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Year of first isolation: |
2008 |
| Formula: | C30H48O9 |
| Molecular weight: | 552 |
| Occurence in plants: |
Silene viridiflora [Caryophyllaceae] »  ![Wikipedia: Silene viridiflora [Caryophyllaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC1(OC(C(O1)(C)C2CCC3(C2(CCC4C3=CC(=O)C5(C4(CC(C(C5)O)O)C)O)C)O)CCC(C)(CO)O)C | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@](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(CO)(C)O)OC(O1)(C)C)O)C)O)C » 
C1[C@]2([C@@](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(CO)(C)O)OC(O1)(C)C)O)C)O)C »
C1[C@]2([C@@](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(CO)(C)O)OC(O1)(C)C)O)C)O)C »
| | IUPAC Name | (2S,3R,5S,9R,10R,13R,14S,17S)-17-[(4R,5R)-5-(3,4-dihydroxy-3-methylbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-2,3,5,14-tetrahydroxy-10,13-dimethyl-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 70684797 | InChiKey
[ ChemIDPlus: search ] | ZJNBRMJTFYQDIR-CUWPXVPYSA-N | | InChI | InChI=1S/C30H48O9/c1-24(2)38-23(9-10-25(3,35)16-31)28(6,39-24)21-8-12-29(36)18-13-22(34)30(37)15-20(33)19(32)14-27(30,5)17(18)7-11-26(21,29)4/h13,17,19-21,23,31-33,35-37H,7-12,14-16H2,1-6H3/t17-,19-,20+,21-,23+,25?,26+,27+,28+,29+,30+/m0/s1 |
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| ESI-MS m/z (relative intensity %) | 575 [M+Na]+ (46), 553 [M+H]+ (100), 537 [M-CH3]+ (5), 535 [M+H-H2O]+ (3), 520 [M+H-H2O-CH3]+ (2), 495 [M+H-acetone]+ (59), 481 (1), 477 (3), 437 (3), 359 (3), 328 (14) | | HR-ESI-MS m/z | 553.3366 [M+H]+ (calc. for C30H49O9, 553.3363) |
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| CD3OD | | 01 | 34.3 | | 02 | 68.6 | | 03 | 70.4 | | 04 | 36.3 | | 05 | 80.4 | | 06 | 202.5 | | 07 | 120.7 | | 08 | 167.4 | | 09 | 39.2 | | 10 | 45.5 | | 11 | 22.65 | | 12 | 32.6 | | 13 | 48.7 | | 14 | 85.3 | | 15 | 31.8 | | 16 | 22.5 | | 17 | 50.5 | | 18 | 17.8 | | 19 | 17.1 | | 20 | 86.0 | | 21 | 22.7 | | 22 | 83.6 | | 23 | 24.0 | | 24 | 37.2 | | 25 | 73.6 | | 26 | 70.7 | | 27 | 23.9 | | 2xMe | | | Me2 | 27.3, 29.5 | | O-C-O | 108.2 |
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| CD3OD | | 01-Ha | 1.73 (m) | | 01-He | 1.73 (m) | | 02-Ha | 3.95 (ddd, 10.0, 7.4, 3.6) | | 03-He | 3.99 (q, 3) | | 04-Ha | 1.77 (dd, 14.9, 3.0) | | 04-He | 2.075 (dd, 14.7, 3.0) | | 07-H | 5.86 (d, 2.8) | | 09-H | 3.19 (ddd, 11.3, 7.0, 2.7) | | 11-Ha | 1.74 (m) | | 11-He | 1.81 (m) | | 12-Ha | 2.12 (td, 13.1, 5.0) | | 12-He | 1.86 (m) | | 15-Ha | 1.61 (m) | | 15-Hb | 1.97 (m) | | 16-Ha | 1.87 (m) | | 16-Hb | 2.03 (m) | | 17-H | 2.31 (dd, 9.4, 8.1) | | 18-Me | 0.83 (s) | | 19-Me | 0.915 (s) | | 21-Me | 1.18 (s) | | 22-H | 3.695 (t, 6) | | 23-Ha | 1.53 (m) | | 23-Hb | 1.55 (m) | | 24-Ha | 1.52 (m) | | 24-Hb | 1.71 (m) | | 26-CH2OH | 3.375 (d, 11), 3.355 (d, 11) | | 27-Me | 1.15 (s) | | Me2CO | 1.39 (s), 1.32 (s) |
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| M.P. | °C ; | | [α]D25 | + 89 ° (c 0.05; MeOH) | | IR (KBr) ν max (cm-1) | | | UV (MeOH) λ max (log ε) | 242 (3.76) ; |
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Permanent link to this datasheet: 5,20,26-TRIHYDROXYECDYSONE 20,22-ACETONIDE
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