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Year of first isolation: |
1989 |
| Formula: | C27H44O6 |
| Molecular weight: | 464 |
| Occurence in plants: |
Tinospora capillipes [Menispermaceae] »  ![Wikipedia: Tinospora capillipes [Menispermaceae]](/images/wikipedia.png)
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| Occurence in animals: |
Hirudo medicinalis [Hirudinidae] »
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| Canonical SMILES | CC12CCC(CC1C(=O)C=C3C2CCC4(C3(CCC4C(C)(C(CCC(C)(C)O)O)O)O)C)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@](C)([C@@H](CCC(C)(C)O)O)O)O)C)C » 
| | IUPAC Name | (3R,5R,9R,10R,13R,14S,17S)-3,14-dihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | 22785-88-2 | | PubChem CID | 11812630 | InChiKey
[ ChemIDPlus: search ] | JNTQSSGVHLUIBL-MBYAXLKMSA-N | | InChI | InChI=1S/C27H44O6/c1-23(2,31)10-9-22(30)26(5,32)21-8-13-27(33)18-15-20(29)19-14-16(28)6-11-24(19,3)17(18)7-12-25(21,27)4/h15-17,19,21-22,28,30-33H,6-14H2,1-5H3/t16-,17+,19+,21+,22-,24-,25-,26-,27-/m1/s1 |
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| FAB-MS (positive mode) m/z | 465.3217 [M+H] + | | CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 464 (M) + |
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| C5D5N | | 01 | 31.71 | | 02 | 27.43 | | 03 | 68.07 | | 04 | 38.62 | | 05 | 51.34 | | 06 | 203.43 | | 07 | 121.63 | | 08 | 166.02 | | 09 | 34.46 | | 10 | 37.95 | | 11 | 21.09 | | 12 | 31.99 | | 13 | 48.09 | | 14 | 84.18 | | 15 | 32.37 | | 16 | 21.40 | | 17 | 50.08 | | 18 | 17.84 | | 19 | 24.41 | | 20 | 76.85 | | 21 | 21.09 | | 22 | 77.54 | | 23 | 27.40 | | 24 | 42.56 | | 25 | 69.56 | | 26 | 29.96 | | 27 | 29.96 |
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| D2O | | 01-Ha | 1.22 | | 01-He | 1.11 | | 02-Ha | 1.4 | | 02-He | 1.95 | | 03-Ha | 3.54 (m, w1/2 = 25) | | 04-Ha | 1.43 | | 04-He | 1.73 | | 05-H | 2.13 (dd, 13, 4) | | 07-H | 5.97 (d, 2.5) | | 09-Ha | 3.20 (m, w1/2 = 22) | | 11-Ha | 1.8 | | 11-He | 1.72 | | 12-Ha | | | 12-He | 1.68 | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.33 (dd, 9, 9) | | 18-Me | 0.86 (s ) | | 19-Me | 0.92 (s ) | | 21-Me | 1.23 (s ) | | 22-H | 3.43 (dd, 10, 2) | | 23-Ha | 1.32 | | 23-Hb | 1.68 | | 24-Ha | | | 24-Hb | | | 26-Me | 1.22 (s ) | | 27-Me | 1.23 (s ) |
| C5D5N | | 01-Ha | | | 01-He | | | 02-Ha | | | 02-He | | | 03-Ha | 3.83 | | 04-Ha | | | 04-He | | | 05-H | 2.29 | | 07-H | 6.23 | | 09-Ha | 3.70 | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 3.02 (t, 9) | | 18-Me | 1,22 (s) | | 19-Me | 0.98 (s) | | 21-Me | 1.59 (s) | | 22-H | 3.88 (brd, 10.1) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.37 (s) | | 27-Me | 1.37 (s) |
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| M.P. | 247 °C | | [α]D28 | + 60.6 ° (c 0.201; MeOH) | | IR (KBr) ν max (cm-1) | 3340, 2960, 1640, (enone), 1558, 1408, 1381, 1299, 1054, 963 | | UV (EtOH) λ max (log ε) | 243 (4.09) |
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| HPTLC | | | TLC | (silica gel Merck plates), solvent CHCl3-MeOH (4:1 v/v) Rf 0.30 (2D20E 0.53) | | GLC | | | HPLC | |
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Calliphora assay: 33% (20-hydroxyecdysone = 100%) |
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| General | GALBRAITH, M.N. et al. (1969) Aust. J. Chem. 22, 1059-1067 |
 | | Bioactivities | BERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 |
| | First isolation | GARCIA, M. et al. (1989) Invertebr. Reprod. Devel. 15, 57-68 |
| | First isolation | SONG, C. et al. (1991) Chin. Chem. Lett. 2, 13-14 |
| | General | SUKSAMRARN, A. et al. (1997) Tetrahedron 53, 3145-3154 |
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Permanent link to this datasheet: 3-EPI-2-DEOXY-20-HYDROXYECDYSONE
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