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17943

Sigma-Aldrich

(24R)-24,25-Dihydroxyvitamin D3

≥98% (vitamin + pre-vitamin, HPLC)

Synonym(s):

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

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100 μG
$877.00

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100 μG
$877.00

About This Item

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

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biological source

synthetic

Quality Level

200

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.[1] It is the one of the most active form of vitamin D[2] and an essential circulating vitamin D3 metabolite.[3]

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).[3]

Biochem/physiol Actions

(24R)-24,25-Dihydroxyvitamin D3 plays an essential role in calcium and phosphorus homeostasis.[1] (24R)-24,25-Dihydroxyvitamin D3 along with 1α,25(OH)2D3 stimulates bone metabolism.[2]
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.

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Product No.
Description
Pricing

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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Certificates of Analysis (COA)

Lot/Batch Number
SLCJ9991
SLBP2385V
SLBR9499V
SLBR3666V
SLBJ5566V

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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
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
24, 25-Dihydroxyvitamin D3 and bone metabolism
van Leeuwen JPTM, et al.
Steroids, 66(3-5), 375-380 (2001)
Anthony W Norman et al.
Molecular and cellular endocrinology, 197(1-2), 1-13 (2002-11-15)
All biologic responses to vitamin D are now known to arise as a consequence of the metabolism of this seco-steroid into its two principal biologically active metabolites 1alpha,25(OH)(2)-vitamin D(3) (1ALPHA;,25(OH)(2)D(3)) and 24R,25(OH)(2)-vitamin D(3) (24R,25(OH)(2)D(3)). 1alpha,25(OH)(2)D(3) is the dominant metabolite and
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
View All Related Papers

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