17943

Sigma-Aldrich

(24R)-24,25-Dihydroxyvitamin D3

≥98% (vitamin + pre-vitamin, HPLC)

Synonym(s):
Secalciferol, (24R)-,24,25-Dihydroxycholecalciferol
Empirical Formula (Hill Notation):
C27H44O3
CAS Number:
Molecular Weight:
416.64
Beilstein/REAXYS Number:
4567039
MDL number:
PubChem Substance ID:
NACRES:
NA.79

Quality Level

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

Related Categories

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).

Packaging

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

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.

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 / PGII

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

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...
Helen L Henry
Best practice & research. Clinical endocrinology & metabolism, 25(4), 531-541 (2011-08-30)
Fundamental to understanding the way in which perturbations in the vitamin D endocrine system can affect human health is an appreciation of the steps involved in the production of the well-recognized active hormonal form, 1,25-dihydroxyvitamin D(3). Thus this paper focuses...
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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