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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 | CC12CCC(CC1C(=O)C=C3C2CCC4(C3(CCC4C(C)(C(CCC(C)(C)O)OP(=O)(O)O)O)O)C)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C[C@]12CC[C@@H](C[C@H]1C(=O)C=C3[C@@H]2CC[C@]4([C@]3(CC[C@@H]4[C@](C)([C@@H](CCC(C)(C)O)OP(=O)(O)O)O)O)C)O » 
| | IUPAC Name | [(2R,3R)-2-[(3S,5R,9R,10R,13R,14S,17S)-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]-2,6-dihydroxy-6-methylheptan-3-yl] dihydrogen phosphate | | CAS-RN | | | PubChem CID | 21122088 | InChiKey
[ ChemIDPlus: search ] | ZZFVYSIMDVDSAY-GLPVALQZSA-N | | InChI | InChI=1S/C27H45O9P/c1-23(2,30)10-9-22(36-37(33,34)35)26(5,31)21-8-13-27(32)18-15-20(29)19-14-16(28)6-11-24(19,3)17(18)7-12-25(21,27)4/h15-17,19,21-22,28,30-32H,6-14H2,1-5H3,(H2,33,34,35)/t16-,17-,19-,21-,22+,24+,25+,26+,27+/m0/s1 |
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| FAB-MS m/z | 565 (M-H+Na)-, 543 (M-H)-, 525 (M-H-18)-, 97, 79 | | HR-MS | | | EI-MS m/z (direct inlet on gold support) | (464), 446, 428, 410, 393; Direct introduction, fast heating m/z: 549 (M-18+Na)+ , (544) (M)+ , 531 (M-2x18+Na)+ (526) (M-18)+ , 513 |
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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 | | | 02-He | | | 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 | 0.89 (s ) 0.92 | | 19-Me | 0.95 (s ) 0.98 | | 21-Me | 1.26 (s ) 1.32 | | 22-H | 4.07 (m, w1/2=22) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.18 (s ) 1.21 | | 27-Me | 1.20 (s ) 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 | RP-HPLC with ion suppression, Retention volume 45 ml (column Partisil-ODS3, 25 cm x 4.6 mm i.d. eluted with MeOH in 20 mM sodium citrate pH 6.5, gradient 1:9 v/v to 7:3 v/v over 30 min, flow-rate 2 ml.min-1 |
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| First isolation | TSOUPRAS, G. et al. (1982) Steroids 40, 551-560 |
 | | 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 | HIRAMOTO, M. et al. (1988) Experientia 44, 623-625 |
| | General | OHNISHI, E. et al. (1989) Insect Biochem. 19, 95-101 |
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Permanent link to this datasheet: 2-DEOXY-20-HYDROXYECDYSONE 22-PHOSPHATE
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