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Vitamin D


DATA No : VVD0237 INFORMANT : Sachiko Yamada

NAME : (5Z,7E)-(3S)-9,10-seco-5,7,10(19)-cholestatrien-3-ol

COMMON NAME: vitamin D3 / cholecalciferol / calciol
SYMBOL: D3
FORMULA: C27H44O MOL.WT (average) : 384.638


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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)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:84-85 degC (Ref. 0001)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-25 +51.9 deg (c = 1.6 in CHCl3) (Ref. 0001)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:(95% EtOH or Hexane) lmax (nm) (e) 264.5 (18200) (Ref. 0001)

IR SPECTRA:

NMR SPECTRA:1H-NMR (d, CDCl3, 300MHz) 0.54 (3 H, s, 18-CH3), 0.87 (6 H, d, J = 6.5 Hz, 26-, 27-CH3), 0.92 (3 H, d, J = 6 Hz, 21-CH3), 2.17 (1 H, ddd, 4.5, 8.6 and 13.9 Hz, 1a-H), 2.28 (1 H, dd, J = 7.5 and 13.2 Hz, 4b-H), 2.39 (1 H, ddd, J = 5.0, 7.7 and 13.9 Hz, 1b-H), 2.56 (1 H, dd, J = 3.6 and 13.2 Hz, 4a-H), 2.82 (1 H, d, J = 12 Hz, 9b-H), 3.94 (1 H, dddd, J = 3.6, 3.8, 7.5 and 7.6 Hz, 3a-H), 4.82 (1 H, d, J = 2.5 Hz, 19-H), 5.05 (1 H, dt, J = 2.5 and 1.2 Hz, 19-H), 6.03 (1 H, d, J = 11.2 Hz, 7-H), 6.25 (1 H, d, J = 11.2 Hz, 6-H) (Ref. 0002)
1H-NMR (d, CDCl3, 300MHz) spectrum (Ref. 0004)
13C-NMR (d, CDCl3, 22.6MHz) 32.1 (1), 35.3 (2), 69.2 (3), 46.0 (4), 135.3 (5), 122.5 (6) 117.8 (7), 142.2 (8), 29.1 (9),* 145.3 (10), 22.4 (11), 40.6 (12), 46.0 (13), 56.5 (14),** 23.7 (15), 27.8 (16),* 56.7 (17),** 11.9 (18), 112.5 (19), 36.2 (20), 18.9 (21), 36.2 (22), 24.0 (23), 39.6 (24), 28.1 (25),* 22.7 (26), 22.9 (27); * and **, the assignments may be interchanged. (Ref. 0003)

MASS SPECTRA:m/z 384 (M+), 351, 325, 271, 253, 158, 136, 118; spectrum (Ref. 0015)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Upon sunlight irradiation, 7-dehydrocholesterol (provitamin D3) on the skin isomerizes to previtamin D3 which in turn isomerizes to vitamin D3 at skin temperature. (Ref. 0005/0006)
CHEMICAL SYNTHESIS
Synthesis from cholesterol acetate via photochemical isomerization of the corresponding 5,7-diene (provitamin D3) followed by thermal isomerization. (Ref. 0007)
By convergent method from des-AB-cholestan-8-one and A-ring precursor using Wittig-Horner coupling. (Ref. 0286)
METABOLISM
Vitamin D3 is hydroxylated by vitamin D 25-hydroxylase (CYP27) in the liver (Ref. 0016/0017) to yield 25-OHD3 and then by 1a-hydroxylase (CYP24B1) (Ref. 0030/0031) in the kidney to afford 1,25-(OH)2D3 (Ref. 0026/0027) , the biologically active form of vitamin D3.
GENETIC INFORMATION

