and DeLuca, H. F.
TITLE:Isolation and characterization of 1 alpha-hydroxy-23-carboxytetranorvitamin D: a major metabolite of 1,25-dihydroxyvitamin D3 PubMed ID:486408
JOURNAL:Biochemistry.
VOL:18 PAGE : 3977-3983 (1979)
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[0073]
AUTHOR:Reddy, G. S., and Tserng, K. Y.
TITLE:Calcitroic acid, end product of renal metabolism of 1,25-dihydroxyvitamin D3 through C-24 oxidation pathway PubMed ID:2719932
JOURNAL:Biochemistry.
VOL:28 PAGE : 1763-1769 (1989)
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[0228]
AUTHOR:Ostrem, V. K., Lau, W. F., Lee, S. H., Perlman, K., Prahl, J., Schnoes, H. K., and DeLuca, H. F.
TITLE:Induction of monocytic differentiation of HL-60 cells by 1,25-dihydroxyvitamin D analogs PubMed ID:3477545
JOURNAL:J Biol Chem.
VOL:262 PAGE : 14164-14171 (1987)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.