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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/REAXYS Number:
4270041
MDL number:
MFCD00867077
UNSPSC Code:
12352205
eCl@ss:
34058003
PubChem Substance ID:
57647690
NACRES:
NA.79

biological source

synthetic

Quality Level

200

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

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
BCCF9309
BCCF2261
BCCC3494
BCCB4415
BCCB0132

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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
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
Alberto Lo Gullo et al.
PloS one, 10(8), e0134602-e0134602 (2015-08-05)
Suboptimal vitamin D status was recently acknowledged as an independent predictor of cardiovascular diseases and all-cause mortality in several clinical settings, and its serum levels are commonly reduced in Rheumatoid Arthritis (RA). Patients affected by RA present accelerated atherosclerosis and
Peter Daley et al.
The Lancet. Infectious diseases, 15(5), 528-534 (2015-04-13)
Vitamin D has immunomodulatory effects that might aid clearance of mycobacterial infection. We aimed to assess whether vitamin D supplementation would reduce time to sputum culture conversion in patients with active tuberculosis. We did this randomised, double-blind, placebo-controlled, superiority trial
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Articles

Vitamin D and Prevention of Human Disease

Vitamin D2 (ergocalciferol) is naturally synthesized from ergosterol by invertebrates, fungi, and plants in response to ultraviolet B irradiation, while vitamin D3 synthesis (cholecalciferol) is uniquely initiated in the skin of vertebrates. During sun exposure, ultraviolet B photons are absorbed by 7-dehydrocholesterol, which is found within the plasma membranes of epidermal and dermal skin layers. This reaction yields an unstable derivative of 7-dehydrocholesterol, named precholecalcitrol, which rapidly rearranges to vitamin D3. Vitamin D binding protein (DBP) is a carrier protein responsible for drawing vitamin D3 from the plasma membrane into the dermal capillaries within the extracellular space.

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