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Year of first isolation: |
1984 |
| Formula: | C29H47O10P |
| Molecular weight: | 586 |
| Occurence in plants: |
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| Occurence in animals: |
Schistocerca gregaria [Orthoptera] »  ![Wikipedia: Schistocerca gregaria [Orthoptera]](/images/wikipedia.png)
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| Canonical SMILES | | 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)OP(=O)([O-])[O-])O)C)C » 
| | IUPAC Name | (2S,3R)-2-((2S,3R,5R,9R,10R,13R,14S,17R)-3-acetoxy-2,14-dihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-hydroxy-6-methylheptan-3-yl phosphate | | CAS-RN | | | PubChem CID | | InChiKey
[ ChemIDPlus: search ] | YVVCFCZXAOUYIG-OQSRUVMCSA-L | | InChI | InChI=1S/C29H47O10P/c1-16(24(39-40(35,36)37)9-10-26(3,4)33)18-8-12-29(34)20-13-22(31)21-14-25(38-17(2)30)23(32)15-27(21,5)19(20)7-11-28(18,29)6/h13,16,18-19,21,23-25,32-34H,7-12,14-15H2,1-6H3,(H2,35,36,37)/p-2/t16-,18+,19-,21-,23-,24+,25+,27+,28+,29+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | | | FAB-MS m/z | 607 (M-H+Na)-, 585 (M-H)-, 97, 79 | | 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 | |
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| CD3OD | | 01-Ha | | | 01-He | | | 02-Ha | | | 03-He | | | 04-Ha | | | 04-He | | | 05-H | 5.82, 5.84 (mixture of 2- and 3-acetates) | | 07-H | | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.74 (s ) | | 19-Me | 0.99 (s ) | | 21-Me | 0.98 (d, 6) | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.17 | | 27-Me | 1.185 | | O-Ac | 2.06, 2.18 (mixture of 2- and 3-acetates) |
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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 | | | GLC | | | HPLC | (exists as an equilibrium mixture of 2/3 acetates and gives rise to 2 peaks); RP-HPLC (ion suppression mode) : Retention volume 17 ml [Waters Resolve column, 150 mm x 4.6 mm i.d., solvent MeOH-20 mM Na citrate pH 6.5 30:70 v/v, flow-rate 1 ml.min-1] |
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Permanent link to this datasheet: ECDYSONE 3(/2)-ACETATE 22-PHOSPHATE
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