25,26-Dihydroxyvitamin D3 - CAS 29261-12-9
Catalog number: 29261-12-9
Category: Inhibitor
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Molecular Formula:
C27H44O3
Molecular Weight:
416.64
COA:
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Targets:
VD/VDR
Description:
Α hydroxylated metabolite of Vitamin D3
Purity:
>98%
Synonyms:
(6R)-2-methyl-6-[(1R,3aS,4E,7aR)-octahydro-4-[(2Z)-2-[(5S)-5-hydroxy-2-methylenecyclohexylidene]ethylidene]-7a-methyl-1H-inden-1-yl]-1,2-Heptanediol; (3β,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,25,26-triol; 9,10-Secocholesta-5,7,10(19)-triene-3β,25,26-triol; 25,26-Dihydroxycholecalciferol; 25,26-Dihydroxyvitamin D
MSDS:
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InChIKey:
QOWCBCXATJITSI-ZLNGONTQSA-N
InChI:
InChI=1S/C27H44O3/c1-19-9-12-23(29)17-22(19)11-10-21-8-6-16-27(4)24(13-14-25(21)27)20(2)7-5-15-26(3,30)18-28/h10-11,20,23-25,28-30H,1,5-9,12-18H2,2-4H3/b21-10+,22-11-/t20-,23+,24-,25+,26?,27-/m1/s1
Canonical SMILES:
CC(CCCC(C)(CO)O)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C
1.Evaluation of the total fetomaternal vitamin D relationships at term: evidence for racial differences.
Hollis BW;Pittard WB 3rd J Clin Endocrinol Metab. 1984 Oct;59(4):652-7.
The present study assessed the total fetomaternal vitamin D relationship at term in 12 white and 10 black mothers and their infants. Antirachitic sterols were extracted from plasma, chromatographed, and finally quantitated using competitive protein binding assays. Compounds quantitated included vitamins D2 and D3, 25-hydroxyvitamin D2, 25-hydroxyvitamin D3, 24,25-dihydroxyvitamin D2, 24,25-dihydroxyvitamin D3, 25,26-dihydroxyvitamin D3, 1,25-dihydroxyvitamin D2, and 1,25-dihydroxyvitamin D3. There was a strong correlation between maternal and neonatal plasma concentrations of all antirachitic sterols measured with the exception of vitamins D2 and D3. Vitamins D2 and D3, although detectable in maternal plasma, were undetectable in neonatal plasma. Racial comparisons demonstrated that vitamin D3, 25-hydroxyvitamin D3, 24,25-hydroxyvitamin D3, and 25,26-(OH)2-D3 were significantly (P less than 0.05) higher in white than in black mothers. Total 25-hydroxyvitamin D and 24,25-hydroxyvitamin D were also significantly (P less than 0.05) higher in white than in black mothers. A similar pattern was found in black and white infants except for 25,26-(OH)2-D3. Black mothers and their infants had significantly (P less than 0.
2.Synthesis of 1,25-dihydroxycholecalciferol and 24,25-dihydroxycholecalciferol by calvarial cells. Characterization of the enzyme systems.
Puzas JE;Turner RT;Howard GA;Brand JS;Baylink DJ Biochem J. 1987 Jul 15;245(2):333-8.
The synthesis of 1,25-dihydroxycholecalciferol [1,25(OH)2D3] and 24,25-dihydroxycholecalciferol [24,25(OH)2D3] from 25-hydroxycholecalciferol [25(OH)D3] has previously been shown to occur in cells isolated from bone. The main findings of the present study are that the enzyme systems which catalyse these syntheses are: (1) active at 'in vitro' substrate concentrations over the range of 2-50 nM; (2) regulatable in a complex way by 1,25(OH)2D3, 24,25(OH)2D3, 25,26-dihydroxycholecalciferol and 25(OH)D3, but not by cholecalciferol ('vitamin D3'); and (3) have relatively short half-lives (approx. 5 h).
3.25-hydroxyvitamin D hydroxylation. Evidence for a dioxygenase activity of solubilized renal mitochondrial cytochrome P-450.
Warner M J Biol Chem. 1983 Oct 10;258(19):11590-3.
Upon solubilization and partial purification, renal mitochondrial P-450 catalyzes both the 1 alpha- and 24-hydroxylations of 25-hydroxyvitamin D3 in the absence of NADPH. Neither 1 alpha,25-dihydroxyvitamin D3 nor 24,25-dihydroxyvitamin D3 is further metabolized by the enzyme. Under similar conditions, P-450 obtained from hepatic microsomes or adrenal mitochondria is inactive as a 25-hydroxyvitamin D3 hydroxylase. Both hydroxylations are heat-sensitive and are inhibited by 1 alpha,25-dihydroxyvitamin D3, 24,25-dihydroxyvitamin, 25,26-dihydroxyvitamin D3, EDTA, menadione, dithiothreitol, and cadmium but not by carbon monoxide. Cumene hydroperoxide does not facilitate either hydroxylation and no lipid peroxides can be detected in the system either prior to or after incubation with the substrate. Based on these data, it is proposed that during these hydroxylations P-450 is acting as a dioxygenase. The first step in the sequence of reactions is postulated to be a P-450-catalyzed formation of a hydroperoxide at carbon 1 of a substrate molecule. This is followed by the 25-hydroxyvitamin D hydroperoxide-supported, P-450-catalyzed hydroxylation of another molecule of substrate at either the 1 alpha or the 24 position.
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CAS 29261-12-9 25,26-Dihydroxyvitamin D3

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