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Year of first isolation: |
2005 |
| Formula: | C29H44O8 |
| Molecular weight: | 520 |
| Occurence in plants: |
Cyathula capitata [Amaranthaceae] »  ![Wikipedia: Cyathula capitata [Amaranthaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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![25-EPI,28-EPI-CYASTERONE [cf. 28-EPI-ISOCYASTERONE]](images/ecdy/385.gif)
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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](C[C@H]1[C@H](C(=O)O[C@H]1C)C)O)O)O)C)C » 
| | IUPAC Name | (3R,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 | 11455183 | InChiKey
[ ChemIDPlus: search ] | NEFYSBQJYCICOG-LGVKSGJWSA-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-/m1/s1 |
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| EI-MS m/z (relative intensity %) | | | CI-MS (NH3) m/z | | | HR-FABMS m/z | 521.3109 [M+H]+, C29H45O8 requires 521.3114 |
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| C5D5N | | 01 | 37.9 | | 02 | 68.1 | | 03 | 68.0 | | 04 | 32.4 | | 05 | 51.3 | | 06 | 203.4 | | 07 | 121.6 | | 08 | 165.8 | | 09 | 34.4 | | 10 | 38.6 | | 11 | 21.0 | | 12 | 31.9 | | 13 | 48.0 | | 14 | 84.0 | | 15 | 31.7 | | 16 | 21.6 | | 17 | 49.9 | | 18 | 17.7 | | 19 | 24.4 | | 20 | 76.6 | | 21 | 21.3 | | 22 | 74.9 | | 23 | 26.6 | | 24 | 39.8 | | 25 | 39.5 | | 26 | 180.0 | | 27 | 17.4 | | 28 | 78.6 | | 29 | 12.8 |
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| C5D5N | | 01-Ha | 1.94 | | 01-He | 2.15 (dd, 13.1, 4.7) | | 02-Ha | 4.19 (brd, 11.5) | | 03-He | 4.23 (brs, w1/2=7.4) | | 04-Ha | 1.81 | | 04-He | 2.03 | | 05-H | 3.02 (dd, 13.2, 3.7) | | 07-H | 6.27 (d, 2.1) | | 09-H | 3.59 (brt, 9.9) | | 11-Ha | 1.74 | | 11-He | 1.89 | | 12-Ha | 2.57 (td, 13.0, 4.2) | | 12-He | 1.98 | | 15-Ha | 1.89 | | 15-Hb | 2.18 | | 16-Ha | 2.49 (m) | | 16-Hb | 2.05 | | 17-H | 2.89 | | 18-Me | 1.22 (s) | | 19-Me | 1.08 (s) | | 21-Me | 1.59 (s) | | 22-H | 3.82 (brd, 11.5) | | 23-Ha | 1.69 | | 23-Hb | 1.85 | | 24-H | 3.14 | | 25-H | 2.89 (m) | | 27-Me | 1.28 (d, 7.5) | | 28-H | 4.65 (qui, 6.7) | | 29-Me | 1.29 (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) | 241.2 (4.11) ; |
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| HPLC | RP-HPLC, column Shimadzu STR PREP-ODS, 6x15 mm i.d.), solvent MeOH-H2O (10:8), flow-rate 1 ml.min-1, ret. 17.2 min (cyasterone : 13.8 min) | | GLC | | | HPTLC | | | TLC | Silica plates, solvent CHCl3-MeOH (10:1), developed 3 times, Rf 0.35 |
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Permanent link to this datasheet: 25-EPI,28-EPI-CYASTERONE [cf. 28-EPI-ISOCYASTERONE]
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