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Merck
CN

55171

Sigma-Aldrich

(23R)-23,25-Dihydroxyvitamin D3

≥99.0% (HPLC)

Synonym(s):

(23R)-23,25-Dihydroxycholecalciferol

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About This Item

Empirical Formula (Hill Notation):
C27H44O3
CAS Number:
81738-09-2
Molecular Weight:
416.64
MDL number:
MFCD12912385
UNSPSC Code:
12352200
PubChem Substance ID:
329758085

Key Documents

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Quality Level

100

Assay

≥99.0% (HPLC)

form

powder or crystals

color

colorless to white

shipped in

dry ice

storage temp.

−20°C

SMILES string

C[C@H](C[C@@H](O)CC(C)(C)O)[C@H]1CC[C@H]2\C(CCC[C@]12C)=C\C=C3\C[C@@H](O)CCC3=C

InChI

1S/C27H44O3/c1-18-8-11-22(28)16-21(18)10-9-20-7-6-14-27(5)24(12-13-25(20)27)19(2)15-23(29)17-26(3,4)30/h9-10,19,22-25,28-30H,1,6-8,11-17H2,2-5H3/b20-9+,21-10-/t19-,22+,23-,24-,25+,27-/m1/s1

InChI key

JVBPQHSRTHJMLM-WORHRCAZSA-N

Application

able to increase the plasma lactone concentration

Biochem/physiol Actions

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. 23,25-Dihydroxyvitamin D3 is synthesized by the human placenta and by kidney cortex mitochondria.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P310

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBL3639V
BCBH1725V
1406530V
1406530

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L Cancela et al.
Journal of steroid biochemistry, 28(5), 479-484 (1987-11-01)
Mouse skin fibroblasts in culture were used to study the regulation of 1,25-dihydroxycholecalciferol (1,25(OH)2D3) induced 24 hydroxylase (24-OH-ase) under the influence of 3 agents: (1) 24,25-Dihydroxycholecalciferol (24,25(OH)2D3), 62.5 10(-9) M, which led to a significant decrease in the 1,25(OH)2D3-induced 24-OH-ase
Metabolic pathway to 25-hydroxyvitamin D3-26,23-lactone from 25-hydroxyvitamin D3.
S Ishizuka et al.
FEBS letters, 138(1), 83-87 (1982-02-08)
J I Pedersen et al.
The Biochemical journal, 250(2), 527-532 (1988-03-01)
Incubation of 25-hydroxyvitamin D3 with kidney cortex mitochondria from 1,25-dihydroxyvitamin D3-treated guinea pigs resulted in the formation of 23,25-dihydroxyvitamin D3 as the major product. The identity of the product was verified by g.c.-m.s. and quantification was performed by h.p.l.c. The
T F Vlasova et al.
Voprosy pitaniia, (1)(1), 55-59 (1986-01-01)
Some aspects of amino acid metabolism in rats exposed to 30 days of hypokinesia were explored. The animals were placed on the diets with varying Ca/P ratio, containing 24, 25-dihydroxycholecalciferol (24, 25 (OH)2)D3, an active vitamin D3 metabolite. It was
Binding properties of 23S,25-dihydroxyvitamin D3: an in vivo metabolite of vitamin D3.
R L Horst et al.
Biochemical and biophysical research communications, 106(3), 1006-1011 (1982-06-15)
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