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Year of first isolation: |
1978 |
| Formula: | C29H46O8 |
| Molecular weight: | 522 |
| Occurence in plants: |
Lychnis flos-culculi [Caryophyllaceae] »  ![Wikipedia: Lychnis flos-culculi [Caryophyllaceae]](/images/wikipedia.png)
Ajuga reptans [Lamiaceae (alt. Labiatae)] »
Cyanotis arachnoidea [Commelinaceae] »
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| Occurence in animals: |
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| Canonical SMILES | CC(=O)OC1CC2(C3CCC4(C(CCC4(C3=CC(=O)C2CC1O)O)C(C)(C(CCC(C)(C)O)O)O)C)C | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H]([C@H]1OC(=O)C)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,14S,17S)-3,14-dihydroxy-10,13-dimethyl-6-oxo-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-2-yl] acetate | | CAS-RN | | | PubChem CID | 11060408 | InChiKey
[ ChemIDPlus: search ] | TXLUXHSVMYTTCI-FORVDKSSSA-N | | InChI | InChI=1S/C29H46O8/c1-16(30)37-22-15-26(4)17-7-11-27(5)23(28(6,35)24(33)9-10-25(2,3)34)8-12-29(27,36)18(17)13-20(31)19(26)14-21(22)32/h13,17,19,21-24,32-36H,7-12,14-15H2,1-6H3/t17-,19-,21+,22-,23-,24+,26+,27+,28+,29+/m0/s1 |
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| CI-MS (NH3) m/z | 540, 523 (MH)+, 505, 487, 469, 405 (MH - C22-C27)+, 387, 345, 329 | | EI-MS m/z (relative intensity %) | 522, 486, 468, 405 (58), 388 (100), 387 (86), 373, 345, 343 (13), 329, 311, 291, 285, 269, 258, 231, 199, 183, 161, 143, 119, 99, 81 |
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| C5D5N | | 01 | 33.63 $ | | 02 | 72.50 | | 03 | 65.09 | | 04 | 32.55 $ | | 05 | 51.09 | | 06 | 202.81 | | 07 | 121.55 | | 08 | 166.20 | | 09 | 34.25 | | 10 | 38.70 | | 11 | 21.06 & | | 12 | 31.89 * | | 13 | 47.94 | | 14 | 84.09 | | 15 | 31.64 * | | 16 | 21.35& | | 17 | 49.94 | | 18 | 17.78 | | 19 | 24.19 | | 20 | 76.75 | | 21 | 21.58 & | | 22 | 77.43 | | 23 | 27.40 | | 24 | 42.58 | | 25 | 69.51 | | 26 | 29.84 | | 27 | 30.16 | | CH3COO | 20.10; 170.40, |
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| CDCl3 | | 01-Ha | 1.55 | | 01-He | 1.82 | | 02-Ha | 5.01 (m, w1/2=22) | | 03-He | 4.11 (m, w1/2=8) | | 04-Ha | 1.6 | | 04-He | 1.85 | | 05-H | 2.51 (dd, 13, 4) | | 07-H | 5.84 (d, 2.5) | | 09-Ha | 3.09 (m, w1/2=21) | | 11-Ha | 1.70 | | 11-He | 1.80 | | 12-Ha | | | 12-He | | | 14-H | -- | | 15-Ha | | | 15-Hb | | | 16-Ha | 2.0 | | 16-Hb | 1.75 | | 17-H | 2.34 (m ) | | 18-Me | 0.86 (s ) | | 19-Me | 0.99 (s ) | | 21-Me | 1.21 (s ) | | 22-H | 3.44 (d br, 10) | | 23-Ha | 1.35 | | 23-Hb | 1.65 | | 24-Ha | | | 24-Hb | | | 25-H | -- | | 26-Me | 1.24 (s ) | | 27-Me | 1.25 (s ) | | O-Ac | 2.08 (s ) |
| C5D5N | | 01-Ha | | | 01-He | | | 02-Ha | 5.25 (w1/2=22.5) | | 03-He | 4.29 (w1/2=7.0) | | 04-Ha | | | 04-He | | | 05-H | 3.04 | | 07-H | 6.25 | | 09-Ha | 3.65 (w1/2=20) | | 11-Ha | | | 11-He | | | 12-Ha | 2.50 | | 12-He | | | 14-H | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | 3.02 | | 17-H | | | 18-Me | 1.20 | | 19-Me | 1.07 | | 21-Me | 1.57 | | 22-H | 3.86 (w1/2=15.0) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | 1.38 | | 27-Me | 1.38 | | O-Ac | 1.98 |
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| M.P. | 219-220 °C ; | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3410 (OH), 1658 (cyclohexenone), 1715, 1260. | | UV (EtOH) λ max (log ε) | 243 (4.043) ; |
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| HPTLC | | | TLC | | | GLC | | | HPLC | 1- Retention time 8.7 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); 2-Retention time 13.2 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); 3-Retention time 15.0 min [Spherisorb-5ODS2 250 mm x 4.6 mm i.d., solvent ACN- 0.1% TFA in H2O 23:77 v/v, flow-rate 1 ml.min-1] (20E 5.5 min). |
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Drosophila melanogaster BII cell assay: EC50 = 4.0 x 10-7M |
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| General | GALBRAITH, M.N. et al. (1969) Aust. J. Chem. 22, 1045-1046 |
 | | First isolation | NIEN, S.-L. et al. (1978) Acta Chim. Sinica 36, 137-141 |
| | General | GIRAULT, J.-P. et al. (1990) J. Nat. Prod. 53, 279-293 |
| | General | CALGANO, M.P. et al. (1995) Eur. J. Entomol. 92, 287-294 |
| | General | DANIELI, B. et al. (1997) Tetrahedron 53, 5855-5862 |
| | Bioactivities | DINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 |
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Permanent link to this datasheet: 20-HYDROXYECDYSONE 2-ACETATE
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