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Year of first isolation: |
1979 |
| Formula: | C27H42O5 |
| Molecular weight: | 446 |
| Occurence in plants: |
Silene praemixta [Caryophyllaceae] »  ![Wikipedia: Silene praemixta [Caryophyllaceae]](/images/wikipedia.png)
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| Occurence in animals: |
Locusta migratoria [Orthoptera] »
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![SILENOSTERONE [= 3-DEHYDRO-2-DEOXYECDYSONE]](images/ecdy/291.gif)
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| Canonical SMILES | CC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CCC(=O)C4)C)C)O)C(CCC(C)(C)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](CC(=O)C1)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(C)(C)O)O)O)C)C » 
| | IUPAC Name | (5R,9R,10R,13R,14S,17R)-17-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-14-hydroxy-10,13-dimethyl-1,2,4,5,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthrene-3,6-dione | | CAS-RN | | | PubChem CID | 15251159 | InChiKey
[ ChemIDPlus: search ] | PDQPHVPWJVSDEA-IHTFJKPZSA-N | | InChI | InChI=1S/C27H42O5/c1-16(22(29)9-10-24(2,3)31)18-8-13-27(32)20-15-23(30)21-14-17(28)6-11-25(21,4)19(20)7-12-26(18,27)5/h15-16,18-19,21-22,29,31-32H,6-14H2,1-5H3/t16-,18+,19-,21-,22+,25+,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 446 (M)+ (0.3), 428 (5), 413 (4), 410 (8), 400 (3), 395 (10), 377 (3), 359 (3), 341 (8), 330 (7), 312 (10), 297 (10), 283 (14), 282 (16), 261 (10), 233 (33), 232 (25), 231 (17), 99 (100), 81 (92). | | HR-MS | |
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| C5D5N | | 01 | | | 02 | | | 03 | | | 04 | | | 05 | | | 06 | | | 07 | | | 08 | | | 09 | | | 10 | | | 11 | | | 12 | | | 13 | | | 14 | | | 15 | | | 16 | | | 17 | | | 18 | | | 19 | | | 20 | | | 21 | | | 22 | | | 23 | | | 24 | | | 25 | | | 26 | | | 27 | |
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| C5D5N | | 01-Ha | | | 01-Hb | | | 02-Ha | | | 03-He | | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 6.00 | | 09-Ha | 3.45 | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.60 (s ) | | 19-Me | 0.94 (s ) | | 21-Me | 1.15 (d ) | | 22-H | 3.90 | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.25 (s ) | | 27-Me | 1.25 (s ) |
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| M.P. | 115-117 °C | | [α]D28 | + 86.9 ? 2° (c 0.92; MeOH) | | IR (KBr) ν max (cm-1) | 3420 (OH), 1710 (CO), 1660 (cyclohexenone) | | UV (EtOH) λ max (log ε) | 246 (4.05) |
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| HPTLC | | | TLC | on silica gel : Rf 0.46 (CHCl3-EtOH 9:1) | | GLC | | | HPLC | |
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Drosophila melanogaster BII cell assay: EC50 = 4.6 x 10-5M |
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| First isolation | SAATOV, Z. et al. (1979) Khim. Prir. Soedin., 793-797 |
 | | General | TSOUPRAS, G. et al. (1982) Thesis, Strasbourg, France |
| | General | TSOUPRAS, G. et al. (1983) Tetrahedron 39, 1789-1796 |
| | Bioactivities | DINAN, L. et al. (2003) In: Studies in Natural Products Chemisty (ed. Atta-ur-Rahman), Elsevier, Amsterdam, 29, 3-71 |
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Permanent link to this datasheet: SILENOSTERONE [= 3-DEHYDRO-2-DEOXYECDYSONE]
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