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Year of first isolation: |
2007 |
| Formula: | C29H44O8 |
| Molecular weight: | 520 |
| Occurence in plants: |
Microsorum scolopendria [Polypodiaceae] »  ![Wikipedia: Microsorum scolopendria [Polypodiaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC1C(C(OC1=O)C)CC(C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)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@](C)([C@@H](CC1[C@@H](OC(=O)[C@H]1C)C)O)O)O)C)C » 
| | IUPAC Name | (3S,4S,5S)-4-[(2R,3R)-2,3-dihydroxy-3-[(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]butyl]-3,5-dimethyloxolan-2-one | | CAS-RN | | | PubChem CID | 11260931 | InChiKey
[ ChemIDPlus: search ] | NEFYSBQJYCICOG-OENMBAOESA-N | | InChI | InChI=1S/C29H44O8/c1-14-16(15(2)37-25(14)34)10-24(33)28(5,35)23-7-9-29(36)18-11-20(30)19-12-21(31)22(32)13-26(19,3)17(18)6-8-27(23,29)4/h11,14-17,19,21-24,31-33,35-36H,6-10,12-13H2,1-5H3/t14-,15-,16-,17-,19-,21+,22-,23-,24+,26+,27+,28+,29+/m0/s1 |
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| HR-MS | | | CI-MS (NH3) m/z | 538 [M+H+NH3]+, 521 [M+H]+, 520 [M+H+NH3-H2O]+, 503 [M+H-H2O]+, 485 [M+H-2H2O]+, 411; 279, 174, 136. |
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| D2O | | 01 | 37.8 | | 02 | 69.8 | | 03 | 69.8 | | 04 | 33.7 | | 05 | 52.8 | | 06 | 211.1 | | 07 | 123.7 | | 08 | n.d. | | 09 | 36.6 | | 10 | 40.8 | | 11 | 22.4 | | 12 | 33.5 | | 13 | 50.0 | | 14 | 87.8 | | 15 | 33.0 | | 16 | 22.4 | | 17 | 51.5 | | 18 | 19.7 | | 19 | 25.7 | | 20 | 80.6 | | 21 | 21.9 | | 22 | 76.8 | | 23 | 31.2 | | 24 | 44.6 | | 25 | 50.7 | | 26 | 187.4 | | 27 | 12.5 | | 28 | 86.3 | | 29 | 21.8 |
| C5D5N | | 01 | 38.2 | | 02 | 68.3 | | 03 | 68.2 | | 04 | 32.6 | | 05 | 51.6 | | 06 | 203.9 | | 07 | 121.8 | | 08 | 166.5 | | 09 | 34.7 | | 10 | 39.0 | | 11 | 21.3 | | 12 | 32.3 | | 13 | 48.7 | | 14 | 84.6 | | 15 | 32.0 | | 16 | 21.6 | | 17 | 50.2 | | 18 | 16.1 | | 19 | 24.7 | | 20 | 77.2 | | 21 | 21.6 | | 22 | 75.5 | | 23 | 29.7 | | 24 | 44.7 | | 25 | 38.9 | | 26 | 180.1 | | 27 | 11.5 | | 28 | 79.6 | | 29 | 20.0 |
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| D2O | | 01-Ha | 1.38 (t, 12.8) | | 01-He | 1.88 | | 02-Ha | 3.99 (w1/2 = 22) | | 03-He | 4.07 (w1/2) = 8) | | 04-Ha | 1.75 | | 04-He | 1.75 | | 05-H | 2.34 (t, 8.8) | | 07-H | 5.97 (d, 2) | | 09-H | 3.11 (w1/2 = 22) | | 11-Ha | 1.73 | | 11-He | 1.86 | | 12-Ha | 1.99* | | 12-He | 1.96* | | 15-Ha | 1.97 | | 15-Hb | 2.07 | | 16-Ha | 1.90* | | 16-Hb | 1.76* | | 17-H | 2.26 (t, 9.2) | | 18-Me | 0.87 (s) | | 19-Me | 1.000 (s) | | 21-Me | 1.250 (s) | | 22-H | 3.54 (dd, 9.9, 2.8) | | 23-Ha | 1.51 | | 23-Hb | 1.49 | | 24-Ha | 2.49 (m) | | 25-H | 3.09 (m) | | 27-Me | 1.175 (d, 7.5) | | 28-Ha | 4.59 (dq, 6.4, 6.2) | | 29-Me | 1.446 (d, 6.4) |
| C5D5N | | 01-Ha | 1.92 | | 01-He | 2.14 | | 02-Ha | 4.17 (w1/2 = 22) | | 03-He | 4.22 (w1/2 = 8) | | 04-Ha | 1.79 | | 04-He | 2.05 | | 05-H | 3.01 (dd, 13.0, 3.9) | | 07-H | 6.27 (d, 2.2) | | 09-H | 3.59 (w1/2 = 22) | | 11-Ha | 1.75 | | 11-He | 1.90 | | 12-Ha | 2.60* | | 12-He | 2.04* | | 15-Ha | 1.93* | | 15-Hb | 2.21* | | 16-Ha | 2.47 (m)* | | 16-Hb | 2.05* | | 17-H | 2.88 (t, 9.2) | | 18-Me | 1.224 (s) | | 19-Me | 1.073 (s) | | 21-Me | 1.221 (s) | | 22-H | 3.86 (db, 9.4) | | 23-Ha | 1.68 | | 23-Hb | 1.7 | | 24-Ha | 2.58 | | 25-H | 3.04 (qui, 8) | | 27-Me | 1.215 (d, 8.1) | | 28-Ha | 4.32 (qui, 6.4) | | 29-Me | 1.243 (d, 6.6) |
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| M.P. | - °C ; | | [α]D20 | +- ° (c ; MeOH) | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | () ; |
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| HPLC | NP-HPLC Kromasil column (250 x 4.6 mm i.d.) solvent dichloro-methane-isopropanol-water (125:30:1.5), flow-rate 1 ml/min, ret. 10.2 min (20E: 27.8 min) ;
RP-HPLC Spherisorb 5ODS2 column (250 x 4.6 mm i.d.) solvent methanol-water (45:55), flow-rate 0.7 ml/min, ret 11.5 min (20E: 10.9 min) | | HPTLC | | | TLC | |
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Permanent link to this datasheet: 24,28-DIEPI-CYASTERONE
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