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C1357

Sigma-Aldrich

Cholecalciferol

meets USP testing specifications

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:
24892404
NACRES:
NA.21

Agency

USP/NF
meets USP testing specifications

Quality Level

200

Assay

97.0-103.0%

form

crystalline

color

white

mp

83-86 °C (lit.)

application(s)

pharmaceutical (small molecule)

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 (vitamin D3), a fat-soluble steroid is produced in the skin.

Application

Cholecalciferol has been used:
  • to induce arterial medial calcification (AMC) in mice
  • to study its impact in vascular remodeling associated with vascular calcification (VC) in murine model of obesity and insulin resistance (ob/ob mice)
  • to study its effect on anchorage dependent growth of RWPE2-W99 cells in monolayer culture

Biochem/physiol Actions

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.

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Product No.
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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Expansive vascular remodeling and increased vascular calcification response to cholecalciferol in a murine model of obesity and insulin resistance
Carmo LS, et al.
Arteriosclerosis, Thrombosis, and Vascular Biology, 39(2), 200-211 (2019)
Cholecalciferol (vitamin D 3) inhibits growth and invasion by up-regulating nuclear receptors and 25-hydroxylase (CYP27A1) in human prostate cancer cells
Tokar EJ and Webber MM
Clinical & Experimental Metastasis, 22(3), 275-284 (2005)
Chronic Kidney Disease-Mineral and Bone Disorder
Handbook of Dialysis Therapy, 685-697 (2016)
Runx2 expression in smooth muscle cells is required for arterial medial calcification in mice
Lin ME, et al.
The American Journal of Pathology, 185(7), 1958-1969 (2015)
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
View All Related Papers

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