|
|
|
|
Year of first isolation: |
1977 |
| Formula: | C27H42O7 |
| Molecular weight: | 478 |
| Occurence in plants: |
Serratula strangulata [Asteraceae] »  ![Wikipedia: Serratula strangulata [Asteraceae]](/images/wikipedia.png)
|
| Occurence in animals: |
Calliphora erythrocephala [Diptera] »
Pieris brassicae [Lepidoptera] »
Locusta migratoria [Orthoptera] »
|
|
| |
| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(CC(C(=O)C4)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)O)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@](C)([C@@H](CCC(C)(C)O)O)O)O)C)C » 
| | IUPAC Name | (2S,5R,9R,10R,13R,14S,17S)-2,14-dihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,4,5,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthrene-3,6-dione | | CAS-RN | | | PubChem CID | 101254420 | InChiKey
[ ChemIDPlus: search ] | WCHJQYCCTKKLLC-JSDLXWKJSA-N | | InChI | InChI=1S/C27H42O7/c1-23(2,32)9-8-22(31)26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,20-22,30-34H,6-11,13-14H2,1-5H3/t15-,17-,20-,21-,22+,24+,25+,26+,27+/m0/s1 |
| |
| CI-MS (NH3) m/z | 479 (M+H)+, 461, 443, 425, 361, 343 | | EI-MS m/z (relative intensity %) | 478 (M)+(<1), 460 (<1), 442 (1), 427 (5), 424 (11), 409 (2), 406 (3), 361 (14), 345 (24), 343 (73), 342 (27), 327 (16), 326 (27), 325 (27), 283 (20), 269 (22), 189 (18), 161 (10), 143 (24), 99 (100), 81 (73). | | HR-MS | |
|
|
| D2O* | | 01 | 40.92 (A) 38.61 (B) | | 02 | 73.89 (A) 72.89 (B) | | 03 | 213.67 (A) 96.38 (B) | | 04 | 46.34 (A) 41.51 (B) | | 05 | 59.60 (A) 56.60 (B) | | 06 | 205.97 (A) 208.99 (B) | | 07 | 123.07 (A) 123.53 (B) | | 08 | 171.14 (A) 170.94 (B) | | 09 | 37.16 (A) 36.57 (B) | | 10 | 40.92 (A) 40.62 (B) | | 11 | 22.76 | | 12 | 33.40 | | 13 | 49.90 (A) 49.82 (B) | | 14 | 87.49 | | 15 | 32.77 | | 16 | 22.58 | | 17 | 51.63 | | 18 | 19.52 | | 19 | 24.06 (A) 25.06 (B) | | 20 | 80.38 | | 21 | 22.12 | | 22 | 79.75 | | 23 | 28.46 | | 24 | 43.01 | | 25 | 74.07 | | 26 | 29.97 | | 27 | 30.57 |
|
| C5D5N | | 01-Ha | | | 01-He | | | 02-Ha | | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 1.24 (s ) | | 19-Me | 1.06 (s ) | | 21-Me | 1.62 (s ) | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.38 (s ) | | 27-Me | 1.38 (s ) |
| D2O* | | 01-Ha | 1.55 (A) 1.3 (B) | | 01-He | 2.5 (A) 2.0 (B) | | 02-Ha | 4.70 (dd, 12.6, 6.5) (A) 3.92 (dd, 12.1, 4.6) | | 04-Ha | 2.75 (t, 14.1) (A) 1.7 (B) | | 04-He | 2.39 (A) 1.8 (B) | | 05-H | 2.56 (dd, 14.1, 4.1) (A) 2.34 (dd, ~9.5, 5) | | 07-H | 6.04 (d, 2.5) (A) 5.99 (B) | | 09-Ha | 3.44 (m, w1/2=22) (A) 3.14 (B) | | 11-Ha | 1.85 (A) 1.75 (B) | | 11-He | 1.95 (A) 1.85 (B) | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.33 (A) 2.33 (B) | | 18-Me | 0.90 (A) 0.87 (B) | | 19-Me | 1.08 (A) 0.99 (B) | | 21-Me | 1.26 (A) 1.26 (B) | | 22-H | 3.43 (A) 3.43 (B) | | 23-Ha | 1.30 (A) | | 23-Hb | 1.63 (B) | | 24-Ha | | | 24-Hb | | | 26-Me | 1.24 (A) 1.24 (B) | | 27-Me | 1.24 (A) 1.24 (B) |
|
| |
| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 1700 (C=O), 1640 (cyclohexenone). | | UV (EtOH) λ max (log ε) | |
| |
| TLC | Rf 0.44 (silica plates, CH2Cl2-MeOH 4:1 v/v); Rf 0.41 (silica plates, CHCl3-MeOH 4:1 v/v); Rf 0.77 (silica plates, CHCl3-MeOH 9:2 v/v, continuous development for 2.5 hours) | | GLC | | | RP-HPLC | Retention volume 22 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] (20E : 22 ml); | | NP-HPLC | Retention volume 27 ml [column APS-Hypersil, 25 cm long, 4.6 mm i.d., solvent CH2Cl2-MeOH-iPrOH 95:1:4 v/v/v, flow-rate 3 ml.min-1] (20E : 97 ml) |
| |
| |
| First isolation | KOOLMAN, J.A. et al. (1977) Hoppe-Seyler´s Z. Physiol. Chem. 358, 1339-1344 |
 | | General | DINAN, L. et al. (1978) Steroids 32, 629-638 |
| | 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 | GIRAULT, J.-P. et al. (1989) Arch. Insect Biochem. Physiol. 10, 199-213 |
| | General | SOMME-MARTIN, G. et al. (1990) Arch. Insect Biochem. Physiol. 15, 43-56 |
|
| |
Permanent link to this datasheet: 3-DEHYDRO-20-HYDROXYECDYSONE
|
|
