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Vitamin D


DATA No : VVD0395 INFORMANT : Sachiko Yamada

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

COMMON NAME: (24R)-24,25-dihydroxyvitamin D2 / (24R)-24,25-dihydroxyergocalciferol
SYMBOL: 24R,25-(OH)2D2
FORMULA: C28H44O3 MOL.WT (average) : 428.647


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BIOLOGICAL ACTIVITY

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. 0149)
(EtOH) lmax (nm) 265, lmin (nm) 228 (Ref. 0193)

IR SPECTRA:

NMR SPECTRA:1H-NMR (d, CDCl3) 4.84 and 5.08 (each 1H, br s, 19-H2), 5.64 (2H, m, 22- and 23-H) (Ref. 0193)

MASS SPECTRA:m/z 428 (M+), 395, 370, 337, 271, 253, 136, 118 (Ref. 0149)
m/z 428 (M+), 395, 370, 337, 271, 253, 136, 118,59 (Ref. 0150)
m/z 428.3271 (Ref. 0193)

OTHER SPECTRA:
CHROMATOGRAM DATA
HPLC : Zorbax-SIL column, 5.5% / 94.5% : isopropyl alcohol / hexane, 2ml/min (Ref. 0150)
SOURCE

CHEMICAL SYNTHESIS
Asymmetric synthesis of (24R)- and (24S)-24,25-(OH)2D2 from C(22) steroid aldehyde via reduction of 3b,25-dihydroxy-5,22-cholestadien-24-one as a key step, the stereochemistry at C(24) being determined by X-ray analysis. The configuration of 24,25-(OH)2D2 produced by kidney was determined to be R using these synthetic compounds. (Ref. 0151)
Asymmetric synthesis of (24R)- and (24S)-24,25-(OH)2D2 from C(22) steroid aldehyde via triazoline adduct of 3b-acetoxy-25-hydroxy-5,7,22-cholestadien-24-one. (Ref. 0152)
METABOLISM
24,25-Dihydroxyvitamin D2 was biologically generated from synthetic 25-hydroxyvitamin D2 using an isolated perfused rat kidney incubated under normocalcemic and normophosphatemic conditions. (Ref. 0150)
GENETIC INFORMATION

NOTE

REFERENCES
[0149]
AUTHOR:Jones, G.; Schnoes, H. K.; Levan, L.; DeLuca, H. F.
TITLE:Isolation and Identification of 24-Hydroxyvitamin D2 and 24,25-Dihydroxyvitamin D2. PubMed ID:6970013
JOURNAL:Arch Biochem. Biophys.
VOL:202 PAGE : 450 -457 (1980)
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[0150]
AUTHOR:Jones, G., Rosenthal, A., Segev, D., Mazur, Y., Frolow, F., Halfon, Y., Rabinovich, D., and Shakked, Z.
TITLE:Isolation and identification of 24,25-dihydroxyvitamin D2 using the perfused rat kidney PubMed ID:311655
JOURNAL:Biochemistry.
VOL:18 PAGE : 1094-1011 (1979)
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[0151]
AUTHOR:Jones, G.; Rosenthal, A.; Segev, D.; Mazur, Y.; Frolow, F.; Halfon, Y.; Rabinovich, D.; Shakked, Z.
TITLE:24(R),25-Dihydroxyvitamin D2 Synthesis, Determination of Absolute Configuration by X-Ray Analysis and Identification as a Kidney Metabolite of Vitamin D2.
JOURNAL:Tetrahedron Lett.
VOL:2 PAGE : 177 -180 (1979)
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[0152]
AUTHOR:Katsumi, K.; Okano, T.; Kobayashi, T.; Miyata, O.; Naito, T.; Ninomiya, I.
TITLE:Synthesis of Diastereomeric 24,25-Dihydroxyvitamin D2 and Separation of Its (24R)-and (24S)-Isomers.
JOURNAL:Chem. Pharm. Bull.
VOL:32 PAGE : 3744 -3746 (1984)
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[0193]
AUTHOR:Katsumi, K., Okano, T., Ono, Y., Maegaki, E., Nishimura, K., Baba, M., Kobayashi, T., Miyata, O., Naito, T., and Ninomiya, I.
TITLE:Syntheses of 24,25-dihydroxyvitamin D2, 24,25-dihydroxy-22-dehydrovitamin D3, 25-hydroxy-24-oxo-22-dehydrovitamin D3 and 22,24,25-trihydroxyvitamin D3 PubMed ID:3496978
JOURNAL:Chem Pharm Bull (Tokyo).
VOL:35 PAGE : 970-979 (1987)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.