739677

Sigma-Aldrich

1α,25-Dihydroxyvitamin D2 solution

100 μg/mL in ethanol, 95% (CP)

Synonym(s):
1α,25-Dihydroxycalciferol solution
Empirical Formula (Hill Notation):
C28H44O3
CAS Number:
Molecular Weight:
428.65
EC Number:
PubChem Substance ID:
NACRES:
NA.24

Quality Level

assay

95% (CP)

form

liquid

concentration

100 μg/mL in ethanol

application(s)

mass spectrometry (MS): suitable

color

colorless

storage temp.

−20°C

SMILES string

CC(O)(C)[C@@H](C)/C=C/[C@@H](C)[C@H]1CCC([C@]1(C)CCC/2)C2=C\C=C(C[C@@H](O)C[C@@H]3O)/C3=C

InChI

1S/C28H44O3/c1-18(9-10-19(2)27(4,5)31)24-13-14-25-21(8-7-15-28(24,25)6)11-12-22-16-23(29)17-26(30)20(22)3/h9-12,18-19,23-26,29-31H,3,7-8,13-17H2,1-2,4-6H3/b10-9+,21-11+,22-12-/t18-,19+,23-,24-,25?,26+,28-/m1/s1

InChI key

ZGLHBRQAEXKACO-KPKHAADHSA-N

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General description

1α,25-Dihydroxyvitamin D2 is an active form of vitamin D2. It is also known as ercalcitriol or 1α,25-dihydroxyergocalciferol. It was first isolated from mitochondria of chick kidney.

Pictograms

FlameExclamation mark

Signal Word

Danger

Hazard Statements

Precautionary Statements

RIDADR

UN1170 - class 3 - PG 2 - Ethanol, solution

WGK Germany

WGK 1

Flash Point(F)

57.2 °F - closed cup

Flash Point(C)

14.0 °C - closed cup

Certificate of Analysis
Certificate of Origin
Yuka Inaba et al.
Journal of medicinal chemistry, 52(5), 1438-1449 (2009-02-06)
To identify novel vitamin D receptor (VDR) ligands that induce a novel architecture within the ligand-binding pocket (LBP), we have investigated eight 22-butyl-1alpha,24-dihydroxyvitamin D(3) derivatives (3-10), all having a butyl group as the branched alkyl side chain. We found that...
Convergent synthesis of double point modified analogs of 1α, 25-dihydroxyvitamin D2 for biological evaluation
Nadkarni S, et al.
The Journal of Steroid Biochemistry and Molecular Biology, 164, 45-49 (2016)
Pierre Antony et al.
Journal of medicinal chemistry, 53(3), 1159-1171 (2010-01-15)
The vitamin D nuclear receptor is a ligand-dependent transcription factor that controls multiple biological responses such as cell proliferation, immune responses, and bone mineralization. Numerous 1 alpha,25(OH)(2)D(3) analogues, which exhibit low calcemic side effects and/or antitumoral properties, have been synthesized....
Angsuma Wongmayura et al.
Bioorganic & medicinal chemistry letters, 22(4), 1756-1760 (2012-01-31)
Vitamin D receptor (VDR) is a nuclear receptor for 1α,25-dihydroxyvitamin D(3) (1α,25(OH)(2)D(3)), and is an attractive target for multiple clinical applications. We recently developed novel non-secosteroidal VDR ligands bearing a hydrophobic p-carborane cage, thereby establishing the utility of this spherical...
Marc Lamblin et al.
Journal of medicinal chemistry, 53(20), 7461-7465 (2010-10-05)
Vitamin D receptor (VDR) antagonists have therapeutic potential in treatment of allergic conditions and hypercalcemia driven by granulomatous diseases. We have identified an o-aminoanilide analogue of the hormonal form of vitamin D with a dienyl side chain that functions as...
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This application shows an Ascentis Express F5 provided rapid resolution of the isobaric vitamin D metabolites. MS detection provides the necessary secondary resolution.
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The metabolic role and health implications of the various vitamin D isoforms are of current clinical interest. Therefore, it is important to have an analytical method that will resolve all of the known isoforms with necessary sensitivity and specificity
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