|
|
|
|
Year of first isolation: |
1973 |
| Formula: | C27H45O10P |
| Molecular weight: | 560 |
| Occurence in plants: |
|
|
| Occurence in animals: |
Manduca sexta [Lepidoptera] »  ![Wikipedia: Manduca sexta [Lepidoptera]](/images/wikipedia.png)
|
|
| |
| Canonical SMILES | CC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)OP(=O)(O)O)C)C)O)C(CCC(C)(CO)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H]([C@H]1OP(=O)([O-])[O-])O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(CO)(C)O)O)O)C)C » 
C1[C@]2([C@@H](C[C@H]([C@H]1OP(=O)([O-])[O-])O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(CO)(C)O)O)O)C)C »
C1[C@]2([C@@H](C[C@H]([C@H]1OP(=O)([O-])[O-])O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(CO)(C)O)O)O)C)C »
| | IUPAC Name | [(2S,3R,5R,9R,10R,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-6-oxo-17-[(2S)-3,6,7-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-2-yl] dihydrogen phosphate | | CAS-RN | | | PubChem CID | 66869499 | InChiKey
[ ChemIDPlus: search ] | KAAIKLQKKVDABE-YHEWSBQBSA-N | | InChI | InChI=1S/C27H45O10P/c1-15(20(29)7-8-24(2,32)14-28)16-6-10-27(33)18-11-21(30)19-12-22(31)23(37-38(34,35)36)13-25(19,3)17(18)5-9-26(16,27)4/h11,15-17,19-20,22-23,28-29,31-33H,5-10,12-14H2,1-4H3,(H2,34,35,36)/t15-,16+,17-,19-,20?,22+,23-,24?,25+,26+,27+/m0/s1 |
| |
| EI-MS m/z (relative intensity %) | | | FAB-MS m/z | 559 (M-H)-, 543 (M-OH)-, 97 (H2PO4)-, 79 (PO3)- | | HR-MS | |
|
|
| 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 | |
|
| D2O | | 01-Ha | | | 01-He | | | 02-Ha | 4.300 (m br ) | | 03-He | 4.235 | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 14-H | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.748 (s ) | | 19-Me | 1.005 (s ) | | 21-Me | 0.948 (d, ) | | 22-H | 3.702 (d, ) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-CH2-OH | 3.468 (s , 2H) | | 27-Me | 1.183 (s ) |
|
| |
| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | 240 (?) ; |
| |
| HPTLC | NP-HPTLC : Rf 0.15 (precoated plates for nanoTLC, Silicagel 60F254, Merck, solvent CHCl3-MeOHl-10NNH4OH 15:35:3.5) | | TLC | | | GLC | | | HPLC | RP-HPLC, Retention time 10.5 min (column IBM C8, 15 cm long, 4.6 mm i.d., eluted isocratically with EtOH-30mM aqueous NaH2PO4, pH 5, 26:74 v/v, flow-rate 1 ml.min-1). |
| |
| |
| |
Permanent link to this datasheet: 26-HYDROXYECDYSONE 2-PHOSPHATE
|
|
