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Year of first isolation: |
2007 |
| Formula: | C27H44O7 |
| Molecular weight: | 480 |
| 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 | CC12CCC3C(=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=C1[C@@H]2CC[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,9R,10R,13R,14R,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 11386092 | InChiKey
[ ChemIDPlus: search ] | NKDFYOWSKOHCCO-MQVWFXNHSA-N | | InChI | InChI=1S/C27H44O7/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/h12,15,17,19-22,29-34H,6-11,13-14H2,1-5H3/t15-,17-,19+,20-,21-,22+,24+,25+,26+,27-/m0/s1 |
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| FAB-MS m/z (relative intensity %) | 503 [M+Na](34), 481 [M+H](41), 463 [M+H-H2O](25), 445 [M+H-2H2O](65), 427 [M+H-3H2O](37), 363 (41), 303 (71), 279 (80), 211 (100). | | HR-MS | 481.3158 for C27H45O7, calculated 481.3165 | | CI-MS (NH3) m/z | |
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| CD3OD | | 01 | 37.23 | | 02 | 68.66 | | 03 | 68.41 | | 04 | 33.34 | | 05 | 51.01 | | 06 | 206.12 | | 07 | 123.12 | | 08 | 167.68 | | 09 | 37.41 | | 10 | 39.27 | | 11 | 22.25 | | 12 | 41.67 | | 13 | 52.64 | | 14 | 85.68 | | 15 | 40.75 | | 16 | 24.64 | | 17 | 56.61 | | 18 | 19.24 | | 19 | 24.64 | | 20 | 77.64 | | 21 | 20.45 | | 22 | 78.44 | | 23 | 27.41 | | 24 | 42.20 | | 25 | 71.24 | | 26 | 28.84 | | 27 | 29.88 |
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| CD3OD | | 01-Ha | 1.43 | | 01-He | 1.80 | | 02-Ha | 3.86 | | 03-He | 3.94 | | 04-Ha | 1.59 | | 04-He | 1.73 | | 05-H | 2.36 | | 07-H | 6.29 | | 09-H | 2.85 | | 11-Ha | 1.68 | | 11-He | 1.79 | | 12-Ha | 1.77 | | 12-He | 1.67 | | 15-Ha | 2.28 | | 15-Hb | 1.43 | | 16-Ha | 2.08 | | 16-Hb | 1.89 | | 17-H | 1.98 | | 18-Me | 1.26 | | 19-Me | 0.94 | | 21-Me | 1.29 | | 22-H | 3.50 | | 23-Ha | 1.58 | | 23-Hb | 1.29 | | 24-Ha | 1.80 | | 24-Hb | 1.43 | | 26-Me | 1.19 | | 27-Me | 1.21 |
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| M.P. | C ; | | [α]D20 | +- ° (c ; MeOH) | | IR (KBr) ν max (cm-1) | 3380 (OH), 1653 (C=O), 1063 (C-O) | | UV (EtOH) λ max (log ε) | () ; |
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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. 22.1 min (20E : 21.0 min). | | GLC | | | HPTLC | | | TLC | |
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Permanent link to this datasheet: 14-EPI-20-HYDROXYECDYSONE
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