17936

Sigma-Aldrich

1α,25-Dihydroxyvitamin D3

≥97.0% (HPLC)

Synonym(s):
1α,25-Dihydroxycholecalciferol, Calcitriol
Empirical Formula (Hill Notation):
C27H44O3
CAS Number:
Molecular Weight:
416.64
Beilstein/REAXYS Number:
7559394
EC Number:
MDL number:
eCl@ss:
34058003
PubChem Substance ID:
NACRES:
NA.79

Quality Level

assay

≥97.0% (HPLC)

form

crystals

color

white to off-white

storage temp.

−70°C

SMILES string

[H][C@@]1(CC[C@@]2([H])C(\CCC[C@]12C)=C\C=C3\C[C@@H](O)C[C@H](O)C3=C)[C@H](C)CCCC(C)(C)O

InChI

1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10+,21-11-/t18-,22-,23-,24+,25+,27-/m1/s1

InChI key

GMRQFYUYWCNGIN-NKMMMXOESA-N

Gene Information

human ... VDR(7421)

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General description

1α,25-Dihydroxyvitamin D3, also referred as calcitriol, is a calcitrophic hormone. It is the most biologically active metabolite of vitamin D produced in proximal tubular cells in the kidney.

Application

1α,25-Dihydroxyvitamin D3 has been used to study its effect on transplantation success of human muscle precursor cells (hMPCs) in severe combined immunodeficient (SCID) mice in-vitro.

Packaging

100 μg in poly bottle
1 mg in poly bottle
Bottomless glass bottle. Contents are inside inserted fused cone.

Biochem/physiol Actions

1α,25-Dihydroxyvitamin D3 modulates energy metabolism by facilitating various metabolic processes, such as Ca2+ signaling and modulation of glucocorticoids, by affecting adipocyte apoptosis and by regulating the expression and production of multiple cytokines. In addition, it also modulates phosphorus homeostasis through actions in the intestine, kidney and bone. 1α,25-Dihydroxyvitamin D3 exhibits antiproliferative effects and is used as a potent therapeutic for human prostate cancer.
Biologically active form of vitamin D3 in calcium absorption and deposition. 1α,25-Dihydroxyvitamin D3 has widespread effects on cellular differentiation and proliferation, and can modulate immune responsiveness, and central nervous system function. Recent studies suggest that 1α,25-dihydroxyvitamin D3 acts as a chemopreventive agent against several malignancies including cancers of the prostate and colon and shows synergy with other anticancer compounds.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 2811 6.1 / PGI

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Treatment of early recurrent prostate cancer with 1, 25-dihydroxyvitamin D3 (calcitriol)
Gross C, et al.
The Journal of Urology, 159(6), 2035-2040 (1998)
Calcitriol and energy metabolism
Zemel M B and Sun X
Nutr. Rev, 66(suppl-2), S139-S146 (2008)
Inhibition of T lymphocyte mitogenesis by 1, 25-dihydroxyvitamin D3 (calcitriol).
Rigby WF, et al.
The Journal of Clinical Investigation, 74(4), 1451-1455 (1984)
1, 25-dihydroxyvitamin D3 increases the transplantation success of human muscle precursor cells in SCID mice
Stephan L, et al.
Cell Transplantation, 16(4), 391-402 (2007)
Handbook of Hormones: Comparative Endocrinology for Basic and Clinical Research (2015)

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