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Year of first isolation: |
1982 |
| Formula: | C27H45O8P |
| Molecular weight: | 528 |
| Occurence in plants: |
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| Occurence in animals: |
Bombyx mori [Bombycidae] »  ![Wikipedia: Bombyx mori [Bombycidae]](/images/wikipedia.png)
Locusta migratoria [Orthoptera] »
Schistocerca gregaria [Orthoptera] »
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| Canonical SMILES | CC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CCC(C4)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]1CC[C@@]2([C@@]1(CC[C@H]3C2=CC(=O)[C@H]4[C@@]3(CC[C@@H](C4)O)C)C)O)[C@@H](CCC(C)(C)O)OP(=O)(O)O » 
| | IUPAC Name | [(2S,3R)-2-[(3S,5R,9R,10R,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-6-methylheptan-3-yl] dihydrogen phosphate | | CAS-RN | | | PubChem CID | 21121820 | InChiKey
[ ChemIDPlus: search ] | AOKIBCRWTSJHIE-XNSSJAPWSA-N | | InChI | InChI=1S/C27H45O8P/c1-16(23(35-36(32,33)34)9-10-24(2,3)30)18-8-13-27(31)20-15-22(29)21-14-17(28)6-11-25(21,4)19(20)7-12-26(18,27)5/h15-19,21,23,28,30-31H,6-14H2,1-5H3,(H2,32,33,34)/t16-,17-,18+,19-,21-,23+,25+,26+,27+/m0/s1 |
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| CI-MS (isobutane) m/z | 431 | | EI-MS m/z (relative intensity %) | | | FAB-MS m/z | 549 (M-H+Na)-, 527 (M-H)-, 509 (M-H-18)-, 329, 301 (ecdysone nucleus), 251, 239, 199, 97, 79 | | HR-MS | |
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| CD3OD | | 01 | | | 02 | | | 03 | 65.6 (d ) | | 04 | | | 05 | | | 06 | | | 07 | | | 08 | | | 09 | | | 10 | | | 11 | | | 12 | | | 13 | -- | | 14 | 85.6 (s ) | | 15 | | | 16 | | | 17 | | | 18 | | | 19 | | | 20 | | | 21 | | | 22 | 79.1 (d ) | | 23 | | | 24 | | | 25 | 71.8 (s ) | | 26 | | | 27 | |
| D2O | | 01 | 29.50 (t ) | | 02 | 28.20 (t ) | | 03 | 66.04 (d) | | 04 | 32.80 (t ) | | 05 | 52.21(d) | | 06 | 210.00 (s ) | | 07 | 121.00 (d ) | | 08 | 170.00 (s ) | | 09 | 35.50 (d ) | | 10 | 37.60 (s ) | | 11 | 21.80 (t ) | | 12 | 32.10 (t ) | | 14 | 86.70 (s ) | | 15 | 31.70 (t ) | | 16 | 24.60 (t ) | | 17 | 48.76 (d ) | | 18 | 16.57 (q ) | | 19 | 24.40 (q ) | | 20 | 40.80 (d ) | | 21 | 13.60 (q ) | | 22 | 81.09 (d ) | | 23 | 24.90 (t ) | | 24 | 41.24 (t ) | | 25 | 73.02 (s ) | | 26 | 29.00 (q ) | | 27 | 29.20 (q ) |
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| CD3OD | | 01-Ha | | | 01-He | | | 02-Ha | | | 03-He | 3.98 (m, w1/2=18) | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 5.80 (d, 2) | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.74 (s ) | | 19-Me | 0.96 (s ) | | 21-Me | 0.97 (d, 8) | | 22-H | 4.20 (m, w1/2=22) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.17 (s ) | | 27-Me | 1.19 (s ) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | 244 (?) ; |
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| HPTLC | | | TLC | | | GLC | | | HPLC | Ion-exchange-HPLC Retention volume 19 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: 2-DEOXYECDYSONE 22-PHOSPHATE
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