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Year of first isolation: |
2004 |
| Formula: | C27H44O8 |
| Molecular weight: | 496 |
| Occurence in plants: |
Silene italica ssp. nemoralis [Caryophyllaceae] »  ![Wikipedia: Silene italica ssp. nemoralis [Caryophyllaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC12CCC3(C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)O)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@]2(CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O)C)O)C » 
| | IUPAC Name | (2S,3R,5R,9R,10S,13R,14S,17S)-2,3,9,14-tetrahydroxy-10,13-dimethyl-17-[(2R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,5,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 91390253 | InChiKey
[ ChemIDPlus: search ] | AHHRNGCAWAPZKG-KCLJKRFISA-N | | InChI | InChI=1S/C27H44O8/c1-22(2,32)8-7-21(31)25(5,33)19-6-9-26(34)20-13-16(28)15-12-17(29)18(30)14-24(15,4)27(20,35)11-10-23(19,26)3/h13,15,17-19,21,29-35H,6-12,14H2,1-5H3/t15-,17+,18-,19-,21?,23+,24-,25+,26+,27-/m0/s1 |
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| HRESI-MS | MH+ = 497.3119, calculated for C27H45O8, 497.3114 | | CI-MS (NH3) m/z | | | ESI-MS m/z (relative intensity %) | 497 (14) [M+H]+, 479 (10), 461 (11), 446 (10), 441 (10), 436 (20), 423 (17), 361 (12), 339 (32), 324 (34), 317 (30), 301 (100) |
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| DMSO-d5 | | 01 | 35.7 | | 02 | 68.5 | | 03 | 67.7 | | 04 | 25.3 | | 05 | 48.4 | | 06 | 201.2 | | 07 | 122.0 | | 08 | 164.5 | | 09 | 72.8 | | 10 | 42.3 | | 11 | 25.3 | | 12 | 31.4 | | 13 | 44.4 | | 14 | 83.4 | | 15 | 30.6 | | 16 | 20.4 | | 17 | 50.3 | | 18 | 22.5 | | 19 | 20.9 | | 20 | 75.6 | | 21 | 20.5 | | 22 | 76.3 | | 23 | 26.1 | | 24 | 41.4 | | 25 | 68.7 | | 26 | 29.0 | | 27 | 30.0 |
| CD3OD | | 01 | 37.2 | | 02 | 70.6 | | 03 | 69.9 | | 04 | 26.3 | | 05 | 50.3 | | 06 | 204.4 | | 07 | 124.3 | | 08 | 166.4 | | 09 | 75.3 | | 10 | 44.2 | | 11 | 27.0 | | 12 | 32.9 | | 13 | 46.2 | | 14 | 85.9 | | 15 | 32.3 | | 16 | 21.8 | | 17 | 52.4 | | 18 | 23.4 | | 19 | 21.6 | | 20 | 78.1 | | 21 | 20.8 | | 22 | 78.7 | | 23 | 27.6 | | 24 | 42.6 | | 25 | 71.5 | | 26 | 29.1 | | 27 | 29.8 |
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| DMSO-d5 | | 01-Ha | 1.43 (dt, 14.8, 2.3) | | 01-He | 1.74 | | 02-Ha | 3.67 (q, 2.2) | | 03-He | 2.96 (dt, 12.0, 3.5) | | 04-Ha | 2.11 (dt, 12.6, 3.5) | | 04-He | 1.79 (dt, 12.2, 4.9) | | 05-H | 2.52 | | 07-H | 5.61 (s) | | 11-Ha | 1.52 (dd, 13.7, 8.7) | | 11-He | 2.21 (dt, 13.4, 9.6) | | 12-Ha | 1.86 (dd, 13.6, 9.6) | | 12-He | 1.67 (13.8, 8.8) | | 15-Ha | 1.65 | | 15-Hb | 1.75 | | 16-Ha | 1.55 | | 16-Hb | 1.89 (qd, 12.0, 1.9) | | 17-H | 2.34 (t, 9.1) | | 18-Me | 1.13 (s) | | 19-Me | 1.24 (s) | | 21-Me | 1.07 (s) | | 22-H | 3.115 (d, 10.6) | | 23-Ha | 1.15 | | 23-Hb | 1.50 | | 24-Ha | 1.26 1.444 (ddd, 13.0, 11.7, 4.0) | | 24-Hb | 1.66 | | 26-Me | 1.06 (s) | | 27-Me | 1.09 (s) |
| CD3OD | | 01-Ha | 1.67 | | 01-He | 1.86 | | 02-Ha | 3.88 (d, 3.1) | | 03-He | 3.195 (dt, 12.1, 3.5) | | 04-Ha | 2.34 (dt, 13.6, 3.9) | | 04-He | 2.01 | | 05-H | 2.72 (dt, 4.5, 2.3) | | 07-H | 5.82 (s) | | 11-Ha | 1.69 | | 11-He | 2.37 (dt, 14.0, 9.8) | | 12-Ha | 2.04 | | 12-He | 1.83 | | 15-Ha | 1.73* | | 15-Hb | 1.97* | | 16-Ha | 1.73* | | 16-Hb | 1.99* | | 17-H | 2.46 (t, 8.8) | | 18-Me | 1.235 (s) | | 19-Me | 1.37 (s) | | 21-Me | 1.21 (s) | | 22-H | 3.32 | | 23-Ha | 1.315 | | 23-Hb | 1.71 | | 24-Ha | | | 24-Hb | 1.81 | | 26-Me | 1.19 (s) | | 27-Me | 1.205 (s) |
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| M.P. | - °C ; | | [α]D24 | +14 ? ° (c 0.1 ; MeOH) | | IR (KBr) ν max (cm-1) | 3450, 3400, 1660 | | UV (MeOH) λ max (log ε) | 206 (1.8) ; 243 (3.8) |
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| HPLC | NP silica, CH2Cl2-iPrOH-H2O (125:40:3) | | GLC | | | HPTLC | | | TLC | silica gel Merck, EtOAc-EtOH-H2O (8:1:0.5) |
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Permanent link to this datasheet: 9β,20-DIHYDROXYECDYSONE
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