Chemistry:Calcitroic acid
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| IUPAC name
(3R)-3-[(1R,3aR,4E,7aR)- 4-[(2Z)-2-[(3R,5R)-3,5- Dihydroxy-2-methylene-cyclohexylidene]ethylidene] -7a-methyl-2,3,3a,5,6,7-hexahydro-1H -inden-1-yl]butanoic acid
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3D model (JSmol)
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PubChem CID
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| Properties | |
| C23H34O4 | |
| Molar mass | 374.514 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Calcitroic acid (1α-hydroxy-23-carboxy-24,25,26,27-tetranorvitamin D3) is a major metabolite of 1α,25-dihydroxyvitamin D3 (calcitriol).[1] Around 1980, scientists first reported the isolation of calcitroic acid from the aqueous extract of radioactively treated animals' livers and intestines. Subsequent researches confirmed calcitroic acid to be a part of enterohepatic circulation.[1] Often synthesized in the liver and kidneys, calcitroic acid is generated in the body after vitamin D is first converted into calcitriol, an intermediate in the fortification of bone through the formation and regulation of calcium in the body.[1] These pathways managed by calcitriol[2] are thought to be inactivated[3] through its hydroxylation by the enzyme CYP24A1, also called calcitriol 24-hydroxylase.[4] Specifically, It is thought to be the major route to inactivate vitamin D metabolites.[3] The hydroxylation and oxidation reactions will yield either calcitroic acid via the C24 oxidation pathway or 1,25(OH2)D3-26,23-lactone via the C23 lactone pathway.[5]
Hydroxylation and further metabolism of calcitriol in the liver and the kidneys yields calcitroic acid, a water-soluble compound that is excreted in bile.[1]
In case where a higher concentration of this acid is used in vitro, studies determined that calcitroic acid binds to vitamin D receptor (VDR) and induces gene transcription.[1]
The compound has been prepared in the laboratory.[2]
References
- ↑ 1.0 1.1 1.2 1.3 1.4 "Calcitroic Acid-A Review". ACS Chemical Biology 11 (10): 2665–2672. October 2016. doi:10.1021/acschembio.6b00569. PMID 27574921.
- ↑ 2.0 2.1 Meyer, Daniel; Rentsch, Lara; Marti, Roger (2014). "Efficient and scalable total synthesis of calcitroic acid and its 13C-labeled derivative". RSC Adv. 4 (61): 32327–32334. doi:10.1039/c4ra04322g. ISSN 2046-2069. Bibcode: 2014RSCAd...432327M. http://dx.doi.org/10.1039/c4ra04322g.
- ↑ 3.0 3.1 "Cytochrome P450-mediated metabolism of vitamin D". Journal of Lipid Research 55 (1): 13–31. January 2014. doi:10.1194/jlr.R031534. PMID 23564710.
- ↑ "Metabolism of vitamin D3 by cytochromes P450". Frontiers in Bioscience 10: 119–34. January 2005. doi:10.2741/1514. PMID 15574355. http://www.bioscience.org/2005/v10/af/1514/fulltext.htm.
- ↑ Feldman, David, ed (November 2017). Biochemistry, physiology and diagnostics. Vitamin D / 4th ed.-in-chief David Feldman (4th ed.). Amsterdam: Elsevier Academic Press. ISBN 978-0-12-809965-0.
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