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{{short description|Fat soluble vitamin}}{{DISPLAYTITLE:Vitamin D5}}
{{chembox
| Verifiedfields = changed
| verifiedrevid = 470631138
| Name=Vitamin D5
| ImageFile=Vitamin D5 structure.svg
| ImageSize=
| IUPACName=(1''S'',3''Z'')-3-[(2''E'')-2-[(1''R'',3a''S'',7a''R'')-1-[(1''R'',4''S'')-4-ethyl-1,5-dimethylhexyl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1''H''-inden-4-ylidene]ethylidene]-4-methylene-1-cyclohexanol
| OtherNames= Sitocalciferol (5''Z'',7''E'')-(3''S'')-9,10-secoporiferasta-5,7,10(19)-trien-3-ol
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7826639
| ChEBI = 33279
| InChI = 1/C29H48O/c1-7-23(20(2)3)12-10-22(5)27-16-17-28-24(9-8-18-29(27,28)6)13-14-25-19-26(30)15-11-21(25)4/h13-14,20,22-23,26-28,30H,4,7-12,15-19H2,1-3,5-6H3/b24-13+,25-14-/t22-,23+,26+,27-,28+,29-/m1/s1
| InChIKey = RMDJVOZETBHEAR-GHTRHTQZBN
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C29H48O/c1-7-23(20(2)3)12-10-22(5)27-16-17-28-24(9-8-18-29(27,28)6)13-14-25-19-26(30)15-11-21(25)4/h13-14,20,22-23,26-28,30H,4,7-12,15-19H2,1-3,5-6H3/b24-13+,25-14-/t22-,23+,26+,27-,28+,29-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = RMDJVOZETBHEAR-GHTRHTQZSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=71761-06-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0W2I161LCL
| PubChem=9547700
| SMILES = O[C@@H]1CC(\C(=C)CC1)=C\C=C2/CCC[C@]3([C@H]2CC[C@@H]3[C@H](C)CC[C@H](CC)C(C)C)C
}}
|Section2={{Chembox Properties
| C=29 | H=48 | O=1
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
}}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
}}
}}
'''Vitamin D5''' ('''sitocalciferol''') is a form of [[vitamin D]].
== Research ==
[[structural analog|Analogs]] of [[calcitriol]], a form of vitamin D3, have been proposed for use as antitumor agents. Studies on vitamin D3 have shown inhibition of cell proliferation in [[prostate cancer]], but high doses of vitamin D3 result in [[Hypercalcaemia|hypercalcemia]]. The effects of vitamin D5 on prostate cancer have also been studied, and unlike vitamin D3, vitamin D5 does not cause [[Hypercalcaemia|hypercalcemia]] while inhibiting tumor cell proliferation. The most researched analogue of vitamin D5 as an antitumor agent is 1α-hydroxyvitamin D5.

=== 1α-Hydroxyvitamin D5 ===

1α-Hydroxyvitamin D5 is a chemical derivative of vitamin D5. The motive to study 1α-hydroxyvitamin D5 as a potential pharmaceutical drug stemmed from the tendency of calcitriol, a natural metabolite produced in the [[kidney]], to cause toxic hypercalcemia in patients when dosed at concentrations needed to interrupt [[prostate cancer]] cells' cycle and stimulate [[apoptosis]]. And while supplementation with [[dexamethasone]] decreases hypercalcemia, bypassing it with an equally effective tumor suppressant would reduce patient cost and stress. Thus, the therapeutic effects of 1α-Hydroxyvitamin D5 as a potential antitumor agent without the side effects of calcitriol became a topic of study.

1α-Hydroxyvitamin D5 was first synthesized in 1997 by researchers in the Department of Chemistry at the [[University of Chicago]], under Robert M. Moriarty and Dragos Albinescu. By 2005, the group had revised its synthesis method for a more streamlined, higher yield-producing route. It involved the photochemical conversion of precursor [[7-Dehydrositosterol|7-dehydrositosteryl]] acetate to contain a conjugated triene system, a hallmark of this analog, followed by [[hydroxylation]], [[photoisomerization]], and [[Protecting group|deprotection]] steps. Their overall yield was 48%.

== See also ==
* [[7-Dehydrositosterol]]
* [[Calcipotriene]]

{{Vitamin}}

{{二次利用|date=11 December 2023}}
[[Category:Vitamin D]]

Vitamin D5/en - Revision history

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