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Year of first isolation: |
2008 |
| Formula: | C30H48O7 |
| Molecular weight: | 520 |
| Occurence in plants: |
Leuzea carthamoides [Asteraceae] »  ![Wikipedia: Leuzea carthamoides [Asteraceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC(CCC1C(OC(O1)(C)C)(C)C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)CO | 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)CO)OC(O1)(C)C)O)C)C » 
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)CO)OC(O1)(C)C)O)C)C »
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)CO)OC(O1)(C)C)O)C)C »
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-17-[(4R,5R)-5-(4-hydroxy-3-methylbutyl)-2,2,4-trimethyl-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 | 101851581 | InChiKey
[ ChemIDPlus: search ] | SFPZTLYGGVFTEJ-HMDHKIHQSA-N | | InChI | InChI=1S/C30H48O7/c1-17(16-31)7-8-25-29(6,37-26(2,3)36-25)24-10-12-30(35)19-13-21(32)20-14-22(33)23(34)15-27(20,4)18(19)9-11-28(24,30)5/h13,17-18,20,22-25,31,33-35H,7-12,14-16H2,1-6H3/t17?,18-,20-,22+,23-,24-,25+,27+,28+,29+,30+/m0/s1 |
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| FAB-MS | 543 (45) [M+Na]+, 521 (80) [M+H]+, 503 (100) [M+H-H20]+, 445 (20), 427 (15), 329 (20), 301 (22), 279 (12), 249 (19). | | EI-MS m/z (relative intensity %) | | | HRESI-MS | 543.3282 [M+Na]+ (calculated for C30H48O7 Na : 543.3290) | | CI-MS (NH3) m/z | |
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| CD3OD | | 01 | 37.35 | | 02 | 68.72 | | 03 | 68.49 | | 04 | 32.87 | | 05 | 51.77 | | 06 | 206.43 | | 07 | 122.15 | | 08 | 167.56 | | 09 | 35.14 | | 10 | 39.21 | | 11 | 21.51 | | 12 | 32.32 | | 13 | 48.44 | | 14 | 85.34 | | 15 | 31.72 | | 16 | 22.43 | | 17 | 50.46 | | 18 | 17.69 | | 19 | 24.45 | | 20 | 85.75 | | 21 | 22.54 | | 22 | 83.13 | | 23 | 27.43 | | 24 | 32.05 | | 25 | 37.01 | | 26 | 68.23 | | 27 | 17.04 | | Me | 29.36, 27.19 | | OCO | 107.98 |
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| CD3OD | | 01-Ha | 1.43 (dd, 13.2, 12.0) | | 01-He | 1.78 (dd, 13.2, 4.3) | | 02-Ha | 3.83 (ddd, 12.0, 4.3, 3.2) | | 03-He | 3.95 (q, 3, 3, 3) | | 04-Ha | 1.68-1.78 | | 04-He | 1.68-1.78 | | 05-H | 2.38 (dd, 12.8, 4.7) | | 07-H | 5.82 (d, 2.6) | | 09-Ha | 3.15 (ddd, 11.5, 7.0, 2.6) | | 11-Ha | 1.69 | | 11-He | 1.80 | | 12-Ha | 2.11 (td, 13, 13, 4.8) | | 12-He | 1.85 | | 15-Ha | 1.63 | | 15-Hb | 1.96 | | 16-Ha | 1.86 | | 16-Hb | 2.04 | | 17-H | 2.29 (dd, 9.6, 8.2) | | 18-Me | 0.826 (s) | | 19-Me | 0.963 (s) | | 21-Me | 1.162 (s) | | 22-H | 3.69 (dd, 9.4, 2.9) | | 23-Ha | 1.47 | | 23-Hb | 1.47 | | 24-Ha | 1.15 | | 24-Hb | 1.68 | | 25-H | 1.63 | | 26-Me | 3.36 (dd, 10.7, 5.8), 3.43 (dd, 10.7, 6.4) | | 27-Me | 0.937 (d, 6.6) | | Me2C= | 1.39 (s), 1.32 (s) |
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| M.P. | °C ; | | [α]D20 | + 42.9 ° (c 0.29; EtOH) | | IR (KBr) ν max (cm-1) | 3429 (OH), 1655 (C=O), 1109, 1055 (C-O) | | UV (MeOH) λ max (log ε) | |
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| HPLC | RP-HPLC Separon SGX C-18 (250 x 4 mm), solvent methanol-water (linear grad of 10-70%), flow-rate 0,6 ml/min (Ret 55.0 min); NP-HPLC Silasorb 600 (250 x 4 mm) solvent dichloromethane-isopropanol-water (84:15:1), flow-rate 0.8 ml/min (Ret 28.0 min); and two other systems. | | GLC | | | HPTLC | | | TLC | |
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Permanent link to this datasheet: INOKOSTERONE 20,22-ACETONIDE
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