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Year of first isolation: |
1973 |
| Formula: | C27H44O7 |
| Molecular weight: | 480 |
| Occurence in plants: |
Silene repens [Caryophyllaceae] »  ![Wikipedia: Silene repens [Caryophyllaceae]](/images/wikipedia.png)
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| Occurence in animals: |
Manduca sexta [Lepidoptera] »
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| Canonical SMILES | CC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)C(CCC(C)(CO)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(CO)(C)O)O)O)C)C » 
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(CO)(C)O)O)O)C)C »
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(CO)(C)O)O)O)C)C »
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17R)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2S,3R)-3,6,7-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | 52717-49-4 | | PubChem CID | 22295962 | InChiKey
[ ChemIDPlus: search ] | CHEZKCVMQIAGLX-PBUSDRRUSA-N | | InChI | InChI=1S/C27H44O7/c1-15(20(29)7-8-24(2,33)14-28)16-6-10-27(34)18-11-21(30)19-12-22(31)23(32)13-25(19,3)17(18)5-9-26(16,27)4/h11,15-17,19-20,22-23,28-29,31-34H,5-10,12-14H2,1-4H3/t15-,16+,17-,19-,20+,22+,23-,24?,25+,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | 498 (M+H+NH3)+, 481 (M+H)+, 463, 445, 431, 427, 331 | | EI-MS m/z (relative intensity %) | 480 (M)+ (<1), 462 (9), 444 (33), 426 (17), 413 (12), 395 (8), 330 (9), 300 (100), 291 (45), 285 (26), 267 (29), 211 (40), 181 (60), 115 (45), 93 (38). | | ESI-MS | 519 [M+K]+, 503 [M+Na]+, 481 [M+H]+, 463 [M+H-H2O]+, 445 [M+H-2H2O]+, 427 [M+H-3H2O]+, ... |
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| CD3OD | | 01 | 37.2 | | 02 | 68.0 | | 03 | 67.5 | | 04 | 32.5 | | 05 | 51.5 | | 06 | 206.5 | | 07 | 122.0 | | 08 | 167.5 | | 09 | 35.3 | | 10 | 39.1 | | 11 | 22.4 | | 12 | 32.0 | | 13 | 48.9 | | 14 | 85.1 | | 15 | 31.6 | | 16 | 27.8 | | 17 | 48.5 | | 18 | 17.5 | | 19 | 24.1 | | 20 | 43.1 | | 21 | 12.9 | | 22 | 76.9 | | 23 | 26.3 | | 24 | 40.8 | | 25 | 74.2 | | 26 | 71.2 | | 27 | 25.9 |
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| CD3OD | | 01-Ha | 1.43 (dd, 13.1,12.1) | | 01-He | 1.84 (dd, 13.1,4.0) | | 02-Ha | 3.85 (ddd, 12.1,4.0, 3.2) | | 03-He | 4.00 (m) | | 04-Ha | 1.60 (m) | | 04-He | 1.72 (m) | | 05-H | 2.41 (dd, 12.0, 4.5) | | 07-H | 5.90 (d, 2.4) | | 09-Ha | 3.14 (ddd, 12.0, 7.3, 2.4) | | 11-Ha | 1.83 (m) | | 11-He | 1.69 (m) | | 12-Ha | 2.10 (ddd, 13.1, 12.9, 5.1) | | 12-He | 1.89 (m) | | 15-Ha | 1.52 (m) | | 15-Hb | 2.03 (m) | | 16-Ha | 1.96 (m) | | 16-Hb | 1.68 (m) | | 17-H | 2.43 (m) | | 18-Me | 0.85 (s) | | 19-Me | 0.98 (s) | | 20-H | 1.76 (m) | | 21-Me | 0.94 (d, 6.9) | | 22-H | 3.38 (m) | | 23-Ha | 1.62 (m) | | 23-Hb | 1.26 (m) | | 24-Ha | 1.78 (m) | | 24-Hb | 1.11 (m) | | 26-CH2-O- | 3.59 (dd, 11.1, 5.5); 3.47 (11.1, 6.2) | | 27-Me | 1.05 (s) |
| D2O | | 01-Ha | | | 01-He | | | 02-Ha | 3.99 | | 03-He | 4.08 | | 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 | 0.745 | | 19-Me | 1.005 | | 20-H | | | 21-Me | 0.938, 0.953 | | 22-H | 3.70 (d, 5.6) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-CH2-O- | 3.465 | | 27-Me | 1.183 |
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| M.P. | 252-256 °C ; | | [α]D20 | | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | 245 (4.064) ; |
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| HPTLC | | | TLC | Rf 0.08 [Preparative silica gel G, CHCl3-EtOH 8:2 v/v] (20E 0.15) | | GLC | | | HPLC | NP-HPLC, Retention volume 124 ml [column APS-Hypersil, 25 cm long, 4.6 mm i.d., solvent CH2Cl2-MeOH-iPrOH 95:3:2 v/v/v] (20E : 54 ml); Retention volume 31 ml [column Partisil 10 ODS, 25 cm long, 4.6 mm i.d., solvent MeOH-H2O 25:75 v/v] (20E 31 ml) |
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Musca assay: 7-10% (20-hydroxyecdysone = 100%) |
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| First isolation | KAPLANIS, J.N. et al. (1973) Science 180, 307-308 |
 | | 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 | THOMPSON, M.J. et al. (1985) Aust. J. Chem. 2, 227-236 |
| | Identification | OLENNIKOV, D.N. et al. (2019) Chem. Nat. Compd. 55/4, 770 |
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Permanent link to this datasheet: 26-HYDROXYECDYSONE
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