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Year of first isolation: |
1996 |
| Formula: | C27H44O7 |
| Molecular weight: | 480 |
| Occurence in plants: |
Serratula tinctoria [Asteraceae] »  ![Wikipedia: Serratula tinctoria [Asteraceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)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)O)O)O)C)C » 
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3S)-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 | | | PubChem CID | 10767085 | InChiKey
[ ChemIDPlus: search ] | NKDFYOWSKOHCCO-ZPEWUMIJSA-N | | InChI | InChI=1S/C27H44O7/c1-23(2,32)9-8-22(31)26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-34H,6-11,13-14H2,1-5H3/t15-,17-,19+,20-,21-,22-,24+,25+,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | 498 (M+H+NH3)+, 481, 463, 445, 427, 403, 380 (M+H+NH3- C22--C27)+, 363, 345 | | EI-MS m/z (relative intensity %) | | | FAB-MS (glycerol) m/z (relative intensity %) | 481 (M+H)+ (30), 463 (78), 445 (100), 427.6 (36), 411.5 (23), 393 (20), 371 (42), 347 (40), 331 (57), 329 (72), 303 (70), 301 (93) |
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| D2O | | 01 | 36.3 | | 02 | 68.3 | | 03 | 68.2 | | 04 | 32.4 | | 05 | 51.4 | | 06 | | | 07 | 122.1 | | 08 | | | 09 | 35.1 | | 10 | 39.1 | | 11 | | | 12 | 32.1 | | 13 | 48.0 | | 14 | 86.3 | | 15 | | | 16 | | | 17 | 50.2 | | 18 | 18.1 | | 19 | 24.2 | | 20 | 78.6 | | 21 | 21.3 | | 22 | 78.6 | | 23 | | | 24 | 41.7 | | 25 | 73.0 | | 26 | 28.3 | | 27 | 29.3 |
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| D2O | | 01-Ha | 1.4 (t, 13) | | 01-Hb | 1.85 | | 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 ) | | 07-H | 5.99 (d, 2.5) | | 09-Ha | 3.10 (m, w1/2 = 22) | | 11-Ha | 1.75 | | 11-He | 1.85 | | 12-Ha | 1.95 | | 12-He | | | 15-Ha | 2.05 (m ) | | 15-Hb | 1.65 | | 16-Ha | 1.85 | | 16-Hb | 1.9 | | 17-H | 2.55 (t ) | | 18-Me | 0.85 (s ) | | 19-Me | 1.00 (s ) | | 21-Me | 1.27 (s ) | | 22-H | 3.35 (d, 10) | | 23-Ha | 1.45 | | 23-Hb | 1.8 | | 24-Ha | 1.8 | | 24-Hb | 1.53 | | 26-Me | 1.238 (s ) | | 27-Me | 1.243 (s ) |
| C5D5N | | 01-Ha | | | 01-Hb | | | 02-Ha | 4.00-4.35 | | 03-He | 4.00-4.35 | | 04-Ha | | | 04-He | | | 05-H | 2.85-3.15 | | 07-H | 6.22 (d, 2) | | 09-Ha | 3.40-3.75 | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 3.40-3.75 | | 18-Me | 1.22 (s ) | | 19-Me | 1.08 (s ) | | 21-Me | 1.71 (s ) | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.40 (s ) | | 27-Me | 1.40 (s ) |
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| M.P. | 259-260 °C | | [α]D20 | | | IR (KBr) ν max (cm-1) | 1650 (unsaturated CO) | | UV (EtOH) λ max (log ε) | |
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| HPTLC | | | TLC | Rf 0.14, solvent CH2Cl2-EtOH (96%) 85:15 v/v (20E 0.18) | | GLC | | | HPLC | NP-HPLC, Column Zorbax-SIL9.4x250 mm, flow-rate 4 ml.min-1, Ret 26.4 min, Solvent CH2Cl2-iPrOH-H2O 125:40:3 v/v/v, (20E 17.6 min); Ret 16.4 min, Solvent Cyclohexane-iPrOH-H2O 80:40:3 v/v/v, (20E 13.4 min) |
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Calliphora assay: 0% (20-hydroxyecdysone = 100%) |
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| General | KERB, U. et al. (1968) Tetrahedron Lett. 4277-4280 |
 | | Bioactivities | BERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 |
| | General | HEDTMAN, U. et al. (1991) Tetrahedron 47, 3753-3772 |
| | First isolation | BÁTHORI, M. et al. (1998) J. Nat. Prod. 61, 415-417 |
| | Identification | VOKÁČ, K. et al. (2002) Collect. Czech. Chem. Commun. 67, 124-139 |
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Permanent link to this datasheet: 22-EPI-20-HYDROXYECDYSONE
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