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Vitamin D


DATA No : VVD0014 INFORMANT : Sachiko Yamada

NAME : (5Z,7E)-(1S,3R)-1,3-dihydroxy-24-nor- 9,10-seco-5,7,10(19)-cholatrien-23-oic acid

COMMON NAME: 1a-hydroxy-24,25,26,27-tetranorvitamin D3 23-carboxylic acid / calcitroic acid
SYMBOL: 1a-OH-24,25,26,27-tetranor-D3 23-carboxylic acid
FORMULA: C23H34O4 MOL.WT (average) : 374.514


Download ChemDraw structure data
BIOLOGICAL ACTIVITY
Bone Mineral Mobilization and Intestinal Calcium Transport Activity of Calcitroic Acid. (Ref. 0072)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:122-126 degC (Ref. 0074)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (nm) (emax) 262 (18000), lmin (nm) (emin) 226 (10000) (Ref. 0074)
Me-ester : lmax (nm) (emax) 264 (18000) (Ref. 0071)

IR SPECTRA:

NMR SPECTRA:1H-NMR (d, CDCl3) 6.43, 6.06 (2H, ABq, J = 11 Hz, 6-, 7-H), 5.56 (1H, br s, 19E-H), 5.04 (1H, br s, 19Z-H), 4.46 (1H, m, 1b-H), 4.26 (1H, m, 3a-H), 2.80 (1H, m, 9b-H), 0.99 (3H, d, J = 6 Hz, 21-H), 0.59 (3H, s, 18-H) (Ref. 0074)
Me-ester : 1H-NMR (d, CDCl3) 0.58 (3H, s, 18-CH3), 0.99 (3H, d, J = 5.9 Hz, 21-CH3), 3.67 (3H, s, COOCH3), 4.23 (1H, m, 3a-H), 4.43 (1H, m, 1b-H), 5.00 (1H, s, 19(Z)-H), 5.33 (1H, s, 19(E)-H), 6.02 (1H, d, J = 11.0 Hz, 7-H), 6.38 (1H, d, J = 11.0 Hz, 6-H) (Ref. 0071)

MASS SPECTRA:Me-ester : m/z 388, 370, 352 , 152, 134, 287, 269, 251. Spectrum (Ref. 0070)

OTHER SPECTRA:
CHROMATOGRAM DATA
HPLC : (Ref. 0070/0073)
SOURCE
Isolation from rat liver. (Ref. 0070)
Isolation and identification from vitamin D supplemented rat kidney homogenates incubated with 24,25-(OH)2D3. (Ref. 0118)
CHEMICAL SYNTHESIS
From C(22)-steroid carboxylic acid via one-carbon homologation, conversion to tetranor-vitamin D3 23-carboxylic acid and 1a-hydroxylation of the corresponding 3,5-cyclovitamin D. (Ref. 0071)
From 3b-acetoxypregn-7-ene-22-carboxaldehyde. (Ref. 0074)
METABOLISM
A final catabolite produced from the active vitamin D3 metabolite, 1,25-(OH)2D3, via 24-hydroxylation pathway.(Ref. 0034/0065/0066/0067/0068/0069/0070/0073)
GENETIC INFORMATION

NOTE

REFERENCES
[0034]
AUTHOR:Kleiner-Bossaller, A.; DeLuca, H. F.
TITLE:Formation of 1,24,25-Trihydroxyvitamin D3 from 1,25-Dihydroxyvitamin D3.
JOURNAL:Biochim. Biophys. Acta
VOL:338 PAGE : 489 -495 (1974)
[TOP]

[0065]
AUTHOR:Holick, M. F., Kleiner-Bossaller, A., Schnoes, H. K., Kasten, P. M., Boyle, I. T., and DeLuca, H. F.
TITLE:1,24,25-Trihydroxyvitamin D3. A metabolite of vitamin D3 effective on intestine PubMed ID:4355503
JOURNAL:J Biol Chem.
VOL:248 PAGE : 6691-6696 (1973)
[TOP]

[0066]
AUTHOR:Tanaka, Y., Castillo, L., and DeLuca, H. F.
TITLE:The 24-hydroxylation of 1,25-dihydroxyvitamin D3 PubMed ID:838723
JOURNAL:J Biol Chem.
VOL:252 PAGE : 1421-1424 (1977)
[TOP]

