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Year of first isolation: |
2002 |
| Formula: | C27H44O7 |
| Molecular weight: | 480 |
| Occurence in plants: |
Diploclisia glaucescens [Menispermaceae] »  ![Wikipedia: Diploclisia glaucescens [Menispermaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(C(C(CC4)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | [C@@H]1([C@]2([C@@H](CC[C@H]1O)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)O » 
| | IUPAC Name | (1S,2R,5R,9R,10R,13R,14S,17S)-1,2,14-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 | 10863772 | InChiKey
[ ChemIDPlus: search ] | RWIUQUIFSRGGMV-KSEYKKGQSA-N | | InChI | InChI=1S/C27H44O7/c1-23(2,32)11-10-21(30)26(5,33)20-9-13-27(34)17-14-19(29)16-6-7-18(28)22(31)25(16,4)15(17)8-12-24(20,27)3/h14-16,18,20-22,28,30-34H,6-13H2,1-5H3/t15-,16-,18+,20-,21+,22+,24+,25+,26+,27+/m0/s1 |
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| EI-MS m/z (relative intensity %) | | | FAB-MS m/z | 481, 463, 445, 427HRFAB -MS m/z |
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| CD3OD | | 01 | 73.78 | | 02 | 68.94 | | 03 | 27.64 | | 04 | 25.62 | | 05 | 52.12 | | 06 | 206.14 | | 07 | 121.70 | | 08 | 167.14 | | 09 | 35.76 | | 10 | 43.65 | | 11 | 21.93 | | 12 | 32.56 | | 13 | 49.00 | | 14 | 85.08 | | 15 | 31.78 | | 16 | 21.39 | | 17 | 50.58 | | 18 | 18.03 | | 19 | 20.16 | | 20 | 77.91 | | 21 | 21.05 | | 22 | 78.44 | | 23 | 27.37 | | 24 | 42.39 | | 25 | 71.30 | | 26 | 28.97 | | 27 | 29.69 |
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| CD3OD | | 01-Ha | 3.72 (d, 2.4) | | 02-Ha | 3.95 (m) | | 03-Ha | 162 (m) | | 03-He | 1.73 (m) | | 04-Ha | 1.52 (m) | | 04-He | 1.63 (m) | | 05-H | 2.29 (dd, 11.6, 5.6) | | 07-H | 5.78 (d, 2.4) | | 09-H | 3.14 (td, 8, 2) | | 11-Ha | 1.70 (m) | | 11-He | ? | | 12-Ha | ? | | 12-He | 1.90 (m) | | 15-Ha | 2.00 (m) | | 15-Hb | ? | | 16-Ha | ? | | 16-Hb | 1.70 (m) | | 17-H | 2.39 (t, 9.2) | | 18-Me | 0.89 (s) | | 19-Me | 1.03 (s) | | 21-Me | 1.19 (s) | | 22-H | 3.30 (m) | | 23-Ha | 1.26 (m) | | 23-Hb | 1.28 (m) | | 24-Ha | 1.79 (m) | | 24-Hb | 1.44 (m) | | 26-Me | 1.18 (s) | | 27-Me | 1.18 (s) |
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| M.P. | 152-155 °C ; | | [α]D20 | + 63.3 ° (c 0.72; MeOH) | | IR (CHCl3) ν max (cm-1) | 3450, 1660, 1640 | | UV (EtOH) λ max (log ε) | 241 (-) ; |
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| RP-HPLC | STR Prep-ODS 20x250 mm, MeOH-H2O (4:6 v/v), flow-rate 5 ml.min-1 | | HPTLC | | | TLC | |
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Permanent link to this datasheet: 3-DEOXY-1β,20-DIHYDROXYECDYSONE
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