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Year of first isolation: |
2007 |
| Formula: | C27H42O7 |
| Molecular weight: | 478 |
| 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 | CC12CC=C3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)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=C1C2=CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O)C)C » 
| | IUPAC Name | (2S,3R,5R,10S,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 12021128 | InChiKey
[ ChemIDPlus: search ] | LUFONRHFFBQBJJ-MFLHRAQLSA-N | | InChI | InChI=1S/C27H42O7/c1-23(2,32)9-8-22(31)26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h6,12,17,19-22,29-34H,7-11,13-14H2,1-5H3/t17-,19+,20-,21-,22+,24+,25+,26+,27+/m0/s1 |
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| HR-MS | | | ESI-MS m/z (positive ion mode) | 479 [M+H]+, 461.6 [M+H-H2O]+, 443 [M+H-2H2O]+, 427 [M+H-3H2O]+, 345 [M-C20-C27]+ | | CI-MS (NH3) m/z | |
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| CD3OD | | 01 | 37.5 | | 02 | 68.9 | | 03 | 68.4 | | 04 | 35.9 | | 05 | 51.7 | | 06 | n.d. | | 07 | 119.4 | | 08 | 156.7 | | 09 | 136.3 | | 10 | 41.1 | | 11 | 134.0 | | 12 | 39.2 | | 13 | 48.1 | | 14 | 84.6 | | 15 | 31.6 | | 16 | 22.0 | | 17 | 50.7 | | 18 | 18.3 | | 19 | 31.6 | | 20 | 78.0 | | 21 | 21.0 | | 22 | 78.6 | | 23 | 27.5 | | 24 | 42.5 | | 25 | 71.6 | | 26 | 29.1 | | 27 | 29.8 |
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| CD3OD | | 01-Ha | 1.70 (dd, 13.5, 11.9) | | 01-He | 2.08 (dd, 11.5, 4.0) | | 02-Ha | 3.72 (ddd, 11.9, 3.9, 3.1) | | 03-He | 3.85 (q, 2.8) | | 04-Ha | 1.60 | | 04-He | 1.76 (dt, 14.0, 3.9) | | 05-H | 2.45 (dd, 12.6, 3.7) | | 07-H | 5.75 (d, 1.0) | | 09-Ha | - | | 11-H | 6.29 (dt, 6.6, 2.0) | | 12-Ha | 2.74 (dd, 17.6, 2.5) | | 12-He | 2.42 (dd, 18.0, 6.8) | | 15-Ha | 1.79 | | 15-Hb | 1.95 | | 16-Ha | 1.80 | | 16-Hb | 1.99 | | 17-H | 2.50 (t, 8.9) | | 18-Me | 0.90 (s) | | 19-Me | 1.11 (s) | | 21-Me | 1.211 (s) | | 22-H | 3.34 | | 23-Ha | 1.31 | | 23-Hb | 1.64 | | 24-Ha | 1.44 | | 24-Hb | 1.81 | | 26-Me | 1.19 (s) | | 27-Me | 1.206 (s) |
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| M.P. | - °C ; | | [α]D29 | - 17 ° (c 0.5; MeOH) | | UV (MeOH) max (log ) | 299 (3.33) ; | | IR (KBr) ν max (cm-1) | |
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| HPLC | NP-HPLC column Zorbax-SIL (250x4.6 mm), solvent cyclohexane-iso-PrOH-H2O (100:40:3), flow-rate 1 ml/min, ret. 26.1 min (20E : 21.0 min). | | GLC | | | HPTLC | | | TLC | Silica, |
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Permanent link to this datasheet: 25-HYDROXYDACRYHAINANSTERONE
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