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Year of first isolation: |
1990 |
| Formula: | C29H42O8 |
| Molecular weight: | 490 |
| Occurence in plants: |
Silene otites [Caryophyllaceae] »  ![Wikipedia: Silene otites [Caryophyllaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CCC(C4)O)C)C)O)C(CCC(C)(C)O)OC(=O)C | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H](C1)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(C)(C)O)OC(=O)C)O)C)C » 
| | IUPAC Name | [(2S,3R)-2-[(3S,5R,9R,10R,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-6-methylheptan-3-yl] acetate | | CAS-RN | | | PubChem CID | 15607749 | InChiKey
[ ChemIDPlus: search ] | AXPOMMVUGJHIFF-GTCSVZCFSA-N | | InChI | InChI=1S/C29H46O6/c1-17(25(35-18(2)30)10-11-26(3,4)33)20-9-14-29(34)22-16-24(32)23-15-19(31)7-12-27(23,5)21(22)8-13-28(20,29)6/h16-17,19-21,23,25,31,33-34H,7-15H2,1-6H3/t17-,19-,20+,21-,23-,25+,27+,28+,29+/m0/s1 |
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| CI-MS (NH3) m/z | 508 (M+H+NH3)+, 491 (MH)+, 473 (M+H-18)+, 455, 431, 413, 397, 396 | | EI-MS m/z (relative intensity %) | | | 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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| CD3OD | | 01-Ha | | | 01-Hb | | | 02-Ha | | | 02-He | | | 03-He | 3.96 (m, w1/2=12) | | 04-Ha | | | 04-He | | | 05-H | 2.33 (dd, 12, 4) | | 07-H | 5.80 (d, 2.5) | | 09-Ha | 3.20 | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 14-H | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.70 (s ) | | 19-Me | 0.96 (s ) | | 21-Me | 0.98 (d, 6.5) | | 22-H | 4.87 (d ) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.18 (s ) | | 27-Me | 1.19 (s ) | | Me-CO- | 2.04 (s ) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | |
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| HPTLC | | | TLC | Rf 0.59 (EtOAc/MeOH/NH4OH, 85:10:5) (20E 0.18); Rf 0.57 (CH2Cl2-EtOH, 85:15) (20E 0.15) | | GLC | | | HPLC | NP-HPLC, Retention time 5.4 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2- iPrOH-H2O125:40:3 v/v/v, flow-rate 1 ml.min-1] (20E : 16.8 min); Retention time 8.2 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2- iPrOH-H2O 125:25:2 v/v/v, flow-rate 1 ml.min-1] (20E 37.4 min) |
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Drosophila melanogaster BII cell assay: EC50 = 1.4 x 10-6M |
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Permanent link to this datasheet: 2-DEOXYECDYSONE 22-ACETATE
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