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Vitamin D


DATA No : VVD0258 INFORMANT : Sachiko Yamada

NAME : (5Z,7E)-(1S,3R)-9,10-seco-5,7,10(19)-cholestatriene-1,3-diol

COMMON NAME: 1a-hydroxyvitamin D3 / 1a-hydroxycholecalciferol
SYMBOL: 1a-OHD3
FORMULA: C27H44O2 MOL.WT (average) : 400.637


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BIOLOGICAL ACTIVITY
Intestinal calcium transport and bone mineral mobilization response to 1a-OH-D3 and 25-OH-D3 in anephric rats. : Table(Ref. 0168)
Intestinal calcium transport and bone calcium mobilization response of rats to 1a-OH-D3. Results are means of six rats ; S.E., standard error. : Table (Ref. 0172)
HL-60 human promyelocytes differentiation : ED50 in nitro blue tetrazplium reduction, phagocytic activity, and nonspecific acid esterase activity are 9.3 times 10-7 M, 1.0 times 10-6 M and 1.0 times 10-6 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)
Treatment of psoriasis : A case of psoriasis with senile osteoporosis is reported in which skin lesions were cured two and half months after the start of administration of 0.75 mg/day of 1a-OHD3. (Ref. 0248)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:134-136 degC (Ref. 0167)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-25 +28.0 deg (c = 0.6 in Et2O) (Ref. 0167)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:(Et2O) lmax (nm) (emax) 264-265 (18000) (Ref. 0167)

IR SPECTRA:(CHCl3) 895m, 912m, 952m, 1040s, 1645m, 3450m, 3600s cm-1 (Ref. 0167)

NMR SPECTRA:1H-NMR (d, CDCl3) 3.58 (1H, d, J = 12 Hz, 6- or 7-H), 3.99 (1H, d, J = 12 Hz, 6- or 7-H), 4.66 (1H, m, 19-H), 4.99 (1H, m, 19-H), 5.45-6.05 (2H, m, >CH-O), 9.12 (9H, d, J = 6 Hz, MeCH<), 9.45 (3H, s, 18-H) (Ref. 0167)

MASS SPECTRA:m/z 382 (5.2%), 364 (16.2%), 149 (26.0%), 134 (6.1%), 128 (30.4%), 121 (67.5%), 119 (32.0%), 95 (49.4%), 83 (50.5%), 81 (59%), 71 (58.5%), 69 (76.3%), 57 (100%) (Ref. 0167)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS
From cholesterol. (Ref. 0035)
From 1,4,6-cholestatrien-3-one via its regio- and stereoselective epoxidation followed by deconjugative reduction to yield 1a-hydroxycholesterol as the key step. (Ref. 0166)
Total synthesis from 9a-chloro-des-AB-cholestan-8-one and optically active A-ring synthon having C(6)-C(7) linker part as ethyl group. (Ref. 0167)
From 1,4-cholestadien-3-one via steps of deconjugation followed by reduction, hydroboration, bromination, dehydrobromination, and photochemical and thermal isomerizations. (Ref. 0168)
Synthesis of 1a-hydroxyprovitamin D3 from 1,4,6-cholestatrien-3-one via steps of deconjugation followed by reduction, protection of 5,7-diene, epoxidation, and reduction. (Ref. 0169/0170)
From vitamin D3 via SeO2 oxidation of 3,5-cyclo-vitamin D derivative. (Ref. 0171)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0035]
AUTHOR:Semmler, E. J.; Holick, M. F.; Schnoes, H. K.; DeLuca, H. F.
TITLE:The Synthesis of 1a,25-Dihydroxycholecalciferol : A Metabolically Active from of Vitamin D3.
JOURNAL:Tetrahedron Lett.
VOL:40 PAGE : 4147 -4150 (1972)
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[0166]
AUTHOR:Barton, D. H., Hesse, R. H., Pechet, M. M., and Rizzardo, E.
TITLE:A convenient synthesis of 1 -hydroxy-vitamin D 3 PubMed ID:4348493
JOURNAL:J Am Chem Soc.
VOL:95 PAGE : 2748-2749 (1973)
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[0167]
AUTHOR:Harrison, R. G., Lythgoe, B., and Wright, P. W.
TITLE:Calciferol and its relatives. (part)XVIII. Total synthesis of 1alpha-hydroxy vitamin D3 PubMed ID:4376813
JOURNAL:J Chem Soc [Perkin 1].
VOL: PAGE : 2654-2657 (1974)
[TOP]

[0168]
AUTHOR:Kaneko, C., Yamada, S., Sugimoto, A., Eguchi, Y., and Ishikawa, M.
TITLE:Synthesis and biological activity of 1alpha-hydroxyvitamin D3 PubMed ID:4813304
JOURNAL:Steroids.
VOL:23 PAGE : 75-92 (1974)
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[0169]
AUTHOR:Kaneko, C.; Sugimoto, A.; Eguchi, Y.; Yamada, S.; Ishikawa, M.
TITLE:A New Synthetic Method of 1a-Hydroxy-7-dehydrocholecalciferol.
JOURNAL:Tetrahedron
VOL:30 PAGE : 2701 -2705 (1974)
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[0170]
AUTHOR:Guest, D.; W.; Williams, D. H.
TITLE:A Modified Synthesis of 1a-Hydroxyvitamin D3.
JOURNAL:J. Chem. Soc. Perkin I
VOL: PAGE : 1695 -1697 (1979)
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[0171]
AUTHOR:Paaren, H. E., Hamer, D. E., Schnoes, H. K., and DeLuca, H. F.
TITLE:Direct C-1 hydroxylation of vitamin D compounds: convenient preparation of 1alpha-hydroxyvitamin D3, 1alpha, 25-dihydroxyvitamin D3, and 1alpha-hydroxyvitamin D2 PubMed ID:209448
JOURNAL:Proc Natl Acad Sci U S A.
VOL:75 PAGE : 2080-2081 (1978)
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[0172]
AUTHOR:Holick, M. F., Semmler, E. J., Schnoes, H. K., and DeLuca, H. F.
TITLE:1 -Hydroxy derivative of vitamin D 3: a highly potent analog of 1,25-dihydroxyvitamin D 3 PubMed ID:4348463
JOURNAL:Science.
VOL:180 PAGE : 190-191 (1973)
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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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[0248]
AUTHOR:Morimoto, S., and Kumahara, Y.
TITLE:A patient with psoriasis cured by 1 alpha-hydroxyvitamin D3 PubMed ID:4069059
JOURNAL:Med J Osaka Univ.
VOL:35 PAGE : 51-54 (1985)
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