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29447

Sigma-Aldrich

(24S)-24,25-Dihydroxyvitamin D3

≥95.0% (HPLC)

Sinónimos:

(24S)-24,25-Dihydroxycholecalciferol

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About This Item

Fórmula empírica (notación de Hill):
C27H44O3
Número de CAS:
55700-58-8
Peso molecular:
416.64
MDL number:
MFCD11114064
UNSPSC Code:
12352200
PubChem Substance ID:
329753335

assay

≥95.0% (HPLC)

form

powder or crystals

color

colorless to white

mp

114.6 °C

storage temp.

−20°C

SMILES string

C[C@H](CC[C@H](O)C(C)(C)O)[C@H]1CC[C@H]2\C(CCC[C@]12C)=C\C=C3\C[C@@H](O)CCC3=C

InChI

1S/C27H44O3/c1-18-8-12-22(28)17-21(18)11-10-20-7-6-16-27(5)23(13-14-24(20)27)19(2)9-15-25(29)26(3,4)30/h10-11,19,22-25,28-30H,1,6-9,12-17H2,2-5H3/b20-10+,21-11-/t19-,22+,23-,24+,25+,27-/m1/s1

InChI key

FCKJYANJHNLEEP-WQUHCOROSA-N

Biochem/physiol Actions

Cholecalciferol is an inactive form of vitamin D3 which undergoes various levels of hydroxylation to form active vitamin D3 analogs. 1α-Hydroxyvitamin D3 (alfacalcidol) is a synthetic analog that is metabolized to 1,25-dihydroxycholecalciferol, the biologically active form of vitamin D3. Other analogues of cholecalciferol result from different hydroxylations. 24S,25-Dihydroxyvitamin D3 should not be confused with 24R,25-Dihydroxyvitamin D3.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Related product

Referencia del producto
Descripción
Precios

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class

6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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José Pérez Sestelo et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 8(12), 2747-2752 (2002-10-24)
Vitamin D3 active metabolites 24R,25-(OH)2-D3, 24S,25-(OH)2-D3, and 1 alpha, 24R,25-(OH)3-D3 were synthesized by a convergent and stereoselective approach. In the synthetic route, the stereogenic center at C-24 was generated through ultrasonically induced aqueous conjugate addition of iodide 6 to Seebach's
S Ishizuka et al.
Archives of biochemistry and biophysics, 234(1), 97-104 (1984-10-01)
Tritium-labeled 24,25-dihydroxyvitamin D3 was prepared both in vitro, by using chick kidney homogenates, and in vivo in rats from [26,27-methyl-3H]25-hydroxyvitamin D3. These compounds were mixed with synthetic 24(R),25- and 24(S),25-dihydroxyvitamin D3, converted to the corresponding trimethylsilyl ether derivatives, and analyzed
H L Henry et al.
The Journal of nutrition, 106(6), 724-734 (1976-06-01)
The ability of 24R, 25- and 24S, 25-dihydroxycholecalciferol to stimulate intestinal calcium transport and bone calcium mobilization in chicks was measured. Enhancement of intestinal calcium transport by 325 or 130 nmoles of either compound was maximal by 24 hours. The
Anjali Verma et al.
Steroids, 150, 108447-108447 (2019-07-16)
Vitamin D has long been prescribed as a supplement to breast cancer patients. This is partially motivated by data indicating that low serum vitamin D, measured as 25-hydroxyvitamin D3 [25(OH)D3], is associated with worsened cancer prognosis and decreased survival rates
Anjali Verma et al.
Molecular cancer research : MCR, 19(1), 99-111 (2020-10-22)
Vitamin D3 and its metabolites have antitumorigenic properties in vitro and in vivo; however, clinical trials and retrospective studies on the effectiveness of vitamin D3 oral supplementation against cancer have been inconclusive. One reason for this may be that clinical

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