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Year of first isolation: |
1981 |
| Formula: | C29H46O7 |
| Molecular weight: | 506 |
| Occurence in plants: |
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| Occurence in animals: |
Schistocerca gregaria [Orthoptera] »  ![Wikipedia: Schistocerca gregaria [Orthoptera]](/images/wikipedia.png)
Locusta migratoria [Orthoptera] »
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| Canonical SMILES | CC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)OC(=O)C)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]([C@H]1O)OC(=O)C)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 | [(2S,3R,5R,9R,10R,13R,14S,17R)-17-[(2S)-3,6-dihydroxy-6-methylheptan-2-yl]-2,14-dihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate | | CAS-RN | | | PubChem CID | 53893325 | InChiKey
[ ChemIDPlus: search ] | HSADMKYEQWKERB-NIVYSHQQSA-N | | InChI | InChI=1S/C29H46O7/c1-16(22(31)9-10-26(3,4)34)18-8-12-29(35)20-13-23(32)21-14-25(36-17(2)30)24(33)15-27(21,5)19(20)7-11-28(18,29)6/h13,16,18-19,21-22,24-25,31,33-35H,7-12,14-15H2,1-6H3/t16-,18+,19-,21-,22?,24-,25+,27+,28+,29+/m0/s1 |
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| CI-MS (NH3) m/z (relative intensity %) | 524 (M+H+NH3)+ (0.1), 506 (0.3), 489 (10), 488 (10), 447 (2), 446 (2), 429 (12), 99 (100). | | EI-MS m/z (relative intensity %) | 470 (M-2x18)+ (2), 428 (M-18-60)+ (1), 410 (2), 395 (8), 390 (M-C22--C27)+ (3), 342 (10), 99 (100). | | HR-MS | |
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| C5D5N | | 01 | | | 02 | | | 03 | | | 04 | | | 05 | | | 06 | | | 07 | | | 08 | | | 09 | | | 10 | | | 11 | | | 12 | | | 13 | | | 14 | | | 15 | | | 16 | | | 17 | | | 18 | | | 19 | | | 20 | | | 21 | | | 22 | | | 23 | | | 24 | | | 25 | | | 26 | | | 27 | | | 28 | | | 29 | |
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| CDCl3 | | 01-Ha | | | 01-He | | | 02-Ha | 4.05 (m, w1/2=20) | | 03-He | 5.23 (m, w1/2=7) | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 5.87 (d ) | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 14-H | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.71 (s ) | | 19-Me | 1.03 (s ) | | 21-Me | 0.97 (d, 7) | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | 1.27 (s ) | | 27-Me | 1.27 (s ) | | O-Ac | 2.14 (s, 3H) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | |
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| HPTLC | | | TLC | Rf on silica gel 0.62 (CHCl3-MeOH 4:1) (E : 0.37; 20E : 0.30) | | GLC | | | HPLC | 1-Retention volume 128 ml [Whatman Magnum 9 Partisil ODS-3, 50 cm x 9.4 mm i.d., eluted with a linear gradient (40 min) of 40 --> 80% MeOH-H2O] (20E 82 ml, E 110 ml, E2Ac 145 ml); 2-Retention time 9.1 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 31.5 min) |
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Permanent link to this datasheet: ECDYSONE 3-ACETATE
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