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Vitamin D


DATA No : VVD0351 INFORMANT : Sachiko Yamada

NAME : (5Z,7E,22E)-(3S)-9,10-seco-5,7,10(19),22-ergostatetraen-3-ol

COMMON NAME: vitamin D2 / ergocalciferol / ercalciol
SYMBOL: D2
FORMULA: C28H44O MOL.WT (average) : 396.648


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BIOLOGICAL ACTIVITY
Effect of vitamins D2 and D3 on serum calcium and phosphorus and on bone ash in rachitic chicks was evaluated. Dose-response curves based on the 3 parameters indicated a flatter response to vitamin D2 than vitamin D3. When based on CD50 (curative dose giving a response midway between animals on rachitogenic and standard chick diets), the vitamin D3 to D2 efficacy ratio was estimated at about 8:1 to 11:1. (Ref. 0273)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:115-116 degC (Ref. 0139)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D +48.2 deg (in CHCl3), +85 degC (in benzene) (Ref. 0139)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (nm) (emax) 265 (18300) (Ref. 0139)

IR SPECTRA:887 cm-1 (Ref. 0139)

NMR SPECTRA:1H-NMR (d, CCl4, 100MHz) 0.57 (3 H, s, 18-CH3), 2.24 (1 H, dd, J = 13 and 7.4 Hz, 4-H), 2.51 (1 H, dd, J = 13 and 3.7 Hz, 4-H), 2.80 (1 H, dd, J = 10.5 and 2.5 Hz, 14-H), 3.82 (1 H, tt, J = 7.4 and 3.7 Hz, 3-H), 4.73 (1 H, d, J = 2.4 Hz, 19-H), 4.97 (1 H, dt, J = 2.4 and 1.0 Hz, 19-H), 5.17 (2 H, m, 22- and 23-H), 5.94 (1 H, dd, J = 11.3 and 0.8 Hz, 7-H), 6.14 (1 H, d, J = 11.3 Hz, 6-H) (Ref. 0140)
13C-NMR (d, CCl4, 22.6MHz) 32.0 (1), 35.3 (2), 69.2 (3), 46.2 (4), 135.4 (5), 122.4 (6), 117.8 (7), 142.2 (8), 29.1 (9),* 145.3 (10), 22.4 (11), 40.4 (12), 46.0 (13), 56.5 (14), 23.7 (15), 27.8 (16),* 56.5 (17), 12.3 (18), 112.5 (19), 40.4 (20), 19.7 (21), 132.0 (22), 135.7 (23), 42.8 (24), 33.2 (25), 20.0 (26), 21.1 (27), 17.7 (28) (Ref. 0003) * The assignments may be interchanged.

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS
From ergosterol by photochemical followed by thermal isomerization. (Ref. 0272/0290)
By convergent method using Wittig-Horner coupling of the A-ring fragment with Windaus-Grundmann ketone. (Ref. 0286)
METABOLISM
Metabolism of vitamin D2 is similar to that of vitamin D3 : Vitamin D2 is first metabolized to 25-hydroxyvitamin D2 (Ref. 0263) and then to 1a,25-dihydroxyvitamin D2. (Ref. 0146)
25-Hydroxyvitamin D2 is metabolized to 24R,25-dihydroxyvitamin D2 in normocalcemic and normophosphatemic animals receiving adequate intakes of vitamin D. (Ref. 0150/0264)
GENETIC INFORMATION

NOTE

REFERENCES
[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)
[TOP]

[0139]
AUTHOR:Inhoffen, H. H.; Quinkert, G.; Hess, H. J.; Erdnann, H. M.
TITLE:Studien in der Vitamin D-Reihe XVI.
JOURNAL:Chem. Ber.
VOL:89 PAGE : 2273 -2284 (1956)
[TOP]

[0140]
AUTHOR:La Mar, G. N., and Budd, D. L.
TITLE:Elucidation of the solution conformation of the A ring in vitamin D using proton coupling constants and a shift reagent PubMed ID:4547774
JOURNAL:J Am Chem Soc.
VOL:96 PAGE : 7317-7324 (1974)
[TOP]

[0146]
AUTHOR:Jones, G., Schnoes, H. K., and DeLuca, H. F.
TITLE:Isolation and identification of 1,25-dihydroxyvitamin D2 PubMed ID:1078978
JOURNAL:Biochemistry.
VOL:14 PAGE : 1250-1256 (1975)
[TOP]

[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)
[TOP]

[0263]
AUTHOR:Suda, T., DeLuca, H. F., Schnoes, H. K., and Blunt, J. W.
TITLE:The isolation and identification of 25-hydroxyergocalciferol PubMed ID:5307049
JOURNAL:Biochemistry.
VOL:8 PAGE : 3515-3520 (1969)
[TOP]

[0264]
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)
[TOP]

[0272]
AUTHOR:Windaus, von A.; Linsert, O.; Luttringhaus, A.; Weidlich, G.
TITLE:Uber das krystallisierte Vitamin D2.
JOURNAL:Ann.
VOL:492 PAGE : 226 -241 (1932)
[TOP]

[0273]
AUTHOR:Chen, P. S., Jr., and Bosmann, H. B.
TITLE:Effect Of Vitamins D2 And D3 On Serum Calcium And Phosphorus In Rachitic Chicks PubMed ID:14171311
JOURNAL:J Nutr.
VOL:83 PAGE : 133-139 (1964)
[TOP]

[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)
[TOP]

[0290]
AUTHOR:Askew, F. A.; Bourdillon, R. B.; Bruce, H. M.; Callow, R. K.; Philpot, J. St. L.; Webster, T. A.
TITLE:Crystalline Vitamin D.
JOURNAL:Proc. Roy. Soc. (London)
VOL:109 PAGE : 488 -506 (1932)
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