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Year of first isolation: |
2005 |
| Formula: | C29H46O7 |
| Molecular weight: | 506 |
| Occurence in plants: |
Serratula coronata [Asteraceae] »  ![Wikipedia: Serratula coronata [Asteraceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC1OC(C(O1)(C)C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)CCC(C)(C)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@]1(C)[C@@H](CCC(C)(C)O)OC(O1)C)O)C)C » 
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-17-[(2R,4R,5R)-5-(3-hydroxy-3-methylbutyl)-2,4-dimethyl-1,3-dioxolan-4-yl]-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 12094560 | InChiKey
[ ChemIDPlus: search ] | NCPGKYAKIIXLRA-RUVATRSJSA-N | | InChI | InChI=1S/C29H46O7/c1-16-35-24(9-10-25(2,3)33)28(6,36-16)23-8-12-29(34)18-13-20(30)19-14-21(31)22(32)15-26(19,4)17(18)7-11-27(23,29)5/h13,16-17,19,21-24,31-34H,7-12,14-15H2,1-6H3/t16-,17+,19+,21-,22+,23+,24-,26-,27-,28-,29-/m1/s1 |
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| HR-MS | | | EI-MS m/z (relative intensity %) | | | CI-MS (NH3) m/z | 524 [M + H + NH3]+, 507 [M + H]+, 489, 471, 463, 445, 427, 411, 409, 391, 370, 346, 279, 272, 246, 299, 187, 160, 143, 124, 99 |
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| D2O | | 01 | 36.1 (t) | | 02 | 68.5 (d) | | 03 | 68.5 (d) | | 04 | 32.3 (t) | | 05 | 51.4 (d) | | 06 | ? | | 07 | 122.1 (d) | | 08 | ? | | 09 | 34.9 (d) | | 10 | 39.1 (s) | | 11 | ? | | 12 | 31.7 (t) | | 13 | 48.2 (s) | | 14 | 86.1 (s) | | 15 | ? | | 16 | ? | | 17 | 51.1 (d) | | 18 | 18.0 (q) | | 19 | 24.3 (q) | | 20 | 87.3 (s) | | 21 | 24.9 (q) | | 22 | 86.1 (d) | | 23 | ? | | 24 | 41.7 (t) | | 25 | 72.8 (s) | | 26 | 29.0 (qq) | | 27 | 29.0 (q) | | MeCH< | 21.3 (q), 102.5 (d) |
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| D2O | | (minor) | 1.35 (d, 5.0); 5.36 (q, 5.0) | | 01-Ha | 1.38 (t, 13.4) | | 01-He | 1.88 (m) | | 02-Ha | 3.99 (m, w1/2 = 22) | | 03-He | 4.07 (m, w1/2 = 8) | | 04-Ha | 1.75 (t) | | 04-He | 1.75 (t) | | 05-H | 2.36 (t) | | 07-H | 5.97 (d, 2.5) | | 09-Ha | 3.11 (m, w1/2 = 22) | | 11-Ha | 1.73 (m) | | 11-He | 1.86 (m) | | 12-Ha | 1.95 (m) | | 12-He | 1.75 (m) | | 15-Ha | 1.65 (m) | | 15-Hb | 2.05 (m) | | 16-Ha | 1.88* (m) | | 16-Hb | 1.74* (m) | | 17-H | 2.31 (t, 9) | | 18-Me | 0.86 (s) | | 19-Me | 1.00 (s) | | 21-Me | 1.25 (s) | | 22-H | 3.85 (m, w1/2=18) | | 23-Ha | 1.63 (m) | | 23-Hb | 1.63 (m) | | 24-Ha | 1.75 (m) | | 24-Hb | 1.75 (m) | | 26-Me | 1.24 (s) | | 27-Me | 1.25 (s) | | MeCH< | 1.40 (d, 5.0); 5.15 (q, 5.0) |
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| M.P. | ? °C ; | | [α]D20 | ? ° (c ; MeOH) | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | ? (?) ; |
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| HPLC | NP-HPLC Zorbax-SIL (250 x 9.4 mm) solvent dichloromethane-isopropanol-water (125:15:1), flow-rate 4 ml/min (Ret 35.5 min); Kromasil (250x 4.6 mm), solvent cyclohexane-isopropanol-water (100:30:2), flow-rate 1 ml/min (Ret 15.3 min). | | HPTLC | | | TLC | |
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Permanent link to this datasheet: 20-HYDROXYECDYSONE 20,22-ETHYLIDENE
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