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17938

Sigma-Aldrich

25-Hydroxyvitamin D3 monohydrate

≥99.0% (HPLC)

Synonym(s):

25-Hydroxycholecalciferol

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About This Item

Empirical Formula (Hill Notation):
C27H44O2 · H2O
CAS Number:
63283-36-3
Molecular Weight:
418.65
Beilstein:
4270041
MDL number:
MFCD00867077
UNSPSC Code:
12352205
eCl@ss:
34058003
PubChem Substance ID:
57647690
NACRES:
NA.79

biological source

synthetic

Assay

≥99.0% (HPLC)

form

powder or crystals

color

white to off-white

shipped in

dry ice

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)CCCC(C)(C)O

InChI

1S/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/b21-11+,22-12-/t20-,23+,24-,25+,27-/m1/s1

InChI key

JWUBBDSIWDLEOM-DTOXIADCSA-N

Gene Information

human ... VDR(7421)

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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. 25-dihydroxycholecalciferol is a the major circulating form of vitamin D3 and a physiological precursor of 1α,25-Dihydroxycholecalciferol. The conversion is catalyzed by 25-Hydroxyvitamin D3 1-α-hydroxylase (VD3 1A hydroxylase) also known ascytochrome p450 27B1 (CYP27B1).

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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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H F DeLuca
Biochemical Society transactions, 10(3), 147-158 (1982-06-01)
Cholecalciferol must be regarded as a pro-hormone rather than a vitamin, since it is normally produced in skin under the influence of ultraviolet light. Cholecalciferol must be metabolized in liver to 25-hydroxycholecalciferol and subsequently to 1,25-dihydroxycholecalciferol before it can act
Matthew J Rowling et al.
The Journal of nutrition, 136(11), 2754-2759 (2006-10-24)
The major circulating form of vitamin D is 25-hydroxycholecalciferol [25(OH)D3], which is delivered to target tissues in complex with the serum vitamin D binding protein (DBP). We recently observed that mammary cells can metabolize 25(OH)D3 to 1,25-dihydroxycholecalciferol [1,25(OH)(2)D3], the vitamin
Carly M Kemmis et al.
The Journal of nutrition, 136(4), 887-892 (2006-03-22)
1alpha,25-dihydroxycholecalciferol [1alpha,25(OH)2D3], the active form of cholecalciferol, is a negative growth regulator of breast cancer cells. CYP27B1 is a cytochrome P450-containing hydroxylase expressed in kidney and other tissues that generates 1alpha,25(OH)2D3 from an inactive vitamin D precursor 25-hydroxycholecalciferol [25(OH)D3]. In
Kazuya Omi et al.
Clinical chemistry, 61(4), 627-635 (2015-02-20)
Small molecules classified as haptens are generally measured by competitive immunoassay, which is theoretically inferior to noncompetitive sandwich immunoassay in terms of sensitivity and specificity. We created a method for developing sandwich immunoassays to measure haptens on the basis of
Marina V Antunes et al.
Therapeutic drug monitoring, 37(6), 733-744 (2015-04-09)
In view of the large variability on therapeutic response and the multiple factors associated to tamoxifen (TAM) metabolic activation, this study aimed to evaluate the effect of CYP2D6 and CYP3A4 phenotypes, drug interactions, and vitamin D exposure on TAM metabolism
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