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Year of first isolation: |
1972 |
| Formula: | C27H42O6 |
| Molecular weight: | 462 |
| Occurence in plants: |
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| Occurence in animals: |
Calliphora erythrocephala [Diptera] »  ![Wikipedia: Calliphora erythrocephala [Diptera]](/images/wikipedia.png)
Pieris brassicae [Lepidoptera] »
Locusta migratoria [Orthoptera] »
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| Canonical SMILES | CC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(=O)C4)O)C)C)O)C(CCC(C)(C)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](CC(=O)[C@H]1O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(C)(C)O)O)O)C)C » 
| | IUPAC Name | (2S,5R,9R,10R,13R,14S,17R)-17-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-2,14-dihydroxy-10,13-dimethyl-1,2,4,5,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthrene-3,6-dione | | CAS-RN | 39750-00-0 | | PubChem CID | 5460083 | InChiKey
[ ChemIDPlus: search ] | GDSSFVCRVUQMRG-OSCDMYCUSA-N | | InChI | InChI=1S/C27H42O6/c1-15(20(28)8-9-24(2,3)32)16-7-11-27(33)18-12-21(29)19-13-22(30)23(31)14-25(19,4)17(18)6-10-26(16,27)5/h12,15-17,19-20,23,28,31-33H,6-11,13-14H2,1-5H3/t15-,16+,17-,19-,20+,23-,25+,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | 463 (M+H)+, 445, 427, | | EI-MS m/z (relative intensity %) | 462 (M)+ (<1), 444 (3), 426 (7), 411 (4), 346 (3), 328 (18), 298 (10), 248 (18), 126 (20), 117 (12), 99 (100), 81 (71). |
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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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| C5D5N | | 01-Ha | 1.72 | | 01-He | 2.73 | | 02-Ha | 4.88 | | 03-He | -- | | 04-Ha | 2.48 | | 04-He | 2.70 | | 05-H | 2.70 | | 07-H | 6.23 | | 09-Ha | 3.89 | | 11-Ha | 1.69 | | 11-He | 1.91 | | 12-Ha | 1.87 | | 12-He | 2.60 | | 15-Ha | 2.02 | | 15-Hb | 1.86 | | 16-Ha | 2.19 | | 16-Hb | 1.60 | | 17-H | 2.58 | | 18-Me | 0.743 (s ) | | 19-Me | 1.070 (s ) | | 20-H | 2.16 | | 21-Me | 1.329 (d, 6.5) | | 22-H | 4.09 | | 23-Ha | 1.90 | | 23-Hb | 1.90 | | 24-Ha | 2.31 | | 24-Hb | 1.80 | | 26-Me | 1.402 (s ) | | 27-Me | 1.406 (s ) |
| D2O* | | 01-Ha | 1.49 (A) 1.24 (B) | | 01-He | 2.45 (A) 1.94 (B) | | 02-Ha | 4.65 (A) 3.84 (B) | | 03-He | | | 04-Ha | 2.27 (A) 1.72 (B) | | 04-He | 2.64 (A) 1.66 (B) | | 05-H | 2.49 (A) 2.26 (B) | | 07-H | 5.96 (A) 5.91 (B) | | 09-Ha | 3.38 (A) 3.05 (B) | | 11-Ha | 1.75 (A) 1.64 (B) | | 11-He | 1.90 (A) 1.80 (B) | | 12-Ha | 1.59 (A) 1.55 (B) | | 12-He | 2.00 (A) 1.95 (B) | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.70 (A) 0.66 (B) | | 19-Me | 1.00 (A) 0.92 (B) | | 20-H | 1.73 (A) 1.73 (B) | | 21-Me | 0.88 (A) 0.87 (B) | | 22-H | 3.63 (A) 3.63 (B) | | 23-Ha | 1.45 (A) 1.45 (B) | | 23-Hb | 1.29 (A) 1.29 (B) | | 24-Ha | 1.37 (A) 1.37 (B) | | 24-Hb | 1.65 (A) 1.65 (B) | | 26-Me | 1.15 (A) 1.15 (B) | | 27-Me | 1.16 (A) 1.16 (B) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 1720 (C=O), 1660 (cyclohexenone). | | UV (EtOH) λ max (log ε) | 242 (?) ; |
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| HPTLC | | | TLC on silica | Rf 0.88 (CHCl3-EtOH 9:2 v/v) (E : 0.45); Rf 0.50 (CHCl3-EtOH 4:1 v/v); Rf 0.62 (CHCl3-EtOH 4:1 v/v, continuous development for 2.5 hours) | | GLC | | | HPLC | 1- Retention volume 35 ml [column Partisil-10 ODS, 25 cm long, 4.6 mm i.d., solvent linear gradient (40 min) of MeOH-H2O from 2:3 to 3:2, flow-rate 2 ml.min-1] (E : 35 ml). 2- Retention volume 12 ml [column APS-Hypersil, 25 cm long, 4.6 mm i.d., solvent CH2Cl2-MeOH-iPrOH 95:2:3 v/v/v, flow-rate 3 ml.min-1] (E : 44 ml) |
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Drosophila melanogaster BII cell assay: EC50 = 6.0 x 10-6M | Calliphora assay: 10% (20-hydroxyecdysone = 100%) |
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| First isolation | KARLSON, P. et al. (1972) Hoppe-Seyler´s Z. Physiol. Chem. 358, 1610-1614 |
 | | General | DINAN, L. et al. (1978) Steroids 32, 629-638 |
| | Bioactivities | BERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 |
| | General | DINAN, L. et al. (1981) J. Chromatogr. 205, 139-145 |
| | General | BLAIS, C. et al. (1984) Hoppe-Seyler´s Z. Physiol. Chem. 365, 809-817 |
| | General | MILNER, N.P. et al. (1985) Biochem. J. 231, 369-374 |
| | Bioactivities | DINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 |
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Permanent link to this datasheet: 3-DEHYDROECDYSONE
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