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Year of first isolation: |
1974 |
| Formula: | C27H44O6 |
| Molecular weight: | 464 |
| Occurence in plants: |
Serratula strangulata [Asteraceae] »  ![Wikipedia: Serratula strangulata [Asteraceae]](/images/wikipedia.png)
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| Occurence in animals: |
Manduca sexta [Lepidoptera] »
Pieris brassicae [Lepidoptera] »
Spodoptera littoralis [Lepidoptera] »
Bombyx mori [Bombycidae] »
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| Canonical SMILES | CC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)C(CCC(C)(C)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(C)(C)O)O)O)C)C » 
| | IUPAC Name | (2S,3S,5R,9R,10R,13R,14S,17R)-17-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 23724769 | InChiKey
[ ChemIDPlus: search ] | UPEZCKBFRMILAV-LVRQXCCVSA-N | | InChI | InChI=1S/C27H44O6/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/h12,15-17,19-20,22-23,28,30-33H,6-11,13-14H2,1-5H3/t15-,16+,17-,19-,20+,22-,23-,25+,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 446 (M-18)+ (1), 431 (3), 428 (16), 413 (8), 410 (4), 395 (4), 348 (14), 330 (30), 315 (14), 301 (14), 300 (30), 285 (13), 279 (26), 250 (29), 249 (18), 173 (13), 161 (13), 145 10), 126 (16), 121 (14), 117 (14), 109 (17), 107 (10), 105 (13), 99 (100), 81 (77). | | HR-MS | |
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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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| CD3OD | | 01-Ha | | | 01-He | | | 02-Ha | 3.63 (m, w1/2=21) | | 03-He | 3.34 (m, w1/2=22) | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 5.82 (d, 2.4) | | 09-Ha | 3.17 (m ) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.725 | | 19-Me | 0.949 | | 21-Me | 0.944 | | 22-H | 3.59 (brd, 10.6) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.185 | | 27-Me | 1.193 |
| D2O | | 01-Ha | | | 01-He | | | 02-Ha | 3.77 | | 03-He | 3.51 | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 5.99 (m) | | 09-Ha | 3.11 (m) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.757 | | 19-Me | 0.966 | | 21-Me | 0.981 | | 22-H | 3.71 | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.244 | | 27-Me | 1.250 |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | |
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| TLC on silica | Rf 0.35 (CHCl3-EtOH 4:1 v/v); Rf 0.41 (CHCl3-MeOH 4:1 v/v); Rf 0.33 (CHCl3-EtOH 9:2 v/v, continuous development fro 2.5 hours); Rf 0.52 (CHCl3-EtOH 65:35 v/v) (E : 0.47)); Rf 0.41 (CHCl3-MeOH 90:15 v/v, multiple development ) (E : 0.34) | | NP-HPLC | Retention volume 68 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) | | RP-HPLC | 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) |
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Musca assay: 10-20% (20-hydroxyecdysone = 100%) |
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| First isolation | NIGG, H.N. et al. (1974) Lipids 9, 971-974 |
 | | General | DINAN, L. et al. (1978) Steroids 32, 629-638 |
| | General | KAPLANIS, J.N. et al. (1979) Steroids 34, 333-345 |
| | Bioactivities | BERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 |
| | General | LAFONT, R. et al. (1980) Steroids 36, 185-207 |
| | General | DINAN, L. et al. (1981) J. Chromatogr. 205, 139-145 |
| | General | MILNER, N.P. et al. (1985) Biochem. J. 231, 369-374 |
| | First isolation | KAMBA, M. et al. (1995) J. Seric. Sci. Jpn. 64, 333-343 |
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Permanent link to this datasheet: 3-EPI-ECDYSONE
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