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Year of first isolation: |
1990 |
| Formula: | C40H58O13 |
| Molecular weight: | 746 |
| 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 | CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)OC5C(C(C(C(O5)CO)O)O)O)OC(=O)C6=CC=CC=C6)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O[C@H]1C(C([C@@H](C(O1)CO)O)O)O)OC(=O)c1ccccc1)O)O)C)C » 
| | IUPAC Name | [(2R)-2-hydroxy-6-methyl-2-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-3-yl] benzoate | | CAS-RN | | | PubChem CID | 66869437 | InChiKey
[ ChemIDPlus: search ] | ADATWESZSSNTDT-YEPBJDLISA-N | | InChI | InChI=1S/C40H58O13/c1-36(2,53-35-33(47)32(46)31(45)28(20-41)51-35)14-13-30(52-34(48)21-9-7-6-8-10-21)39(5,49)29-12-16-40(50)23-17-25(42)24-18-26(43)27(44)19-37(24,3)22(23)11-15-38(29,40)4/h6-10,17,22,24,26-33,35,41,43-47,49-50H,11-16,18-20H2,1-5H3/t22-,24-,26+,27-,28+,29-,30?,31+,32-,33+,35?,37+,38+,39+,40+/m0/s1 |
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| CI-MS (NH3) m/z | 747 (MH)+, 729, 643, 625, 607, 463, 445, 427, 363, 345 | | 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 | |
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| CD3OD | | 01-Ha | | | 01-He | | | 02-Ha | 3.82 (m ) | | 03-He | 3.94 (m, w1/2=8) | | 04-Ha | | | 04-He | | | 05-H | 2.37 (dd, 5, 12) | | 07-H | 5.81 (d, 2) | | 09-Ha | ~3.1-3.2 | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.46 (m ) | | 18-Me | 0.88 (s ) | | 19-Me | 0.95 (s ) | | 21-Me | 1.41 (s ) | | 22-H | 5.14 (d br, 10) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.22 (s ) | | 27-Me | 1.22 (s ) | | C6H5-CO- m | 7.49 (t, 7) (2H) | | C6H5-CO- o | 8.08 (t, 7) (2H) | | C6H5-CO- p | 7.61 (t, 7) (1H) | | glu-1´ | 4.41 (d, 7.6) | | glu-2´ | 3.12 | | glu-6´ | 3.78 (dd, 12.3,2.2) | | glu-6´´ | 3.62 |
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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 on silica | Rf 0.48 (EtOAc-EtOH-H2O, 8:2:1) (20E 0.61); Rf 0.25 (CHCl3-MeOH-Me2CO 6:2:1) (20E 0.47) | | GLC | | | NP-HPLC | Retention time 24.6 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O, 125:40:3 v/v/v, flow-rate 1 ml.min-1] (20E : 16.8 min) |
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Permanent link to this datasheet: 20-HYDROXYECDYSONE 22-BENZOATE 25-GLUCOSIDE
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