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17943

Sigma-Aldrich

(24R)-24,25-Dihydroxyvitamin D3

≥98% (vitamin + pre-vitamin, HPLC)

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

biological source

synthetic

Quality Level

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

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This Item
1793617938705888
vibrant-m

17943

(24R)-24,25-Dihydroxyvitamin D3

vibrant-m

17936

1α,25-Dihydroxyvitamin D3

vibrant-m

17938

25-Hydroxyvitamin D3 monohydrate

vibrant-m

705888

25-Hydroxyvitamin D3 (6,19,19-d3)

assay

≥98% (vitamin + pre-vitamin, HPLC)

assay

≥97.0% (HPLC)

assay

≥99.0% (HPLC)

assay

≥98% (CP)

color

colorless to white

color

white to off-white

color

white to off-white

color

white to off-white

form

powder or crystals

form

crystals

form

powder or crystals

form

powder

storage temp.

−20°C

storage temp.

−70°C

storage temp.

−20°C

storage temp.

−20°C

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

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.

pictograms

Skull and crossbonesHealth hazard

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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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
24R, 25-Dihydroxyvitamin D3 and 1alpha, 25-dihydroxyvitamin D3 are both indispensable for calcium and phosphorus homeostasis
Norman AW, et al.
Life Sciences, 27(3), 229-237 (1980)
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
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
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

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