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Year of first isolation: |
1992 |
| Formula: | C31H48O9 |
| Molecular weight: | 564 |
| Occurence in plants: |
Serratula tinctoria [Asteraceae] »  ![Wikipedia: Serratula tinctoria [Asteraceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC(=O)OC1CC2C(=O)C=C3C(C2(CC1O)C)CCC4(C3(CCC4C(C)(C(CCC(C)(C)O)OC(=O)C)O)O)C | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H]([C@H]1O)OC(=O)C)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)C)O)O)C)C » 
| | IUPAC Name | [(2S,3R,5R,9R,10R,13R,14S,17S)-17-[(2R,3R)-3-acetyloxy-2,6-dihydroxy-6-methylheptan-2-yl]-2,14-dihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate | | CAS-RN | | | PubChem CID | 101642418 | InChiKey
[ ChemIDPlus: search ] | SWWDJZZNTORSLE-VIEKNRERSA-N | | InChI | InChI=1S/C31H48O9/c1-17(32)39-24-15-21-22(34)14-20-19(28(21,5)16-23(24)35)8-12-29(6)25(9-13-31(20,29)38)30(7,37)26(40-18(2)33)10-11-27(3,4)36/h14,19,21,23-26,35-38H,8-13,15-16H2,1-7H3/t19-,21-,23-,24+,25-,26+,28+,29+,30+,31+/m0/s1 |
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| CI-MS (NH3) m/z | 582 (M+H+NH3)+, 565 (M+H)+, 547, 529, 504, 487, 469, 453, 422, 387, 362, 345, 327 | | 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 | | | 28 | | | 29 | |
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| CDCl3 | | 01-Ha | | | 01-Hb | | | 02-Ha | 4.0 (m, w1/2=22) | | 03-He | 5.20 (m, w1/2=8) | | 04-Ha | | | 04-He | | | 05-H | 2.50 (dd, 14,4.5) | | 07-H | 5.84 | | 09-Ha | 3.04 (m, w1/2=22) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.34 (m ) | | 18-Me | 0.84 (s ) | | 19-Me | 1.01 (s ) | | 21-Me | 1.24 (s ) | | 22-H | 4.85 (dd, 10,2) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.21 (s ) | | 27-Me | 1.23 (s ) | | CH3CO-(03) | 2,11 (s, 3H) | | CH3CO-(22) | 2.10 (s, 3H) |
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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, Rt 15.3 min (Column Zorbax-Sil, 25 cm x 4.6 mm i.d., solvent isoC8-iPrOH-H2O, 100:30:2 v/v/v, flow-rate 1ml.min-1) (20E 22.6 min); RP-HPLC, Rt 19.5 min (Column Spherisorb-5ODS2, 25 cm x 4.6 mm i.d., solvent linear gradient 20 to 70% ACN in 1? TFA in H2O, flow-rate 1ml.min-1) (20E 12.3 min). |
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Permanent link to this datasheet: 20-HYDROXYECDYSONE 3,22-DIACETATE
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