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Year of first isolation: |
1984 |
| Formula: | C27H44O9S |
| Molecular weight: | 544 |
| Occurence in plants: |
Silene brahuica [Caryophyllaceae] »  ![Wikipedia: Silene brahuica [Caryophyllaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)C(CCC(C)(C)O)OS(=O)(=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@H](C)[C@@H](CCC(C)(C)O)OS(=O)(=O)[O-])O)C)C » 
| | IUPAC Name | [(2S,3R)-6-hydroxy-6-methyl-2-[(2S,3R,5R,9R,10R,13R,14S,17R)-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]heptan-3-yl] sulfate | | CAS-RN | | | PubChem CID | 21607616 | InChiKey
[ ChemIDPlus: search ] | XXYLBDMUDDPFID-LAMJOLGYSA-M | | InChI | InChI=1S/C27H44O9S/c1-15(23(36-37(33,34)35)8-9-24(2,3)31)16-7-11-27(32)18-12-20(28)19-13-21(29)22(30)14-25(19,4)17(18)6-10-26(16,27)5/h12,15-17,19,21-23,29-32H,6-11,13-14H2,1-5H3,(H,33,34,35)/p-1/t15-,16+,17-,19-,21+,22-,23+,25+,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 428 (4), 410 (57), 392 (57), 380 (18), 377 (16), 359 (7), 349 (6), 336 (8), 322 (8), 312 (20), 297 (8), 295 (9), 282 (38), 267 (21), 265 (14), 255 (14), 225 (20), 211 (13), 126 (20), 109 (19), 99 (100), 81 (43), 69 (19). | | FAB-MS (negative-ion mode) m/z (relative intensity %) | 565 (M-H)- (40), 543 (M-Na) (100), 525 (M-Na-H2O) (50) | | HR-MS | |
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| C5D5N | | 01 | 37.8 | | 02 | 68.1 | | 03 | 68.1 | | 04 | 32.0 | | 05 | 51.2 | | 06 | 203.3 | | 07 | 121.5 | | 08 | 165.6 | | 09 | 34.5 | | 10 | 38.6 | | 11 | 21.1 | | 12 | 31.4 | | 13 | 47.6 | | 14 | 83.9 | | 15 | 32.0 | | 16 | 26.5 | | 17 | 48.2 | | 18 | 15.9 | | 19 | 24.4 | | 20 | 39.7 | | 21 | 13.8 | | 22 | 82.9 | | 23 | 24.0 | | 24 | 41.1 | | 25 | 69.8 | | 26 | 30.3 * | | 27 | 29.5 * |
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| C5D5N | | 01-Ha | | | 01-Hb | | | 02-Ha | 4.15 (dt, 12.3, 4.4, 3.5) | | 03-He | 4.23 (br d, w1/2 = 9) | | 04-Ha | | | 04-He | | | 05-H | 3.00 (q, 13.2. 4.4) | | 07-H | 6.2 (d, 2.4) | | 09-Ha | 3.54 (m ) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.79 (s ) | | 19-Me | 1.01 (s ) | | 20-H | 3.09 (m, ?3J 21.4) | | 21-Me | 1.27 (d, 7) | | 22-H | 5.21 (m, ?3J 15.1) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.31 (s ) | | 27-Me | 1.32 (s ) |
| D2O | | 01-Ha | 1.6 | | 01-Hb | 1.9 | | 02-Ha | 3.99 (m, w1/2 = 22) | | 03-He | 4.07 (m, w1/2 = 8) | | 04-Ha | 1.8 | | 04-He | 1.8 | | 05-H | 2.34 (t ) | | 07-H | 5.97 (d, 2.5) | | 09-Ha | 3.11 (m, w1/2 = 22) | | 11-Ha | 1.8 | | 11-He | 1.9 | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 1.9 | | 18-Me | 0.75 (s ) | | 19-Me | 1.00 (s ) | | 20-H | 2.3 (m, w1/2 = 26) | | 21-Me | 0.99 (d, 7) | | 22-H | 4.4 (db, w1/2 = 8) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.23 (s ) | | 27-Me | 1.24 (s ) |
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| M.P. | 224-226 °C | | [α]D20 | + 63.3 ? 2° (c 0.91, MeOH) | | IR (KBr) ν max (cm-1) | 3210-3445 (OH), 1652 (cyclohexenone), 1235 (sulfate) | | UV (EtOH) λ max (log ε) | 245 (4.15) |
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| HPTLC | | | TLC | (on silica), eluent CHCl3-MeOH-H2O (80:32:0.3) | | GLC | | | HPLC | Column Spherisorb 5ODS2, 4.6x250 mm, flow-rate 1 ml.min-1. A-Gradient (in 60 min) 8 to 40% ACN in 0.1% TFA (pH 2), Ret. 16.7 min (E : 33.0 min); B-Isocratic 15% ACN in 0.1% TFA, Ret. 10.5 min (E : 72.2 min); C-Gradient (in 60 min) 8 to 40% ACN in 20 mM Tris-HClO4 (pH 7.5), Ret. 13.8 min (E : 33.0 min) |
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Permanent link to this datasheet: ECDYSONE 22-SULFATE
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