THC Science

5-Dehydroepisterol
Names
	IUPAC name Campesta-5,7,24(241)-trien-3β-ol
	Systematic IUPAC name (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
	Other names 24-Methylcholesta-5,7,24(28)-trienol, ergosta-5,7,24(28)-trien-3β-ol, campesta-7,24(28)-dien-3β-ol
Identifiers
CAS Number	23582-83-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	9069833 ;
KEGG	C15780 ;
PubChem CID	10894570;
CompTox Dashboard (EPA)	DTXSID90447480 ;
	InChI InChI=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 Key: ZEPNVCGPJXYABB-LOIOQLKMSA-N ; 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 Key: ZEPNVCGPJXYABB-LOIOQLKMBD;
	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;
Properties
Chemical formula	C28H44O
Molar mass	396.648 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

5-Dehydroepisterol is a sterol and an intermediate in steroid biosynthesis, particularly synthesis of brassinosteroids.^[1] It is formed from episterol through action of ERG3, the C-5 sterol desaturase in the yeast^[2] and is then converted into 24-methylenecholesterol by 7-dehydrocholesterol reductase.^[3]

Episterol and 5-dehydroepisterol are found in Leishmania.^[4]^[5]

References[edit]

^ Pathway ko00100 at KEGG Pathway Database.
^ Reaction R07491 at KEGG Pathway Database.
^ Reaction R07492 at KEGG Pathway Database.
^ Goad LJ, Holz GG, Beach DH (June 1985). "Sterols of ketoconazole-inhibited Leishmania mexicana mexicana promastigotes". Mol Biochem Parasitol. 15 (3): 257–79. doi:10.1016/0166-6851(85)90089-1. PMID 4033689.
^ Rodrigues JC, Attias M, Rodriguez C, Urbina JA, Souza W (February 2002). "Ultrastructural and Biochemical Alterations Induced by 22,26-Azasterol, a Δ24(25)-Sterol Methyltransferase Inhibitor, on Promastigote and Amastigote Forms of Leishmania amazonensis". Antimicrob Agents Chemother. 46 (2): 487–99. doi:10.1128/AAC.46.2.487-499.2002. PMC 127026. PMID 11796362.

Names


IUPAC name Campesta-5,7,24(24¹)-trien-3β-ol
Systematic IUPAC name (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
Other names 24-Methylcholesta-5,7,24(28)-trienol, ergosta-5,7,24(28)-trien-3β-ol, campesta-7,24(28)-dien-3β-ol
Identifiers
CAS Number	23582-83-4^Y
3D model (JSmol)	Interactive image
ChemSpider	9069833^N
KEGG	C15780^Y
PubChem CID	10894570
CompTox Dashboard (EPA)	DTXSID90447480
InChI InChI=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^N Key: ZEPNVCGPJXYABB-LOIOQLKMSA-N^N 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 Key: ZEPNVCGPJXYABB-LOIOQLKMBD
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
Properties
Chemical formula	C₂₈H₄₄O
Molar mass	396.648 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references