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Year of first isolation: |
1982 |
| Formula: | C27H45O9P |
| Molecular weight: | 544 |
| Occurence in plants: |
Spinacia oleracea [Amaranthaceae] »  ![Wikipedia: Spinacia oleracea [Amaranthaceae]](/images/wikipedia.png)
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| Occurence in animals: |
Locusta migratoria [Orthoptera] »
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| Canonical SMILES | CC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)OP(=O)(O)O)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)OP(=O)([O-])[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 | [(2S,3R,5R,9R,10R,13R,14S,17R)-17-[(2S,3R)-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] dihydrogen phosphate | | CAS-RN | | | PubChem CID | 101672230 | InChiKey
[ ChemIDPlus: search ] | ALZRZRFBTMQEBA-HNPHCAPQSA-N | | InChI | InChI=1S/C27H45O9P/c1-15(20(28)8-9-24(2,3)31)16-7-11-27(32)18-12-21(29)19-13-23(36-37(33,34)35)22(30)14-25(19,4)17(18)6-10-26(16,27)5/h12,15-17,19-20,22-23,28,30-32H,6-11,13-14H2,1-5H3,(H2,33,34,35)/t15-,16+,17-,19-,20+,22-,23+,25+,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (direct inlet on gold support) | 549 (M-18+Na)+, 544 (M)+, 531, 526, 513, 464 (ecdysone)+, 447, 428, ? | | 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 | | | 07-H | | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.76 | | 19-Me | ? | | 20-H | | | 21-Me | 0.94 (d, 4) | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.22 | | 27-Me | 1.22 |
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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 | Retention time 7.7 min [column Lichroprep C18 10 ?m, 250 mm long, 4 mm i.d., eluted with a gradient 12 to 44% (in 32 min, gradient former Waters M660, curve 7) of CH3CN in 20 mM tris-HCl, pH 7.5, flow-rate 1 ml.min-1] |
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| First isolation | TSOUPRAS, G. et al. (1982) Thesis, Strasbourg, France |
 | | General | LAGUEUX, M. et al. (1984) In: Biosynthesis, Metabolism and Mode of Action of Invertebrate Hormones (eds., Hoffmann J.A., Porchet M.), Springer-Verlag, Berlin, pp. 168-180 |
| | General | GREBENOK, R.J. et al. (1994) Phytochemistry 36, 1399-1408 |
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Permanent link to this datasheet: ECDYSONE 3-PHOSPHATE
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