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Year of first isolation: |
2008 |
| Formula: | C29H48O8 |
| Molecular weight: | 524 |
| 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 | CCC(CC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)O)C(C)(CO)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@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CC(C(CO)(C)O)CC)O)O)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@](C)([C@@H](C[C@H]([C@@](CO)(C)O)CC)O)O)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@](C)([C@@H](C[C@H]([C@](CO)(C)O)CC)O)O)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@](C)([C@@H](C[C@@H]([C@@](CO)(C)O)CC)O)O)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@](C)([C@@H](C[C@@H]([C@](CO)(C)O)CC)O)O)O)C)C »
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-17-[(2R,3R,5R)-5-ethyl-2,3,6,7-tetrahydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 101851587 | InChiKey
[ ChemIDPlus: search ] | ZBEOVYLJIQOXKK-YPNFDIQASA-N | | InChI | InChI=1S/C29H48O8/c1-6-16(27(4,35)15-30)11-24(34)28(5,36)23-8-10-29(37)18-12-20(31)19-13-21(32)22(33)14-25(19,2)17(18)7-9-26(23,29)3/h12,16-17,19,21-24,30,32-37H,6-11,13-15H2,1-5H3/t16-,17+,19+,21-,22+,23+,24-,25-,26-,27?,28-,29-/m1/s1 |
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| HR-ESI-MS m/z | 547.3276 [M+Na]+ (calculated for C29H48O8Na : 547.3247) | | ESI-MS/MS m/z | 525 [M+H]+, 507 [M+H-H20]+, 489 [M+H-2H20]+, 471 [M+H-3H2O]+, 453 [M+H-4H2O]+ |
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| CD3OD | | 01 | 37.36 | | 02 | 68.71 | | 03 | 68.51 | | 04 | 32.87 | | 05 | 51.80 | | 06 | 206.44 | | 07 | 122.14 | | 08 | 167.86 | | 09 | 35.10 | | 10 | 39.26 | | 11 | 21.63 | | 12 | 32.49 | | 13 | ~49.17 | | 14 | 85.19 | | 15 | 31.81 | | 16 | 21.63 | | 17 | 50.39 | | 18 | 18.03 | | 19 | 24.41 | | 20 | 77.91 | | 21 | 20.82 | | 22 | 77.57 | | 23 | 33.40 | | 24 | 45.30 | | 25 | 76.41 | | 26 | 69.08 | | 27 | 21.01 | | 28 | 25.04 | | 29 | 14.30 |
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| CD3OD | | 01-Ha | 1.43 | | 01-He | 1.79 | | 02-Ha | 3.84 (ddd, 12.0, 4.2, 3.0) | | 03-He | 3.95 (q, 3, 3, 3) | | 04-Ha | 1.68-1.76 | | 04-He | 1.68-1.76 | | 05-H | 2.39 (dd, 12.8, 4.8) | | 07-H | 5.81 (d, 2.6) | | 09-Ha | 3.16 (m, 11.5, 7, 2.6) | | 11-Ha | 1.71 | | 11-He | 1.80 | | 12-Ha | 2.13 (td, 13, 13, 5) | | 12-He | 1.87 | | 15-Ha | 1.96 | | 15-Hb | 1.62 | | 16-Ha | 1.78 | | 16-Hb | 2.04 | | 17-H | 2.39 (dd, 10.0, 8.8) | | 18-Me | 0.896 (s) | | 19-Me | 0.967 (s) | | 21-Me | 1.196 (s) | | 22-H | 3.45 (dd, 10.8, 2.4) | | 23-Ha | 1.45 | | 23-Hb | 1.37 | | 24-H | 1.66 | | 26-Ha | 3.58 (d, 11.7) | | 26-Hb | 3.35 (d, 11.7) | | 27-Me | 1.061 (s) | | 28-Ha | 1.79 | | 28-Hb | 1.20 | | 29-Me | 1.030 (t, 7.4, 7.4) |
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| M.P. | °C ; | | [α]D20 | + 64.0 ° (c 0.075; EtOH) | | IR (KBr) ν max (cm-1) | 3409 (OH), 1654 (C=O), 1056 (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: 26-HYDROXYMAKISTERONE C
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