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{{chembox |
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{{chembox |
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| verifiedrevid = 377857801 |
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|ImageFile=5-Dehydroepisterol.png |
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| verifiedrevid = 444444056 |
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|ImageSize=200px |
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| ImageFile=5-Dehydroepisterol.png |
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|IUPACName=(3''S'',10''R'',13''R'')-17--10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1''H''-cyclopentaphenanthren-3-ol |
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| ImageSize=220px |
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|OtherNames=24-Methylcholesta-5,7,24(28)-trienol, ergosta-5,7,24(28)-trien-3β-ol, campesta-7,24(28)-dien-3β-ol |
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| ImageFile1 = 5-Dehydroepisterol molecule ball.png |
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| ImageSize1 = 250 |
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| ImageAlt1 = Ball-and-stick model of 5-dehydroepisterol |
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| IUPACName=Campesta-5,7,24(24<sup>1</sup>)-trien-3β-ol |
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| SystematicName=(1''R'',3a''R'',7''S'',9a''R'',9b''S'',11a''R'')-9a,11a-Dimethyl-1--2,3,3a,6,7,8,9,9a,9b,10,11,11a-dodecahydro-1''H''-cyclopentaphenanthren-7-ol |
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| OtherNames=24-Methylcholesta-5,7,24(28)-trienol, ergosta-5,7,24(28)-trien-3β-ol, campesta-7,24(28)-dien-3β-ol |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo=23582-83-4 |
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| CASNo=23582-83-4 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG=C15780 |
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| KEGG=C15780 |
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| PubChem=23724572 |
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| PubChem = 10894570 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| SMILES=CC(C)C(=C)CCC(C)C1CCC2C1(CCC3C2=CC=C4C3(CCC(C4)O)C)C |
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| ChemSpiderID = 9069833 |
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| InChI=1/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9-10,18,20,22,24-26,29H,3,7-8,11-17H2,1-2,4-6H3/t20-,22+,24-,25+,26+,27+,28-/m1/s1 |
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| SMILES = O4C/C3=C/C=C1\(CC2(1CC2(C)CCC(=C)/C(C)C)C)3(C)CC4 |
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| InChI = 1/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9-10,18,20,22,24-26,29H,3,7-8,11-17H2,1-2,4-6H3/t20-,22+,24-,25+,26+,27+,28-/m1/s1 |
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| InChIKey = ZEPNVCGPJXYABB-LOIOQLKMBD |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9-10,18,20,22,24-26,29H,3,7-8,11-17H2,1-2,4-6H3/t20-,22+,24-,25+,26+,27+,28-/m1/s1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = ZEPNVCGPJXYABB-LOIOQLKMSA-N |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>28</sub>H<sub>44</sub>O |
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| Formula=C<sub>28</sub>H<sub>44</sub>O |
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| MolarMass=396.648 g·mol<sup>−1</sup> |
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| MolarMass=396.648 g·mol<sup>−1</sup> |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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'''5-Dehydroepisterol''' is a ] and an ] in ], particularly synthesis of ]s.<ref>{{KEGG pathway|ko00100}}</ref> It is formed from ] through action of the ] ],<ref>{{KEGG reaction|R07491}}</ref> and is then converted into ] by ].<ref>{{KEGG reaction|R07492}}</ref> |
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'''5-Dehydroepisterol''' is a ] and an ] in ], particularly synthesis of ]s.<ref>{{KEGG pathway|ko00100}}</ref> It is formed from ] through action of ], the ] in the yeast<ref>{{KEGG reaction|R07491}}</ref> and is then converted into ] by ].<ref>{{KEGG reaction|R07492}}</ref> |
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Episterol and 5-dehydroepisterol are found in '']''.<ref>{{cite journal |author=Goad LJ, Holz GG, Beach DH |title=Sterols of ketoconazole-inhibited ''Leishmania mexicana mexicana'' promastigotes |journal=Mol Biochem Parasitol |volume=15 |issue=3 |pages=257–79 |year=1985 |month=June |pmid=4033689 |doi=10.1016/0166-6851(85)90089-1}}</ref><ref>{{cite journal |author=Rodrigues JC, Attias M, Rodriguez C, Urbina JA, Souza W |title=Ultrastructural and biochemical alterations induced by 22,26-azasterol, a delta(24(25))-sterol methyltransferase inhibitor, on promastigote and amastigote forms of ''Leishmania amazonensis'' |journal=Antimicrob Agents Chemother |volume=46 |issue=2 |pages=487–99 |year=2002 |month=February |pmid=11796362 |pmc=127026 |url=http://aac.asm.org/cgi/pmidlookup?view=long&pmid=11796362 |doi=10.1128/AAC.46.2.487-499.2002}}</ref> |
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Episterol and 5-dehydroepisterol are found in '']''.<ref>{{cite journal |vauthors =Goad LJ, Holz GG, Beach DH |title=Sterols of ketoconazole-inhibited ''Leishmania mexicana mexicana'' promastigotes |journal=Mol Biochem Parasitol |volume=15 |issue=3 |pages=257–79 |date=June 1985 |pmid=4033689 |doi=10.1016/0166-6851(85)90089-1}}</ref><ref>{{cite journal |vauthors =Rodrigues JC, Attias M, Rodriguez C, Urbina JA, Souza W |title=Ultrastructural and Biochemical Alterations Induced by 22,26-Azasterol, a Δ24(25)-Sterol Methyltransferase Inhibitor, on Promastigote and Amastigote Forms of Leishmania amazonensis |journal=Antimicrob Agents Chemother |volume=46 |issue=2 |pages=487–99 |date=February 2002 |pmid=11796362 |pmc=127026 |url=|doi=10.1128/AAC.46.2.487-499.2002}}</ref> |
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==References== |
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==References== |
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<references/> |
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<references/> |
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{{Cholesterol and steroid intermediates}} |
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{{steroid-stub}} |
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{{DEFAULTSORT:Dehydroepisterol, 5-}} |
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{{DEFAULTSORT:Dehydroepisterol, 5-}} |
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{{steroid-stub}} |
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