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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:
67-97-0
Molecular Weight:
384.64
Beilstein:
2339331
EC Number:
200-673-2
MDL number:
MFCD00078131
eCl@ss:
34058003
PubChem Substance ID:
24893192
NACRES:
NA.26

biological source

synthetic (organic)

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.

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.

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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

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

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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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
Stefan Pilz et al.
Hypertension (Dallas, Tex. : 1979), 65(6), 1195-1201 (2015-03-25)
Vitamin D deficiency is a risk factor for arterial hypertension, but randomized controlled trials showed mixed effects of vitamin D supplementation on blood pressure (BP). We aimed to evaluate whether vitamin D supplementation affects 24-hour systolic ambulatory BP monitoring values
Anders Burild et al.
Steroids, 98, 72-79 (2015-03-01)
Information regarding the endogenous storages of vitamin D3 after cutaneous vitamin D synthesis compared to oral vitamin D3 supplementation is sparse. Furthermore it is not known whether vitamin D3 can be stored for later use during periods of shortages of
View All Related Papers

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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