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Year of first isolation: |
1981 |
| Formula: | C27H44O5 |
| Molecular weight: | 448 |
| Occurence in plants: |
Blechnum vulcanicum [Blechnaceae] »  ![Wikipedia: Blechnum vulcanicum [Blechnaceae]](/images/wikipedia.png)
Acanthophyllum gypsophiloides [Caryophyllaceae] »
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| Occurence in animals: |
Schistocerca gregaria [Orthoptera] »
Bombyx mori [Bombycidae] »
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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 | (3R,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 | | | PubChem CID | 21724361 | InChiKey
[ ChemIDPlus: search ] | CRAPXAGGASWTPU-DUIYOXMUSA-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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| EI-MS m/z (relative intensity %) | 448 (M)+ (0.2), 430 (2), 412 (5), 397 (5), 396 (3), 379 (3), 361 (1), 332 (8), 314 (11), 299 (5), 284 (6), 283 (9), 263 (8), 251 (5), 99 (100), 81 (54). | | EI* m/z (relative intenzity %) | 430 (4), 394 (4), 343 (5), 332(8), 284 (18), 99 (100), 81 (68) | | CI-MS (isobutane) m/z | 449 (M+H)+ |
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| C5D5N | | 01 | 35.6 (t ) | | 02 | 31.2 (t ) | | 03 | 69.1 (d ) | | 04 | 34.3 (t ) | | 05 | 57.2 (d ) | | 06 | 201.9 (s ) | | 07 | 121.3 (d ) | | 08 | 165.8 (s ) | | 09 | 34.0 (d ) | | 10 | 36.8 (s ) | | 11 | 20.8 (t ) | | 12 | 31.6 (t ) | | 13 | 47.6 (s ) | | 14 | 83.8 (s ) | | 15 | 31.9 (t ) | | 16 | 26.7 (t ) | | 17 | 48.3 (d ) | | 18 | 15.8 (q ) | | 19 | 23.9 (q ) | | 20 | 43.0 (d ) | | 21 | 15.7 (q ) | | 22 | 74.0 (d ) | | 23 | 25.6 (t ) | | 24 | 42.5 (t ) | | 25 | 69.7 (s ) | | 26 | 30.0 (q ) | | 27 | 30.3 (q ) |
| DMSO-d6 | | 01 | 28.40 | | 02 | 27.91 | | 03 | 62.61 | | 04 | 31.75 | | 05 | 50.18 | | 06 | 201.96 | | 07 | 119.93 | | 08 | 164.84 | | 09 | 33.16 | | 10 | 35.77 | | 11 | 20.30 | | 12 | 30.43 | | 13 | 46.92 | | 14 | 82.75 | | 15 | 30.16 | | 16 | 25.45 | | 17 | 46.92 | | 18 | 15.03 | | 19 | 23.45 | | 20 | 41.49 | | 21 | 12.60 | | 22 | 72.27 | | 23 | 24.14 | | 24 | 40.96 | | 25 | 68.55 | | 26 | 29.49 | | 27 | 28.97 |
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| DMSO-d6 | | 01-Ha | 1.375 | | 01-He | 1.488 | | 02-Ha | 1.643 | | 02-He | 1.529 | | 03-He | 3.827 | | 04-Ha | 1.692 | | 04-He | 1.405 | | 05-H | 2.274 | | 07-H | 5.643 | | 09-Ha | 3.076 | | 11-Ha | 1.635 | | 11-He | 1.503 | | 12-Ha | 2.026 | | 12-He | 1.623 | | 15-Ha | 1.847 | | 15-Hb | 1.527 | | 16-Ha | 1.843 | | 16-Hb | 1.383 | | 17-H | 1.952 | | 18-Me | 0.617 | | 19-Me | 0.881 | | 20-H | 1.616 | | 21-Me | 0.851 | | 22-H | 3.430 | | 23-Ha | 1.366 | | 23-Hb | 1.177 | | 24-Ha | 1.655 | | 24-Hb | 1.281 | | 26-Me | 1.094 | | 27-Me | 1.080 |
| CD3OD | | 01-Ha | | | 01-He | | | 02-Ha | | | 03-Ha | 3.57 (m, w1/2=22) | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 5.82 (d, 2.2) | | 09-Ha | 3.18 (m ) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.726 (s) | | 19-Me | 0.915 (s) | | 21-Me | 0.944 (d, 6) | | 22-H | 3.59 (brd, 10.5) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.186 (s) | | 27-Me | 1.186 (s) |
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| M.P. | 264-265 °C ; | | [α]D20 | + 98 ° (CHCl3) | | IR (KBr) ν max (cm-1) | 3450 (OH), 1650 (cyclohexenone) ; | | UV (EtOH) λ max (log ε) | 243 (4.061) ; |
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| HPTLC | | | TLC | NP-TLC on silica gel, Rf 0.60 (CHCl3-MeOH 4:1 v/v) (0.56 for 2DE) | | GLC | | | NP-HPLC | CH2Cl2-iPrOH-MeOH 87:10:3 v/v/v (Russel et al.); | | RP-HPLC | Reverse-phase column (15 cm long, 4.6 mm i.d.) eluted at 1 ml.min-1 with a linear gradient (20 min) 40-> 80% methanol in H2O, retention time 20.0 min) (20E 9.4 min). |
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| First isolation | RUSSEL, G.B. et al. (1981) Phytochemistry 20, 2407-2410 |
 | | First isolation | ISAAC, R.E. et al. (1981) Chem. Commun., 418-420 |
| | General | HETRU, C. et al. (1985) Methods Enzymol. 111, 411-419 |
| | General | REES, H.H. et al. (1985) Methods Enzymol. 111, 377-410 |
| | First isolation | KAMBA, M. et al. (1995) J. Seric. Sci. Jpn. 64, 333-343 |
| | Identification | TULEUOV, B.I. et al. (2018) Russian Chemical Bulletin, International Edition 67(4): 633-666 |
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Permanent link to this datasheet: 3-EPI-2-DEOXYECDYSONE
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