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Merck
CN

17943

(24R)-24,25-Dihydroxyvitamin D3

≥98% (vitamin + pre-vitamin, HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C27H44O3
CAS Number:
55721-11-4
Molecular Weight:
416.64
UNSPSC Code:
12352205
NACRES:
NA.79
PubChem Substance ID:
57647691
MDL number:
MFCD00941417
Beilstein/REAXYS Number:
4567039

Key Documents

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Product Name

(24R)-24,25-Dihydroxyvitamin D3, ≥98% (vitamin + pre-vitamin, HPLC)

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

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 key

FCKJYANJHNLEEP-XRWYNYHCSA-N

biological source

synthetic

assay

≥98% (vitamin + pre-vitamin, HPLC)

Quality Level

200

color

white to off-white

storage temp.

−20°C

Related Categories

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.

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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

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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Certificates of Analysis (COA)

Lot/Batch Number
SLCJ9991
SLBP2385V
SLBR9499V
SLBR3666V
SLBJ5566V

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J D Bashutski et al.
Journal of dental research, 90(8), 1007-1012 (2011-05-11)
Vitamin D regulates calcium and immune function. While vitamin D deficiency has been associated with periodontitis, little information exists regarding its effect on wound healing and periodontal surgery outcomes. This longitudinal clinical trial assessed outcomes of periodontal surgery and teriparatide
Hulya Taskapan
International urology and nephrology, 44(4), 1135-1144 (2012-04-03)
Deficiency of 1,25-dihydroxyvitamin D [1,25(OH)(2)D] and excessive fibroblast growth factor (FGF23) are suggested to be associated with increased mortality in patients with chronic kidney disease (CKD). Generally, 24-hydroxylation has been considered the first step in the degradation pathway of 1,25(OH)(2)D
Yanping Lin et al.
Current eye research, 37(10), 871-878 (2012-05-29)
This study was designed to measure vitamin D metabolites in the aqueous and vitreous humor and in tear fluid, and to determine if dietary vitamin D3 supplementation affects these levels. We also determined if the corneal epithelium can synthesize vitamin
Vishwanath P Hiremath et al.
Oral health & preventive dentistry, 11(1), 61-69 (2013-03-20)
To assess the anti-inflammatory effect of vitamin D on gingivitis at various doses. In this randomized controlled trial, daily oral vitamin D supplementation was given in doses of 2000 IU for group A, 1000 IU for group B, 500 IU
Robin A Kremsdorf et al.
The Journal of clinical endocrinology and metabolism, 98(3), 1207-1213 (2013-02-09)
High-protein diets, which are popular for weight loss, contain large quantities of phosphorus. Phosphorus excess and consequent changes in phosphorus regulatory hormones are implicated in vascular calcification and cardiovascular disease. We tested the hypothesis that a moderate increase in dietary
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