D1530

Sigma-Aldrich

1α,25-Dihydroxyvitamin D3

≥99% (HPLC)

Synonym(s):
1α,25-Dihydroxycholecalciferol, Calcitriol
Empirical Formula (Hill Notation):
C27H44O3
CAS Number:
Molecular Weight:
416.64
Beilstein/REAXYS Number:
7559394
EC Number:
MDL number:
eCl@ss:
34058003
PubChem Substance ID:
NACRES:
NA.79

Quality Level

assay

≥99% (HPLC)

application(s)

HPLC: suitable

storage temp.

−20°C

SMILES string

[H][C@@]1(CC[C@@]2([H])C(\CCC[C@]12C)=C\C=C3\C[C@@H](O)C[C@H](O)C3=C)[C@H](C)CCCC(C)(C)O

InChI

1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10+,21-11-/t18-,22-,23-,24+,25+,27-/m1/s1

InChI key

GMRQFYUYWCNGIN-NKMMMXOESA-N

Gene Information

human ... VDR(7421)

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Biochem/physiol Actions

Biologically active form of vitamin D3 in calcium absorption and deposition. 1α,25-Dihydroxyvitamin D3 has widespread effects on cellular differentiation and proliferation, and can modulate immune responsiveness, and central nervous system function. Recent studies suggest that 1α,25-dihydroxyvitamin D3 acts as a chemopreventive agent against several malignancies including cancers of the prostate and colon and shows synergy with other anticancer compounds.
Cholecalciferol is an inactive form of vitamin D3 which undergoes various levels of hydroxylation to form active vitamin D3 analogs. 1α-Hydroxyvitamin D3 (alfacalcidol is a synthetic analog that is metabolized to 1,25-dihydroxycholecalciferol, the biologically active form of vitamin D3 in calcium absorption and deposition. 1α,25-Dihydroxyvitamin D3 has widespread effects on cellular differentiation and proliferation, and can modulate immune responsiveness, and central nervous system function. Recent studies suggest that 1α,25-dihydroxyvitamin D3 acts as a chemopreventive agent against several malignancies including cancers of the prostate and colon and shows synergy with other anticancer compounds.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 2811 6.1 / PGI

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  4. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  5. How can I dissolve Product D1530, ?,25-Dihydroxyvitamin D3, for cell culture use?

    1?,25-Dihydroxyvitamin D3 is soluble in serveral organic solvents, including methanol, ethanol, ethyl acetate, and tetrahydrofuran. For cell culture use, a 10 μM stock solution can be prepared and diluted to the working concentration in cell culture media.

  6. What is the best way to store stock solutions of Product D1530, 1?,25-Dihydroxyvitamin D3?

    1?,25-Dihydroxyvitamin D3 is both air and light sensitive, so should be stored under inert gas at either -20 or -70°C.  The length of time a stock solution can be stored depends on how carefully air is excluded from the solution. If care is taken to exclude air, stock solutions may be stable indefinitely at -20°C.

  7. I can't see anything in the vial. How should Product D1530, 1´,25-Dihydroxyvitamin D3, look?

    D1530 is packaged by dispensing a solution into the vials, then drying them under inert gas. The product will be a thin film in the bottom of the vial, so it may appear to be empty by visual inspection.

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

  9. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Maurizio Cutolo et al.
Vitamins and hormones, 86, 327-351 (2011-03-23)
Epidemiological evidence indicates a significant association between vitamin D deficiency and an increased incidence of autoimmune diseases. The presence of vitamin D receptors (VDRs) in the cells of the immune system and the fact that several of these cells produce...
Maria Plesa et al.
Journal of asthma and allergy, 13, 249-264 (2020-09-29)
Airway fibroblasts are major contributors to the histopathological feature of airway remodeling in asthma by their implication in the cell invasiveness and profibrogenic secretory phenotype observed in subepithelial fibrosis. 1,25 Dihydroxy vitamin D3 (1,25(OH)2D3) is an important therapeutic agent that...
Beth J Kirby et al.
Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research, 28(9), 1987-2000 (2013-03-19)
Pregnancy invokes a doubling of intestinal calcium absorption whereas lactation programs skeletal resorption to provide calcium to milk. Postweaning bone formation restores the skeleton's bone mineral content (BMC), but the factors that regulate this are not established. We used Pth-null...
Joao F de Brito Galvao et al.
Journal of veterinary emergency and critical care (San Antonio, Tex. : 2001), 23(2), 134-162 (2013-04-10)
To review the inter-relationships between calcium, phosphorus, parathyroid hormone (PTH), parent and activated vitamin D metabolites (vitamin D, 25(OH)-vitamin D, 1,25(OH)2 -vitamin D, 24,25(OH)2 -vitamin D), and fibroblast growth factor-23 (FGF-23) during chronic kidney disease (CKD) in dogs and cats....
Edwin C Y Chow et al.
American journal of physiology. Endocrinology and metabolism, 304(9), E977-E989 (2013-03-14)
The vitamin D receptor (VDR) maintains a balance of plasma calcium and 1α,25-dihydroxyvitamin D3 [1,25(OH)2D3], its natural active ligand, by directly regulating the calcium ion channel (TRPV6) and degradation enzyme (CYP24A1), and indirectly regulating the parathyroid hormone (PTH) for feedback...
Articles
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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