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Year of first isolation: |
2008 |
Formula: | C43H62O14 |
Molecular weight: | 802 |
Occurence in plants: |
Microsorum membranifolium [Polypodiaceae] »
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Occurence in animals: |
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Canonical SMILES | | Isomeric SMILES [ PubChem: search | XML ] [ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H](C1)OC(=O)/C=C/c1cc(c(cc1)O[C@H]1C(C([C@@H](C(O1)CO)O)O)O)OC)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O)C)C »
| IUPAC Name | (3S,5R,9R,10R,13R,14S,17S)-14-hydroxy-10,13-dimethyl-6-oxo-17-((2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl)-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl (E)-3-(3-methoxy-4-(((2S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)acrylate | CAS-RN | | PubChem CID | | InChiKey [ ChemIDPlus: search ] | HVDSIPJIWNFTLE-OZUXEFNISA-N | InChI | InChI=1S/C43H62O14/c1-39(2,51)15-14-33(46)42(5,52)32-13-18-43(53)26-21-28(45)27-20-24(11-16-40(27,3)25(26)12-17-41(32,43)4)55-34(47)10-8-23-7-9-29(30(19-23)54-6)56-38-37(50)36(49)35(48)31(22-44)57-38/h7-10,19,21,24-25,27,31-33,35-38,44,46,48-53H,11-18,20,22H2,1-6H3/b10-8+/t24-,25-,27-,31?,32-,33+,35+,36?,37?,38+,40+,41+,42+,43+/m0/s1 |
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HR-MS | | EI-MS m/z (relative intensity %) | | FAB-MS m/z | 841 [M+K] +, 825 [M+Na]+, 803 [MH]+, 785 [MH-H2O]+, 767 [MH-2H2O]+, 749 [MH-3H2O]+, 641 [MH-sugar]+, 623 [MH-sugar-H2O]+, 605 [MH-sugar-2H2O]+, 447 [ecdysteroid core+H-H2O]+, 429, 411, 393, 345, 329, 327, 309, 241 |
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CD3OD | 01 | 30.1 | 02 | 26.3 | 03 | 69.4 | 04 | 26.3 | 05 | 53.0 | 06 | 206.1 | 07 | 121.7 | 08 | | 09 | 37.3 | 10 | 37.3 | 11 | 21.4 | 12 | 32.5 | 13 | 49.0 | 14 | 85.4 | 15 | 31.7 | 16 | 21.4 | 17 | 50.5 | 18 | 17.9 | 19 | 24.2 | 20 | 77.7 | 21 | 20.8 | 22 | 78.3 | 23 | 27.3 | 24 | 42.2 | 25 | 71.1 | 26 | 29.0 | 27 | 29.3 | [CH3-O] | 56.7 | [Ferulate] 1'' | 130.4 | [Ferulate] 2'' | 112.3 | [Ferulate] 3'' | 150.7 | [Ferulate] 4'' | 149.5 | [Ferulate] 5'' | 117.1 | [Ferulate] 6'' | 123.4 | [Ferulate] 7'' | 145.8 | [Ferulate] 8'' | 117.5 | [Ferulate] 9'' | 168.0 | [sugar] 1' | 102.1 | [sugar] 2' | 74.85 | [sugar] 3' | 77.6 | [sugar] 4' | 71.29 | [sugar] 5' | 78.06 | [sugar] 6' | 62.41 |
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CD3OD | 01-Ha | 1.46 | 01-He | 1.76 | 02-Ha | 1.87 | 02-He | 1.94 | 03-He | 5.18 (m, w1/2 = 13) | 04-Ha | 1.77 | 04-He | 1.87 | 05-H | 2.40 (dd, 12.3, 4) | 07-H | 5.84 (d, 2.4) | 09-H | 3.27 | 11-Ha | 1.68 | 11-He | 1.76 | 12-Ha | 2.15 (dt, 13.8, 4.8) | 12-He | 1.88 | 15-Ha | 2.00 | 15-Hb | 1.63 | 16-Ha | 2.00 | 16-Hb | 1.76 | 17-H | 2.42 (t, 9.9) | 18-Me | 0.907 (s) | 19-Me | 0.97(s) | 21-Me | 1.203 (s) | 22-H | 3.35 | 23-Ha | 1.31 | 23-Hb | 1.69 | 24-Ha | 1.81 | 24-Hb | 1.46 | 26-Me | 1.197 (s) | 27-Me | 1.211 (s) | [Ferulate] 2f | 7.31 (s, w1/2 = 3) | [Ferulate] 5f | 7.19 AA' | [Ferulate] 6f | 7.19 AA' | [Ferulate] 7f | 7.66 (d, 15.8) | [Ferulate] 8f | 6.50 (d, 15.8) | [Ferulate] MeO-3f | 3.92 (s) | [sugar] 1' | 4.98 (d, 7.3) | [sugar] 2' | 3.53 (dd, 7.5, 9) | [sugar] 3' | 3.48 (t, 9) | [sugar] 4' | 3.43 (dd, 9.5, 8.6) | [sugar] 5' | 3.45 (ddd, 9.5, 5.2, 2.2) | [sugar] 6' | 3.70 (dd, 12, 5) | [sugar] 6'' | 3.89 (dd, 12.2, 1.8) |
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M.P. | °C ; | [α]D20 | ° (c ; MeOH) | IR (KBr) ν max (cm-1) | | UV (EtOH) λ max (log ε) | 240, 294, 317 () ; |
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HPLC | RP-HPLC column ACE C18 (15x0.46 cm) eluted with a linear gradient (15 to 35% acetonitrile/isopropanol (5/2) in 0.1% TFA over 40 min, flow rate 1 mL/min, Ret 32.9 min (20E 9.8 min, 2dE 25.8 min)NP-HPLC column Zorbax-SIL (25x0.46 cm), eluted with cyclohexane/isopropanol/water (100/50/3), flow-rate 1 mL/min, Ret 34.3 min (20E 17.1 min, 2dE 8.5 min) | HPTLC | | TLC | |
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Permanent link to this datasheet: 2-DEOXY-20-HYDROXYECDYSONE 3-[4-(1-β-D-GLUCOPYRANOSYL)]-FERULATE
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