A precursor to calcitriol
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Vitamin D3

Item No. 11792

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3Z-[2E-[(1R,3aS,7aR)-1S-[1R,5-dimethylhexyl]octahydro-7a-methyl-4H-inden-4-ylidene]ethylidene]-4-methylene-cyclohexanol
CAS Number
67-97-0
Synonyms
  • Cholecalciferol
  • NSC 375571
Molecular Formula
C27H44O
Formula Weight
384.6
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 2 mg/mlEthanol: 30 mg/ml
λmax
213, 265 nm
SMILES
C=C1CC[C@H](O)C/C1=C/C=C2[C@@](CC[C@@]3([C@H](C)CCCC(C)C)[H])([H])[C@]3(C)CCC/2
InChi Code
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
Origin
Animal/Lanolin
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 g

    $43

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    5 g

    $172

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    10 g

    $301

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    Product Description

    Vitamin D3 is a biologically inactive precursor to calcitriol (Item No. 71820) that is converted to active metabolites in vivo.1,2 Vitamin D3 is obtained from dietary sources, including fish, or formed in the epidermis via photolytic conversion of 7-dehydro cholesterol (Item No. 14612) to previtamin D3 by UVB radiation, followed by isomerization to vitamin D3.3,4 Vitamin D3 can then be converted to 25-hydroxy vitamin D3 (Item No. 9000683) in the liver by the cytochrome P450 (CYP) isoform CYP2R1 before being converted to calcitriol by CYP27B1 in the kidney.2,3 Formulations containing vitamin D3 have been used in the treatment of osteoporosis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lehmann, B., Genehr, T., Knuschke, P., et al. UVB-induced conversion of 7-dehydrocholesterol to 1α,25-dihydroxyvitamin D3 in an in vitro human skin equivalent model. J. Invest. Dermatol. 117(5), 1179-1185 (2001).

    2. Holick, M.F. Vitamin D deficiency. N. Engl. J. Med. 357(3), 266-281 (2007).

    3. Rosen, C.J. Vitamin D insufficiency. N. Engl. J. Med. 364(3), 248-254 (2011).

    4. Chen, T.C., Chimeh, F., Lu, Z., et al. Factors that influence the cutaneous synthesis and dietary sources of vitamin D. Arch. Biochem. Biophys. 460(2), 213-217 (2007).

    Product Citations

    Cherian, M.T., Lin, W., Wu, J., et al. CINPA1 is an inhibitor of constitutive androstane receptor that does not activate pregnane X receptor. Mol. Pharmacol. 87(5), 878-889 (2015).