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Year of first isolation: |
2003 |
| 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,9S,10S,13R,14S,17S)-2,3,9,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R)-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 | 10097359 | InChiKey
[ ChemIDPlus: search ] | AHHRNGCAWAPZKG-GLRNUJIGSA-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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| EI-MS m/z (relative intensity %) | 460 (2), 442 (2), 424 (2), 410 (4), 392 (4), 379 (1), 374 (6), 361 (59), 343 (43), 325 (19), 316 (1), 301 (94), 283 (96), 250 (54), 232 (28), 211 (40), 161 (22), 143 (46), 125 (40), 99 (62), 81 (100), 69 (63) | | ESI-MS-MS m/z | 503 [M + Li]+ , 485 [M + Li - H2O]+ | | HREI-MS | 460.5998 [M - 2 H20]+, calculated for C27H40O6 460.5962 |
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| CD3OD | | 01 | 37.6 | | 02 | 69.7 | | 03 | 69.8 | | 04 | 36.3 | | 05 | 51.4 | | 06 | 206.7 | | 07 | 123.8 | | 08 | 162.6 | | 09 | 76.6 | | 10 | 43.0 | | 11 | 30.9 | | 12 | 29.6 | | 13 | 49.1 | | 14 | 87.2 | | 15 | 31.6 | | 16 | 21.4 | | 17 | 50.4 | | 18 | 18.5 | | 19 | 29.6 | | 20 | 78.0 | | 21 | 21.2 | | 22 | 78.6 | | 23 | 27.5 | | 24 | 42.5 | | 25 | 71.4 | | 26 | 29.1 | | 27 | 29.9 |
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| CD3OD | | 01-Ha | 1.38 (t) | | 01-He | 2.06 (d) | | 02-Ha | 4.45 (dt 10.4, 3.9) | | 03-He | 3.96 (q, 2.6) | | 04-Ha | 2.44 (td, 13.3, 2.3) | | 04-He | 1.74 (d) | | 05-H | 2.56 (dd, 13.3, 3.9) | | 07-H | 5.85 (s) | | 11-Ha | 1.95 | | 11-He | 2.04 | | 12-Ha | 2.19 (td, 13.1, 4.6) | | 12-He | 1.83 (d) | | 15-Ha | 1.67 | | 15-Hb | 1.98 | | 16-Ha | 1.71 | | 16-Hb | 2.01 | | 17-H | 2.45 | | 18-Me | 0.89 (s) | | 19-Me | 1.01 (s) | | 21-Me | 1.22 (s) | | 22-H | 3.32 (dd) | | 23-Ha | 1.31 (q) | | 23-Hb | 1.66 (t) | | 24-Ha | 1.44 (td, 11.6, 4.2) | | 24-Hb | 1.81 (t) |
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| M.P. | 269-271 °C ; | | [α]D24 | - 10 ° (c 0.05; MeOH) | | IR (KBr) ν max (cm-1) | 3460, 3380, 1660 | | UV (MeOH) λ max (log ε) | 228 (3.7) ; |
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Permanent link to this datasheet: 9α,20-DIHYDROXYECDYSONE
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