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Year of first isolation: |
2007 |
| Formula: | C27H42O5 |
| Molecular weight: | 446 |
| Occurence in plants: |
Serratula wolffii [Asteraceae] »  ![Wikipedia: Serratula wolffii [Asteraceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC(=CCCC(C)(C)O)C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)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/CCC(C)(C)O)/C)O)C)C » 
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(=CCCC(C)(C)O)/C)O)C)C »
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17R)-2,3,14-trihydroxy-17-[(E)-6-hydroxy-6-methylhept-2-en-2-yl]-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 102086068 | InChiKey
[ ChemIDPlus: search ] | CMIUBJTVLMVMSY-ARXHBIMOSA-N | | InChI | InChI=1S/C27H42O5/c1-16(7-6-10-24(2,3)31)17-9-12-27(32)19-13-21(28)20-14-22(29)23(30)15-25(20,4)18(19)8-11-26(17,27)5/h7,13,17-18,20,22-23,29-32H,6,8-12,14-15H2,1-5H3/b16-7+/t17-,18+,20+,22-,23+,25-,26-,27-/m1/s1 |
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| CI-MS (NH3) m/z | | | HRESI-MS m/z | 447.3025 [M+H]+, calculated for C27H42O5 447.3021 | | Electrospray-MS m/z (relative intensity) | 485 [M+K]+ (69), 429 [M+H-H2O]+ (93), 411 [M+H-2H2O]+ (6), 393 [M+H-3H2O]+ (7), 347 (6), 320 (4) |
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| CD3OD | | 01 | 37.6 | | 02 | 68.85 | | 03 | 68.67 | | 04 | 33.0 | | 05 | 52.0 | | 06 | 206.7 | | 07 | 121.9 | | 08 | 167.9 | | 09 | 35.4 | | 10 | 39.5 | | 11 | 21.8 | | 12 | 31.1 | | 13 | 48.9 | | 14 | 85.0 | | 15 | 32.3 | | 16 | 24.1 | | 17 | 54.3 | | 18 | 17.7 | | 19 | 24.6 | | 20 | 134.7 | | 21 | 18.4 | | 22 | 127.7 | | 23 | 24.4 | | 24 | 45.0 | | 25 | 71.5 | | 26 | 29.3 | | 27 | 29.3 |
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| CD3OD | | 01-Ha | 1.43 (dd, 13.4, 12.2) | | 01-He | 1.79 (m) | | 02-Ha | 3.84 (ddd, 12.0, 4.2, 3.3) | | 03-He | 3.96 (m) | | 04-Ha | 1.76 (m) | | 04-He | 1.70 (dt, 14.2, 4.5) | | 05-H | 2.39 (dd, 12.7, 4.5) | | 07-H | 5.81 (d, 2.6) | | 09-H | 3.18 (ddd, 11.2, 7.2, 2.6) | | 11-Ha | 1.63 (m) | | 11-He | 1.84 (m) | | 12-Ha | 2.09 (td, 13.0, 8.0) | | 12-He | 1.54 (ddd, 13.0, 5.3, 1.7) | | 15-Ha | 1.66 (m) | | 15-Hb | 2.02 (m) | | 16-Ha | 1.83 (m) | | 16-Hb | 1.95 (tdd, 12.0, 9.2, 2.3) | | 17-H | 2.90 (t, 9.2) | | 18-Me | 0.57 (s) | | 19-Me | 0.96 (s) | | 21-Me | 1.69 (s) | | 22-H | 5.30 (t, 7.5) | | 23-Ha | 2.13 (m) | | 23-Hb | 2.13 (m) | | 24-Ha | 1.50 (m) | | 24-Hb | 1.50 (m) | | 26-Me | 1.20 (s) | | 27-Me | 1.20 (s) |
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| M.P. | 231-233 °C ; | | [α]D28 | + 71 ° (c 0.025 ; MeOH) | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | 242 nm (4.387) |
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| HPLC | NP-HPLC cyclohexane-isopropanol-water 100:40:3 | | GLC | | | HPTLC | | | TLC | |
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Permanent link to this datasheet: 20,22-DIDEHYDROTAXISTERONE
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