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Year of first isolation: |
1998 |
| Formula: | C27H42O7 |
| Molecular weight: | 478 |
| Occurence in plants: |
Froelichia floridana [Amaranthaceae] »  ![Wikipedia: Froelichia floridana [Amaranthaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(CC(=O)C(C4)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](C1=O)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 | (3S,5R,9R,10R,13R,14S,17S)-3,14-dihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,3,4,5,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthrene-2,6-dione | | CAS-RN | | | PubChem CID | 10790832 | InChiKey
[ ChemIDPlus: search ] | RRGYPIOLUPMGCP-FJWASMFLSA-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/h12,15,17,19,21-22,29,31-34H,6-11,13-14H2,1-5H3/t15-,17-,19-,21-,22+,24+,25+,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | | | LSI-MS | 569 [M-H+glycerol] -, 477 [M-H] - |
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| C5D5N | | 01 | 49.0 | | 02 | 210.0 | | 03 | 74.6 | | 04 | 36.0 | | 05 | 55.6 | | 06 | -- | | 07 | 120.9 | | 08 | -- | | 09 | 35.8 | | 10 | 42.7 | | 11 | 20.6 | | 12 | 31.5 | | 13 | 48.0 | | 14 | 83.1 | | 15 | 31.3 | | 16 | 21.1 | | 17 | 49.7 | | 18 | 17.6 | | 19 | 22.7 | | 20 | 76.5 | | 21 | 21.4 | | 22 | 77.3 | | 23 | 27.3 | | 24 | 42.4 | | 25 | 69.3 | | 26 | 29.9 | | 27 | 29.8 |
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| C5D5N | | 01-Ha | 2.35 (d, 13.7) | | 01-He | 2.70 (d, 13.7) | | 02-H | ? | | 03-Ha | 4.54 (dd: 7.2, 11.0) | | 04-Ha | 2.00 (m) | | 04-He | 2.40 (m) | | 05-H | 2.80 (dd: 3.9, 13.7) | | 07-H | 6.17 (d: 2.3) | | 09-H | 3.25 (m) | | 11-Ha | 1.70 | | 11-He | 1.88 | | 12-Ha | 2.05 | | 12-He | 2.45 | | 15-Ha | 1.95 | | 15-Hb | 2.10 | | 16-Ha | 2.46 | | 16-Hb | 2.15 | | 17-H | 2.90 (t: 9.7) | | 18-Me | 1.15 (s) | | 19-Me | 1.06 (s) | | 21-Me | 1.52 (s) | | 22-H | 3.83 (t: 9.4) | | 23-Ha | 1.72 | | 23-Hb | 2.14 | | 24-Ha | 2.25 | | 24-Hb | 1.82 | | 26-Me | 1.36 (s) | | 27-Me | 1.36 (s) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | 242.4 (4.106) ; |
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| HPTLC | | | TLC | | | GLC | | | HPLC | NP-HPLC - Zorbax-SIL semi-preparative column eluted with CH2Cl2-iPrOH-H2O (125: 40: 3), flow-rate 2 mL/min, (Ret 15 min; 20E 31 min) |
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Drosophila melanogaster BII cell assay: EC50 = 4.0 x 10-7M |
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Permanent link to this datasheet: 2-DEHYDRO-3-EPI-20-HYDROXYECDYSONE
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