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Year of first isolation: |
2008 |
| Formula: | C28H44O8 |
| Molecular weight: | 508 |
| 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(C)C1(CC(C(O1)(C)C2CCC3(C2(CC(C4C3=CC(=O)C5C4(CC(C(C5)O)O)C)O)C)O)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]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@]1(O[C@@](C[C@H]1O)(C(C)C)CO)C)O)C)O)C » 
| | IUPAC Name | (2S,3R,5R,9R,10R,11R,13R,14S,17S)-2,3,11,14-tetrahydroxy-17-[(2R,3S,5R)-3-hydroxy-5-(hydroxymethyl)-2-methyl-5-propan-2-yloxolan-2-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 | 101851588 | InChiKey
[ ChemIDPlus: search ] | KFWPEZQKCIZSHF-VGKHSYQCSA-N | | InChI | InChI=1S/C28H44O8/c1-14(2)27(13-29)12-22(34)26(5,36-27)21-6-7-28(35)16-9-17(30)15-8-18(31)19(32)10-24(15,3)23(16)20(33)11-25(21,28)4/h9,14-15,18-23,29,31-35H,6-8,10-13H2,1-5H3/t15-,18+,19-,20+,21-,22-,23+,24-,25+,26+,27-,28+/m0/s1 |
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| HR-ESI-MS | 531.2943 [M+Na]+ (calculated for C28H44O8Na : 531.2934) | | ESI-MS/MS m/z | 509 [M+H]+, 491 [M+H-H20]+, 473 [M+H-2H20]+, 455 [M+H-3H2O]+, 437 [M+H-4H2O]+, 419 [M+H-5H2O]+, 389, 345, 299, 281, 173, 155, 137. |
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| CD3OD | | 01 | 39.80 | | 02 | 68.94 | | 03 | 68.55 | | 04 | 33.40 | | 05 | 52.79 | | 06 | 206.91 | | 07 | 122.65 | | 08 | 166.17 | | 09 | 42.93 | | 10 | 39.11 | | 11 | 69.66 | | 12 | 43.87 | | 13 | 49.0** | | 14 | 84.65 | | 15 | 32.31 | | 16 | 23.33 | | 17 | 52.19 | | 18 | 19.04 | | 19 | 24.59 | | 20 | 89.72* | | 21 | 27.60 | | 22 | 82.62 | | 23 | 41.33 | | 24 | 89.56* | | 25 | 40.37 | | 26 | 18.12 | | 27 | 18.60 | | 28 | 64.41 |
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| CD3OD | | 01-Ha | 1.37 (dd, 12.8, 11.8) | | 01-He | 2.60 (dd, 12.8, 4.0) | | 02-Ha | 4.01 (ddd, 11.8, 4.0, 3.0) | | 03-He | 3.95 (q, 3, 3, 3) | | 04-Ha | 1.77 | | 04-He | 1.69 | | 05-H | 2.33 (dd, 13.2, 4.0) | | 07-H | 5.82 (dd, 2.6, 0.7) | | 09-Ha | 3.15 (dd, 9.2, 2.6) | | 11-Ha | 4.06 (ddd, 10.9, 9.2, 5.7) | | 12-Ha | 2.24 (dd, 12.2, 10.9) | | 12-He | 2.14 (dd, 12.2, 5.7) | | 15-Ha | 1.89 | | 15-Hb | 1.54 | | 16-Ha | 2.07 | | 16-Hb | 2.28 | | 17-H | 2.66 (dd, 9.8, 8.2) | | 18-Me | 0.850 (s) | | 19-Me | 1.053 (s) | | 21-Me | 1.226 (s) | | 22-H | 3.82 (bd, 5.6, 0.5) | | 23-Ha | 2.34 (dd, 14.3, 5.6) | | 23-Hb | 1.87 (dd, 14.3, 0.5) | | 25-H | 1.81 | | 26-Me | 0.924 (d, 7.1) | | 27-Me | 0.985 (d, 7.0) | | 28-Ha | 3.62 (d, 10.8) | | 28-Hb | 3.54 (d, 10.8) |
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| M.P. | °C ; | | [α]D20 | + 213 ° (c 0.02; EtOH) | | IR (KBr) ν max (cm-1) | 3390 (OH), 1658 (C=O), 1051, 1037, (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: CARTHAMOLEUSTERONE
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