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C9756

Sigma-Aldrich

Cholecalciferol

≥98% (HPLC)

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Synonym(s):
(+)-Vitamin D3, 7-Dehydrocholesterol activated, Activated 7-dehydrocholesterol, Calciol
Empirical Formula (Hill Notation):
C27H44O
CAS Number:
Molecular Weight:
384.64
Beilstein/REAXYS Number:
2339331
EC Number:
MDL number:
UNSPSC Code:
12352209
eCl@ss:
34058003
PubChem Substance ID:
NACRES:
NA.26

biological source

synthetic (organic)

Quality Level

assay

≥98% (HPLC)

form

powder

technique(s)

HPLC: suitable

color

white to off-white

mp

83-86 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(C)CCC[C@@H](C)[C@@]1([H])CC[C@@]([C@]1(C)CCC/2)([H])C2=C\C=C(C[C@@H](O)CC3)/C3=C

InChI

1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h12-13,19,21,24-26,28H,3,6-11,14-18H2,1-2,4-5H3/b22-12+,23-13-/t21-,24+,25-,26+,27-/m1/s1

InChI key

QYSXJUFSXHHAJI-YRZJJWOYSA-N

Gene Information

human ... VDR(7421)

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General description

Cholecalciferol acts as a hormone precursor since it requires two stages of metabolism: first to 25-hydroxycholecalciferol; then to 1α, 25-dihydroxycholecalciferol. One unit (U.S.P. or international) is defined as the activity of 0.025 μg of vitamin D3 contained in the USP vitamin D reference standard.
Cholecalciferol is sourced either through the diet or exposing skin to ultraviolet rays. Oral administration of vitamin D3 is readily absorbed and is stored in adipose tissue.

Application


  • Alterations in regulators of the renal-bone axis, inflammation and iron status in older people with early renal impairment and the effect of vitamin D supplementation.: This study delves into the significant roles of cholecalciferol in modulating the renal-bone axis, inflammatory responses, and iron metabolism in elderly patients with renal impairment. Through vitamin D supplementation, researchers observed pivotal changes that could guide future therapeutic strategies (Christodoulou M et al., 2024).

  • Investigating the effects of 25-hydroxyvitamin D3 on clinical outcomes in multiple sclerosis patients: A randomized, double-blind clinical trial- a pilot study.: This clinical trial assesses the efficacy of cholecalciferol in improving the health outcomes of patients with multiple sclerosis. The use of cholecalciferol potentially enhances neurological function and reduces disease progression, illustrating its vital role in neurodegenerative disease management (Maghbooli Z et al., 2024).

  • Vitamin D regulates COVID-19 associated severity by suppressing the NLRP3 inflammasome pathway.: This pivotal research links cholecalciferol to the reduction of COVID-19 severity through its regulatory effects on the NLRP3 inflammasome pathway. The findings underscore the potential of vitamin D as a modulatory agent in the immune response against viral infections (Khalil B et al., 2024).

  • Effects of Vitamin D Supplementation on Central Hemodynamic Parameters and Autonomic Nervous System in Obese or Overweight Individuals.: This randomized controlled trial explores how cholecalciferol supplementation can affect cardiovascular and autonomic functions in obese or overweight patients, providing insights into its benefits beyond bone health and into cardiovascular regulation (Faria ACC et al., 2024).


Biochem/physiol Actions

Deficiency of vitamin D is often observed in chronic kidney disease.
Vitamin D acts through a receptor that is a member of the ligand-dependent transcription factor superfamily. Modulates the proliferation and differentiation of both normal and cancer cells. Has antiproliferative and antimetastatic effects on breast, colon, and prostate cancer cells. Activated vitamin D receptors in intestine and bone maintain calcium absorbance and homeostasis.

Storage and Stability

Cholecalciferol C9756 is packaged under argon gas. If it is stored unopened at 2-8°C and protected from light, this product should be stable for a minimum of three years. Unused portions should be stored under nitrogen or argon gas. Deterioration is negligible after storage of one year in amber-evaculated ampules at refrigerator temperatures. It is oxidized and inactivated by moist air within a few days.

pictograms

Skull and crossbonesHealth hazard

signalword

Danger

Hazard Classifications

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

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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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Clinical Veterinary Toxicology, 448-448 (2003)
Cholecalciferol supplementation in hemodialysis patients: effects on mineral metabolism, inflammation, and cardiac dimension parameters
Matias P, et al.
Clinical journal of the American Society of Nephrology : CJASN, CJN-06510909 (2010)
Lin Fu et al.
Journal of immunology (Baltimore, Md. : 1950), 203(5), 1198-1207 (2019-07-19)
It is increasingly recognized that excessive glucocorticoids induce fetal intrauterine growth restriction (IUGR). Placental 11β-hydroxysteroid dehydrogenase 2 (11β-HSD2), a glucocorticoid-catalyzing enzyme, prevents active glucocorticoids from maternal circulation into the fetus, thus protecting against IUGR. Previous studies demonstrated gestational LPS exposure
Bich Tran et al.
The American journal of clinical nutrition, 99(1), 156-161 (2013-10-11)
Observational data suggested that supplementation with vitamin D could reduce risk of infection, but trial data are inconsistent. We aimed to examine the effect of oral vitamin D supplementation on antibiotic use. We conducted a post hoc analysis of data
Hongliu Ding et al.
Neurology, 81(17), 1531-1537 (2013-09-27)
To conclusively test for a specific association between the biological marker 25-hydroxy-vitamin D3, a transcriptionally active hormone produced in human skin and liver, and the prevalence and severity of Parkinson disease (PD). We used liquid chromatography/tandem mass spectrometry to establish

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