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C9774

Sigma-Aldrich

Cholecalciferol

analytical standard

Synonym(s):

(+)-Vitamin D3, 7-Dehydrocholesterol activated, Activated 7-dehydrocholesterol, Calciol

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About This Item

Empirical Formula (Hill Notation):
C27H44O
CAS Number:
67-97-0
Molecular Weight:
384.64
Beilstein:
2339331
EC Number:
200-673-2
MDL number:
MFCD00078131
UNSPSC Code:
12352205
eCl@ss:
34058003
PubChem Substance ID:
24893197
NACRES:
NA.77

biological source

synthetic (organic - wool)

Quality Level

200

grade

analytical standard

Assay

≥97.0%

form

crystalline

packaging

pkg of 250 mg

color

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, also called vitamin D3, promotes the absorption of calcium and phosphorus in the body to regulate bone growth. It is most commonly found in humans and animals and is produced in our skin when exposed to sunlight. It is used to treat and prevent bone disorders (such as rickets, osteomalacia).

Application

Cholecalciferol has been used as an internal standard in high-performance liquid chromatography (HPLC) to analyze serum vitamin D levels. It has also been used as a standard in liquid chromatography-electrospray ionization tandem mass spectrometry (LC-ESI-MS/MS) to quantify vitamin D3 in sunflower oil.
Cholecalciferol may be used as an analytical reference standard for the determination of the analyte in pharmaceutical formulations by liquid chromatography.

Biochem/physiol Actions

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. 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.

Packaging

Packaged in flame-sealed ampules under Argon

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Description
Pricing

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H300 + H310 + H330,H372

Hazard Classifications

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

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Stability of vitamin D3 and vitamin D2 in oil, fish and mushrooms after household cooking
Lovznjak P and Jakobsen J
Food Chemistry, 254(4), 144-149 (2018)
Vitamin D serum levels are associated with handgrip strength but not with muscle mass or length of hospital stay after hip fracture
Gumieiro DN, et al.
Nutrition, 31(7-8), 931-934 (2015)
Genetic polymorphisms of vitamin D metabolism genes and serum level of vitamin D in colorectal cancer
Vidigal VM, et al.
The International Journal of Biological Markers, 32(4), 441-446 (2017)
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 (2010)
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