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Vitamin D


DATA No : VVD0372 INFORMANT : Sachiko Yamada

NAME : (5Z,7E,22E)-(3S,24R)-9,10-seco-5,7,10(19),22-ergostatetraene-3,25-diol

COMMON NAME: 24-epi-25-hydroxyvitamin D2 / 24-epi-25-hydroxyergocalciferol
SYMBOL: 24-epi-25-OHD2
FORMULA: C28H44O2 MOL.WT (average) : 412.648


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BIOLOGICAL ACTIVITY
HL-60 human promyelocytes differentiation : ED50 in nitro blue tetrazplium reduction, phagocytic activity, and nonspecific acid esterase activity are 3.0 times 10-7 M, 2.8 times 10-7 M and 2.8 times 10-7 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:[a]d-25 +50.7 deg (c = 0.2 in EtOH) (Ref. 0232)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (nm) (emax) 265 (17300) (Ref. 0232)

IR SPECTRA:(KBr) 3401 (OH), 1643, 1630 (C=C), 971 cm-1 (trans C=C) (Ref. 0232)

NMR SPECTRA:1H-NMR (d, CDCl3) 0.57 (s, 18-H), 0.99 (d, J = 7 Hz, 28-H), 1.03 (d, J = 7 Hz, 21-H), 1.14 and 1.16 (2 s, 26- and 27-H), 3.94 (m, 1H, 3a-H), 4.82 and 5.03 (2 narrow m, 2 times 1H, 19(Z)- and 19(E)-H), 5.20-5.40 (m, 2H, 22- and 23-H), 6.04 and 6.22 (2 d, J = 11 Hz, 2 times 1H, 7- and 6-H) (Ref. 0232)

MASS SPECTRA:m/z (relative intensity) 412 (M+, 62), 394 (M+-H2O, 12), 379 (M+-H2O-Me, 31), 271 (M+-side chain, 44), 253 (M+-side chain-H2O, 55), 136 (100), 118 (67), 59 (38) (Ref. 0232)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[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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[0232]
AUTHOR:Morzycki, J. W.; Schnoes, H. K.; DeLuca, H. F.
TITLE:Synthesis of 25-Hydroxyvitamin D2 and Its 24-Epimer.
JOURNAL:J. Org. Chem.
VOL:49 PAGE : 2148 -2151 (1984)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.