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Vitamin D


DATA No : VVD0007 INFORMANT : Sachiko Yamada

NAME : (5Z,7E)-(1S,3R,20S)-9,10-seco-5,7,10(19)-pregnatriene-1,3,20-triol

COMMON NAME: (20S)-1a,20-dihydroxy-22,23,24,25,26,27-hexanorvitamin D3 / (20S)-1a,20-dihydroxy-22,23,24,25,26,27-hexanorcholecalciferol
SYMBOL: 1a,20S-(OH)2-22,23,24,25,26,27-hexanor-D3
FORMULA: C21H32O3 MOL.WT (average) : 332.477


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BIOLOGICAL ACTIVITY
The antiproliferation activity towards HL-60 was <1/217 of 22-oxacalcitriol (OCT). The binding affinity for bovine thymus vitamin D receptor was 1/929 of OCT. (Ref. 0213)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-20 55.10 deg (c = 0.01 in EtOH) (Ref. 0212)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA: lmax (EtOH) (nm) 263, lmin (nm) 227 (Ref. 0212)

IR SPECTRA:(neat) 3375, 2920, 2865, 1050 cm-1 (Ref. 0212)

NMR SPECTRA:1H-NMR (d, CDCl3) 0.55 (3H, s), 1.23 (3H, d, J = 6.6 Hz), 2.33 (1H, dd, J = 6.0 and 13.1 Hz), 2.61 (1H, dd, J = 2.9 and 13.1 Hz), 2.85 (1H, dd, J = 2.9 and 10.8 Hz), 3.25-3.57 (4H, m), 3.62-3.76 (1H, m), 4.17-4.31 (1H, m), 4.37-4.51 (1H, m), 5.00 (1H, s), 5.33 (1H, s), 6.04 (1H, d, J = 11.7 Hz), 6.37 (1H, d, J = 11.7Hz) (Ref. 0212)

MASS SPECTRA:m/z 332 (M+), 134 (100%) (Ref. 0212)

OTHER SPECTRA:Colorless foam. (Ref. 0213)
HRMS Calcd 332.2351, Found 332.2369 (Ref. 0212)
CHROMATOGRAM DATA
1)Flash column chromatography with CH2Cl2-EtOH (10 : 1). 2)Fash column chromatography with AcOEt. 3)Flash column chromatography with CH2Cl2-EtOH (10 : 1). (Ref. 0213)
SOURCE

CHEMICAL SYNTHESIS
Synthesis from dehydroepiandrostertone via the 5,7-diene by photochemical method. (Ref. 0212/0213)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0212]
AUTHOR:Kubodera, N.; Watanabe, H.; Hatakeyama, S.; Tazumi, K.; Takano S.
TITLE:Synthesis of Postulated Metabolites of 1a,25-Dihydroxy-22-oxavitamin D3.
JOURNAL:Bioorg. Med. Chem. Lett.
VOL:4 PAGE : 753 -756 (1994)
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[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.