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Year of first isolation: |
2012 |
| Formula: | C42H60O14 |
| Molecular weight: | 788 |
| Occurence in plants: |
Microsorum membranifolium [Polypodiaceae] »  ![Wikipedia: Microsorum membranifolium [Polypodiaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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![E-2-DEOXY-20-HYDROXYECDYSONE 3-[4-(1-β-D-GLUCOPYRANOSYL)]-CAFFEATE](images/ecdy/509.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)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)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-hydroxy-4-(((2S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)acrylate | | CAS-RN | | | PubChem CID | | InChiKey
[ ChemIDPlus: search ] | NMXNBBASNVMDAZ-QDTHBUKISA-N | | InChI | InChI=1S/C42H60O14/c1-38(2,51)14-13-32(46)41(5,52)31-12-17-42(53)25-20-27(44)26-19-23(10-15-39(26,3)24(25)11-16-40(31,42)4)54-33(47)9-7-22-6-8-29(28(45)18-22)55-37-36(50)35(49)34(48)30(21-43)56-37/h6-9,18,20,23-24,26,30-32,34-37,43,45-46,48-53H,10-17,19,21H2,1-5H3/b9-7+/t23-,24-,26-,30?,31-,32+,34+,35?,36?,37+,39+,40+,41+,42+/m0/s1 |
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| HR-ESI-MS | 811.38726 [M+Na]+, calculated for C42H60O14Na, 811.38753 | | CI-MS (NH3) m/z | | | ESI-MS m/z (relative intensity %) | |
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| CD3OD | | 01 | 30.1 | | 02 | | | 03 | 69.5 | | 04 | | | 05 | 53.1 | | 06 | | | 07 | 121.8 | | 08 | | | 09 | 37.8 | | 10 | | | 11 | | | 12 | 32.4 | | 13 | 49.0 | | 14 | 85.6 | | 15 | 31.6 | | 16 | 21.4 | | 17 | 50.5 | | 18 | 17.9 | | 19 | 24.2 | | 20 | 77.7 | | 21 | 20.9 | | 22 | 78.3 | | 23 | 27.3 | | 24 | 42.3 | | 25 | 71.3 | | 26 | 28.9 | | 27 | 29.7 | | C-1' | 103.3 | | C-1'' | 131.0 | | C-2' | 74.6 | | C-2'' | 115.9 | | C-3' | 77.5 | | C-3'' | 148.4 | | C-4' | 71.2 | | C-4'' | 148.7 | | C-5' | 78.1 | | C-5'' | 117.9 | | C-6' | 62.3 | | C-6'' | 122.2 | | C-7'' | 146.0 | | C-8'' | 117.3 | | C-9'' | 168.1 |
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| CD3OD | | 01-Ha | | | 01-He | | | 02-Ha | | | 02-He | | | 03-He | 5.16 (br, s, w1/2=13) | | 04-Ha | 1.77 | | 04-He | 1.87 | | 05-H | 2.38 (dd, 12.3, 4.0) | | 07-H | 5.84 (d, 2.1) | | 09-H | 3.28 H-2 | | 11-Ha | 1.68 H-5 | | 11-He | 1.76 H-6 | | 12-Ha | 2.15 H-7 | | 12-He | 1.86 H-8 | | 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 | 0.908 (s) | | 19-Me | 1.010 (s) | | 21-Me | 1.203 (s) | | 22-H | 3.36 | | 23-Ha | 1.31 | | 23-Hb | 1.69 | | 24-Ha | 1.81 | | 24-Hb | 1.44 | | 26-Me | 1.197 (s) | | 27-Me | 1.211 (s) | | H-1' | 4.86 (d, 7.3) | | H-2' | 3.53 | | H-2'' | 7.14 (d, 1.8) | | H-3' | 3.48 | | H-4' | 3.42 | | H-5' | 3.46 | | H-5'' | 7.21 (d, 8.6) | | H-6' (Ha) | 3.72 (dd, 12.5, 5.3) | | H-6' (He) | 3.91 (dd, 12.2, 1.8) | | H-6'' | 7.08 (dd, 8.3, 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) | 242, 290, 313 () ; |
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| HPLC | RP-HPLC column ACE C18 (150 mm, 4.6 mm i.d., particle size 5 m), eluted with a linear gradient (15% to 35% acetonitrile/isopropanol [5:2 v/v] in water containing 0.1% trifluoroacetic acid in 40 min, flow-rate of 1 mL/min (Ret 25.7 min, 20E 7.5 min).NP-HPLC column ACE 5 SIL (150 mm, 4.6 mm i.d., particle), eluted at a flow-rate of 1 mL/min with dichloromethane-isopropanol-water (125:30:2, v/v/v) (Ret 15.9 min, 20E 16.0 min) or with cyclohexane-isopropanol-water (100:40:3, v/v/v) (Ret 15.6 min, 20E 9.4 min). | | NP-HPLC | NP-HPLC column ACE 5 SIL (150 mm, 4.6 mm i.d., particle), eluted at a flow-rate of 1 mL/min with dichloromethane-isopropanol-water (125:30:2, v/v/v) (Ret 15.9 min, 20E 16.0 min) or with cyclohexane-isopropanol-water (100:40:3, v/v/v) (Ret 15.6 min, 20E 9.4 min). |
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Permanent link to this datasheet: E-2-DEOXY-20-HYDROXYECDYSONE 3-[4-(1-β-D-GLUCOPYRANOSYL)]-CAFFEATE
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