Reaction #155358

ord-a2dadd22025a409987662a0f64ebd88e

Reaction equation

C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@]2(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@@H]12
D3
C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@]2(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@@H]12
cholecalciferol
C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@]2(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@@H]12
7-Dehydrocholesterol
C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@]2(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@@H]12
cholecalciferol
C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@]2(C)[C@@H]([C@H](C)CCCC(C)(C)O)CC[C@@H]12
25-Hydroxyvitamin D
C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@]2(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@@H]12
7-DHC
C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@]2(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@@H]12
7-DHC
→
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
7-DHC

Reactants

C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@]2(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@@H]12
D3
C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@]2(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@@H]12
cholecalciferol
—
vitamin D
C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@]2(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@@H]12
7-Dehydrocholesterol
C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@]2(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@@H]12
cholecalciferol
C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@]2(C)[C@@H]([C@H](C)CCCC(C)(C)O)CC[C@@H]12
25-Hydroxyvitamin D
C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@]2(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@@H]12
7-DHC
C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@]2(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@@H]12
7-DHC

Reagents

None

Solvents

CCO
ethanol
CCO
ethanol
CCO
ethanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Filtrationfiltered with a 0.22 mm pore size
  2. 2
    Filtrationfilter before use
  3. 3
    OtherFourteen different groups were prepared
  4. 4
    Othereight were non irradiated

Procedure

For the treatment with vitamin D metabolites, stock solutions of 2 mM 7-Dehydrocholesterol (7-DHC, Sigma St. Louis, Mo., USA), 2 μM cholecalciferol (D3, Sigma St. Louis, Mo., USA), and 2 μM 25-Hydroxyvitamin D (25-D3, Sigma St. Louis, Mo., USA) were prepared in absolute ethanol and filtered with a 0.22 mm pore size filter before use. Fourteen different groups were prepared; eight were non irradiated: 7-DHC at different doses (20 nmols, 2 nmols, 0.2 nmols, 2×10−2 nmols, and 2×10−3 nmols), 2×10−2 nmols D3, 2×10−2 nmols 25-D3 and ethanol. And six were UV-irradiated: 7-DHC at the same different doses (20 nmols, 2 nmols, 0.2 nmols, 2×10−2 nmols, and 2×10−3 nmols) and ethanol.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08821568B2uspto-grants-2014_09