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Vitamin D


DATA No : VVD0273 INFORMANT : Sachiko Yamada

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

COMMON NAME: 25-hydroxyvitamin D3 / 25-hydroxycholecalciferol / calcidiol
SYMBOL: 25-OHD3
FORMULA: C27H44O2 MOL.WT (average) : 400.637


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BIOLOGICAL ACTIVITY
Activities of vitamin D3 in intestinal calcium transport and bone calcium mobilization were compared with those of 25-OHD3: Tables (Ref. 0014)
Antirachitic Activity (IU/mg)(the standard line test assay for vitamin D activity as described in The United States Pharmacopoeia): 25-OHD3 56 pm 6 ; vitamin D3, 40 pm 4. (Ref. 0019)
HL-60 human promyelocytes differentiation: ED50 in nitro blue tetrazplium reduction, phagocytic activity, and nonspecific acid esterase activity are 8.4 times 10-7 M, 8.0 times 10-7 M and 8.0 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:96-106 degC (Ref. 0262)
95-100 degC (Ref. 0298)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-25 +88.1 deg (c = 0.5 in EtOH) (Ref. 0262)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:(EtOH) lmax (nm) (e) 265 (18000) (Ref. 0014)
lmax (nm) (e) 265 (17700) (Ref. 0298)

IR SPECTRA:(KBr) 3500, 3360, 3080, 3030, 1650, 1635, 1050, 900, 880, 860, 765 cm-1 (Ref. 0298)

NMR SPECTRA:1H-NMR (d, CDCl3, 100MHz) 0.54 (3H, s), 0.90 (3H, d, J = 8 Hz), 1.22 (6H, s), 4.80 and 5.00 (each 1H, s), 5.97 and 6.25 (each 1H, d, J = 12 Hz) (Ref. 0014)
1H-NMR (d) 0.54 (3H, s, 18-CH3), 0.93 (3H, d, J = 5 cps, 21-CH3), 1.21 (6H, s, 26- and 27-CH3), 3.90 (1H, bm, 3-CH), 4.81 and 5.04 (2H, 2d, =CH2), 6.02 (1H, d, J = 12 cps, 7-CH), 6.21 (1H, d, J = 12 cps, 6-CH) (Ref. 0298)

MASS SPECTRA:m/z 400, 367, 341, 271, 253, 158, 136, 118; spectrum(Ref. 0014/0015)

OTHER SPECTRA:X-ray crystal structure (Ref. 0274)
CHROMATOGRAM DATA
HPLC: (Ref. 0023)
SOURCE
Isolation and identification: from plasma of pigs (Ref. 0015/0021) ; from human plasma. (Ref. 0019)
Concentration in human plasma : 10-40 ng/ml (Ref. 0020)
CHEMICAL SYNTHESIS
Synthesis from 25-hydroxycholesterol acetate and 3b-acetoxy-27-nor-cholest-5-en-25-one by standard photochemical method via 5,7-cholestadiene-3b,25-diol. (Ref. 0014)
8b,25-Dihydroxy-3,5-cyclovitamin D derivative was synthesized in a convergent method from 25-hydroxylated Grundman's ketone and A-ring precursor and the title compound was prepared from the 3,5-cyclovitamin D by cycloreversion followed by photochemical isomerization. (Ref. 0262)
METABOLISM
Biosynthesis: Hydroxylation of D3 by vitamin D 25-hydroxylase (CYP27) in the liver. (Ref. 0016/0017)
Further metabolism : 1a-Hydroxylation in the kidney to give 1a,25-(OH)2D3 under vitamin D deficient conditions. (Ref. 0017/0018/0022)
24-Hydroxylation to give 24R,25-(OH)2D3 in tissues possessing vitamin D receptor under vitamin D supplemented conditions. (Ref. 0017/0018)
26-Hydroxylation to give 25,26-(OH)2D3. (Ref. 0126)
GENETIC INFORMATION

NOTE

REFERENCES
[0014]
AUTHOR:Blunt, J. W., and DeLuca, H. F.
TITLE:The synthesis of 25-hydroxycholecalciferol. A biologically active metabolite of vitamin D3 PubMed ID:4307413
JOURNAL:Biochemistry.
VOL:8 PAGE : 671-675 (1969)
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[0015]
AUTHOR:Blunt, J. W., DeLuca, H. F., and Schnoes, H. K.
TITLE:25-hydroxycholecalciferol. A biologically active metabolite of vitamin D3 PubMed ID:4300699
JOURNAL:Biochemistry.
VOL:7 PAGE : 3317-3322 (1968)
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[0016]
AUTHOR:Masumoto, O., Ohyama, Y., and Okuda, K.
TITLE:Purification and characterization of vitamin D 25-hydroxylase from rat liver mitochondria PubMed ID:2844763
JOURNAL:J Biol Chem.
VOL:263 PAGE : 14256-14260 (1988)
[TOP]

