:5-Dehydroepisterol

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| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 444444056

| ImageFile=5-Dehydroepisterol.png

| ImageSize=220px

| ImageFile1 = 5-Dehydroepisterol molecule ball.png

| ImageSize1 = 250

| ImageAlt1 = Ball-and-stick model of 5-dehydroepisterol

| IUPACName=Campesta-5,7,24(241)-trien-3β-ol

| SystematicName=(1R,3aR,7S,9aR,9bS,11aR)-9a,11a-Dimethyl-1-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,3a,6,7,8,9,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[a]phenanthren-7-ol

| OtherNames=24-Methylcholesta-5,7,24(28)-trienol, ergosta-5,7,24(28)-trien-3β-ol, campesta-7,24(28)-dien-3β-ol

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo=23582-83-4

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG=C15780

| PubChem = 10894570

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 9069833

| SMILES = O[C@@H]4C/C3=C/C=C1\[C@H](CC[C@]2([C@H]1CC[C@@H]2[C@H](C)CCC(=C)/C(C)C)C)[C@@]3(C)CC4

| 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

| InChIKey = ZEPNVCGPJXYABB-LOIOQLKMBD

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = ZEPNVCGPJXYABB-LOIOQLKMSA-N

}}

|Section2={{Chembox Properties

| Formula=C28H44O

| MolarMass=396.648 g·mol−1

| Appearance=

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|Section3={{Chembox Hazards

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5-Dehydroepisterol is a sterol and an intermediate in steroid biosynthesis, particularly synthesis of brassinosteroids.{{KEGG pathway|ko00100}} It is formed from episterol through action of ERG3, the C-5 sterol desaturase in the yeast{{KEGG reaction|R07491}} and is then converted into 24-methylenecholesterol by 7-dehydrocholesterol reductase.{{KEGG reaction|R07492}}

Episterol and 5-dehydroepisterol are found in Leishmania.{{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}}{{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}}

References

{{Cholesterol and steroid intermediates}}

{{steroid-stub}}

{{DEFAULTSORT:Dehydroepisterol, 5-}}

Category:Sterols