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Year of first isolation: |
2007 |
| Formula: | C27H46O6 |
| Molecular weight: | 466 |
| Occurence in plants: |
Taxus cuspidata [Taxaceae] »  ![Wikipedia: Taxus cuspidata [Taxaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC(C)CCC(C(C)(C1CCC2(C1(CCC3C2CC(=O)C4C3(CC(C(C4)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)CC1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)C)O)O)O)C)C » 
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C[C@H]1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)C)O)O)O)C)C »
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C[C@@H]1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)C)O)O)O)C)C »
| | IUPAC Name | (2S,3R,5R,8R,9S,10R,13R,14R,17S)-17-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-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 | 101187643 | InChiKey
[ ChemIDPlus: search ] | XKRVOXLOQKYJKV-ORCMZSNMSA-N | | InChI | InChI=1S/C27H46O6/c1-15(2)6-7-23(31)26(5,32)22-9-11-27(33)17-12-19(28)18-13-20(29)21(30)14-24(18,3)16(17)8-10-25(22,27)4/h15-18,20-23,29-33H,6-14H2,1-5H3/t16-,17+,18-,20+,21-,22-,23+,24+,25+,26+,27+/m0/s1 |
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| EI-MS m/z (relative intensity %) | | | CI-MS (NH3) m/z | | | HR-FABMS m/z | 489.3193 [M+Na]+, calc. for C27H46O6Na 489.3192, 505.2921 [M+K]+, calc for C27H46O6K 505.2931 |
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| CDCl3 | | 01 | 37.2 | | 02 | 67.1 | | 03 | 67.8 | | 04 | 31.9 | | 05 | 53.3 | | 06 | 215.1 | | 07 | 37.0 | | 08 | 39.1 | | 09 | 32.8 | | 10 | 40.0 | | 11 | 20.2 | | 12 | 32.2 | | 13 | 47.8 | | 14 | 84.7 | | 15 | 32.3 | | 16 | 20.4 | | 17 | 49.3 | | 18 | 17.4 | | 19 | 22.9 | | 20 | 76.9 | | 21 | 20.3 | | 22 | 76.6 | | 23 | 29.3 | | 24 | 36.3 | | 25 | 27.9 | | 26 | 22.9 | | 27 | 22.5 |
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| CDCl3 | | 01-Ha | 1.38 (m) | | 01-He | 1.81 (m) | | 02-Ha | 3.82 (dt, 12.3, 3.8) | | 03-He | 4.04 (ddd, 2.9) | | 04-Ha | 1.99 (m) | | 04-He | 1.84 (m) | | 05-H | 2.42 (dd, 13.5, 3.9) | | 07-Ha | 2.55 (dd, 14.3, 12.0) | | 07-He | 2.06 (dd, 14.3, 3.6) | | 08-H | 2.14 (m) | | 09-H | 2.18 (m) | | 11-Ha | 1.46 (m) | | 11-He | 1.79 (m) | | 12-Ha | 1.84 (m) | | 12-He | 1.60 (m) | | 15-Ha | 1.35 (m) | | 15-Hb | 1.84 (m) | | 16-Ha | 1.65 (m) | | 16-Hb | 1.99 (m) | | 17-H | 2.21 (t, 9.3) | | 18-Me | 1.00 (s) | | 19-Me | 0.91 (s) | | 21-Me | 1.18 (s) | | 22-H | 3.38 (br, d, 8.6) | | 23-Ha | 1.46 (m) | | 23-Hb | 1.22 (m) | | 24-Ha | 1.44 (m) | | 24-Hb | 1.21 (m) | | 25-H | 1.54 (m) | | 26-Me | 0.91 (d, 6.4) | | 27-Me | 0.90 (d, 6.4) |
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| M.P. | °C ; | | [α]D22 | + 76 ° (c 0.20; MeOH) | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | () ; |
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| HPLC | | | HPTLC | | | TLC | Rf 0.40 (EtOAc-EtOH 100:6) |
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Permanent link to this datasheet: 7,8-DIHYDROPONASTERONE A
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