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Year of first isolation: |
1987 |
| Formula: | C34H48O8 |
| Molecular weight: | 584 |
| Occurence in plants: |
Silene tatarica [Caryophyllaceae] »  ![Wikipedia: Silene tatarica [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)O)O)OC(=O)C5=CC=CC=C5)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)O)O)OC(=O)c1ccccc1)O)C)C » 
| | IUPAC Name | [(2R)-3,6-dihydroxy-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-2-yl] benzoate | | CAS-RN | | | PubChem CID | 18394233 | InChiKey
[ ChemIDPlus: search ] | MVLGAWKWMMILCK-HFIPMGTHSA-N | | InChI | InChI=1S/C34H48O8/c1-30(2,40)14-13-28(38)33(5,42-29(39)20-9-7-6-8-10-20)27-12-16-34(41)22-17-24(35)23-18-25(36)26(37)19-31(23,3)21(22)11-15-32(27,34)4/h6-10,17,21,23,25-28,36-38,40-41H,11-16,18-19H2,1-5H3/t21-,23-,25+,26-,27-,28?,31+,32+,33+,34+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 485 (M - C22-C27) (5), 470 (1), 468 (1), 452 (2), 439 (15), 426 (35), 411 (10), 408 (5), 393 (5), 353 (5), 301 (5), 122 (benzoic acid) (100), 105 (90), 77 (40). | | 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 | | | 28 | | | 29 | |
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| C5D5N | | 01-Ha | | | 01-He | | | 02-Ha | 4.10 (m ) | | 03-He | 4.10 (m ) | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 6.12 | | 09-Ha | 3.45 (m ) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 14-H | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 1.08 (s ) | | 19-Me | 0.97 (s ) | | 21-Me | 1.65 (s ) | | 22-H | 3.66 (m ) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | 1.22 (s ) | | 27-Me | 1.22 (s ) |
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| M.P. | 232-233 °C | | [α]D20 | + 34.4 ? 2 ° (c 0.9 ; MeOH). | | IR (KBr) ν max (cm-1) | 3400-3480 (OH), 1665 (cyclohexenone), 1710, 1287 (benzyl est | | UV (EtOH) λ max (log ε) | 232 (4.08) |
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Galleria mellonella in vivo assay: ED50 = 15.6 ug/g | Sarcophaga bullata in vivo assay: ED50 = 2.6 ug/g |
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Permanent link to this datasheet: 20-HYDROXYECDYSONE 20-BENZOATE
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