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Year of first isolation: |
1970 |
| Formula: | C27H44O5 |
| Molecular weight: | 448 |
| Occurence in plants: |
Blechnum minus [Blechnaceae] »  ![Wikipedia: Blechnum minus [Blechnaceae]](/images/wikipedia.png)
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| Occurence in animals: |
Bombyx mori [Bombycidae] »
Locusta migratoria [Orthoptera] »
Schistocerca gregaria [Orthoptera] »
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| Canonical SMILES | CC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CCC(C4)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](C1)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 | (3S,5R,9R,10R,13R,14S,17R)-17-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-3,14-dihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | 31575-91-4 | | PubChem CID | 13939876 | InChiKey
[ ChemIDPlus: search ] | CRAPXAGGASWTPU-VQOIUDCISA-N | | InChI | InChI=1S/C27H44O5/c1-16(22(29)9-10-24(2,3)31)18-8-13-27(32)20-15-23(30)21-14-17(28)6-11-25(21,4)19(20)7-12-26(18,27)5/h15-19,21-22,28-29,31-32H,6-14H2,1-5H3/t16-,17-,18+,19-,21-,22+,25+,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | 466 (M+H+NH3)+, 449 (MH)+, 431, 415, 413, 333, 315 | | EI-MS m/z | 448, 430, 412, 361, 332, 314, 284, 99, 81 | | HR-MS | |
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| C5D5N | | 01 | 29.48 (t ) | | 02 | 29.07 (t ) | | 03 | 64.06 (d ) | | 04 | 33.07 (t ) | | 05 | 51.61 (d ) | | 06 | 203.20 (s ) | | 07 | 121.30 (d ) | | 08 | 166.01 (s ) | | 09 | 34.40 (d ) | | 10 | 36.96 (s ) | | 11 | 21.00 (t ) | | 12 | 31.70 (t ) | | 13 | 48.00 (s ) | | 14 | 84.01 (s ) | | 15 | 31.70 (t ) | | 16 | 25.50 (t ) | | 17 | 48.32 (d ) | | 18 | 15.80 (q ) | | 19 | 24.30 (q ) | | 20 | 42.99 (d ) | | 21 | 13.60 (q ) | | 22 | 73.90 (d ) | | 23 | 26.70 (t ) | | 24 | 42.46 (t ) | | 25 | 69.60 (s ) | | 26 | 29.98 (q ) | | 27 | 30.20 (q ) |
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| CD3OD | | 01-Ha | | | 01-He | | | 02-Ha | | | 03-He | 4.09 (m, w1/2=22) | | 04-Ha | | | 04-He | | | 05-H | 2.41 (dd, 12, 4) | | 07-H | 5.96 (d, 2) | | 09-Ha | 3.14 (m, w1/2=22) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.02 (m ) | | 18-Me | 0.74 (s ) | | 19-Me | 0.98 (s ) | | 21-Me | 0.94 (d, 6.5) | | 22-H | 3.69 (m, w1/2=16) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.24 (s ) | | 27-Me | 1.24 (s ) |
| C5D5N | | 01-Ha | | | 01-He | | | 02-Ha | | | 03-He | | | 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 | 0.74 (s ) | | 19-Me | 1.05 (s ) | | 21-Me | 1.28 (d, 7) | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.38 (s ) | | 27-Me | 1.38 (s ) |
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| M.P. | 231-232 °C ; | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3450 (OH), 1650 (cyclohexenone) | | UV (EtOH) λ max (log ε) | 244 (4,111) ; |
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| TLC | (silica plates) Rf 0.43 (solvent : EtOAc-MeOH-NH4OH 85:10:5 v/v/v) (20E : 0.18); Rf 0.40 (solvent : CH2Cl2-EtOH 85:15 v/v) (20E : 0.15); Rf 0.38 (solvent CHCl3-EtOH 4:1 v/v) (20E :0.15) RP-TLC (C18 bonded silica gel) Rf 0.19 (solvent MeOH-H2O 65:35 v/v) (20E : 0.47) | | GLC | as TMS ether on 1.5% OV101, 285°C, derivatized for 5h at 120°C, retention time 5.9 min (E : 6.9 min). | | HPLC | NP-HPLC, Retention time 11.6 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2- iPrOH-H2O, 125:25:2 v/v/v, flow-rate 1 ml.min-1] (20E 37.4 min); RP-HPLC, Retention time 34.1 min [Spherisorb-5ODS2 250 mm x 4.6 mm i.d., solvent ACN-0.1% TFA 23:77 v/v, flow-rate 1 ml.min-1] (20E : 5.5 min) |
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Drosophila melanogaster BII cell assay: EC50 = 5.0 x 10-5M | Drosophila melanogaster BII cell assay: EC50 = 2.0 x 10-5M | Galleria mellonella in vivo assay: ED50 = 15.6 ug/g | Sarcophaga bullata in vivo assay: ED50 = 31.3 ug/g | Calliphora assay: 100% (20-hydroxyecdysone = 100%) |
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| First isolation | CHONG, Y.K. et al. (1970) J. Chem. Soc., Chem. Commun., 1217-1218 |
 | | First isolation | OHNISHI, E. et al. (1971) Science 197, 66-67 |
| | General | GALBRAITH, M.N. et al. (1975) Experientia 31, 873 |
| | Bioactivities | BERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 |
| | General | DIEHL, P.A. et al. (1985) Methods Enzymol. 111, 377-410 |
| | General | HETRU, C. et al. (1985) Methods Enzymol. 111, 411-419 |
| | General | WILSON, I.D. et al. (1985) J. Chromatogr. 318, 373-377 |
| | General | BIELBY, C.R. et al. (1986) J. Chromatogr. 351, 57-64 |
| | General | GIRAULT, J.-P. et al. (1990) J. Nat. Prod. 53, 279-293 |
| | Bioactivities | SLÁMA, K. et al. (1993) Insect Biochem. Molec. Biol. 23, 181-185 |
| | Bioactivities | DINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 |
| | Bioactivities | DINAN, L. et al. (2003) In: Studies in Natural Products Chemisty (ed. Atta-ur-Rahman), Elsevier, Amsterdam, 29, 3-71 |
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Permanent link to this datasheet: 2-DEOXYECDYSONE
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