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Year of first isolation: |
1990 |
| Formula: | C41H52O9 |
| Molecular weight: | 688 |
| Occurence in plants: |
Silene scabrifolia [Caryophyllaceae] »  ![Wikipedia: Silene scabrifolia [Caryophyllaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)OC(=O)C5=CC=CC=C5)OC(=O)C6=CC=CC=C6)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)OC(=O)c1ccccc1)OC(=O)c1ccccc1)O)O)C)C » 
| | IUPAC Name | [(2R,3R)-6-benzoyloxy-2-hydroxy-6-methyl-2-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]heptan-3-yl] benzoate | | CAS-RN | | | PubChem CID | 21626592 | InChiKey
[ ChemIDPlus: search ] | JYQAIQIHWVPEBH-YGSULJDDSA-N | | InChI | InChI=1S/C41H52O9/c1-37(2,50-36(46)26-14-10-7-11-15-26)19-18-34(49-35(45)25-12-8-6-9-13-25)40(5,47)33-17-21-41(48)28-22-30(42)29-23-31(43)32(44)24-38(29,3)27(28)16-20-39(33,41)4/h6-15,22,27,29,31-34,43-44,47-48H,16-21,23-24H2,1-5H3/t27-,29-,31+,32-,33-,34+,38+,39+,40+,41+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 548 (M - C6H5COOH)+ (0.8), 530 (1), 515 (0.2), 512 (0.2), 479 (0.2), 467 (0.2), 462 (0.4), 450 (2.8), 444 (5), 426 (28), 408 (30), 393 (13), 375 (30), 363 (42), 357 (28), 345 (28), 329 (13), 301 (30), 250 (50), 163 (30), 122 (98), 105 (100), 99 (17), 81 (30), 77 (54), 51 (50). | | HR-MS | |
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| C5D5N | | 01 | 37.9 | | 02 | 68.0 | | 03 | 68.0 | | 04 | 32.2 | | 05 | 51.4 | | 06 | 202.2 | | 07 | 121.0 | | 08 | 165.5 | | 09 | 34.3 | | 10 | 38.7 | | 11 | 21.5 | | 12 | 31.8 | | 13 | 48.0 | | 14 | 83.8 | | 15 | 31.8 | | 16 | 22.2 | | 17 | 50.4 | | 18 | 17.5 | | 19 | 24.3 | | 20 | 76.5 | | 21 | 21.2 | | 22 | 80.9 | | 23 | 25.4 | | 24 | 39.1 | | 25 | 82.3 | | 26 | 25.6 | | 27 | 25.9 | | C6H5- | 1' 131.7, 131.7; 2', 6' 129.8; 130.1; | | contin. | 3´,5´ 128.8, 128.8; 4´ 133.0, 133.1 | | O-C=O | 166.9 |
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| C5D5N | | 01-Ha | | | 01-He | | | 02-Ha | 4.0-4.3 | | 03-He | 4.0-4.3 | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 6.22 | | 09-Ha | 3.52 | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 1.18 | | 19-Me | 1.06 | | 21-Me | 1.73 | | 22-H | 5.66 | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.54 | | 27-Me | 1.54 | | C6H5-CO- | 7.39 (6H), 8.25 (4H) |
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| M.P. | | | [α]D20 | + 80.1 ? 2 ° (c 0.22 , MeOH) | | IR (KBr) ν max (cm-1) | 3460-3520 (OH), 1670 (C=O), 1720, 1295, 1610, 1590, 730 (ben | | UV (EtOH) λ max (log ε) | 235 (4.10) ; |
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Galleria mellonella in vivo assay: ED50 = 31.2 ug/g | Sarcophaga bullata in vivo assay: ED50 = 104.0 ug/g |
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Permanent link to this datasheet: 20-HYDROXYECDYSONE 22,25-DIBENZOATE
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