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Year of first isolation: |
1990 |
| Formula: | C34H48O7 |
| Molecular weight: | 568 |
| Occurence in plants: |
Silene tatarica [Caryophyllaceae] »  ![Wikipedia: Silene tatarica [Caryophyllaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC12CCC(CC1C(=O)C=C3C2CCC4(C3(CCC4C(C)(C(CCC(C)(C)O)OC(=O)C5=CC=CC=C5)O)O)C)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@H](C[C@H](C1)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)OC(=O)c1ccccc1)O)O)C)C » 
| | IUPAC Name | [(2S,3R)-2-[(3S,10R,13R,14S,17S)-3,14-dihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2,6-dihydroxy-6-methylheptan-3-yl] benzoate | | CAS-RN | | | PubChem CID | 11273072 | InChiKey
[ ChemIDPlus: search ] | LWSLYKYCCRDVSS-YBEYOQQVSA-N | | InChI | InChI=1S/C34H48O7/c1-30(2,38)15-14-28(41-29(37)21-9-7-6-8-10-21)33(5,39)27-13-18-34(40)24-20-26(36)25-19-22(35)11-16-31(25,3)23(24)12-17-32(27,34)4/h6-10,20,22-23,25,27-28,35,38-40H,11-19H2,1-5H3/t22-,23?,25?,27-,28+,31+,32+,33-,34+/m0/s1 |
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| CI-MS (NH3) m/z | 569 (MH)+, 551, 533, 447 (MH -benzoic acid)+, 429, 411, 347 (MH - C22-C27 - benzoic acid)+, 329, ? | | EI-MS m/z (relative intensity %) | | | FAB-HR-MS | 569.3479 [M+H]+, C34H49O7 requires 569.3477. |
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| C5D5N | | 01 | | | 02 | | | 03 | | | 04 | | | 05 | | | 06 | | | 07 | | | 08 | | | 09 | | | 10 | | | 11 | | | 12 | | | 13 | | | 14 | | | 15 | | | 16 | | | 17 | | | 18 | | | 19 | | | 20 | | | 21 | | | 22 | | | 23 | | | 24 | | | 25 | | | 26 | | | 27 | |
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| CD3OD | | 01-Ha | | | 01-Hb | | | 02-Ha | | | 03-He | 3.98 (m b, w1/2=12) | | 04-Ha | | | 04-He | | | 05-H | 2.38 (dd, 12, 5) | | 07-H | 5.81 (d, 2.5) | | 09-Ha | 3.20 (m, w1/2=22) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.47 (t, 8.5) | | 18-Me | 0.89 (s ) | | 19-Me | 0.95 (s ) | | 21-Me | 1.42 (s ) | | 22-H | 5.15 (dd, 12, 2) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.15 (s ) | | 27-Me | 1.16 (s ) | | C6H5-CO- m | 7.48 (t, 7) [meta, 2H] | | C6H5-CO- o | 8.07 (t, 7) [ortho, 2H] | | C6H5-CO- p | 7.60 (t, 7) [para, 1H] |
| C5D5N | | 01-Ha | | | 01-Hb | | | 02-Ha | | | 03-He | 4.13 (br, s) | | 04-Ha | | | 04-He | | | 05-H | 2.98 (m) | | 07-H | 6.24 (d, 1.8) | | 09-Ha | 3.55 (m) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 3.11 (t, 9.1) | | 18-Me | 1.21 (s ) | | 19-Me | 1.05 (s ) | | 21-Me | 1.78 (s ) | | 22-H | 5.79 (dd, 10.5, 1.7) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.30 (s ) | | 27-Me | 1.31 (s ) | | C6H5-CO- m | | | C6H5-CO- o | | | C6H5-CO- p | |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3404, 2964, 1698, 1649, 1449, 1380, 1281, 1116, 1039, 946, 8 | | UV (EtOH) λ max (log ε) | |
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| HPTLC | | | TLC | | | HPLC | NP-HPLC, Retention time 6.9 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O 125:40:3 v/v/v, flow-rate 1 ml.min-1] (20E : 16.8 min); Retention time 11.1 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O 125:25:2 v/v/v, flow-rate 1 ml.min-1] (20E 37.4 min) |
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Drosophila melanogaster BII cell assay: EC50 = 6.3 x 10-6M |
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Permanent link to this datasheet: 2-DEOXY-20-HYDROXYECDYSONE 22-BENZOATE
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