NOTE

REFERENCES
[0001]
AUTHOR:Huber, W.; Ewing, G. W.; Kriger, J.
TITLE:The Absorption Spectra of the Vitamins and Provitamins D.
JOURNAL:J. Amer. Chem. Soc.
VOL:67 PAGE : 609 -617 (1945)
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[0002]
AUTHOR:Wing, R. M., Okamura, W. H., Rego, A., Pirio, M. R., and Norman, A. W.
TITLE:Studies on vitamin D and its analogs. VIII. Solution conformations of vitamin D3 and 1 alpha, 25-dihydroxyvitamin D3 by high-resolution proton magnetic resonance spectroscopy PubMed ID:170323
JOURNAL:J Am Chem Soc.
VOL:97 PAGE : 4980-4985 (1975)
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[0003]
AUTHOR:Tsukida, K., Akutsu, K., and Saiki, K.
TITLE:Carbon-13 nuclear magnetic resonance spectra of vitamins D and related compounds PubMed ID:178846
JOURNAL:J Nutr Sci Vitaminol (Tokyo).
VOL:21 PAGE : 411-420 (1975)
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[0004]
AUTHOR:Wing, R. M., Okamura, W. H., Pirio, M. R., Sine, S. M., and Norman, A. W.
TITLE:Vitamin D in solution: conformations of vitamin D3, 1alpha,25-dihydroxyvitamin D3, and dihydrotachysterol3 PubMed ID:4377759
JOURNAL:Science.
VOL:186 PAGE : 939-941 (1974)
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[0005]
AUTHOR:Holick, M. F., Richtand, N. M., McNeill, S. C., Holick, S. A., Frommer, J. E., Henley, J. W., and Potts, J. T., Jr.
TITLE:Isolation and identification of previtamin D3 from the skin of rats exposed to ultraviolet irradiation PubMed ID:218609
JOURNAL:Biochemistry.
VOL:18 PAGE : 1003-1008 (1979)
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[0006]
AUTHOR:Holick, M. F., MacLaughlin, J. A., Clark, M. B., Holick, S. A., Potts, J. T., Jr., Anderson, R. R., Blank, I. H., Parrish, J. A., and Elias, P.
TITLE:Photosynthesis of previtamin D3 in human skin and the physiologic consequences PubMed ID:6251551
JOURNAL:Science.
VOL:210 PAGE : 203-205 (1980)
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[0007]
AUTHOR:Windaus, A.; Lettre, H.; Schenck, F.
TITLE:Uder das 7-Dehydro-cholesterin.
JOURNAL:Ann.
VOL:520 PAGE : 98 -106 (1935)
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[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)
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[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)
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[0026]
AUTHOR:Holick, M. F., Schnoes, H. K., DeLuca, H. F., Suda, T., and Cousins, R. J.
TITLE:Isolation and identification of 1,25-dihydroxycholecalciferol. A metabolite of vitamin D active in intestine PubMed ID:4326883
JOURNAL:Biochemistry.
VOL:10 PAGE : 2799-2804 (1971)
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[0027]
AUTHOR:Holick, M. F., Schnoes, H. K., and DeLuca, H. F.
TITLE:Identification of 1,25-dihydroxycholecalciferol, a form of vitamin D3 metabolically active in the intestine PubMed ID:4323790
JOURNAL:Proc Natl Acad Sci U S A.
VOL:68 PAGE : 803-804 (1971)
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[0030]
AUTHOR:Takeyama, K., Kitanaka, S., Sato, T., Kobori, M., Yanagisawa, J., and Kato, S.
TITLE:25-Hydroxyvitamin D3 1alpha-hydroxylase and vitamin D synthesis PubMed ID:9295274
JOURNAL:Science.
VOL:277 PAGE : 1827-1830 (1997)
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[0031]
AUTHOR:Shinki, T., Shimada, H., Wakino, S., Anazawa, H., Hayashi, M., Saruta, T., DeLuca, H. F., and Suda, T.
TITLE:Cloning and expression of rat 25-hydroxyvitamin D3-1alpha-hydroxylase cDNA PubMed ID:9371776
JOURNAL:Proc Natl Acad Sci U S A.
VOL:94 PAGE : 12920-12925 (1997)
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[0286]
AUTHOR:Lythgoe, B.; Moran, T. A.; Nambudiry, M. E. N.; Tideswell, J.; Wright, P. W.
TITLE:Calciferol and its Relatives. Part 22. A Direct Total Synthesis of Vitamin D2 and Vitamin D3.
JOURNAL:J. C. S. Perkin I
VOL: PAGE : 590 -595 (1978)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.