Calcitroic acid

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Calcitroic acid
Names
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
Identifiers
3D model (
JSmol
)
ChemSpider
  • InChI=1/C23H34O4/c1-14(11-22(26)27)19-8-9-20-16(5-4-10-23(19,20)3)6-7-17-12-18(24)13-21(25)15(17)2/h6-7,14,18-21,24-25H,2,4-5,8-13H2,1,3H3,(H,26,27)/b16-6+,17-7-/t14-,18+,19-,20+,21-,23-/m1/s1
    Key: MBLYZRMZFUWLOZ-FEUSBDLHBT
  • O=C(O)C[C@@H](C)[C@H]3CC[C@H]2C(=C\C=C1/C(=C)[C@H](O)C[C@@H](O)C1)\CCC[C@@]23C
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).

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. ^
    PMID 27574921
    .
  2. ^
    ISSN 2046-2069
    .
  3. ^
    PMID 23564710
    .
  4. PMID 15574355
    .
  5. ISBN 978-0-12-809965-0
    .


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