|
|
|
|
Year of first isolation: |
1978 |
| Formula: | C27H44O3 |
| Molecular weight: | 416 |
| Occurence in plants: |
|
|
| Occurence in animals: |
Locusta migratoria [Orthoptera] »  ![Wikipedia: Locusta migratoria [Orthoptera]](/images/wikipedia.png)
|
|
| |
| Canonical SMILES | CC(C)CCCC(C)C1CCC2(C1(CCC3C2=CC(=O)C4C3(CCC(C4)O)C)C)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C[C@H](CCCC(C)C)[C@H]1CC[C@@]2([C@@]1(CC[C@H]3C2=CC(=O)[C@H]4[C@@]3(CC[C@@H](C4)O)C)C)O » 
| | IUPAC Name | (3S,5R,9R,10R,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | 39219-57-3 | | PubChem CID | 15942885 | InChiKey
[ ChemIDPlus: search ] | FADCOUQPHXGWQS-ZCDXYYCTSA-N | | InChI | InChI=1S/C27H44O3/c1-17(2)7-6-8-18(3)20-11-14-27(30)22-16-24(29)23-15-19(28)9-12-25(23,4)21(22)10-13-26(20,27)5/h16-21,23,28,30H,6-15H2,1-5H3/t18-,19+,20-,21+,23+,25-,26-,27-/m1/s1 |
| |
| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 416 (M)+ (30), 398 (12), 388 (100), 383 (15), 355 (20), 313 (6), 302 (3), 285 (7), 233 (68) | | HR-MS | M+ found 416.3285, calc. 416.3290 |
|
|
| CD3OD | | 01 | | | 02 | | | 03 | 66.4 | | 04 | | | 05 | 53.2 | | 06 | 207.4 | | 07 | 122.6 | | 08 | 169.3 | | 09 | | | 10 | | | 11 | 23.0 | | 12 | | | 13 | | | 14 | 86.8 | | 15 | | | 16 | | | 17 | 52.8 | | 18 | 17.2 | | 19 | 25.3 | | 20 | | | 21 | 20.3 | | 22 | | | 23 | | | 24 | | | 25 | 30.0 | | 26 | 23.8 | | 27 | 24.4 |
|
| CD3OD | | 01-Ha | | | 01-He | | | 02-Ha | | | 03-He | 4.01 | | 04-Ha | | | 04-He | | | 05-H | 2.45 | | 07-H | 5.83 | | 09-Ha | 3.23 | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.74 | | 19-Me | 1.00 | | 21-Me | 0.95 | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | 0.91 | | 27-Me | 0.94 |
| CDCl3 | | 01-Ha | | | 01-He | | | 02-Ha | | | 03-He | 4.10 (m ) | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 5.90 | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.69 | | 19-Me | 1.00 | | 21-Me | | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | 0.87 (d, 5) | | 27-Me | 0.87 (d, 5) |
|
| |
| M.P. | 172-173 °C | | [α]D28 | + 80.4 ° (c 5.6; MeOH) | | IR (KBr) ν max (cm-1) | 3450 (OH), 1660 (cyclohexenone), 1450, 1380, 1035 | | UV (MeOH) λ max (log ε) | 245 (4.079) |
| |
| HPTLC | | | TLC | | | GLC | | | HPLC | RP-HPLC : column Spherisorb 5-ODS-2, solvent linear gradient (in 30 min) of 20% to 100% ACN-iPrOH (5:2) in 0.1% TFA in H2O, flow-rate 1 ml.min-1, Rt 35.9 min (2DE : 17.0 min) |
| |
Calliphora assay: 33% (20-hydroxyecdysone = 100%) |
| |
| General | HORN, D.H.S. et al. (1971) In: Marcel Dekker Inc., New York, pp. 333-459 |
 | | General | BOLLENBACHER, W.E. et al. (1977) Steroids 29, 47-63 |
| | First isolation | HETRU, C. et al. (1978) Life Sci. 22, 2141-2154 |
| | Bioactivities | BERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 |
| | General | HAAG, T. et al. (1985) J. J. Labelled Compd. Radiopharm. 22, 547-557 |
|
| |
Permanent link to this datasheet: 2,22,25-TRIDEOXYECDYSONE
|
|
