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 |
Activities of vitamin D
3 in intestinal calcium transport and bone calcium mobilization were compared with those of 25-OHD
3: Tables (
Ref. 0014)
Antirachitic Activity (IU/
mg)(the standard line test assay for vitamin D activity as described in The United States Pharmacopoeia): 25-OHD
3 56
6 ; vitamin D
3, 40
4. (
Ref. 0019)
HL-60 human promyelocytes differentiation: ED50 in nitro blue tetrazplium reduction, phagocytic activity, and nonspecific acid esterase activity are 8.4
10
-7 M, 8.0
10
-7 M and 8.0
10
-7 M, respectively, when 1,25-(OH)
2D
3 shows the respective ED50 values of 1.0
10
-8 M, 1.0
10
-8 M and 1.1
10
-8 M, respectively. (
Ref. 0228)
| PHYSICAL AND CHEMICAL PROPERTIES |
| MELTING POINT | : | 96-106  C (Ref. 0262)
95-100 C (Ref. 0298) |
|
| BOILING POINT | : | |
|
| REFRACTIVE INDEX | : | |
|
| OPTICAL ROTATION | : | [a] +88.1 (c = 0.5 in EtOH) (Ref. 0262) |
|
| DENSITY | : | |
|
| SOLUBILITY | : | |
| 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)
|
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)
Synthesis from 25-hydroxycholesterol acetate and 3
b-acetoxy-27-nor-cholest-5-en-25-one by standard photochemical method via 5,7-cholestadiene-3
b,25-diol. (
Ref. 0014)
8
b,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)
Biosynthesis: Hydroxylation of D
3 by vitamin D 25-hydroxylase (CYP27) in the liver. (
Ref. 0016/
0017)
Further metabolism : 1
a-Hydroxylation in the kidney to give 1
a,25-(OH)
2D
3 under vitamin D deficient conditions. (
Ref. 0017/
0018/
0022)
24-Hydroxylation to give 24R,25-(OH)
2D
3 in tissues possessing vitamin D receptor under vitamin D supplemented conditions. (
Ref. 0017/
0018)
26-Hydroxylation to give 25,26-(OH)
2D
3. (
Ref. 0126)
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
[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) |
Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.
