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739677

Sigma-Aldrich

1α,25-Dihydroxyvitamin D2 solution

100 μg/mL in ethanol, 95% (CP)

Synonym(s):

1α,25-Dihydroxycalciferol solution

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About This Item

Empirical Formula (Hill Notation):
C28H44O3
CAS Number:
60133-18-8
Molecular Weight:
428.65
EC Number:
200-578-6
UNSPSC Code:
12352205
PubChem Substance ID:
329765370
NACRES:
NA.24

Assay

95% (CP)

form

liquid

concentration

100 μg/mL in ethanol

technique(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.

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Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H319

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

57.2 °F - closed cup

Flash Point(C)

14.0 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
MBBC5450
MBBC3809
MBBC1660
MBBB9836V
MBBB7067V

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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)
Laura Sánchez-Abella et al.
Journal of medicinal chemistry, 52(19), 6158-6162 (2009-09-11)
We have synthesized several isomers of 19-nor-vitamin D analogues possessing a hydroxy group at C-2 as well as novel derivatives bearing an epoxy substituent at the A-ring. All vitamins were prepared in convergent syntheses utilizing the modified Julia olefination. 1alpha,2alpha,25-Trihydroxy-19-nor-vitamin
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
Marc Lamblin et al.
Bioorganic & medicinal chemistry, 18(11), 4119-4137 (2010-05-11)
Incorporation of zinc-binding groups into the side-chain of 1alpha,25-dihydroxyvitamin D(3) (1,25D) fully bifunctional hybrid molecules which act both as vitamin D receptor agonists and histone deacetylase inhibitors. These bifunctional hybrids display in vitro antiproliferative activity against the AT84 squamous carcinoma
Masato Shimizu et al.
Bioorganic & medicinal chemistry, 16(14), 6949-6964 (2008-06-10)
Recently, we have found that 16-ene-22-thia-26,27-dimethyl-19-norvitamin D(3) analogs 1a (n=2, 3) are 20 times more active than the natural hormone 1alpha,25-dihydroxyvitamin D(3) in terms of transcriptional activity. To further investigate the effects of the A-ring modification of 1a, b on
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