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Year of first isolation: |
1986 |
| Formula: | C29H46O9 |
| Molecular weight: | 538 |
| Occurence in plants: |
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| Occurence in animals: |
Pycnogonum litorale [pantopod] »  ![Wikipedia: Pycnogonum litorale [pantopod]](/images/wikipedia.png)
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| Canonical SMILES | CC(=O)OC(CCC(C)(CO)O)C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(CO)(C)O)OC(=O)C)O)O)C)C » 
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CC[C@@](CO)(C)O)OC(=O)C)O)O)C)C »
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CC[C@](CO)(C)O)OC(=O)C)O)O)C)C »
| | IUPAC Name | [(2R)-2,6,7-trihydroxy-6-methyl-2-[(2S,3R,5R,9R,10R,13R,14S,17S)-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] acetate | | CAS-RN | | | PubChem CID | 69756175 | InChiKey
[ ChemIDPlus: search ] | GEZOUXGKWUSGFI-YCMAUXCXSA-N | | InChI | InChI=1S/C29H46O9/c1-16(31)38-24(8-9-25(2,35)15-30)28(5,36)23-7-11-29(37)18-12-20(32)19-13-21(33)22(34)14-26(19,3)17(18)6-10-27(23,29)4/h12,17,19,21-24,30,33-37H,6-11,13-15H2,1-5H3/t17-,19-,21+,22-,23-,24?,25?,26+,27+,28+,29+/m0/s1 |
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| CI-MS (NH3) m/z | 556 (M+H+NH3)+, 539 (MH)+, 521, 503, 485, 479 (MH- acetic acid)+, 461, 443, 425, 407, 363, 345 ... | | EI-MS m/z (relative intensity %) | |
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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 | | | 28 | | | 29 | |
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| D2O | | 01-Ha | | | 01-He | | | 02-Ha | 3.98 (m, w1/2=21) | | 03-He | 4.06 (m, w1/2=8) | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 5.97 (d, 2.5) | | 09-Ha | 3.10 (m, w1/2=22) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.86 (s ) | | 19-Me | 1.00 (s ) | | 21-Me | 1.34 (s ) | | 22-H | 4.82 (d, at 80°C) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-CH2-OH | 3.42 (s ) | | 27-Me | 1.14 (s ) |
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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 | 1- Retention time 19.4 and 30.8 min [ Lichrosorb Si 60, 125 mm x 4 mm i.d., solvent CH2Cl2-iPrOH-H2O 125:30:2 v/v/v, flow-rate 2 ml.min-1] (20E : 13.8 min)2-Retention time 8.8 and 10.0 min [ RP-18 Supersphere Merck, 150 mm x 4 mm i.d., solvent ACN in 0.1% TFA in H2O, 16:84 isocratic for 10 min, then linear gradient (in 25 min) to 40:60 v/v, flow-rate 1 ml.min-1] (20E 7.3 min). |
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Permanent link to this datasheet: 20,26-DIHYDROXYECDYSONE 22-ACETATE
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