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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
¥7,493.17

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100 μG
¥7,493.17

About This Item

Empirical Formula (Hill Notation):
C27H44O3
CAS Number:
55721-11-4
Molecular Weight:
416.64
Beilstein:
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

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(24R)-24,25-二羟基维生素 D 3 ≥98% (vitamin + pre-vitamin, HPLC)

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(24R)-24,25-二羟基维生素 D 3

1α,25-二羟基维生素D3 ≥97.0% (HPLC)

17936

1α,25-二羟基维生素D3

25-羟基维生素D3 一水合物 ≥99.0% (HPLC)

17938

25-羟基维生素D3 一水合物

25-羟基维生素 D3 (6,19,19-d3) ≥97 atom % D, ≥98% (CP)

705888

25-羟基维生素 D3 (6,19,19-d3)

assay

≥98% (vitamin + pre-vitamin, HPLC)

assay

≥97.0% (HPLC)

assay

≥99.0% (HPLC)

assay

≥98% (CP)

biological source

synthetic

biological source

-

biological source

synthetic

biological source

-

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

color

colorless to white

color

white to off-white

color

white to off-white

color

white to off-white

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.

related product

Product No.
Description
Pricing

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301 + H311,H330,H372

Hazard Classifications

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

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves
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    Certificates of Analysis (COA)

    Lot/Batch Number
    SLCJ9991
    SLBP2385V
    SLBR9499V
    SLBR3666V
    SLBJ5566V

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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
    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
    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
    View All Related Papers

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