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Year of first isolation: |
2008 |
| Formula: | C43H62O13 |
| Molecular weight: | 786 |
| Occurence in plants: |
Microsorum membranifolium [Polypodiaceae] »  ![Wikipedia: Microsorum membranifolium [Polypodiaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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![2-DEOXYECDYSONE 3-[4-(1-β-D-GLUCOPYRANOSYL)]-FERULATE](images/ecdy/425.gif)
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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@H](C)[C@@H](CCC(C)(C)O)O)O)C)C » 
| | IUPAC Name | (3S,5R,9R,10R,13R,14S,17R)-17-((2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl)-14-hydroxy-10,13-dimethyl-6-oxo-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 ] | KAQKBWAFKZDSON-JNKOWYEPSA-N | | InChI | InChI=1S/C43H62O13/c1-23(30(45)14-15-40(2,3)51)26-13-18-43(52)28-21-31(46)29-20-25(11-16-41(29,4)27(28)12-17-42(26,43)5)54-35(47)10-8-24-7-9-32(33(19-24)53-6)55-39-38(50)37(49)36(48)34(22-44)56-39/h7-10,19,21,23,25-27,29-30,34,36-39,44-45,48-52H,11-18,20,22H2,1-6H3/b10-8+/t23-,25-,26+,27-,29-,30+,34?,36+,37?,38?,39+,41+,42+,43+/m0/s1 |
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| HR-MS | | | EI-MS m/z (relative intensity %) | | | FAB-MS m/z | 825 [M+K] +, 809 [M+Na]+, 787 [MH]+, 769 [MH-H2O]+, 751 [MH-2H2O]+, 625 [MH-sugar]+, 607 [MH-sugar-H2O]+, 431 [ecdysteroid core+H-H2O]+, 413, 395, 377 |
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| CD3OD | | 01 | 30.1 | | 02 | 26.3 | | 03 | 69.4 | | 04 | 30.3 | | 05 | 53.1 | | 06 | 205.6 | | 07 | 121.5 | | 08 | | | 09 | 37.4 | | 10 | 37.4 | | 11 | 21.5 | | 12 | 32.0 | | 13 | 48.2 | | 14 | 85.4 | | 15 | 31.6 | | 16 | 26.9 | | 17 | 48.6 | | 18 | 15.9 | | 19 | 24.2 | | 20 | 43.3 | | 21 | 13.0 | | 22 | 75.0 | | 23 | 25.2 | | 24 | 42.2 | | 25 | 71.1 | | 26 | 29.0 | | 27 | 29.3 | | [Ferul] 1'' | 130.4 | | [Ferul] 2'' | 112.3 | | [Ferul] 3'' | 150.7 | | [Ferul] 4'' | 149.5 | | [Ferul] 5'' | 117.1 | | [Ferul] 6'' | 123.4 | | [Ferul] 8'' | 117.5 | | [Ferul] 9'' | 168.0 | | [Ferul] CH3-O | 56.7 | | [glu] 1' | 102.1 | | [glu] 2' | 74.85 | | [glu] 3' | 77.6 | | [glu] 4' | 71.29 | | [glu] 5' | 78.06 | | [glu] 6' | 62.2 |
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| CD3OD | | 01-Ha | 1.46 | | 01-He | 1.76 | | 02-Ha | 1.87 | | 02-He | 1.94 | | 03-He | 5.16 (m, w1/2 = 14) | | 04-Ha | 1.77 | | 04-He | 1.87 | | 05-H | 2.41 (dd, 12.6, 4.2) | | 07-H | 5.85 (d, 2.0) | | 09-H | 3.27 (m, w1/2 = 26) | | 11-Ha | 1.67 | | 11-He | 1.78 | | 12-Ha | 2.13 (dt, 13.4, 5) | | 12-He | 1.78 | | 15-Ha | 1.98 | | 15-Hb | 1.62 | | 16-Ha | 1.98 | | 16-Hb | 1.51 | | 17-H | 2.06 | | 18-Me | 0.745 (s) | | 19-Me | 1.01 (s) | | 20-H | 1.77 | | 21-Me | 0.957 (d, 6.6) | | 22-H | 3.61 (d, br, 10.1) | | 23-Ha | 1.33 | | 23-Hb | 1.55 | | 24-Ha | 1.79 | | 24-Hb | 1.42 | | 26-Me | 1.20 (s) | | 27-Me | 1.21 (s) | | [Ferul] 2f | 7.31 (s, w1/2 = 3) | | [Ferul] 5f | 7.19 AA' | | [Ferul] 7f | | | [Ferul] 8f | | | [Ferul] MeO | | | [glu] 1' | 4.98 (d, 7.3) | | [glu] 2' | 3.53 (dd, 7.5, 9) | | [glu] 3' | 3.48 (t, 9) | | [glu] 4' | 3.43 (dd, 9.5, 8.6) | | [glu] 5' | 3.45 (ddd, 9.5, 5.2, 2.2) | | [glu] 6' | 3.70 (dd, 12, 5) | | [glu] 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, 394, 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 39.2 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 26.4 min (20E 17.1 min, 2dE 8.5 min) | | HPTLC | | | TLC | |
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Permanent link to this datasheet: 2-DEOXYECDYSONE 3-[4-(1-β-D-GLUCOPYRANOSYL)]-FERULATE
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