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Year of first isolation: |
2004 |
| Formula: | C29H44O8 |
| Molecular weight: | 520 |
| Occurence in plants: |
Eriophyton wallchii [Lamiaceae (alt. Labiatae)] »  ![Wikipedia: Eriophyton wallchii [Lamiaceae (alt. Labiatae)]](/images/wikipedia.png)
Cyathula capitata [Amaranthaceae] »
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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 | (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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| EI-MS m/z (relative intensity %) | | | FAB-MS m/z | 521 [M+1]+, 503 [M+1-H2O]+, 485 [M+1-H2O]+, 449, 431, 363, 347, 345, 303, 285, 249, 201, 183, 157, 121 | | HR-FABMS m/z | 521.3152 [M+H]+, C29H45O8 requires 521.3114 | | HRAPCIMS m/z | 543.2968 [M+Na]+, C29H44O8Na, calcd. 543.2933 |
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| C5D5N | | 01 | 38.0 | | 02 | 68.1 | | 03 | 68.0 | | 04 | 32.5 | | 05 | 51.4 | | 06 | 203.4 | | 07 | 121.8 | | 08 | 165.7 | | 09 | 34.5 | | 10 | 38.7 | | 11 | 21.0 | | 12 | 32.1 | | 13 | 48.2 | | 14 | 84.1 | | 15 | 31.9 | | 16 | 21.4 | | 17 | 50.1 | | 18 | 17.9 | | 19 | 24.5 | | 20 | 76.8 | | 21 | 21.0 | | 22 | 76.5 | | 23 | 30.9 | | 24 | 46.1 | | 25 | 38.7 | | 26 | 179.1 | | 27 | 16.4 | | 28 | 78.7 | | 29 | 14.4 |
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| C5D5N | | 01-Ha | 1.92 (m) 1.92 | | 01-He | 2.14 (d, 13.2) 2.13 (dd, 13.3, 4.6) | | 02-Ha | 4.16 (d, 11.5) 4.16 (dt, 11.0, 3.6) | | 03-He | 4.21 (br s) 4.22 (brs, w1/2=9.4) | | 04-Ha | 1.79 (m) 1.81 | | 04-He | 1.79 (m) 2.03 | | 05-H | 3.00 (dd, 10.2, 2.8) 3.00 (dd, 13.2, 3.7) | | 07-H | 6.28 (s) 6.25 (d, 2.3) | | 09-H | 3.59 (m) 3.59 (brt, 8.6) | | 11-Ha | 1.76 (m) 1.75 | | 11-He | 1.76 (m) 1.90 | | 12-Ha | 2.63 (m) 2.60 (td, 13.0, 4.7) | | 12-He | 2.06 (m) 2.03 | | 15-Ha | 2.22 (m) 1.92 | | 15-Hb | 2.22 (m) 2.22 | | 16-Ha | 2.46 (m) 2.47 | | 16-Hb | 2.06 (m) 2.03 | | 17-H | 2.87 (br t, 9.6) 2.86 (t, 9.2) | | 18-Me | 1.24 (s) 1.21 (s) | | 19-Me | 1.07 (s) 1.05 (s) | | 21-Me | 1.57 (s) 1.58 (s) | | 22-H | 3.88 (d, 10.6) 3.89 (dd, 11.0, 2.1) | | 23-Ha | 1.79 (m) 1.64 | | 23-Hb | 1.79 (m) 1.80 | | 24-H | 2.46 (m) 2.47 | | 25-H | 2.33 (dq, 11.5, 6.5) 2.34 (dq, 11.5, 7.0) | | 27-Me | 1.30 (d, 6.5) 1.18 (d, 7.0) | | 28-H | 4.98 (t, 6.8) 4.98 (dq, 6.8, 6.6) | | 29-Me | 1.17 (d, 7.0) 1.29 (d, 6.6) |
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| M.P. | 248-250 °C ; | | [α]D20 | ? ° (c ; MeOH) | | UV (MeOH) lmax (log e) | 242 (4.11) ; | | IR (KBr) ν max (cm-1) | 3340, 2939, 2877, 1755 (?-lactone), 1665 (???-unsaturated ketone), 1652, 1446, 1385, 1319, 1262, 1228, 1191, 1148, 1053, 953, 927, 878 |
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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. 15.2 min (cyasterone : 13.8 min) | | GLC | | | HPTLC | | | TLC | Silica plates, solvent CHCl3-MeOH (10:1), developed 3 times, Rf 0.38 |
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Permanent link to this datasheet: 28-EPI-CYASTERONE
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