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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 | CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)OC(=O)CO)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(C)(C)O)OC(=O)CO)O)O)C)C » 
| | IUPAC Name | [(2R,3R)-2,6-dihydroxy-6-methyl-2-[(2S,3R,5R,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] 2-hydroxyacetate | | CAS-RN | | | PubChem CID | 21775774 | InChiKey
[ ChemIDPlus: search ] | DWTMLGDZGORWQW-NVKGGLFYSA-N | | InChI | InChI=1S/C29H46O9/c1-25(2,35)9-8-23(38-24(34)15-30)28(5,36)22-7-11-29(37)17-12-19(31)18-13-20(32)21(33)14-26(18,3)16(17)6-10-27(22,29)4/h12,16,18,20-23,30,32-33,35-37H,6-11,13-15H2,1-5H3/t16?,18-,20+,21-,22-,23+,26+,27+,28+,29+/m0/s1 |
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| CI-MS (NH3) m/z | 556 (MH + NH3)+, 539 (MH)+, 521, 503, 480, 463 (MH-glycolic acid)+, 445, 427, 409, 363 (M- side-chain), 345. | | EI-MS m/z (relative intensity %) | | | HR-MS | |
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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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| D2O | | 01-Ha | | | 01-Hb | | | 02-Ha | 3.99 (m, w1/2=21) | | 03-He | 4.07 (m, w1/2=8) | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 5.98 (d, 2.5) | | 09-Ha | 3.11 (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 | 1.33 (s ) | | 22-H | 4.93 (d, w1/2=14) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.21 (s ) | | 27-Me | 1.21 (s ) | | OCOCH2O | 4.31 (s, 2H) |
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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 | NP-HPLC (Merck Lichrosorb Si 60) solvent CH2Cl2-iPrOH-H2O (125:30:2) Ret. 28.2 ml (20E = 27.6 ml).RP-HPLC (Merck Supersphere RP18, 15 cm long, 4 mmcratic for 10 min, then linear gradient 16:84 to 40:60 in 25 min) Ret 7.7 min (20E 7.3 min). |
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Musca assay: 516% (20-hydroxyecdysone = 100%) |
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Permanent link to this datasheet: 20-HYDROXYECDYSONE 22-GLYCOLATE
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