17944

Sigma-Aldrich

1α,25-Dihydroxyvitamin D2

≥97.0% (sum of vitamin and previtamin, HPLC)

Synonym(s):
1α,25-Dihydroxycalciferol
Empirical Formula (Hill Notation):
C28H44O3
CAS Number:
Molecular Weight:
428.65
Beilstein/REAXYS Number:
5635017
MDL number:
PubChem Substance ID:
NACRES:
NA.79

Quality Level

biological source

synthetic

assay

≥97.0% (sum of vitamin and previtamin, HPLC)

form

crystals

color

white to light yellow

storage temp.

−70°C

SMILES string

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

InChI

1S/C28H44O3/c1-18(9-10-19(2)27(4,5)31)24-13-14-25-21(8-7-15-28(24,25)6)11-12-22-16-23(29)17-26(30)20(22)3/h9-12,18-19,23-26,29-31H,3,7-8,13-17H2,1-2,4-6H3/b10-9+,21-11+,22-12-/t18-,19+,23-,24-,25+,26+,28-/m1/s1

InChI key

ZGLHBRQAEXKACO-XJRQOBMKSA-N

Related Categories

Packaging

1 mg in poly bottle
Bottomless glass bottle. Contents are inside inserted fused cone.

Biochem/physiol Actions

Ergocalciferol (vitamin D2) is activated in vivo by hydroxylation to 25-hydroxyergocalciferol and 1α,25-dihydroxycalciferol. Activated Vitamin D2 molecules may be used in a wide range of studies to assess their effects on functions such as immune function and calcium homeostasis.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 17944.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

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 / PGII

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Shigeaki Kato et al.
Current opinion in nephrology and hypertension, 16(4), 297-304 (2007-06-15)
Vitamin D has diverse biological actions, and consequently the mechanisms behind how it regulates gene transcription are diverse. Unlike its well described positive effects on gene transcription, little is known about how vitamin D induces transcriptional repression. Vitamin D-induced transcriptional...
R L Horst et al.
Journal of cellular biochemistry, 88(2), 282-285 (2003-01-10)
1alpha-Hydroxy-23 carboxy-24,25,26,27-tetranorvitamin D(3) (calcitroic acid) is known to be the major water-soluble metabolite produced during the deactivation of 1,25-(OH)(2)D(3). This deactivation process is carried out exclusively by the multicatalytic enzyme CYP24 and involves a series of oxidation reactions at C(24)...
Frederick G Strathmann et al.
Clinical chemistry, 57(9), 1279-1285 (2011-07-20)
1α,25-dihydroxy vitamin D [1,25(OH)(2)D] is the active metabolite of vitamin D. Antibody-based detection methods lack specificity, but when combined with isotope dilution/ultra-performance liquid chromatography (UPLC)-tandem mass spectrometry, immunoextraction provides an attractive method for 1,25(OH)(2)D. We developed a method for simultaneous...
Joanna Wietrzyk et al.
Cancer chemotherapy and pharmacology, 62(5), 787-797 (2008-01-12)
Active and less toxic vitamin D analogs could be useful for clinical applications. In the present study, we evaluated the toxicity and antitumor effect of two new synthetic analogs of vitamin D, namely PRI-1906 [(24E)-24a-Homo-(1S)-1,25-dihydroxyergocalciferol] and its side-chain unsaturated homo...
R A Henik et al.
Journal of the American Veterinary Medical Association, 215(11), 1644-1649 (2003-10-22)
Rickets was diagnosed in a 1-year-old cat with a history of weakness, osteopenia, and recurrent fractures. Processes causing rickets include vitamin D deficiency caused by inadequate, nutrition, lack of exposure to sunlight, defective metabolism of parent vitamin D to active...
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.
Read More
This application shows an Ascentis Express F5 provided rapid resolution of the isobaric vitamin D metabolites. MS detection provides the necessary secondary resolution.
Read More
Related Content
The metabolic role and health implications of the various vitamin D isoforms are of current clinical interest. Therefore, it is important to have an analytical method that will resolve all of the known isoforms with necessary sensitivity and specificity
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