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17943

Sigma-Aldrich

(24R)-24,25-Dihydroxyvitamin D3

≥98% (vitamin + pre-vitamin, HPLC)

Synonyma:

(24R)-,24,25-Dihydroxycholecalciferol, Secalciferol

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About This Item

Empirický vzorec (Hillův zápis):
C27H44O3
Číslo CAS:
55721-11-4
Molekulová hmotnost:
416.64
Beilstein/REAXYS Number:
4567039
MDL number:
MFCD00941417
UNSPSC Code:
12352205
PubChem Substance ID:
57647691
NACRES:
NA.79

biological source

synthetic

assay

≥98% (vitamin + pre-vitamin, HPLC)

form

powder or crystals

color

colorless to white

storage temp.

−20°C

SMILES string

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

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-XRWYNYHCSA-N

General description

(24R)-24,25-Dihydroxyvitamin D3 or secalciferol is produced in kidney. It is the one of the most active form of vitamin D and an essential circulating vitamin D3 metabolite.

Application

(24R)-24,25-Dihydroxyvitamin D3 has been used to assess its function(s) compared with that of 1α,25(OH)2D3, during osteoblastic differentiation of primary human mesenchymal stem cells (hMSCs).

Biochem/physiol Actions

(24R)-24,25-Dihydroxyvitamin D3 plays an essential role in calcium and phosphorus homeostasis. (24R)-24,25-Dihydroxyvitamin D3 along with 1α,25(OH)2D3 stimulates bone metabolism.
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. 24R,25-Dihydroxyvitamin D3 is a catabolite of 25-Dihydroxyvitamin D3 and a putative regulator of developmental bone formation. 24R,25-Dihydroxyvitamin D3 is a substrate for renal 25-hydroxyvitamin D3 1 α-hydroxylase. 24R,25-Dihydroxyvitamin D3 is an endogenous regulator of apo A-I synthesis through a VDR-independent signaling mechanism and an inhibitor of Pi-induced apoptosis through Ca2+, PLD, and PLC signaling and through LPA-LPA1/3-G(αi)-PI(3)K-mdm2-mediated p53 degradation.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

related product

Č. produktu
Popis
Stanovení ceny

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 3 Dermal - Acute Tox. 3 Oral - STOT RE 1 Oral

Storage Class

6.1A - 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

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Kent R Wehmeier et al.
Life sciences, 88(1-2), 110-116 (2010-11-11)
Ligands for the vitamin D receptor (VDR) regulate apolipoprotein A-I (apo A-I) gene expression in a tissue-specific manner. The vitamin D metabolite 24, 25-dihydroxycholecalciferol (24, 25-(OH)(2)D(3)) has been shown to possess unique biological effects. To determine if 24, 25-(OH)(2)D(3) modulates
Thomas Edouard et al.
The Journal of clinical endocrinology and metabolism, 97(4), 1243-1249 (2012-02-10)
Several studies suggest that 24,25-dihydroxyvitamin D [24,25(OH)₂D] may have an effect on bone mass and metabolism. We evaluated the relationship between serum 24,25(OH)₂D levels and bone density and bone metabolism in children with a primary bone disorder-osteogenesis imperfecta (OI). The
Edith K Y Tang et al.
The FEBS journal, 279(19), 3749-3761 (2012-08-07)
CYP27B1 is a mitochondrial cytochrome P450 that catalyses the hydroxylation of 25-hydroxyvitamin D3 at the C1α-position to give the hormonally active form of vitamin D3, 1α,25-dihydroxyvitamin D3. We successfully expressed human CYP27B1 in Escherichia coli and partially purified this labile enzyme
Thomas U Ahearn et al.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology, 21(6), 969-979 (2012-04-28)
Malfunctioning of the adenomatous polyposis coli (APC)/β-catenin signaling pathway is both an early and common event in sporadic colorectal cancer. To assess the potential of APC/β-catenin signaling pathway markers as treatable, preneoplastic biomarkers of risk for colorectal neoplasms, we conducted
T Yamamoto et al.
Experimental cell research, 244(1), 71-76 (1998-10-15)
The effect of the physiological vitamin D metabolite 24R, 25-dihydroxyvitamin D3 [24R,25(OH)2D3] on human osteoblastic cells was assessed. Physiological concentrations (10(-9)-10(-8) M) of 24R, 25(OH)2D3 significantly increased the cyclic guanosine 5'-monophosphate (cGMP) content in the human osteoblastic cells by approximately
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