[0017]
AUTHOR:DeLuca, H. F., and Schnoes, H. K.
TITLE:Metabolism and mechanism of action of vitamin D PubMed ID:183601
JOURNAL:Annu Rev Biochem.
VOL:45 PAGE : 631-666 (1976)
[TOP]

[0018]
AUTHOR:DeLuca, H. F., and Schnoes, H. K.
TITLE:Vitamin D: recent advances PubMed ID:6311080
JOURNAL:Annu Rev Biochem.
VOL:52 PAGE : 411-439 (1983)
[TOP]

[0019]
AUTHOR:Holick, M. F., DeLuca, H. F., and Avioli, L. V.
TITLE:Isolation and identification of 25-hydroxycholecalciferol from human plasma PubMed ID:4332591
JOURNAL:Arch Intern Med.
VOL:129 PAGE : 56-61 (1972)
[TOP]

[0020]
AUTHOR:Wang, X.; Shimizu, M.; Numano, F.; Asaoka, H.; Yamada, S.
TITLE:Multiple Fluorometric Assay of Three Major Vitamin D3 Metabolites (25-Hydroxyvitamin D3, 24,25-Dihydroxyvitamin D3 and 1,25-Dihydroxyvitamin D3) in Plasma and Its Application to Clinical Studies.
JOURNAL:Anal. Sci.
VOL:13 PAGE : 255 -262 (1997)
[TOP]

[0021]
AUTHOR:Blunt, J. W.; DeLuca, H. F.; Schnoes, H. K.
TITLE:25-Hydroxycholecalciferol : A Biologically Active Metabolite of Cholecalciferol.
JOURNAL:Chem. Comm.
VOL: PAGE : 801 - (1968)
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[0022]
AUTHOR:Fraser, D. R., and Kodicek, E.
TITLE:Unique biosynthesis by kidney of a biological active vitamin D metabolite PubMed ID:4319631
JOURNAL:Nature.
VOL:228 PAGE : 764-766 (1970)
[TOP]

[0023]
AUTHOR:Shimizu, M.; Iwasaki, Y.; Ishida, H.; Yamada, S.
TITLE:Determination of 25-hydroxyvitamin D3 in human plasma using a non-radioactive tetranorvitamin D analogue as an internal standard. PubMed ID:8590938
JOURNAL:J. Chromatogr. B.
VOL:672 PAGE : 63 -71 (1995)
[TOP]

[0126]
AUTHOR:DeLuca, H. F., Suda, T., Schnoes, H. K., Tanaka, Y., and Holick, M. F.
TITLE:25,26-dihydroxycholecalciferol, a metabolite of vitamin D3 with intestinal calcium transport activity PubMed ID:4319987
JOURNAL:Biochemistry.
VOL:9 PAGE : 4776-4780 (1970)
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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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[0262]
AUTHOR:Kabat, M. M.; Kiegiel, J.; Cohen, N.; Toth, K.; Wovkulich, P. M.; Uskokovic, M. R.
TITLE:Convergent Synthesis of Vitamin D3 Metabolites. Control of the Stereoselectivity in Samarium-Induced Cyclopropanations of Cyclopentenes.
JOURNAL:J. Org. Chem.
VOL:61 PAGE : 118 -124 (1996)
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[0274]
AUTHOR:Trinh-Toan.; Ryan, R. C.; Simon, G. L.; Calabrese, J. C.; Dahl, L. F.; DeLuca, H. F.
TITLE:Crystal Structure of 25-Hydroxy-vitamin D3 Monohydrate : A Stereochemical Analysis of Vitamin D Molecules.
JOURNAL:J. Chem. Soc. Perkin Trans II
VOL: PAGE : 393 -401 (1977)
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[0298]
AUTHOR:Halkes, S. J.; Van Vliet, N. P.
TITLE:Investigations on Sterols. XXXV. Synthesis of 25-Hydroxycholecalciferol.
JOURNAL:Recueil
VOL:88 PAGE : 1080 -1083 (1969)
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