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Year of first isolation: |
1988 |
| Formula: | C33H54O12 |
| Molecular weight: | 642 |
| Occurence in plants: |
Pfaffia iresinoides [Amaranthaceae] »  ![Wikipedia: Pfaffia iresinoides [Amaranthaceae]](/images/wikipedia.png)
Silene otites [Caryophyllaceae] »
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| Occurence in animals: |
Parascaris equorum [Nematoda] »
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| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)OC5C(C(C(C(O5)CO)O)O)O)O)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@](C)([C@@H](CCC(C)(C)O[C@H]1C(C([C@@H](C(O1)CO)O)O)O)O)O)O)C)C » 
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-17-[(2R)-2,3-dihydroxy-6-methyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-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 | 18394235 | InChiKey
[ ChemIDPlus: search ] | VJAXSGXKVCCJNY-HMWOVMMSSA-N | | InChI | InChI=1S/C33H54O12/c1-29(2,45-28-27(41)26(40)25(39)22(15-34)44-28)9-8-24(38)32(5,42)23-7-11-33(43)17-12-19(35)18-13-20(36)21(37)14-30(18,3)16(17)6-10-31(23,33)4/h12,16,18,20-28,34,36-43H,6-11,13-15H2,1-5H3/t16-,18-,20+,21-,22+,23-,24?,25+,26-,27+,28-,30+,31+,32+,33+/m0/s1 |
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| CI-MS (NH3) m/z | 660 (M + NH4)+, 643 (M+H)+, 625, 607, 480, 463, 445, 427, 363, 345 | | EI-MS m/z (relative intensity %) | | | FAB-MS m/z | 665 [M+Na], 647 [M+Na-H2O], 643 [M+H], 625 [M+H-H2O] | | HR-MS | [M+H] found 643.3656, calc. 643.3694 |
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| C5D5N | | 01 | 37.9 | | 02 | 68.1 | | 03 | 68.0 | | 04 | 32.4 | | 05 | 51.4 | | 06 | 203.7 | | 07 | 121.7 | | 08 | 166.1 | | 09 | 34.4 | | 10 | 38.6 | | 11 | 21.1 | | 12 | 32.0 | | 13 | 48.1 | | 14 | 84.3 | | 15 | 31.7 | | 16 | 21.4 | | 17 | 50.0 | | 18 | 17.9 | | 19 | 24.4 | | 20 | 76.9 | | 21 | 21.7 | | 22 | 77.7 | | 23 | 26.6 | | 24 | 39.8 | | 25 | 77.4 | | 26 | 27.5 | | 27 | 27.6 | | glu-01' | 98.8 | | glu-02' | 75.5 | | glu-03' | 78.7* | | glu-04' | 72.1 | | glu-05' | 78.5* | | glu-06' | 63.4 |
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| C5D5N | | 01-Ha | | | 01-Hb | | | 02-Ha | | | 03-He | | | 04-Ha | | | 04-He | | | 05-H | 2.99 (dd, 13.2, 4) | | 07-H | 6.21 (d, 2.2) | | 09-Ha | 3.55 (br t, 9.0) | | 11-Ha | | | 11-He | | | 12-Ha | 2.52 (dt, 13.2, 4.2) | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | 2.42 (q, 10.4) | | 16-Hb | | | 17-H | 2.94 (t, 8.8) | | 18-Me | 1.18 (s ) | | 19-Me | 1.04 (s ) | | 21-Me | 1.56 (s ) | | 22-H | 3.83 (br d, 9.4) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.31 (s ) | | 27-Me | 1.37 (s ) | | glu-H1´ | 5.00 (d, 7.6) |
| D2O | | 01-Ha | 1.4 | | 01-Hb | 1.9 | | 02-Ha | 3.99 (m, w1/2=22) | | 03-He | 4.07 (m, w1/2=8) | | 04-Ha | 1.75 | | 04-He | 1.75 | | 05-H | 2.34 (t-like ) | | 07-H | 5.97 (d, 2.5) | | 09-Ha | 3.11 (m, w1/2=22) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.32 (m ) | | 18-Me | 0.88 (s ) | | 19-Me | 1.01 (s ) | | 21-Me | 1.25 (s ) | | 22-H | 3.45 | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.30 (s ) | | 27-Me | 1.30 (s ) | | glu-H1' | 4.79 (d, 7.6) | | glu-H1´ | | | glu-H2´ | 3.20 | | glu-H3´ | 3.51 | | glu-H4´ | 3.33 | | glu-H5´ | 3.45 | | glu-H6´ | 3.90 (dd, 12.3, 2.2) | | glu-H6´´ | 3.67 (dd, 12.3, 6.4) |
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| M.P. | 158-163 °C | | [α]D20 | + 26.0° (c 1.5, MeOH) | | IR (KBr) ν max (cm-1) | 3420 (-OH), 1652 (C=O), 1052 (C-O) | | UV (EtOH) λ max (log ε) | 243 (4.02) |
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| HPTLC | | | TLC | Rf 0.20 (CHCl3/MeOH/H2O) 13:7:2, lower phase); Rf 0.33 (EtOAc/EtOH/H2O, 8:2:1) (20E 0.61); Rf 0.13 (CHCl3/MeOH/Me2CO, 6:2:1) (20E 0.47) | | GLC | | | HPLC | Retention time 8.7 min (Reverse-phase, Spherisorb 5ODS2 25 cm long, 4.6 mm i.d., flow-rate 1 ml.min-1, eluted with 17% ACN in 0.1% TFA in water).Retention time 11.5 min (RP-HPLC, Separon SGX-C18 25 cm long, 8 mm i.d., flow-rate 4 ml.min-1, eluted with 40% MeOH in water). |
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Drosophila melanogaster BII cell assay: EC50 = 8.5 x 10-6M |
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| First isolation | NISHIMOTO, N. et al. (1988) Phytochemistry 27, 1665-1668 |
 | | General | GIRAULT, J.-P. et al. (1990) J. Nat. Prod. 53, 279-293 |
| | General | O'HANLON, J.M. et al. (1991) Parasitol. Res. 77, 271-272 |
| | Synthesis | PIS, J. et al. (1994) Tetrahedron 50, 9679-9690 |
| | Bioactivities | HARMATHA, J. et al. (1997) Arch. Insect Biochem. Physiol. 35, 219-225 |
| | Identification | SARKER, S.D. et al. (1998) Biochem. Syst. Ecol. 26, 135-137 |
| | General | LI, X. et al. (2000) Shenyang Yaoke Daxue Xuebao 17, 260-262 |
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Permanent link to this datasheet: 20-HYDROXYECDYSONE 25-β-D-GLUCOSIDE
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