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Year of first isolation: |
1996 |
| Formula: | C27H46O7 |
| Molecular weight: | 482 |
| Occurence in plants: |
Nierembergia hippomanica [Solanaceae] »  ![Wikipedia: Nierembergia hippomanica [Solanaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC(C)CCC(C(C)(C1CCC2(C1(CC(C3C2CC(=O)C4C3(CC(C(C4)O)O)C)O)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)CC1[C@@H]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)C)O)O)O)C)O)C » 
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C[C@H]1[C@@H]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)C)O)O)O)C)O)C »
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C[C@@H]1[C@@H]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)C)O)O)O)C)O)C »
| | IUPAC Name | (2S,3R,5R,8R,9S,10R,11R,13R,14R,17S)-17-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-2,3,11,14-tetrahydroxy-10,13-dimethyl-2,3,4,5,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 15250834 | InChiKey
[ ChemIDPlus: search ] | DFFFEFCBFYMSHZ-KGMAXRKNSA-N | | InChI | InChI=1S/C27H46O7/c1-14(2)6-7-22(32)26(5,33)21-8-9-27(34)16-11-17(28)15-10-18(29)19(30)12-24(15,3)23(16)20(31)13-25(21,27)4/h14-16,18-23,29-34H,6-13H2,1-5H3/t15-,16+,18+,19-,20+,21-,22+,23+,24-,25+,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 467 ([M-15]+, 2), 464 ([M-18]+, 5), 428 (5M-3x18], 2), 413 (2), 381 (4), 363 (84), 345 (41), 327 (28), 309 (16), 285 (8), 267 (10), 189 (12), 157 (11), 145 (41), 127 (9), 109 (33), 101 (2), 83 (75), 71 (36), 67 (33), 55 (100), 43 (94). | | FAB-MS | 483 [MH]+ |
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| C5D5N | | 01 | 43.9 c | | 02 | 65.2 | | 03 | 67.8 d | | 04 | 32.3 a | | 05 | 55.4 | | 06 | 214.5 | | 07 | 40.6 | | 08 | 37.7 b | | 09 | 51.4 | | 10 | 41.2 | | 11 | 67.5 d | | 12 | 43.5 c | | 13 | 60.1 | | 14 | 93.8 | | 15 | 37.9 b | | 16 | 32.9 a | | 17 | 53.3 | | 18 | 26.9 | | 19 | 16.4 | | 20 | 76.7 e | | 21 | 21.5 | | 22 | 77.0 e | | 23 | 31.8 | | 24 | 36.4 | | 25 | 28.7 | | 26 | 22.6 | | 27 | 22.0 |
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| C5D5N | | 01-Ha | 2.00 (m ) | | 01-He | 3.45 (dd, 16, 4) | | 02-Ha | 4.60 (m ) | | 03-He | 4.30 (m ) | | 04-Ha | 1.80 (m ) | | 04-He | 2.20 (dt, 4, 14) | | 05-H | 3.20 (m ) | | 07-Ha | 2.23 (dd, 4, 14) | | 07-He | 1.85 (m ) | | 08-H | 2.30 (m ) | | 09-H | 3.90 (t, 9) | | 11-Ha | 4.68 (m ) | | 12-Ha | 3.42 (t, 12) | | 12-He | 2.70 (dd, 12, 6) | | 15-Ha | 1.95 (m ) | | 15-Hb | 2.10 (m ) | | 16-Ha | 2.10 (m ) | | 16-Hb | 2.50 (m ) | | 17-H | 3.00 (t, 8) | | 18-Me | 1.23 (s ) | | 19-Me | 1.40 (s ) | | 21-Me | 1.53 (s ) | | 22-H | 3.80 (dd, 5, 10) | | 23-Ha ~ | 1.40 | | 23-Hb | 1.68 (m ) | | 24-Ha ~ | 1.50 | | 24-Hb | 1.71 (m ) | | 25-H | 1.58 (m ) | | 26-Me | 0.82 (d, 6) | | 27-Me | 0.82 (d, 6) |
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| M.P. | | | [α]D22 | + 43.2 ° (c 0.01; CHCl3) | | IR (KBr) ν max (cm-1) | 3350 (OH), 2870 (C-C), 1695 (C=O), 2445, 1375, 1265, 1230 | | UV (EtOH) λ max (log ε) | |
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| HPTLC | | | TLC | silica gel, Rf 0.37 (CHCl3-Me2CO, 35:65) (20E : 0.24) | | GLC | | | HPLC | |
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Permanent link to this datasheet: 7,8-DIHYDROAJUGASTERONE C
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