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Year of first isolation: |
2007 |
| Formula: | C27H42O6 |
| Molecular weight: | 462 |
| 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(C(C(C(C4)O)O)O)C)C)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | [C@@H]1([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)O » 
| | IUPAC Name | (1S,2R,3R,5R,9R,10R,13R,14S,17R)-1,2,3,14-tetrahydroxy-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 | 102086069 | InChiKey
[ ChemIDPlus: search ] | RQKPNNORGBQNHF-ONESLGAZSA-N | | InChI | InChI=1S/C27H42O6/c1-15(7-6-10-24(2,3)32)16-9-12-27(33)18-13-20(28)19-14-21(29)22(30)23(31)26(19,5)17(18)8-11-25(16,27)4/h7,13,16-17,19,21-23,29-33H,6,8-12,14H2,1-5H3/b15-7+/t16-,17+,19+,21-,22-,23-,25-,26-,27-/m1/s1 |
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| HRESI-MS m/z | 463.2976 [M+H]+, calculated for C27H42O6 463.2970 | | Electrospray-MS m/z (relative intensity) | 501 [M+K]+ (26), 463 [M+H]+ (4), 445 [M+H-H2O]+ (100), 427 [M+H-2H2O]+ (8), 408 [M+H-3H2O]+ (2), 391 [M+H-4H2O]+ (14), 374 (4), 363 (5), 336 (4) |
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| CD3OD | | 01 | 76.6 | | 02 | 68.6 | | 03 | 71.1 | | 04 | 33.7 | | 05 | 47.0 | | 06 | - | | 07 | 122.2 | | 08 | - | | 09 | 36.0 | | 10 | 44.0 | | 11 | 22.2 | | 12 | 31.1 | | 13 | 48.9 | | 14 | 84.8 | | 15 | 32.3 | | 16 | 24.0 | | 17 | 54.3 | | 18 | 17.7 | | 19 | 20.2 | | 20 | 134.8 | | 21 | 18.4 | | 22 | 127.7 | | 23 | 24.3 | | 24 | 44.9 | | 25 | 71.5 | | 26 | 29.3 | | 27 | 29.3 |
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| CD3OD | | 01-He | 3.82 (br) | | 02-Ha | 3.88 (t, 3.1) | | 03-He | 4.04 (br) | | 04-Ha | 1.78 (m) | | 04-He | 1.83 (m) | | 05-H | 2.61 (dd, 12.8, 4.5) | | 07-H | 5.84 (d, 2.6) | | 09-H | 3.10 (t, br, 8.8) | | 11-Ha | 1.72-1.69 (m) | | 11-He | 1.72-1.69 (m) | | 12-Ha | 2.06 (m) | | 12-He | 1.52 (m) | | 15-Ha | 1.66 (m) | | 15-Hb | 2.05 (m) | | 16-Ha | 1.82 (m) | | 16-Hb | 1.95 (tdd, 12.0, 9.2, 2.2) | | 17-H | 2.89 (t, 9.2) | | 18-Me | 0.59 (s) | | 19-Me | 1.07 (s, br) | | 21-Me | 1.68 (s) | | 22-H | 5.30 (t, 7.0) | | 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. | 218-220 °C ; | | [α]D28 | + 10 ° (c 0.05 ; MeOH) | | IR (KBr) ν max (cm-1) | - | | UV (EtOH) λ max (log ε) | 241 nm (3.95) |
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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: 1-HYDROXY-20,22-DIDEHYDROTAXISTERONE
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