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Year of first isolation: |
2000 |
| Formula: | C27H44O5 |
| Molecular weight: | 448 |
| Occurence in plants: |
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| Occurence in animals: |
Bombyx mori [Bombycidae] »  ![Wikipedia: Bombyx mori [Bombycidae]](/images/wikipedia.png)
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| Canonical SMILES | | 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[C@@H](CC(C)(C)O)O)O)C)C » 
| | IUPAC Name | (3S,5R,9R,10R,13R,14S,17R)-17-((2R,4S)-4,6-dihydroxy-6-methylheptan-2-yl)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | | InChiKey
[ ChemIDPlus: search ] | DOODXECBAIMQQQ-SKYCAMSBSA-N | | InChI | InChI=1S/C27H44O5/c1-16(12-18(29)15-24(2,3)31)19-8-11-27(32)21-14-23(30)22-13-17(28)6-9-25(22,4)20(21)7-10-26(19,27)5/h14,16-20,22,28-29,31-32H,6-13,15H2,1-5H3/t16-,17+,18+,19-,20+,22+,25-,26-,27-/m1/s1 |
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| EI-MS m/z (relative intensity %) | 448 [M]+, 430, 420, 415, 412, 402, 397, 384, 346, 344, 313 (C20 -C22 cleavage - H2O), 303 (C17-C20 cleavage), 285 (C17-C20 cleavage - H2O), 273, 257, 233, 215, 207 | | FAB-MS m/z | 449 [M+H]+ |
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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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| CD3OD | | 01-Ha | | | 01-He | | | 02-Ha | | | 02-He | | | 03-He | 3.97 (m, w1/2 = 9) | | 04-Ha | | | 04-He | | | 05-H | 2.41 (dd, 12.8, 3.7) | | 07-H | 5.80 (d, 2.4) | | 09-H | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.719 (s) | | 19-Me | 0.959 (s) | | 20-H | | | 21-Me | 0.993 (d, 5.9) | | 22-Ha | | | 23-H | 4.03 (m) | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | 1.276 (s) | | 27-Me | 1.236 (s) |
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| M.P. | - °C ; | | [α]D20 | ? ° (c ; MeOH) | | IR (KBr) ν max (cm-1) | | | UV (MeOH) λ max (log ε) | 243 nm (-) ; |
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| HPLC | RP-HPLC column Wakosil 5C18, 250x4.6 mm, flow-rate 1 ml/min, solvent 50% aqueous MeOH for 30 min, then 60% MeOH, Ret 51.5 min (2dE 25.0 min); solvent 55% MeOH, Ret 53.3 min (2dE 18.6 min). | | GLC | | | TLC | Merck Kieselgel 60 F254 (20x20 cm, 1 mm thick), developed twice with CHCl3-MeOH (4:1, v/v), Rf 0.75 (2dE 0.79) |
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Permanent link to this datasheet: 2,22-DIDEOXY-23-HYDROXYECDYSONE
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