[0067]
AUTHOR:Mayer, E., Bishop, J. E., Chandraratna, R. A., Okamura, W. H., Kruse, J. R., Popjak, G., Ohnuma, N., and Norman, A. W.
TITLE:Isolation and identification of 1,25-dihydroxy-24-oxo-vitamin D3 and 1,23,25-trihydroxy-24-oxo-vitamin D3. New metabolites of vitamin D3 produced by a C-24 oxidation pathway of metabolism for 1,25-dihydroxyvitamin D3 present in intestine and kidney PubMed ID:6315697
JOURNAL:J Biol Chem.
VOL:258 PAGE : 13458-13465 (1983)
[TOP]

[0068]
AUTHOR:Napoli, J. L., Pramanik, B. C., Royal, P. M., Reinhardt, T. A., and Horst, R. L.
TITLE:Intestinal synthesis of 24-keto-1,25-dihydroxyvitamin D3. A metabolite formed in vivo with high affinity for the vitamin D cytosolic receptor PubMed ID:6307992
JOURNAL:J Biol Chem.
VOL:258 PAGE : 9100-9107 (1983)
[TOP]

[0069]
AUTHOR:Reddy, G. S., Tserng, K. Y., Thomas, B. R., Dayal, R., and Norman, A. W.
TITLE:Isolation and identification of 1,23-dihydroxy-24,25,26,27-tetranorvitamin D3, a new metabolite of 1,25-dihydroxyvitamin D3 produced in rat kidney PubMed ID:3828305
JOURNAL:Biochemistry.
VOL:26 PAGE : 324-331 (1987)
[TOP]

[0070]
AUTHOR:Esvelt, R. P., Schnoes, H. K., and DeLuca, H. F.
TITLE:Isolation and characterization of 1 alpha-hydroxy-23-carboxytetranorvitamin D: a major metabolite of 1,25-dihydroxyvitamin D3 PubMed ID:486408
JOURNAL:Biochemistry.
VOL:18 PAGE : 3977-3983 (1979)
[TOP]

[0071]
AUTHOR:Esvelt, R. P.; Fivizzani, M. A.; Parren, H. E.; Schnoes, H. K.; DeLuca, H. F.
TITLE:Synthesis of Calcitroic Acid, a Metabolite of 1a, 25-Dihydroxycholecalciferol.
JOURNAL:J. Org. Chem.
VOL:46 PAGE : 456 -458 (1981)
[TOP]

[0072]
AUTHOR:Esvelt, R. P., and De Luca, H. F.
TITLE:Calcitroic acid: biological activity and tissue distribution studies PubMed ID:6261697
JOURNAL:Arch Biochem Biophys.
VOL:206 PAGE : 403-413 (1981)
[TOP]

[0073]
AUTHOR:Reddy, G. S., and Tserng, K. Y.
TITLE:Calcitroic acid, end product of renal metabolism of 1,25-dihydroxyvitamin D3 through C-24 oxidation pathway PubMed ID:2719932
JOURNAL:Biochemistry.
VOL:28 PAGE : 1763-1769 (1989)
[TOP]

[0074]
AUTHOR:DeCosta, B. R.; Makk, N.; Midgley, J. M.; Modi, N. T.; Watt, R. A.; Whalley, W. B.
TITLE:Unsaturated Steroids. Part 12. Synthesis of 1a, 3b-Dihydroxy-24-nor-9,10-secochola-5,7,10(19) trien-23-oic (Calcitroic) Acid and of the Cholic-and 25-Homocholic Acid Analogues.
JOURNAL:J. Chem. Soc. Perkin Trans I
VOL: PAGE : 1331 -1336 (1985)
[TOP]

[0118]
AUTHOR:DeLuca, H. F.; Schnoes, H. K.; (1979) Vitamin D, Basic Research and its Clinical Application. Recent Developments in The Metabolism of Vitamin D., pp445-458, Walter de Gruyter & Co., Berlin New York
TITLE:
JOURNAL:
VOL: PAGE : - ()
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.