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Year of first isolation: |
1982 |
| Formula: | C27H45O9P |
| Molecular weight: | 544 |
| Occurence in plants: |
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| Occurence in animals: |
Schistocerca gregaria [Orthoptera] »  ![Wikipedia: Schistocerca gregaria [Orthoptera]](/images/wikipedia.png)
Locusta migratoria [Orthoptera] »
Bombyx mori [Bombycidae] »
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| Canonical SMILES | CC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)C(CCC(C)(C)O)OP(=O)(O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C[C@@H]([C@H]1CCC2([C@@]1(CC[C@H]3C2=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)C)O)C(CCC(C)(C)O)OP(=O)(O)O » 
| | IUPAC Name | [(2S)-6-hydroxy-6-methyl-2-[(2S,3R,5R,9R,10R,13R,17R)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]heptan-3-yl] dihydrogen phosphate | | CAS-RN | 82183-62-8 | | PubChem CID | 44144521 | InChiKey
[ ChemIDPlus: search ] | FUMILPJJVXGPIT-CWNOQBPDSA-N | | InChI | InChI=1S/C27H45O9P/c1-15(23(36-37(33,34)35)8-9-24(2,3)31)16-7-11-27(32)18-12-20(28)19-13-21(29)22(30)14-25(19,4)17(18)6-10-26(16,27)5/h12,15-17,19,21-23,29-32H,6-11,13-14H2,1-5H3,(H2,33,34,35)/t15-,16+,17-,19-,21+,22-,23?,25+,26+,27?/m0/s1 |
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| CI-MS (isobutane) m/z | 447 | | EI-MS m/z (relative intensity %) | | | FAB-MS m/z | 565 (M-H+Na)-, 543 (M-H)-, 525 (M-H-18)-, 301 (ecdysone nucleus), 251, 223, 221, 199, 97, 79 | | HR-MS | |
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| CD3OD | | 01 | | | 02 | 68.7 (d ) | | 03 | 68.6 (d ) | | 04 | | | 05 | | | 06 | | | 07 | | | 08 | | | 09 | | | 10 | | | 11 | | | 12 | | | 13 | | | 14 | 85.4 (s ) | | 15 | | | 16 | | | 17 | | | 18 | | | 19 | | | 20 | | | 21 | | | 22 | 79.3 (d ) | | 23 | | | 24 | | | 25 | 71.8 (s ) | | 26 | | | 27 | |
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| CD3OD | | 01-Ha | | | 01-He | | | 02-Ha | 3.86 (m, w1/2=21) | | 03-He | 3.97 (m, w1/2=8) | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 5.81 (d, 2) | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.75 (s ) | | 19-Me | 0.97 (s ) | | 21-Me | 0.985 (d, 7) | | 22-H | 4.20 (m, w1/2=20) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.18 (s ) | | 27-Me | 1.19 (s ) |
| D2O | | 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 | 0.70 | | 19-Me | 0.96 | | 21-Me | 0.92 | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.20 | | 27-Me | 1.20 |
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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 volume 16 ml [column Whatman Partisil-SAX 25 cm long, 4.6 mm i.d., eluted with 0.1 M ammonium acetate, flow-rate 2 ml.min-1]. |
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| First isolation | ISAAC, R.E. et al. (1982) Chem. Commun., 249-251 |
 | | General | ISAAC, R.E. et al. (1983) Biochem. J. 213, 533-541 |
| | General | DIEHL, P.A. et al. (1985) Methods Enzymol. 111, 377-410 |
| | General | HETRU, C. et al. (1985) Methods Enzymol. 111, 411-419 |
| | General | OHNISHI, E. et al. (1989) Insect Biochem. 19, 95-101 |
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Permanent link to this datasheet: ECDYSONE 22-PHOSPHATE
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