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Year of first isolation: |
1995 |
| Formula: | C27H44O6 |
| Molecular weight: | 464 |
| Occurence in plants: |
Serratula wolffii [Asteraceae] »  ![Wikipedia: Serratula wolffii [Asteraceae]](/images/wikipedia.png)
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| Occurence in animals: |
Bombyx mori [Bombycidae] »
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| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(CCCC(C)(C)O)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)(CCCC(C)(C)O)O)O)C)C » 
| | IUPAC Name | (2S,3S,5R,9R,10R,13R,14S,17S)-17-[(2S)-2,6-dihydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 101915844 | InChiKey
[ ChemIDPlus: search ] | KFLDRYHMXLUSFO-FTUASRNISA-N | | InChI | InChI=1S/C27H44O6/c1-23(2,31)9-6-10-26(5,32)22-8-12-27(33)17-13-19(28)18-14-20(29)21(30)15-24(18,3)16(17)7-11-25(22,27)4/h13,16,18,20-22,29-33H,6-12,14-15H2,1-5H3/t16-,18-,20-,21-,22-,24+,25+,26-,27+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | | | FAB-MS m/z | 487 (M+Na)+ | | HR-MS | | | ESI-MS m/z (relative intensity %) | 487 (M+Na)+ (0.5), 469 (M+Na-H2O)+ (100) |
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| CD3OD | | 01 | 43.2 | | 02 | 72.3 | | 03 | 75.7 | | 04 | 33.8 | | 05 | 57.6 | | 06 | 204.8 | | 07 | 122.0 | | 08 | 168.4 | | 09 | 36.1 | | 10 | 39.8 | | 11 | 21.6 | | 12 | 32.5 | | 13 | 48.3 | | 14 | 85.5 | | 15 | 31.9 | | 16 | 22.1 | | 17 | 53.5 | | 18 | 18.3 | | 19 | 24.0 | | 20 | 76.1 | | 21 | 26.7 | | 22 | 46.0 | | 23 | 21.9 | | 24 | 45.6 | | 25 | 71.6 | | 26 | 29.3 | | 27 | 29.3 |
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| CD3OD | | 01-Ha | 1.09 (dd, 13.7, 11.9) | | 01-Hb | 2.09 (13.7, 4.6) | | 02-Ha | 3.64 (ddd 11.9, 9.0, 4.6) | | 03-Ha | 3.34 (ddd 11.6, 9.0, 4.4) | | 04-Ha | 1.57 (td, 13.1, 11.6) | | 04-He | 1.75 (dt, 13.1, 4.4) | | 05-H | 2.09 (dd, 13.1, 4.4) | | 07-H | 5.82 (d, 2.8) | | 09-Ha | 3.17 (ddd 11.0, 7.2, 2.4) | | 11-Ha | 1.69 (qd, 13.1, 4.9) | | 11-He | 1.81 (m) | | 12-Ha | 2.14 (td, 13.1, 5.0) | | 12-He | 1.86 (m) | | 15-Ha | 1.62 (ddd 11.9, 9.6, 2.0) | | 15-Hb | 1.95 (m) | | 16-Ha | 1.86 (m) | | 16-Hb | 1.90 (m) | | 17-H | 2.35 (t, 9.0) | | 18-Me | 0.86 (s) | | 19-Me | 0.95 (s) | | 21-Me | 1.28 (s) | | 22-Ha | 1.36 (m) | | 22-Hb | 1.51 (m) | | 23-Ha | 1.42 (m) | | 23-Hb | 1.42 (m) | | 24-Ha | 1.43 (m) | | 24-Hb | 1.43 (m) | | 26-Me | 1.19 (s) | | 27-Me | 1.19 (s) |
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| M.P. | | | [α]D27 | +12 ° (c 0.1; MeOH) | | IR (KBr) ν max (cm-1) | | | UV ( MeOH) λ max (log ε) | 242 (2.42) |
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| NP-HPLC | column Nucleosil 100-5, 15 cm long, 4.6 mm i.d., MeOH-CH2Cl2 (7:93), 1 ml.min-1, Ret 23.5 min. | | TLC | | | GLC | | | RP-HPLC | column Wakosil 5C18, 25 cm long, 4.6 mm i.d., 45% MeOH, isocratic, 1 ml.min-1, Ret 30 min (E 15 min, 2d20E 22.5 min, 2dE 40 min): |
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Permanent link to this datasheet: 3-EPI-22-DEOXY-20-HYDROXYECDYSONE
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